Podcasts about vacation rentals

Send us a message!AI is changing the way travelers search, compare, and book vacation rentals. But what does that mean for direct bookings, local brands, and the websites operators have spent years building?In this episode, Alex and Annie are joined by Richard Vaughton of Yes Consulting and Mark Simpson of Boostly for The Great AI Debate. After taking this conversation to the stage at the Host Planet Roadshow in London, Richard and Mark continue the discussion around what AI could mean for vacation rental marketing, website strategy, and guest acquisition.Richard argues that AI will reshape websites, search, and distribution in ways the industry has not fully prepared for yet. Mark makes the case that strong website infrastructure, brand strategy, PMS connectivity, and niche positioning still matter, especially for operators who want to grow direct bookings.Together, they explore whether AI search will create new opportunities for independent vacation rental companies or make it even harder to compete with OTAs.Episode Chapters:05:29 - How AI is changing the future of vacation rental websites07:10 - The debate between WordPress websites and AI-built websites10:00 - Why website design alone is not enough to drive direct bookings28:25 - How Airbnb, Vrbo, Booking.com, and Expedia continue to shape guest behavior36:29 - Why broad search terms are becoming harder for local operators to compete for18:00 - How AI search could make niche positioning more important21:53 - The growing role of TikTok, creators, and social media in travel discovery46:03 - Why brand trust still matters in an AI-driven search environment48:22 - How PMS data, integrations, and distribution may evolve53:22 - What vacation rental operators should be thinking about now as search changesAs guest behavior shifts, vacation rental operators are being pushed to think more carefully about how people find them, what makes their brand memorable, and how they can stay visible beyond the major booking platforms. Connect with Richard:LinkedIn: https://www.linkedin.com/in/richardvaughton/ Website: https://yes.consulting/ Connect with Mark:LinkedIn: https://www.linkedin.com/in/mrmarksimpson/ Website: https://boostly.co.uk/ ✨ Exclusive Offers to Alex & Annie Listeners: Thinking about the next chapter for your vacation rental business? Connect with Monarch Collective to explore what growth could look like with the right platform behind you.

We're joined this week by Frank Bosi from Hostfully to talk all things AI, PMS platforms, building tech today vs several years ago, growth, winning with software and ops and a LOT more...Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'Connell Frank BosiSave $500 On Onboarding By Signing Up Via This Link

We're joined this week by Luca De Giglio and Richard Vaughton to talk all things SaaS, the growth of agents, building your own PMS platform, coding platforms growth, how Vacation Rental managers should use AI and a lot more... Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'Connell LinkedIn PostLuca De GiglioRichard Vaughton

Research published by MarketerMedia in March 2026 confirmed that 91% of property managers believe timely communications directly impact their guest review scores. Learn how ResortCleaning can help. ResortCleaning City: Orange Beach Address: PO Box 1155 Website: https://www.resortcleaning.com/

We're joined this week by Jan Sahagun of Trellis (backed by YC) to talk all things agents, the future of STR/Vacation Rentals tech, running with lean teams, 150 properties with 1 person and a lot more. Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'Connell Jan SahagunTrellis

ResortCleaning connects vacation rental operators across Airbnb, Guesty, Vacasa, and more than 20 platforms in one housekeeping command center. ResortCleaning City: Orange Beach Address: PO Box 1155 Website: https://www.resortcleaning.com/

We're solo this week to explore a fun thought experiment: what if we had to open our own vacation rental company? How would we operate it? Fund it? Grow it? What types of inventory are we targeting and why? Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'Connell 

https://www.emeraldcoastbyowner.com/blog/rosemary-beach-vacation-rentals-by-owner-cost-and-amenitiesLearn which vacation rental amenities truly elevate your Rosemary Beach getaway. From private pools and beach access to bikes and outdoor kitchens, find out why these features matter and how they transform your 30A experience into something unforgettable. Emerald Coast By Owner City: Destin Address: 15 Todd Point Website: https://www.emeraldcoastbyowner.com

We're joined by an all-star cast from all over the US to talk AI, practical use-cases and growth in tooling that is going to move the needle. JJ King, Jack Zoppa and Jacob Mueller join us to each give one example of how they're using AI in their business spanning hiring, reviews, brand rep and a LOT more. Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'Connell Jamie LaneAirDNA

Today, on the 224th episode of the As The Raven Dreams podcast, we have 13 True Chilling stories. These stories come from the shadowy corners of reality, where everyday life takes an eerie twist & ordinary people experience the extraordinary. Today we will be diving into The Terrors of vacation rentals (like Air BNB), scary things in the middle of nowhere, and other scary stories from listeners! Hey There! Would you like to participate in the postcard exchange? It comes with a free ATRD Sticker! Just Send a post card to the following... Lucas PO BOX 8198 Rochester, MN 55903 If you enjoyed this episode, be sure to like or rate the podcast, and leave me a comment with your thoughts if the platform your on supports it! I upload episodes every 3 days, so there are 2 days between new uploads. The podcast consists of new scary story collections, Glitch in the matrix collections, and also what I call the "Dark Dreams" collections (which are older stories, remastered and layered with rain sounds). If you have a story to submit, would like to find where to listen to the podcast, or want to find me on social media platforms, all of that info can be found at https://www.astheravendreams.com You can also send stories into my subreddit (r/theravensdream) or email them to me at AsTheRavenDreams@gmail.com Want to check out some ATRD Podcast Merch? ➤ https://teechip.com/stores/astheravendreams Or for signed merch ➤ https://ko-fi.com/AsTheRavenDreams I wrote a novel, "The Insomniac's Experiment" by Raven Adams! Check it out on amazon (Or you can email me for a signed copy!) Join Patreon to get early access and support the Podcast! ➤ https://www.patreon.com/AsTheRavenDreams Check out my gaming channel with my pal Ghost_Ink ➤ @superNefariousBros On YouTube Thank you to all of the authors that have stories in todays episode... SonOfaBeach, JudyAndPaul, TeacherTeachingTeachers, GarrettWithAMountainView, Stephen, Just another small town girl, Wade, Rabbit Rabbit , Kisu, Ray Ray, louise, Jane F, Tricia M As Well As Any Author That Has Requested Anonymity. TimeStamps… Ad breaks after Story 1 & Story 5 1 ➤ 1:07 2 ➤ 9:49 3 ➤ 19:54 4 ➤ 28:39 5 ➤ 35:06 6 ➤ 43:56 7 ➤ 46:07 8 ➤ 55:22 9 ➤ 58:18 10 ➤ 1:02:30 11 ➤ 1:14:57 12 ➤ 1:18:13 13 ➤ 1:24:47 ----- Disclaimer ➤ Episodes include a content warning for language and sensitive/disturbing content. Listener discretion is always advised. ALL Audio and visuals on this podcast are copyright of AS THE RAVEN DREAMS / RAVEN ADAMS and may not be duplicated, in any format. Bless This Mess. None of my audio is AI Generated, I am a real person reading real stories into a real microphone. Note: The podcast nor the host endorses any advertisements played during the podcast, ads are not chosen by ATRD or Raven Adams, they are chosen automatically by the advertisement systems by the platforms that host the podcast. I do not endorse, support, or promote any opinions or statements made in any adverts played during the show. #ScaryStories #UnexplainedMysteries #GlitchInTheMatrix Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode, Ryan Moyer shares his expertise in short-term rental investments and property management, focusing on operational excellence, high-end experiential rentals, and strategic growth. Learn how to stay competitive, optimize revenue, and build a strong network in the vacation rental industry.   Professional Real Estate Investors - How we can help you: Investor Fuel Mastermind:  Learn more about the Investor Fuel Mastermind, including 100% deal financing, massive discounts from vendors and sponsors you're already using, our world class community of over 150 members, and SO much more here: http://www.investorfuel.com/apply   Investor Machine Marketing Partnership:  Are you looking for consistent, high quality lead generation? Investor Machine is America's #1 lead generation service professional investors. Investor Machine provides true 'white glove' support to help you build the perfect marketing plan, then we'll execute it for you…talking and working together on an ongoing basis to help you hit YOUR goals! Learn more here: http://www.investormachine.com   Coaching with Mike Hambright:  Interested in 1 on 1 coaching with Mike Hambright? Mike coaches entrepreneurs looking to level up, build coaching or service based businesses (Mike runs multiple 7 and 8 figure a year businesses), building a coaching program and more. Learn more here: https://investorfuel.com/coachingwithmike   Attend a Vacation/Mastermind Retreat with Mike Hambright: Interested in joining a "mini-mastermind" with Mike and his private clients on an upcoming "Retreat", either at locations like Cabo San Lucas, Napa, Park City ski trip, Yellowstone, or even at Mike's East Texas "Big H Ranch"? Learn more here: http://www.investorfuel.com/retreat   Property Insurance: Join the largest and most investor friendly property insurance provider in 2 minutes. Free to join, and insure all your flips and rentals within minutes! There is NO easier insurance provider on the planet (turn insurance on or off in 1 minute without talking to anyone!), and there's no 15-30% agent mark up through this platform!  Register here: https://myinvestorinsurance.com/   New Real Estate Investors - How we can work together: Investor Fuel Club (Coaching and Deal Partner Community): Looking to kickstart your real estate investing career? Join our one of a kind Coaching Community, Investor Fuel Club, where you'll get trained by some of the best real estate investors in America, and partner with them on deals! You don't need $ for deals…we'll partner with you and hold your hand along the way! Learn More here: http://www.investorfuel.com/club   —--------------------

William Parmer shares how education, faith, family support, and bold action helped him move from law enforcement into rental investing, passive income, and the deeper pursuit of buying back his time.See article: https://www.unitedstatesrealestateinvestor.com/create-remarkable-courage-to-buy-back-your-time-with-william-parmer/(00:00) - Introduction to The REI Agent Podcast and William Parmer(00:24) - William's Welcome and Goal to Inspire Investors(00:34) - From Veteran and Law Enforcement Officer to Real Estate Investor(00:46) - COVID Patrol Shifts, Podcast Discovery, and Learning Through Master Passive Income(03:15) - How Real Estate Education Changed William's View of the Paycheck Path(03:56) - Coaching, Cold Feet, and Closing the First Out-of-State Rental(05:56) - William's Family Life and Being a Husband and Father of Four Girls(06:41) - The Kitchen Table Money Conversation With His Wife(08:12) - Choosing Between Single-Family Rentals, Short-Term Rentals, and Mobile Home Parks(08:24) - Why Mobile Home Parks Are More Complex Than Traditional Rentals(10:26) - Mobile Home Parks, Affordability, and Risk Compared With Luxury Rentals(11:16) - Short-Term Rental Risk and Using Long-Term Rental Numbers as the Backup Plan(12:33) - The ABC Plan for Short-Term, Mid-Term, and Long-Term Rental Exits(13:08) - Mid-Term Rentals, Furnished Finder, and Less Management(13:50) - Market Differences in Vacation Rentals, Mid-Term Rentals, and Co-Living(15:12) - Finding Cash-Flowing Long-Term Rentals in Tougher Interest Rate Markets(16:17) - Factoring Property Management Into the Numbers From Day One(17:34) - Researching Appreciation, Local Industries, and Midwest Market Myths(18:21) - William's Zillow and AI Process for Analyzing Out-of-State Markets(21:51) - Using Property Managers for Virtual Market Feedback(22:28) - How to Ask Property Managers About Specific Rental Properties(23:42) - Working With Agents and Property Managers Before Making Offers(24:57) - The Value of Boots-on-Ground Professionals in Repeat Markets(26:29) - Building a Vendor Rolodex Through Local Banks, Managers, and Referrals(27:47) - The Biggest Mistake New Investors Make(28:01) - Analysis Paralysis and Why New Investors Chase Perfect Numbers(29:11) - Why Most Beginner Mistakes Are Not as Catastrophic as They Feel(30:41) - Buying Below Market Value and Focusing on Cash Flow(31:32) - The Hidden Expenses Beginners Forget in Cash-Flow Calculations(32:15) - Why William Recommends Reaching at Least 10 Rentals(33:40) - Mattias's Line in the Sand Against DIY Repairs(35:46) - Local Bank Relationships, ARV Lending, and Flexible Financing(36:37) - How Rental Housing Serves People Who Do Not Want to Own(37:57) - Using Equity, Refinances, and HELOCs to Grow(38:43) - The Golden Nugget: Start With Education(38:58) - Podcasts, Notes, AI Explanations, Books, Coaching, and Meetups(41:11) - Foundational Books for Investors(41:20) - Rich Dad Poor Dad, Cashflow Quadrant, Benjamin Hardy, and Mindset Books(42:24) - Where to Find William Parmer and Breakthrough InvestorContact William Parmerhttps://masterpassiveincome.com/coach/william-parmerhttps://www.facebook.com/william.parmer.2025/https://www.instagram.com/william.c.parmer/https://www.linkedin.com/in/william-cary-parmer-8480382a4/William Parmer's story is a powerful reminder that financial freedom does not begin with perfect confidence. It begins with education, action, and the courage to buy back your time. Keep learning, keep building, and keep moving toward a life that gives your family more options. For more inspiring investor conversations, visit https://reiagent.comIs success destroying your peace? Most pros grind until they break. Download The Investor's Life Balance Sheet: A Holistic Wealth Audit to see if you are building a legacy or heading for burnout. Presented by The REI Agent Podcast & United States Real Estate Investor® https://sendfox.com/lp/m4jrl

Send us a message!In this episode, we welcome back Mike Flaskey, President and Chief Operating Officer of Marriott Vacations Worldwide.Mike shares what brought him back to the industry, what his new role looks like, and how Marriott Vacations Worldwide is approaching loyalty, customer experience, owner engagement, and long-term value.The conversation looks at the timeshare and vacation club model through a hospitality lens, including how major brands build trust, keep owners engaged, and create value beyond the initial sale or stay.Alex, Annie, and Mike also explore what short-term rental operators can learn from Marriott Vacations Worldwide, especially when it comes to consistency, brand standards, guest experience, and creating reasons for people to stay connected over time.Episode Chapters:02:32 - Why Mike returned to the industry and joined Marriott Vacations Worldwide10:06 - How Marriott Vacations Worldwide thinks about loyalty11:02 - The role of Marriott Bonvoy in brand affinity and direct bookings18:53 - What vacation rental operators can learn from timeshare19:30 - How brand standards help build guest trust28:20 - Why lifetime value matters in the customer journey29:00 - Viewing vacation ownership as a subscription business31:09 - Using experiences to strengthen loyalty and engagement40:11 - How Marriott Vacations Worldwide is using AI in sales training41:41 - How AI is changing digital search and hospitality marketing47:52 - Why prepaid vacations create resilience51:43 - What is ahead for Marriott Vacations WorldwideConnect with Mike:LinkedIn: https://www.linkedin.com/in/mike-flaskey-13496094 Instagram: https://www.instagram.com/thevacationdr/reels/ Connect with Marriott Vacations Worldwide:Marriott Vacation Club: https://www.instagram.com/marriottvacationclub/ Westin Vacation Club: https://www.instagram.com/westinvacationclub/ Sheraton Vacation Club: https://www.instagram.com/sheratonvacationclub/ ✨ Exclusive Offer to Alex & Annie Listeners:Automate your short-term rental operations with Hospitable.Start a 14-day free trial and get 25% off your bill for the first 6 months.

We're joined by a favorite guest, Jamie Lane of Airdna to talk all things q1 2026 wrap up, World Cup demand, reading data the right way, how AI is impacting the AirDNA product, future-looking tips for vacation rental managers and a LOT more. Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'Connell Jamie LaneAirDNA

Send us a message!In this episode, Alex & Annie sit down with Pierre-Camille Hamana, founder and CEO of Hospitable, to talk about the evolution of vacation rental software and why adoption across the industry still has so much room to grow.Pierre-Camille shares how his own experience as an Airbnb host in Brussels led to the creation of Smartbnb, which later became Hospitable. What started as a solution for repetitive guest messaging has grown into a broader property management platform supporting communication, operations, channel management, direct bookings, payments, and more.The conversation also explores why many hosts and operators still hesitate to adopt property management software, how Hospitable is working to make software more accessible, and what AI could mean for guest communication, support, direct bookings, and the future of vacation rental distribution.In this episode, we discuss:02:27 - How Pierre-Camille's experience as an Airbnb host led to the creation of Hospitable04:22 - Why guest messaging became the starting point for a larger software platform09:45 - How Hospitable evolved from Smartbnb into a broader property management system20:16 -  Why software adoption remains low across parts of the short-term rental industry21:55 - The challenges that keep smaller hosts and operators from adopting software23:44 - Hospitable's approach to making property management software more accessible17:47 - How self-managers can grow into co-hosts or professional property managers41:47 - The role of AI in guest messaging, customer support, and software usability44:07 - Why AI should make tools easier to use, not simply add more complexity53:07 - What AI agents could mean for OTAs, direct bookings, and property discovery53:07 - Why strong owner service, guest experience, and operational consistency still matter as technology evolvesConnect with Pierre-Camille:LinkedIn: https://www.linkedin.com/in/pchamana/ Connect with Hospitable:Website: https://hospitable.com/partners/alex-annie LinkedIn: https://www.linkedin.com/company/hospitable/ Instagram: https://www.instagram.com/hospitable_com/ Facebook: https://www.facebook.com/hospitable/ ✨ Exclusive Offer to Alex & Annie Listeners:Automate your short-term rental operations with Hospitable.Start a 14-day free trial and get 25% off your bill for the first 6 months.

We're pumped to welcome Michael Friedman, Chief Executive Officer of Simple Life Rentals onto the show to talk all things AI, growth, team, profitability, smart homeowner marketing that works, where we're headed into 2026 and a LOT more.Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'Connell Michael FriedmanSimple Life Rentals

In this Good Morning Hospitality, A Skift Podcast Bonus episode, Brandreth Canaley and Michael Goldin sit down with Tim Rosolio, VP of Vacation Rental Partnerships at Vrbo/Expedia Group, from a standout “Vacation Rental of the Year” property in New Hampshire. Tim breaks down what actually drives performance on Vrbo today, from must-have amenities and pricing strategies to the growing importance of quality, consistency, and reviews in an increasingly saturated market. He shares why the short-term rental “gold rush” is officially over, and what operators need to do now to stay competitive. The conversation also dives into Expedia Group's broader strategy, including the rapid growth of B2B distribution, the expansion of vacation rentals across Expedia's ecosystem, and how new tools like promotions and sponsored listings are changing visibility and bookings. They also tackle AI in travel, where it's already delivering value, where it's overhyped, and why the human element still matters in hospitality. Episode Chapters: 00:00 Snowy New Hampshire Setup 01:08 Why This Rental Won 01:26 How Vrbo Picks Homes 02:35 Hosts Who Go All In 05:22 Amenity Must-Haves 07:57 Boosting Rankings Fast 08:25 Promotions That Convert 10:25 Is The Gold Rush Over 12:44 Quality Over Quantity Era 16:58 Standards And Trust Issues 19:00 Cleaning and Reviewing Data 20:26 Reviews Signal Quality 21:36 Star Ratings Confusion 22:26 B2B Growth Expansion 25:09 AI In Travel Tech 26:32 Keeping Human Hospitality 28:16 OneKey On Vrbo 29:48 Sponsored Listings Launch 33:14 Rapid Fire Wrap Up Connect with Skift LinkedIn: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/company/skift/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ WhatsApp: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://whatsapp.com/channel/0029VaAL375LikgIXmNPYQ0L/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Facebook: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://facebook.com/skiftnews⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Instagram: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.instagram.com/skiftnews/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Threads: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.threads.net/@skiftnews⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Bluesky: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://bsky.app/profile/skiftnews.bsky.social⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ X: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://twitter.com/skift⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Subscribe to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠@SkiftNews⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and never miss an update from the travel industry.

Send us a message!In this special episode, Alex and Annie sit down with Tim Rosolio, Vice President of Vacation Rental Partnerships at Vrbo, for a behind-the-scenes look at Vrbo's Vacation Rentals of the Year program and what it takes to earn that recognition.Recorded on location at Lakefront Escape on Squam Lake, New Hampshire, one of this year's winning properties, the episode offers both a platform perspective and a firsthand look at the kind of hospitality Vrbo is celebrating.Tim shares how Vrbo selects winners from millions of properties across its global network, using a mix of performance data, guest reviews, local market insight, and hospitality storytelling to identify homes that deliver standout guest experiences.The conversation then shifts to David Rose, owner of Lakefront Escape, who shares how he transformed a dated lake house into an award-winning retreat designed with intention, warmth, and usability in mind.From intuitive in-home tech and thoughtful labels to tailored recommendations and architectural details, this episode highlights how exceptional hospitality is built through the details.In this episode, we cover:03:50 - Why Vrbo created the Vacation Rentals of the Year program04:39 - How Vrbo selects its Vacation Rentals of the Year08:04 - What makes a vacation rental experience feel personal and memorable13:35 - Meet David Rose and the story behind Lakefront Escape16:42 - Why intuitive technology matters more than flashy features23:00 - How David Rose designed Lakefront Escape for connection, comfort, and discovery25:20 - Why David chose self-management and how Vrbo supports pricing and promotion26:43 - How personalized recommendations can elevate the guest stay30:34 - How labels, notes, and in-home guidance reduce guest friction32:21 - The Japanese design influence behind the home's guest experience35:27 - How design, layout, and local insight help create repeat guestsThis episode captures both the criteria behind Vrbo's recognition and the real-world hospitality choices that help a property earn it.Connect with:David Rose / Lakefront Escapehttps://www.squamlakehouse.com/ Tim Rosolio / Vrbohttps://www.linkedin.com/in/tim-rosolio-434b2a98/ ✨ Exclusive Offer to Alex & Annie Listeners:Automate your short-term rental operations with Hospitable. Start a 14-day free trial and get 25% off your bill for the first 6 months.

We're thrilled to be joined today by Neely Khan and Rachel Alday to talk all things storytelling, marketing to luxury, being chosen vs being found, AI / LLM discoverability, and a LOT more.Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'Connell Neely KhanRachel AldaykahaniAbode Luxury Rentals

Uncover the hidden fees, breed restrictions, and local laws that can derail your pet-friendly vacation. Learn how direct booking saves money and why communication with property owners is your best tool for a smooth getaway. Find out more at https://www.emeraldcoastbyowner.com/blog/florida-panhandle-vacation-rentals-by-owner-cost-amenities-petfriendly-options Emerald Coast By Owner City: Destin Address: 15 Todd Point Website: https://www.emeraldcoastbyowner.com

Join Scott Bursey as he interviews Kevin Anderson, a real estate expert specializing in luxury villas and ghostwriting. Discover insights on high-end property management, market opportunities, and the value of passion-driven investments.   Professional Real Estate Investors - How we can help you: Investor Fuel Mastermind:  Learn more about the Investor Fuel Mastermind, including 100% deal financing, massive discounts from vendors and sponsors you're already using, our world class community of over 150 members, and SO much more here: http://www.investorfuel.com/apply   Investor Machine Marketing Partnership:  Are you looking for consistent, high quality lead generation? Investor Machine is America's #1 lead generation service professional investors. Investor Machine provides true 'white glove' support to help you build the perfect marketing plan, then we'll execute it for you…talking and working together on an ongoing basis to help you hit YOUR goals! Learn more here: http://www.investormachine.com   Coaching with Mike Hambright:  Interested in 1 on 1 coaching with Mike Hambright? Mike coaches entrepreneurs looking to level up, build coaching or service based businesses (Mike runs multiple 7 and 8 figure a year businesses), building a coaching program and more. Learn more here: https://investorfuel.com/coachingwithmike   Attend a Vacation/Mastermind Retreat with Mike Hambright: Interested in joining a "mini-mastermind" with Mike and his private clients on an upcoming "Retreat", either at locations like Cabo San Lucas, Napa, Park City ski trip, Yellowstone, or even at Mike's East Texas "Big H Ranch"? Learn more here: http://www.investorfuel.com/retreat   Property Insurance: Join the largest and most investor friendly property insurance provider in 2 minutes. Free to join, and insure all your flips and rentals within minutes! There is NO easier insurance provider on the planet (turn insurance on or off in 1 minute without talking to anyone!), and there's no 15-30% agent mark up through this platform!  Register here: https://myinvestorinsurance.com/   New Real Estate Investors - How we can work together: Investor Fuel Club (Coaching and Deal Partner Community): Looking to kickstart your real estate investing career? Join our one of a kind Coaching Community, Investor Fuel Club, where you'll get trained by some of the best real estate investors in America, and partner with them on deals! You don't need $ for deals…we'll partner with you and hold your hand along the way! Learn More here: http://www.investorfuel.com/club   —--------------------

​Comedian Tony P joins the show to discuss why he's accidentally "swinger bait" in Florida and the absolute nightmare of his latest vacation. We also deep dive into the 2026 World Cup price gouging at MetLife Stadium—from $150 train rides to the $255 parking "deals."​Highlights:​World Cup Chaos: Why FIFA told Chuck Schumer to kick rocks while fans face $10,000 tickets.​Albert the Alligator: After 34 years, Tony Cavallaro officially loses his 750lb "best friend."​The Backyard Guests: A hot air balloon emergency lands in a California yard and the passengers act like it's a social call.​Politics vs. Religion: Why are people trading their faith for politicians?​Tony P's Vacation: Rental car rage and why Florida swingers were eyeing him at the bar.​Keywords: NYC Comedy, Tony P, MetLife Stadium World Cup, Albert the Alligator Buffalo, Tony Cavallaro, Podcast Comedy NYC, Swinger Stories, Hot Air Balloon Landing.

We're thrilled to welcome John Suzuki - industry LEGEND - to the podcast to talk all things AI, the future, retirement (and then un-retirement), platforms, young professionals interacting with AI and a LOT more...Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'Connell John SuzukiFinding Better PodcastAmerican Grit BookStaylist

Short-term rentals have matured fast. But many operators are still stuck paying rising distribution costs while losing control of the guest relationship. In this episode, Eric Goldreyer, hospitality entrepreneur and founder of BedandBreakfast.com, former co-founder of TurnKey Vacation Rentals, and creator of Savvy, joins Brian to unpack what's happening behind the scenes in vacation rental distribution. Eric has built, scaled, and sold companies in the space. He also owns and operates a 20-key boutique hotel outside Austin, giving him both strategic and ground-level insight into hospitality operations. This conversation focuses on one core issue: Who owns the guest relationship — and what does that cost you? What We Cover: Why vacation rental distribution costs have increased while hotel distribution costs have decreased The "Airbnb tax" and how it affects long-term profitability Why hosts don't truly own their customer data on major OTAs The difference between transaction fees and customer acquisition costs Why professional property management is separating from gig-economy hosting How book-direct marketplaces are changing the economics of short-term rentals What it takes to scale a property management company nationally Leveraging tech stacks, automation, and AI in modern vacation rental operations How Eric approaches hiring high-performance teams Why hospitality — not just technology — is the real differentiator Eric also shares how his company Savvy is building a book-direct marketplace designed to reduce fees for travelers while giving property managers ownership of their customer relationships. Key Themes Short-term rental profitability OTA dependency risk Distribution strategy Hospitality vs platform control Direct booking models AI in vacation rental tech stacks Resources Mentioned Savvy: https://savvy.com Eric Goldreyer on LinkedIn Sage Hill Inn (Boutique Hotel outside Austin) Today's episode is brought to you by Green Property Management, managing everything from single family homes to apartment complexes in the West Michigan area. https://www.livegreenlocal.com And RCB & Associates, helping Michigan-based real estate investors and small business owners navigate the complex world of health insurance and medicare benefits. https://www.rcbassociatesllc.com

A recent Checkbook investigation found widespread problems with vacation rentals, including fake listings and stolen deposits. Even worse, many victims get little or no help from Booking.com or Vrbo to recover their lost money.In this episode: We share results of our investigation and provide tips on how to protect yourself when booking a vacation rental. One key: Your best move to avoid losing money to scams or bad actors is to book with a credit card.Read our full report about vacation rental scams at Checkbook.org.Not a Checkbook member? ⁠⁠⁠⁠⁠Sign up for a free 30-day trial to access all of our unbiased ratings⁠⁠⁠⁠⁠.

Send us a message!What does it take to grow a vacation rental company without losing the local identity that made it successful in the first place?In this episode, we are joined by Jakob Dwyer, CEO of Awayday, to talk about how the company is scaling through a model built on local leadership, shared support, and strong operational foundations.Instead of forcing every market into the same mold, Awayday supports growth through shared resources across accounting, HR, revenue management, business development, and technology, while local teams continue to lead the day-to-day business. Jakob also shares how that approach influences the way Awayday evaluates partners, supports local operators, and balances growth with owner and guest experience.This conversation offers a clear look at how Awayday is building scale through stronger operations and support without losing the local identity at the core of each business.Episode Chapters:00:00 - Intro to Awayday CEO Jakob Dwyer01:14 - Jakob Dwyer's background in vacation rentals and RealJoy's growth05:52 - How Awayday scales local vacation rental companies10:50 - Why local market knowledge matters in vacation rental growth13:07 - What Awayday looks for in a vacation rental partner18:17 - Founder transitions, succession planning, and exit options23:15 - Why strong vacation rental operations matter more than growth at all costs27:01 - Awayday's onboarding process and value creation strategy31:41 - Shared services, local leadership, and centralized support37:05 - How Awayday is thinking about AI in vacation rental operations46:11 - SOPs, company culture, and empowering vacation rental teams50:57 - Awayday's growth strategy for 2026 and beyond58:43 - Why every team member plays a role in company growthThis episode is brought to you by Awayday. If you are interested in being part of a company that values local leadership, strong operations, and long-term growth, connect with Jakob at jakob@awayday.com.Connect with Jakob:LinkedIn: https://www.linkedin.com/in/jakob-dwyer-19516033/ Connect with Awayday:Website: https://www.awayday.com/ LinkedIn: https://www.linkedin.com/company/awayday-vacation-rentals/ ✨ Exclusive Offer to Alex & Annie Listeners:Streamline your short-term rental operations with Hostfully.Mention the Alex & Annie Podcast when you sign up and get free onboarding ($1000 value).

Stephen Petasky shares his 20-year journey from starting Luxus Group with a syndication of vacation properties to becoming a leader in luxury real estate, short-term rentals, and high-end hospitality. He discusses the evolution of the short-term rental industry, regulatory challenges, the rise of branded residential, and strategies for scaling in a complex luxury market.   Professional Real Estate Investors - How we can help you: Investor Fuel Mastermind:  Learn more about the Investor Fuel Mastermind, including 100% deal financing, massive discounts from vendors and sponsors you're already using, our world class community of over 150 members, and SO much more here: http://www.investorfuel.com/apply   Investor Machine Marketing Partnership:  Are you looking for consistent, high quality lead generation? Investor Machine is America's #1 lead generation service professional investors. Investor Machine provides true 'white glove' support to help you build the perfect marketing plan, then we'll execute it for you…talking and working together on an ongoing basis to help you hit YOUR goals! Learn more here: http://www.investormachine.com   Coaching with Mike Hambright:  Interested in 1 on 1 coaching with Mike Hambright? Mike coaches entrepreneurs looking to level up, build coaching or service based businesses (Mike runs multiple 7 and 8 figure a year businesses), building a coaching program and more. Learn more here: https://investorfuel.com/coachingwithmike   Attend a Vacation/Mastermind Retreat with Mike Hambright: Interested in joining a "mini-mastermind" with Mike and his private clients on an upcoming "Retreat", either at locations like Cabo San Lucas, Napa, Park City ski trip, Yellowstone, or even at Mike's East Texas "Big H Ranch"? Learn more here: http://www.investorfuel.com/retreat   Property Insurance: Join the largest and most investor friendly property insurance provider in 2 minutes. Free to join, and insure all your flips and rentals within minutes! There is NO easier insurance provider on the planet (turn insurance on or off in 1 minute without talking to anyone!), and there's no 15-30% agent mark up through this platform!  Register here: https://myinvestorinsurance.com/   New Real Estate Investors - How we can work together: Investor Fuel Club (Coaching and Deal Partner Community): Looking to kickstart your real estate investing career? Join our one of a kind Coaching Community, Investor Fuel Club, where you'll get trained by some of the best real estate investors in America, and partner with them on deals! You don't need $ for deals…we'll partner with you and hold your hand along the way! Learn More here: http://www.investorfuel.com/club   —--------------------

Welcome to the AoH Operator Series! We're excited to peel back the layers on the smartest minds in short term rentals / vacation rentals who are in the weeds leading teams, building businesses and driving amazing results. We're thrilled to welcome CJ Johnson, Regional Director at Fairly to talk all things about Fairly! We learn how many properties they have (hint: it's already over 1,000 in just over 12~ months), where they are seeing growth, what makes their model unique vs Vacasa/other PMs, how "everyone can win" and a LOT more. Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'Connell CJ JohnsonFairly

This week started with the news that the Myanmar military junta held elections, plus an Italian art heist. Also an F-15 crew ejects over Iran, Gucci Mane kidnapping plot, Australia cop killer shot and killed, Indonesia social media ban for minors update, and a CA vacation rental owner is not only accused of secretly recording his guests having sex, buy having a bound-up child sex doll in his closet. Music: Gucci Mane/"Stick 'em Up"

Send us a message!We're kicking off a new special series, First of the Month Wrangle, in partnership with Lasoh, where we'll dig into the strategies, systems, and blind spots shaping one of the most important and often misunderstood areas of vacation rentals: marketing.Throughout the series, Alex & Annie will be joined by Orlie Benjamin, Founder and CEO of Lasoh, a vacation rental marketing platform built to help operators drive more direct bookings and increase profit through deeper relationships with every guest.Together, they explore what it really takes to build stronger guest relationships, improve direct booking performance, and think more strategically about marketing in vacation rentals.In this first episode, Orlie shares the thinking behind Lasoh and the problem she believes the industry still has not solved. While many of the core systems in vacation rentals are designed to manage properties, pricing, and distribution, far fewer are built to help operators understand guests, strengthen relationships, and market in a way that creates long-term value.The conversation looks at what happens when hospitality gets overshadowed by operations, why guest data matters far beyond the initial booking, and why marketing deserves a bigger role in growth strategy.Episode Chapters:01:56 - Why Orlie Benjamin built Lasoh for vacation rental marketing04:19 - What's missing from most vacation rental PMS platforms07:58 - Vacation rental tech vs. hotel tech: where the gaps still exist09:47 - Asset management vs. guest experience in hospitality11:01 - Why hospitality gets harder to scale in vacation rentals13:42 - Why revenue management and marketing should work together16:33 - The real levers of growth: customers, spend, and repeat stays21:03 - How Lasoh helps operators capture guest data and personalize marketing25:46 - Guest-first marketing vs. inventory-first marketingThis episode sets the tone for the series ahead and offers a valuable perspective for anyone looking to build a more thoughtful, guest-centered marketing strategy.✨ Exclusive offer for Alex & Annie listeners ✨Enjoy 20% off a monthly or annual subscription to Lasoh's Guest Portal or House Manual when you use code: AlexandAnnie.Access the offer here: https://explore.lasoh.io/alex-annie Valid through May 31, 2026.Learn more about Lasoh:Website: https://tinyurl.com/52nvyw8tLinkedIn: https://www.linkedin.com/company/lasoh/ Facebook: https://www.facebook.com/people/Lasohio/61575721958679/ Instagram: https://www.instagram.com/lasoh.ioConnect with Orlie:LinkedIn: https://www.linkedin.com/in/orliebenjamin/ Facebook: https://www.facebook.com/profile.php?id=61585160391720 Instagram: https://www.instagram.com/lasoh.io/#vacationrentals #vacationrentalmarketing #directbookings

We're joined by wunderkid Jack Zoppa to talk all things growth, AI, agents as tools to help your team, scaling to hundreds of units in his 20s, the future and a LOT more... you don't want to miss this one.Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'Connell Jack ZoppaHaven Vacation Rentals

Deputies say disturbing evidence was found inside an Oakhurst vacation rental after owner Christian Parmalee Edwards was arrested for secretly filming guests, including women and at least one child. Investigators seized over 4,000 files of child sexual abuse material and multiple devices, and say Edwards filmed guests through blinds and from inside the home. The loss of small perks and rise of AI have conspired to strip work of all fun; ‘It feels like a funeral in the office right now.’ Please Like, Comment and Follow 'Philip Teresi on KMJ' on all platforms: --- Philip Teresi on KMJ is available on the KMJNOW app, Apple Podcasts, Spotify, YouTube or wherever else you listen to podcasts. -- Philip Teresi on KMJ Weekdays 2-6 PM Pacific on News/Talk 580 AM & 105.9 FM KMJ | Website | Facebook | Instagram | X | Podcast | Amazon | - Everything KMJ KMJNOW App | Podcasts | Facebook | X | Instagram See omnystudio.com/listener for privacy information.

Deputies say disturbing evidence was found inside an Oakhurst vacation rental after owner Christian Parmalee Edwards was arrested for secretly filming guests, including women and at least one child. Investigators seized over 4,000 files of child sexual abuse material and multiple devices, and say Edwards filmed guests through blinds and from inside the home. The loss of small perks and rise of AI have conspired to strip work of all fun; ‘It feels like a funeral in the office right now.’ Please Like, Comment and Follow 'Philip Teresi on KMJ' on all platforms: --- Philip Teresi on KMJ is available on the KMJNOW app, Apple Podcasts, Spotify, YouTube or wherever else you listen to podcasts. -- Philip Teresi on KMJ Weekdays 2-6 PM Pacific on News/Talk 580 AM & 105.9 FM KMJ | Website | Facebook | Instagram | X | Podcast | Amazon | - Everything KMJ KMJNOW App | Podcasts | Facebook | X | Instagram See omnystudio.com/listener for privacy information.

What you'll learn in this episode: ● The difference between short-term and long-term rental markets ● Why vacation-driven markets with limited hotels are the best investment ● How to choose markets that maximize cash flow ● The #1 mistake investors make when buying their first Airbnb ● Why Avery avoids “emerging markets” everyone is hyping online ● How to scale a short-term rental business efficiently (even with a full-time job) ● How to out-host the competition and treat rentals like a real business ● How regulations impact profitability—and how to choose markets that protect you ● Avery's journey from one rental to a 250+ property empire To find out more about Dan Rochon and the CPI Community, you can check these links:Website: No Broke MonthsPodcast: No Broke Months for Salespeople PodcastInstagram: @donrochonxFacebook Page: https://www.facebook.com/NoBrokeMonths/Facebook: Dan RochonLinkedIn: Dan RochonTeach to Sell Preorder: Teach to Sell: Why Top Performers Never Sell – And What They Do Instead

Send us a message!In this episode, Tom Stewart, COO of Resort Realty, joins Alex & Annie to talk about the realities of running a vacation rental business in the Outer Banks, one of the most established and distinctive markets in the industry. They get into what makes the market different, from its geography and seasonality to its mix of inventory and long-standing operating norms.Tom also shares what it takes to keep a legacy operation strong as market conditions change. The conversation explores weather and erosion challenges, guest and owner communication, selective growth, direct bookings, linen and laundry logistics, dynamic pricing, onboarding complexity, and the reset in owner expectations after the COVID boom. If you work in vacation rentals, especially in a mature or highly seasonal market, this episode offers a practical look at what long-term success requires behind the scenes. Episode Chapters:04:20 - Tom Stewart's path into vacation rentals08:18 - What makes the Outer Banks such a unique vacation rental market11:37 - Weather, erosion, road access, and operating through disruption20:56 - Why legacy markets function differently from newer STR markets25:05 - Professionally managed inventory and Resort Realty's direct booking mix27:18 - Growth vs. scale and why selective inventory matters30:41 - Laundry, linens, and simplifying operations at scale36:13 - How Resort Realty approaches dynamic pricing44:16 - Expanding into long-term rentals and building steadier cash flow49:01 - Why onboarding large homes is more complex than it looks54:15 - How owner expectations changed after the COVID boom58:43 - Why pricing and demand look different now1:00:38 - Tom's advice for people getting into vacation rental operationsConnect with Tom:LinkedIn: https://www.linkedin.com/in/tom-s-8b607938/ Website: https://www.resortrealty.com/ ✨ Exclusive Offer to Alex & Annie Listeners:Streamline your short-term rental operations with Hostfully.Mention the Alex & Annie Podcast when you sign up and get free onboarding ($1000 value).

Andrea shares her journey from interior design to specializing in vacation rental design, emphasizing the importance of experience, decision-making, and industry knowledge in creating profitable and memorable short-term rental properties.   Professional Real Estate Investors - How we can help you: Investor Fuel Mastermind:  Learn more about the Investor Fuel Mastermind, including 100% deal financing, massive discounts from vendors and sponsors you're already using, our world class community of over 150 members, and SO much more here: http://www.investorfuel.com/apply   Investor Machine Marketing Partnership:  Are you looking for consistent, high quality lead generation? Investor Machine is America's #1 lead generation service professional investors. Investor Machine provides true 'white glove' support to help you build the perfect marketing plan, then we'll execute it for you…talking and working together on an ongoing basis to help you hit YOUR goals! Learn more here: http://www.investormachine.com   Coaching with Mike Hambright:  Interested in 1 on 1 coaching with Mike Hambright? Mike coaches entrepreneurs looking to level up, build coaching or service based businesses (Mike runs multiple 7 and 8 figure a year businesses), building a coaching program and more. Learn more here: https://investorfuel.com/coachingwithmike   Attend a Vacation/Mastermind Retreat with Mike Hambright: Interested in joining a "mini-mastermind" with Mike and his private clients on an upcoming "Retreat", either at locations like Cabo San Lucas, Napa, Park City ski trip, Yellowstone, or even at Mike's East Texas "Big H Ranch"? Learn more here: http://www.investorfuel.com/retreat   Property Insurance: Join the largest and most investor friendly property insurance provider in 2 minutes. Free to join, and insure all your flips and rentals within minutes! There is NO easier insurance provider on the planet (turn insurance on or off in 1 minute without talking to anyone!), and there's no 15-30% agent mark up through this platform!  Register here: https://myinvestorinsurance.com/   New Real Estate Investors - How we can work together: Investor Fuel Club (Coaching and Deal Partner Community): Looking to kickstart your real estate investing career? Join our one of a kind Coaching Community, Investor Fuel Club, where you'll get trained by some of the best real estate investors in America, and partner with them on deals! You don't need $ for deals…we'll partner with you and hold your hand along the way! Learn More here: http://www.investorfuel.com/club   —--------------------

In this episode, Heather Bayer sits down with Heidie Henriksen, Executive Director of VRNation, to talk about how the organization is helping to strengthen the short-term rental industry through education, collaboration, and community. Heidi shares her 25-year journey in the vacation rental industry - from starting as a host, to working in property management and technology, to now leading a national nonprofit focused on supporting operators across the sector. They discuss the evolution of VRNation, the success of its roadshow events bringing education directly to local markets, and the launch of the new VRNation Pro Academy, designed to raise professional standards across the industry. Heather also shares a quick update from Gulf Shores, Alabama, and talks about the upcoming 2nd cohort of the AI Ambassador Program, launching in early-April. ________________________________________________________________________________________________________

We welcome Chef Franck (Franck Desplechin) to hear a brand-new perspective on fine dining and how we can apply those foundational elements to the service in the short term vacation rental industry. Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'Connell Franck DesplechinChef Franck

Send a textIn this exciting episode of Living the Dream with Curveball, we chat with Carlos Castillo, co-founder of Direct Book Me, a platform revolutionizing the short-term rental industry. With a wealth of travel experience spanning 40 countries and 30 U.S. states, Carlos shares his journey from healthcare to entrepreneurship and his vision for building authentic connections between hosts and guests. He discusses how Direct Book Me empowers property owners by allowing them to retain 100% of their profits while providing travelers with a fee-free booking experience. Carlos emphasizes the importance of trust in the short-term rental space and how his platform aims to foster a trusted community. Tune in as he reveals the unique benefits of direct bookings, the challenges faced with traditional online travel agencies, and the exciting future trends shaping the vacation rental market. Whether you're a host or a traveler, this episode is packed with insights to help you navigate the evolving landscape of short-term rentals. Don't miss out on the chance to learn how to get started with Direct Book Me!Want to be a guest on Living the Dream with Curveball? Send Curtis Jackson a message on PodMatch, here: https://www.podmatch.com/hostdetailpreview/1628631536976x919760049303001600Support the show

Send us a message!Distribution in the vacation rental industry has never been more complex. Property managers today are balancing major OTAs, niche platforms, emerging luxury channels, and an increasingly layered tech stack, all while trying to deliver exceptional guest experiences.In this episode, Alex & Annie sit down with Blake Warner, CEO of BookingPal, to talk about how distribution is evolving and what it takes to build scalable infrastructure in a rapidly maturing industry.Blake shares how BookingPal operates at the center of the ecosystem, connecting property managers, PMS platforms, and global channels, and offers his perspective on where the industry is heading. The conversation explores how distribution strategies are expanding beyond the traditional OTA landscape, the opportunities emerging in luxury and niche channels, and why technology innovation must balance efficiency with simplicity.Drawing from his background in investment banking and capital markets, Blake also discusses the realities of scaling technology companies in the vacation rental space and why consolidation across the tech landscape may be inevitable.Episode Chapters:03:01 Introducing Blake Warner, CEO of BookingPal03:44 Blake's background in investment banking and capital markets04:26 What BookingPal sees across distribution channels heading into 202606:07 The realities of running a channel management business12:32 New BookingPal features and product developments for 202615:30 Is vacation rental tech getting better or more complex?17:05 The explosion of software tools in the STR tech stack20:03 How many channels the average property manager distributes to21:21 Which distribution channels are gaining traction22:53 Luxury platforms and the blurring lines in the ecosystem24:41 Why helping managers focus on hospitality still matters most28:13 Travel agents, discovery, and how distribution expands the market30:05 Why it's difficult for vacation rental companies to go public35:44 How the industry has evolved since pre-COVIDConnect with Blake:LinkedIn: https://www.linkedin.com/in/blakewarner/ Website: https://bookingpal.com/ ✨ Exclusive Offer to Alex & Annie Listeners:Streamline your short-term rental operations with Hostfully.Mention the Alex & Annie Podcast when you sign up and get free onboarding ($1000 value).

In this bonus episode, we are joined by the hosts of the new HGTV series “Wild Vacation Rentals”, Sherry Cola and D'Arcy Carden! You may recognize them from hits like The Good Place and Joy Ride, but for today, they are two besties who take us along as they travel around the US and stay at some of the most unique places. "Wild Vacation Rentals" premieres on Monday, March 2nd at 10:00pm on HGTV!You can find us:Podcast: ACast, iTunes, Spotify, wherever you listen!Instagram & Threads: @twojudgeygirlsTikTok: @twojudgeygirls // @marytwojudgeygirls // @courtneytjgFacebook: www.facebook.com/twojudgeygirlsMerch: www.etsy.com/shop/twojudgeygirlsPatreon: www.patreon.com/twojudgeygirls LTK: @marytwojudgeygirls // @courtneytjg Hosted on Acast. See acast.com/privacy for more information.

Evanston City Council approved a scope of services for the zoning initiative and approved the contentious Vacation Rentals Ordinance amendment at its meeting Monday.

Send us a message!In this episode, Alex & Annie sit down with Tim Hubbard, CEO of Corzly, to break down how a virtual property management model actually works and what it takes to make it successful.Tim started in long-term rental investing before shifting into short-term rentals more than a decade ago. As his portfolio grew across multiple states, and eventually internationally, he built the systems needed to manage properties remotely. That operational backbone became Corzly, a virtual management partner now supporting property managers in more than 40 cities.Tim shares how their white-label backend model works, how they collaborate with on-the-ground teams, and where AI fits into real workflows. Not just automated check-in messages, but layered operational processes that involve owners, cleaners, early check-in requests, and revenue decisions.Episode Chapters:1:04 – From Long-Term Rentals to a 40-City Virtual Operation4:02 – The Idea Behind “Core Operations”5:28 – What Virtual Property Management Actually Means6:08 – Why 10–60 Unit Managers Are Their Sweet Spot7:22 – Running the Backend Without Owning the Listings11:17 – How Much Can You Really Automate With AI?11:58 – The Early Check-In Example That Shows How Complex Workflows Get15:55 – 225 Units Today… 10X Growth This Year?19:58 – The Hardest Part of Scaling Across Markets22:21 – Building Culture With a Fully Global Team27:44 – Developing a 20-Unit Resort in Medellín29:08 – Two Years of Permitting and What It Took to LaunchIf you are exploring growth, efficiency, or a different structure for your management business, this episode offers a clear look at another way to build.Connect with Tim:LinkedIn: https://www.linkedin.com/in/tim-hubbard-str/ Website: https://corzly.com/ ✨ Exclusive Offer to Alex & Annie Listeners:Streamline your short-term rental operations with Hostfully.Mention the Alex & Annie Podcast when you sign up and get free onboarding ($1000 value).

We welcome Scott Eddy to the show to talk storytelling, hospitality, what hotels get right and Vacation Rentals get WRONG, Instagram, thinking about growth in 2026 and a LOT more...Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'Connell Scott Eddy (IG) Scott Eddy (LinkedIn) Scott Eddy Website

Send us a message!In this episode, Alex & Annie sit down with Krista Goodrich and Kymberlee Nguyen, the duo behind Salty Dog Vacations, to talk about what it really takes to build a vacation rental company that guests remember and a team that is proud to be part of it.They share how Salty Dog grew from early investing decisions in Daytona Beach into a full-scale operation, and how their approach to branding goes beyond design choices. It shows up in the details, the guest experience, and the way they protect their people.The conversation also expands into Krista's work in local advocacy and zoning, their broader mission to help more women build wealth through real estate, and how their community has grown through retreats and education.Episode Chapters:08:20 – How local rules, zoning, and community involvement shape what it takes to operate responsibly15:07 – Building a brand guests remember: personality, pet-friendly touches, and guest joy19:37 – Krista's “Boss Lady Investor” work, and why real estate education needs to feel accessible25:00 – How retreats and community experiences can become part of a bigger platform, not just a side project33:32 – What it looks like to build a company culture where your team feels protected and respected35:44 – The moment they fired an owner, and why that decision mattered for the business long term40:25 – Why consistency matters more than “cute ideas,” especially once you are scalingIf you're trying to build a stronger guest experience and a business that holds up as you grow, this one's worth a listen.Connect with Kym & Krista:LinkedIn: https://www.linkedin.com/in/krista-goodrich-2823198/ Podcast: https://www.thebossladyinvestor.com/ Website: https://mysaltydogvacation.com/ ✨ Exclusive Offer to Alex & Annie Listeners:Streamline your short-term rental operations with Hostfully.Mention the Alex & Annie Podcast when you sign up and get free onboarding ($1000 value).

What you'll learn in this episode:● The difference between short-term and long-term rental markets● Why vacation-driven markets with limited hotels are the best investment● How to choose markets that maximize cash flow● The #1 mistake investors make when buying their first Airbnb● Why Avery avoids “emerging markets” everyone is hyping online● How to scale a short-term rental business efficiently (even with a full-time job)● How to out-host the competition and treat rentals like a real business● How regulations impact profitability—and how to choose markets that protect you● Avery's journey from one rental to a 250+ property empire To find out more about Dan Rochon and the CPI Community, you can check these links:Website: No Broke MonthsPodcast: No Broke Months for Salespeople PodcastInstagram: @donrochonxFacebook: Dan RochonLinkedIn: Dan RochonTeach to Sell Preorder: Teach to Sell: Why Top Performers Never Sell – And What They Do Instead

Send us a message!Destination marketing is in a pressure test.Short-term rentals have become a major part of how people travel, yet many DMOs still struggle with how (or whether) to include them. At the same time, AI is speeding up the research-to-booking journey and forcing destinations to rethink what “relevance” even means.In this episode, Alex and Annie sit down with Stuart Butler (President of Visit Myrtle Beach) and Adam Stoker (President of Brand Revolt) to unpack what's getting in the way, what alignment can look like, and why the next version of destination marketing is going to require better coordination across the whole destination economy.You'll hear practical takes on funding dynamics, stakeholder value, the “illusion of relevance” in reporting, and why the future may turn DMO websites into something closer to infrastructure than a traditional marketing channel.Episode Chapters:00:54 – Stuart's background and how he landed in destination work02:27 – Adam's background and how he sees the DMO landscape05:37 – The “illusion of relevance,” metrics, and why DMOs feel behind07:44 – The Indianapolis example, why some DMOs leave STRs out09:28 – Can DMOs stay relevant without vacation rentals11:53 – Why STRs need a seat at the table and what it takes to get one14:34 – What STR operators can do in markets without big PM groups19:16 – Funding reality, stakeholder influence, and how STRs earn attention22:27 – Why getting involved with a DMO teaches you more than you expect23:51 – The bigger DMO question, purpose, scope, and identity30:31 – How performance reporting shaped destination websites30:54 – Why the booking engine path can be a strategic dead end36:49 – Stewardship, community trust, and what destinations are accountable for50:06 – AI as a watershed moment for travel discovery and decision-making57:59 – What destination content needs to look like in an AI-first world1:02:21 – Closing thoughts on websites, infrastructure, and the road aheadConnect with Stuart:LinkedIn: https://www.linkedin.com/in/stuart-butler-50aaa45/ Website: http://www.visitmyrtlebeach.com/ Connect with Adam:LinkedIn: https://www.linkedin.com/in/adamstoker/ Website: https://thebrandrevolt.com/ ✨ Exclusive Offer to Alex & Annie Listeners:Streamline your short-term rental operations with Hostfully.Mention the Alex & Annie Podcast when you sign up and get free onboarding ($1000 value).

Send us a message!Condo-hotels and resort-style properties sit in a tricky middle ground. They are not traditional hotels, but they are not quite vacation rentals either. Many still run on hotel tech stacks, charge hotel-style commissions, and operate with hotel-era assumptions.Meanwhile, guests are increasingly searching on vacation rental channels, homeowners are asking why they cannot find their units online, and off-site managers charging half the commission are pulling inventory away. In our February First-of-the-Month bonus episode, we sit down with Emmanuel Lavoie, CEO of Jetstream, to unpack why so many condo-hotels and resort operators still resist distribution on channels like Airbnb and Vrbo, what it really takes to service this category well, and how AI is starting to reshape channel management.Episode Chapters:01:17 - Leaving a 10-year engineering career for travel tech03:33 - How a Canadian OTA accidentally became a channel manager9:43 - Why resorts still hesitate to embrace Airbnb and Vrbo12:00 - What full-service channel management actually includes13:42 - Why a $10 billion company chose service over cheaper tech15:18 - Off-site managers are winning the homeowner battle16:56 - The challenge of selling non-unique inventory on Airbnb24:12 - Why one listing with 300 reviews beats 50 identical listings30:42 - Building an AI-powered guest communication system35:27 - Using AI for listing content creation at scale38:21 - Empowering frontline teams as AI champions42:09 - The human side of AI disruption44:02 - Where Jetstream is heading nextConnect with Emmanuel:LinkedIn: https://www.linkedin.com/in/emmanuel-lavoie-5b89b924/ Website: https://jetstreamtech.io/ ✨ Exclusive Offer to Alex & Annie Listeners:Streamline your short-term rental operations with Hostfully.Mention the Alex & Annie Podcast when you sign up and get free onboarding ($1000 value).

In this special episode from our Training Series, host Heather Bayer is joined by Brittany Blackman (Discover Freedom) and Sean Kemper (ETI Solutions) - two powerhouse professionals who are bringing serious change to the short-term rental industry through coaching, consulting, and training. Together, they unpack the often unseen emotional weight of solopreneurship, why training isn't just "nice to have" but foundational, and how leaders can prioritize people over process for long-term success. Whether you're doing it all in-house or looking to bring in outside expertise, this episode is a deep dive into the role of real education in our business.  ________________________________________________________________________________________________________

Are we seeing a short-term rental resurgence? Since Airbnb's big boom in 2021, many investors have shied away from the “oversaturated” short-term rental industry. But is now actually the ideal time for you to buy vacation rentals? Today's guests believe there's more opportunity than you might think! Welcome back to the Real Estate Rookie podcast! Today, we're joined by Jamie Lane of AirDNA and John Bianchi of STR Search, who are harnessing the power of real estate data to find cash-flow-rich properties and areas across the U.S. The best part? All of these figures, tools, and strategies are available to rookies, who have an edge in smaller markets where the big players don't want to go. Whether you're buying your first rental property or pivoting to short-term rentals, this episode is chock-full of insights for building a profitable Airbnb business. Jamie and John get into the “20-percent rule” for picking profitable short-term rental markets, the biggest investing mistakes to avoid at all costs, and the huge advantage rookies have in the hospitality space! In This Episode We Cover Why short-term rentals are still a profitable investing strategy in 2025 How to identify high-cash-flow markets using the “20-percent rule” The Airbnb amenities that deliver the greatest return on investment (ROI) The biggest mistakes rookie investors make when analyzing short-term rentals Small versus large markets (and the dangers of going too small) Why “conservative” analysis is needed to find a profitable property And So Much More! Check out more resources from this show on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠BiggerPockets.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.biggerpockets.com/blog/rookie-648 Interested in learning more about today's sponsors or becoming a BiggerPockets partner yourself? Email ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠advertise@biggerpockets.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.  Learn more about your ad choices. Visit megaphone.fm/adchoices