Alex and Annie: The Real Women of Vacation Rentals

Alex and Annie

With more than 35 years of combined experience in vacation rentals, Alex Husner and Annie Holcombe have teamed up to connect the dots between inspiration and opportunity, seeking to find the one story, idea, strategy or decision that led to their guests big A-HA moment. Join them, as they highlight the REAL stories behind the people and brands that have built vacation rentals into the 100 BILLION dollar industry it is today.

  1. 3d ago ·  Video

    What Hotels Get Right (and Wrong) About Vacation Rentals with Aqua-Aston Hospitality’s SVP of Operations, Tom Waithe

    In the hotel world, replacing a dead plant in the lobby is a simple fix. In vacation rental management, that same task can involve multiple stakeholders, HOA approvals, and days of coordination. For Tom Waithe, Senior Vice President of Operations at Aqua-Aston Hospitality, this was one of many surprises after transitioning from a decades-long career with major hotel brands, including Four Seasons and Kimpton. In this episode, Alex & Annie sit down with Tom to explore the operational differences between hotels and vacation rentals, and what the industry can learn from established hotel practices. Drawing from his experience managing both hotels and individually owned vacation rental properties in Hawaii, Tom shares the challenges of maintaining service standards, navigating homeowner relationships, and delivering consistent guest experiences. The conversation also explores the complexities of vacation rental technology, OTA dependence, direct booking strategies, and guest loyalty. Tom offers a valuable perspective on balancing owner returns with guest satisfaction, and why building strong relationships with both is essential to long-term success in hospitality. Episode Chapters: 00:00 - Meet Tom Waithe of Aqua-Aston Hospitality 02:08 - From Four Seasons and Kimpton to Vacation Rental Management 05:42 - The Biggest Surprises Moving from Hotels to Vacation Rentals 10:40 - Managing Hotel Operations vs. Individually Owned Vacation Rentals 14:45 - Can Hotel-Level Service Standards Work in Vacation Rentals? 17:56 - Standardizing Guest Expectations Across Different Rental Units 20:57 - Moving from Hotel Software to a Vacation Rental PMS 25:16 - OTA Dependence, Commissions, and the Direct Booking Challenge 30:07 - Navigating Maui's Tourism and Vacation Rental Challenges 35:46 - Building Guest Loyalty Without Traditional Hotel Rewards 40:25 - Community Relationships and Vacation Rental Advocacy in Hawaii 44:40 - Measuring Success Through Owner Returns and Guest Satisfaction 49:42 - Why Repeat Bookings Are a Powerful Hospitality KPI Connect with Tom: LinkedIn: https://www.linkedin.com/in/tom-waithe-102a987/  Website: https://www.aquaaston.com/ ✨ 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. 👉 Learn more: https://gomonarch.com/partnerships/ List your professionally managed properties on VacationFinder.com with no listing fees or booking commissions. 👉 Get started: https://partners.vacationfinder.com/alexandannie Learn more about dormakaba’s vacation & short-term rental access solutions: 👉 Website: https://dk.world/Vacation26  #vacationrentals #shorttermrentals #hospitality Send us a message!

    What Hotels Get Right (and Wrong) About Vacation Rentals with Aqua-Aston Hospitality’s SVP of Operations, Tom Waithe

  2. Nov 4 ·  Video

    VRMA 2026 Recap: Big Conversations, Bold Predictions & a Few Rumors?

    Nashville was buzzing, and VRMA 2026 brought some of the industry's biggest conversations to the forefront! From major OTA changes and AI developments to industry consolidation and predictions for 2027, this year's conference sparked some fascinating discussions about the future of vacation rentals. And of course, Alex & Annie were right in the middle of it all. In this special episode, we're taking you straight to the VRMA show floor for a mix of industry insight, candid conversations, and a little unexpected fun. We caught up with some of our industry partners and put them on the spot with three burning questions: Where do hospitality professionals actually go on vacation? If their company were a band, who would they be? And the most entertaining question of all: "Rumor has it..." We even kept an unofficial tally, and let's just say the beach won, Bali had a moment, and classic rock is apparently alive and well in vacation rentals. Beyond the laughs and show-floor banter, we also sat down for separate conversations with Jeff Hurst of Furnished Finder, Ian Ackland of Booking.com, and Joel Schoen of Escapia, each bringing a unique perspective on the industry's evolving landscape. Their discussions explore Vrbo's fee changes, opportunities in midterm rentals, industry consolidation, AI, and the future of vacation rental technology and distribution. From the latest industry developments to the unexpected moments that made Nashville memorable, this episode captures the energy, insights, and personalities of VRMA 2026. Episode Chapters: 03:40 - Three burning questions: industry rumors, rock bands, and dream vacations 18:57 - Jeff Hurst on Furnished Finder and the growth of midterm rentals 21:40 - Vrbo's fee changes and the evolving OTA landscape 23:45 - Will AI transform vacation rental distribution? 33:58 - Ian Ackland on Booking.com, trust, and industry partnerships 41:20 - What's next for vacation rental industry consolidation? 45:01 - Joel Schoen on Escapia's latest innovations 47:58 - AI, customer support, and the human side of vacation rental technology Whether you joined us in Nashville or missed the conference this year, tune in for an inside look at the conversations, personalities, and ideas making waves across the vacation rental industry. ✨ 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. 👉 Learn more: https://gomonarch.com/partnerships/ Reach more direct-booking travelers with Savvy. List your professionally managed properties for free. 👉 Get started here: https://savvy.com/list Build a direct booking site designed to get found and convert with CraftedStays. Turn more visitors into direct bookings with less manual work. 👉 Get started: https://craftedstays.co/alexannie/ #vacationrentals #shorttermrentals #VRMA2026 Send us a message!

    VRMA 2026 Recap: Big Conversations, Bold Predictions & a Few Rumors?

  3. Nov 1 ·  Video

    Revenue Reality Check: How to Build a Smarter Revenue Strategy for 2027 with Julie Brinkman

    Your revenue may be up in 2026, but how much of that growth came from a stronger strategy, and what can you learn from those results heading into 2027? As vacation rental operators begin planning for the year ahead, understanding what drove their performance becomes especially important. In this episode of Revenue Reality Check, presented by Beyond, Alex & Annie welcome back Julie Brinkman, CEO of Beyond, for a timely conversation about evaluating revenue performance, identifying missed opportunities, and building a more effective strategy for 2027. Julie explains why portfolio-wide revenue numbers can hide important differences in performance across properties, markets, and inventory types. She shares how operators can use segmentation, historical trends, and market comparisons to understand where their strategies worked and where adjustments may be needed. Through real questions from vacation rental operators, Julie offers practical guidance on setting realistic revenue targets, strengthening owner conversations, and making smarter decisions before the next booking season begins. Episode Chapters 00:00 – Welcome to Revenue Reality Check, presented by Beyond 03:56 – How to evaluate your 2026 revenue performance 07:14 – Using performance data to retain and acquire homeowners 12:22 – Rethinking distribution, direct bookings, and AI search 16:03 – Turning guest data into repeat booking opportunities 20:04 – Why one revenue strategy doesn't work for every property 24:03 – Identifying inventory that may be holding your portfolio back 26:04 – The danger of lowering rates too early 29:46 – Using search demand to make better pricing decisions 30:51 – Setting 2027 revenue targets using historical performance 33:16 – When should you start planning your 2027 revenue strategy? As operators prepare for another year of changing demand and booking behavior, Julie encourages a closer examination of the decisions behind their results and the opportunities available to improve performance. Tune in to this episode of Revenue Reality Check, presented by Beyond, for insights to help you approach 2027 with a more informed and adaptable revenue strategy. Connect with Julie Brinkman LinkedIn: https://www.linkedin.com/in/jrbrinkman/ Connect with Beyond Website: https://beyondpricing.com/ LinkedIn: https://www.linkedin.com/company/beyond-pricing/ Instagram: https://www.instagram.com/beyondpricing/ #vacationrentals #shorttermrentals #revenuemanagement Send us a message!

    Revenue Reality Check: How to Build a Smarter Revenue Strategy for 2027 with Julie Brinkman

  4. Oct 28 ·  Video

    Growing Without Compromising the Guest Experience: Brandon Hall on Hallson Hospitality's Expansion

    Growing a vacation rental portfolio brings new opportunities, but maintaining the quality and consistency that made the business successful becomes increasingly challenging as operations expand. In this episode, Alex & Annie catch up with Brandon Hall, Founder and CEO of Hallson Hospitality, for an on-location conversation in Nashville about the company's next chapter of growth. Brandon shares the news of Hallson Hospitality's merger with Epicbnb, a partnership expected to bring their combined portfolio to approximately 175 properties. He explains how their shared commitment to hospitality standards, strong guest reviews, and thoughtful operations made the merger a natural fit. As the company prepares for its next phase, Brandon shares how Hallson Hospitality is investing in better systems, centralized property information, and AI-powered tools to help teams work more efficiently and maintain service standards across a larger portfolio. Episode Chapters: 02:32 - Welcome to Nashville: Inside Hallson Hospitality's Star Piano Suites 03:14 - Blending boutique hotel service with luxury vacation rentals 04:48 - Why design, branding, and consistency matter to the guest experience 07:12 - Brandon Hall's approach to responsible vacation rental growth 09:50 - Hallson Hospitality's merger with Epicbnb and expansion to 175 properties 11:59 - Expanding into boutique hospitality with Germantown Inn 13:34 - Scaling operations while maintaining quality and service standards 14:08 - How Hallson is using AI and centralized property data to support its team 18:51 - Improving information accuracy across a growing portfolio 19:44 - Integrating the merger and exploring future growth opportunities From strategic partnerships and brand consistency to technology and operational readiness, this episode offers an inside look at how Hallson Hospitality is approaching expansion while keeping the guest experience at the center of its growth strategy. Connect with Brandon: LinkedIn: https://www.linkedin.com/in/brandonhall/  Learn more about Hallson Hospitality: Instagram: https://www.instagram.com/hallson.co/  Website: https://hallson.co/  Facebook: https://www.facebook.com/hallsonco  ✨ 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. 👉 Learn more: https://gomonarch.com/partnerships/ List your professionally managed properties on VacationFinder.com with no listing fees or booking commissions. 👉 Get started: https://partners.vacationfinder.com/alexandannie Learn more about dormakaba’s vacation & short-term rental access solutions: 👉 Website: https://dk.world/Vacation26  #vacationrentals #shorttermrentals #guestexperience Send us a message!

    Growing Without Compromising the Guest Experience: Brandon Hall on Hallson Hospitality's Expansion

  5. Oct 21 ·  Video

    John An Launches Tidewell: Getting Vacation Rental Data Ready for AI

    Your property management system says one thing. Your revenue management platform says another. Your accounting reports tell a different story. So which numbers can you actually trust? As AI becomes more integrated into vacation rental operations, inconsistent data across systems presents a growing challenge for property managers. In this episode, Alex & Annie sit down with John An, Founder and CEO of TechTape, to explore why disconnected systems and conflicting data can lead to misleading reports, unreliable AI insights, and costly business decisions. John also introduces Tidewell by TechTape, a solution designed to bring fragmented data from existing systems into one consistent, trusted foundation. They explore how cleaner, more connected data can give operators greater visibility into their business and support more informed decisions while building a stronger foundation for AI. Episode Chapters: 02:43 - How John's experience as an operator led to TechTape 05:07 - Introducing Tidewell and the problem it solves 06:31 - Why vacation rental systems report different numbers 08:34 - The risks of using AI with inconsistent data 10:29 - Finding operational opportunities through connected data 13:58 - Why consistent definitions of revenue and occupancy matter 16:09 - Making enterprise-level data infrastructure accessible to smaller operators 19:11 - Maintaining historical data through PMS migrations 23:09 - Improving maintenance reporting with connected data 28:18 - Integrating existing software and data sources 31:11 - Building a trustworthy foundation for AI automation Connect with John An: LinkedIn: https://www.linkedin.com/in/john-s-an/  TechTape: https://www.gettechtape.com/  Tidewell: https://www.gettechtape.com/tidewell/  ✨ Exclusive Offers to Alex & Annie Listeners: Get 3 months of Tidewell FREE with your property management system connected, for up to 20 properties. Bring your vacation rental data together and start building a more reliable foundation for reporting, business insights, and AI. 👉 Learn more about Tidewell: https://www.gettechtape.com/tidewell/ 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. 👉 Learn more: https://gomonarch.com/partnerships/ Reach more direct-booking travelers with Savvy. List your professionally managed properties for free. 👉 Get started here: https://savvy.com/list #vacationrentals #shorttermrentals #AI Send us a message!

    John An Launches Tidewell: Getting Vacation Rental Data Ready for AI

  6. Oct 15 ·  Video

    Pour Decisions: When Guests Wreck the Home, Who Pays?

    A high-end vacation rental and a premium nightly rate don't always guarantee well-behaved guests. And when a stay ends with serious property damage, getting the home back in shape can be only part of the headache. In Episode 4 of Pour Decisions: When Stays Go Sideways, presented by Safely, Alex and Annie are joined by Alexandra “Ali” Chaney of 30A Beach Stays & Vacations, alongside Amanda Martins and Zach Grimes of Safely, for a candid conversation about the unpredictable side of vacation rental management. Ali brings firsthand stories of unexpected guest incidents and the challenges of managing damage claims, while Amanda and Zach share insights from Safely's experience helping operators navigate these situations. Together, they explore the realities of guest-related risks, the challenges of recovering costs through booking platforms, and how the right protection and processes can help property managers safeguard the homes entrusted to them. We discuss: 12:55 - Why luxury properties are not immune to destructive guest behavior 14:53 - The challenges of recovering damage costs through booking platforms 21:52 - How the right protection can support homeowner confidence 24:08 - What operators can learn from real guest damage incidents 27:47 - Why documentation and a clear claims process matter 30:14 - How different types of insurance and damage protection work together 36:48 - Where guest waivers fit into a broader protection strategy From shocking guest stories to practical insights on damage protection, this episode offers plenty for property managers to think about before the next stay goes sideways. Connect with Ali: https://www.alexandanniepodcast.com/guests/alexandra-chaney/  Connect with Zach: LinkedIn: https://www.linkedin.com/in/zach-grimes-9242b478/  Connect with Amanda: LinkedIn: https://www.linkedin.com/in/amandakatmartins/  Learn more about Safely: Website: https://safely.com/alex-and-annie LinkedIn: https://www.linkedin.com/company/safely-stay/ Instagram: http://instagram.com/safely/ Facebook: https://www.facebook.com/safelyprotection  This Episode's Cocktail: Ali's Special A classic margarita with a fresh citrus twist. Ingredients: TequilaTriple secSour mixFresh lime juice, optionalFresh orange juice, optionalIceHow to make it: Combine the tequila, triple sec, and sour mix in a shaker with ice. Add fresh orange and lime juice if desired. Shake well and pour into your favorite glass. #vacationrentals #shorttermrentals #damageclaims Send us a message!

    Pour Decisions: When Guests Wreck the Home, Who Pays?

  7. Oct 14 ·  Video

    The Battle for Brand Recognition: Who Gets the Credit for a Five-Star Stay? with Michelle Gilliland of Savvy

    A guest books a beautiful vacation rental, has an incredible stay, and leaves with memories worth sharing. But when they tell others about their experience, whose brand do they remember? In this episode, Alex & Annie sit down with Michelle Gilliland, VP of Sales at Savvy, to explore what it takes to build a recognizable brand in a market where OTAs dominate traveler attention. Drawing from nearly 15 years of experience in the vacation rental industry, Michelle brings a unique perspective on how brands can differentiate themselves, create stronger connections with travelers, and build lasting recognition. The conversation offers a look at Savvy's approach to branding and distribution, along with insights that challenge property managers to think more intentionally about how their businesses are discovered, experienced, and remembered. Episode Chapters: 03:06 - Michelle Gilliland's background at Vrbo, Expedia Group, and Savvy 03:43 - Why property managers deserve greater brand visibility 06:21 - Airbnb's direct booking links and what they mean for operators 12:33 - Why consistency matters throughout the guest experience 17:00 - Should the vacation rental industry establish clearer hospitality standards? 21:48 - Making it easier for travelers to connect directly with property managers 24:58 - Collaboration, community, and building local brand awareness 26:05 - Behind Savvy's unconventional "Death of the Middleman" marketing campaign 31:17 - How referral incentives can encourage more bookings 33:26 - Savvy's approach to brand visibility, distribution, and guest relationships 37:58 - Building a business that is less dependent on major OTAs If you're looking to strengthen your vacation rental brand and stand out in an increasingly competitive market, this is a conversation worth tuning into. Connect with Michelle: LinkedIn: https://www.linkedin.com/in/michellegilliland/ ✨ 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. 👉 Learn more: https://gomonarch.com/partnerships/ Reach more direct-booking travelers with Savvy. List your professionally managed properties for free. 👉 Get started here: https://savvy.com/list Learn more about dormakaba’s vacation & short-term rental access solutions: 👉 Website: https://dk.world/Vacation26  #vacationrentals #shorttermrentals #directbookings Send us a message!

    The Battle for Brand Recognition: Who Gets the Credit for a Five-Star Stay? with Michelle Gilliland of Savvy

  8. Oct 7 ·  Video

    Beyond Google: Winning the New Vacation Rental Search Journey, with Gil Chan of CraftedStays

    The way travelers discover vacation rentals is changing. Traditional Google search still matters, but discovery is increasingly expanding into tools like ChatGPT, Gemini, and Claude, where travelers can describe the kind of trip they want and receive recommendations based on that intent. In this episode, Alex & Annie sit down with Gil Chan, Founder and CEO of CraftedStays, to explore what this shift means for vacation rental operators and the direct booking websites they have spent years building. Gil shares how his experience as a property manager, combined with his background in e-commerce and product development, led him to build CraftedStays around a problem he saw firsthand: vacation rental websites often lack the infrastructure needed to support a seamless, measurable direct booking journey. The conversation also dives into how AI search is changing website strategy, what CraftedStays has learned from its research into AI visibility, and why content, structured data, reviews, and strong local expertise may become even more important as the search journey evolves. Episode Chapters: 05:39 - Why direct bookings are still complicated 06:56 - What vacation rental websites can learn from e-commerce 16:52 - Building a website platform that can evolve faster 18:55 - CraftedStays’ relationship with Google and the development of Aria 22:56 - From Google search to conversational travel discovery 28:34 - Reviews, structured data, and helping AI understand your business 32:07 - What CraftedStays learned from 24,000 AI search queries 36:53 - Using AI to create and optimize direct booking landing pages 48:13 - Where independent operators can compete with OTAs in AI search 50:12 - How to audit your visibility across AI search platforms 55:35 - Why there is no “page two” in AI search Want to dig deeper into AI search? CraftedStays has created a free AI Search Guide for vacation rental operators that breaks down what property managers should be paying attention to as search continues to evolve. 👉 Explore the guide: https://craftedstays.co/ai-search-for-vacation-rentals/ Connect with Gil: LinkedIn: https://www.linkedin.com/in/thegilbertchan/ Learn more about CraftedStays: Website: https://craftedstays.co/alexannie/ ✨ Exclusive Offer to Alex & Annie Listeners: Build a direct booking site designed to get found and convert with CraftedStays. Turn more visitors into direct bookings with less manual work. 👉 Get started: https://craftedstays.co/alexannie/ 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. 👉 Learn more: https://gomonarch.com/partnerships/ Reach more direct-booking travelers with Savvy. List your professionally managed properties for free. 👉 Get started here: https://savvy.com/list #vacationrentals #shorttermrentals #directbookingwebsite Send us a message!

    Beyond Google: Winning the New Vacation Rental Search Journey, with Gil Chan of CraftedStays
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5
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36 Ratings

About

With more than 35 years of combined experience in vacation rentals, Alex Husner and Annie Holcombe have teamed up to connect the dots between inspiration and opportunity, seeking to find the one story, idea, strategy or decision that led to their guests big A-HA moment. Join them, as they highlight the REAL stories behind the people and brands that have built vacation rentals into the 100 BILLION dollar industry it is today.

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