Vacation Rental Success

In this episode, Heather Bayer sits down with Heather Fillmore, co-founder of Utah-based StayLuxe Properties, for an honest and inspiring conversation about resilience, growth, and leadership in the short-term rental space. Heather shares her remarkable journey from surviving a catastrophic flood in Baton Rouge to launching a successful luxury vacation rental brand in Park City, Utah - right in the middle of the COVID pandemic. Make sure you complete The Strategic AI Adoption Survey >>https://www.hostfully.com/survey You will get the chance to win an iPad and get access to '24 Use Cases For AI In Short-Term Rental Properties'. Revolutionize Your Employee Onboarding with THRIVE Essentials: Faster Training, Stronger Teams, Better Results! Discover how THRIVE Essentials accelerates onboarding for new property management staff, boosting performance and reducing turnover. >> THRIVE Essentials Are you listening to this podcast on the move? Get to the show notes here: https://www.vacationrentalformula.com/VRS620

In this episode of the Vacation Rental Success Podcast, host Heather Bayer sits down with Fred Bassili from Hostfully to discuss the evolving role of AI in vacation rental businesses and how short-term rental managers can use AI tools and workflows to scale operations, improve guest communication, and boost owner acquisition. Fred Bassili, a seasoned content and marketing strategist at Hostfully, brings a wealth of experience from both sides of the vacation rental industry - as a former host and now a driving force behind tech adoption and education. With a background in content development and a passion for simplifying complex technologies, Fred is on a mission to help property managers use AI in practical, hospitality-centered ways. His insights come not only from his work at Hostfully, but from years of observing the shift in industry sophistication and tech stack growth among property managers worldwide. Revolutionize Your Employee Onboarding with THRIVE Essentials: Faster Training, Stronger Teams, Bette

Some of the strongest brands in the vacation rental business have been around for decades and are rooted in tradition, family values and local knowledge.  As the next generation stepping into a decades-old family-run vacation rental business, Alexis Miller personifies this legacy as she shares how she's honoring her family’s rich story while ushering in thoughtful innovations to meet today’s fast-paced demands. Cottage Connection of Maine was founded in 1992 by Jeff Miller and Audrey Leeds-Miller, and 33 years later is still going strong.  It’s a lean organisation operationally managed by their daughter Alexis, a graduate of an International business program. Heather and Alexis connected at the VRNation Conference in Austin - over Yorkshire tea bags and a moment of true hospitality. That spirit flows through this episode as Lexi opens up about her journey from her childhood in the business and housekeeping to officially joining the business full-time after college. Revolutionize Your Employee Onboarding with

In this episode of the Vacation Rental Success Podcast, host Heather Bayer shares her top takeaways from the AI for Business Summit in Orlando, diving into the transformative power of artificial intelligence and how vacation rental professionals can leverage it to drive growth, efficiency, and guest experience Revolutionize Your Employee Onboarding with THRIVE Essentials: Faster Training, Stronger Teams, Better Results! Discover how THRIVE Essentials accelerates onboarding for new property management staff, boosting performance and reducing turnover. >> THRIVE Essentials Are you listening to this podcast on the move? Get to the show notes here: https://www.vacationrentalformula.com/VRS617

In this episode of the Vacation Rental Success Podcast, host Heather Bayer sits down with… herself! It’s a podcast within a podcast as Heather explores the power of AI through a hands-on demonstration of Google's NotebookLM, sharing practical examples of how it can be a game-changer for short-term rental businesses. Drawing on her extensive industry experience and recent immersion in AI tools, Heather shares insights into how vacation rental operators can use AI not only to save time and money, but also to transform their business operations. Through a live example of AI-generated podcast content, she showcases how the future of AI isn't something to fear - but a tool to empower. Revolutionize Your Employee Onboarding with THRIVE Essentials: Faster Training, Stronger Teams, Better Results! Discover how THRIVE Essentials accelerates onboarding for new property management staff, boosting performance and reducing turnover. >> THRIVE Essentials Are you listening to this podcast on the move? Get to the show notes

In this no-holds-barred conversation, Heather is joined by longtime friend of the show, Mark Simpson, to unpack the buzz - and backlash - surrounding Airbnb’s newly launched "Services" offering. From liability concerns to insurance gaps, Mark breaks down why this move is raising eyebrows in the host community and what you can do right now to protect your business. Then, we switch gears and dive headfirst into the world of AI in vacation rentals. Mark shares how he’s been helping hosts build custom GPTs, boost productivity, and take back control of their marketing strategies. If you're curious about how to harness AI without feeling overwhelmed, this episode delivers a masterclass in cutting through the fluff and getting to what works. Revolutionize Your Employee Onboarding with THRIVE Essentials: Faster Training, Stronger Teams, Better Results! Discover how THRIVE Essentials accelerates onboarding for new property management staff, boosting performance and reducing turnover. >> THRIVE Essentials Are you list

In this insightful conversation, I welcome back digital marketing expert Conrad O’Connell, founder of BuildUp Bookings, to talk about the dramatic shifts in how people are finding, booking, and experiencing vacation rentals. It’s been nearly a decade since our first conversation, and we’ve both been on quite the journey -personally and professionally. Conrad shares what’s changed (including growing his family and his business) and what’s stayed consistent in the ever-evolving digital landscape. We talk about how Google’s AI-powered search is impacting SEO, how paid ads are gaining traction again, and what content strategies still work in 2025. If you’ve ever felt confused about where to put your marketing dollars - or how to write content that still gets found - this episode is packed with clarity. Revolutionize Your Employee Onboarding with THRIVE Essentials: Faster Training, Stronger Teams, Better Results! Discover how THRIVE Essentials accelerates onboarding for new property management staff, boosting per

In this episode of the Vacation Rental Success Podcast, host Heather Bayer sits down with her son and business partner, Mike Bayer, to discuss the essential role of an "AI Ambassador" in vacation rental businesses. Together, they explore why nominating a dedicated AI advocate can unlock efficiencies, reduce burnout, and help teams fully embrace the transformative potential of artificial intelligence. In this conversation Heather and Mike talk about why companies must move from passive awareness to active implementation. The best way to do this is to empower someone within their business to lead the AI charge and they explain the steps to get this underway. Revolutionize Your Employee Onboarding with THRIVE Essentials: Faster Training, Stronger Teams, Better Results! Discover how THRIVE Essentials accelerates onboarding for new property management staff, boosting performance and reducing turnover. >> THRIVE Essentials Are you listening to this podcast on the move? Get to the show notes here: https://www.vacat

This week on the Vacation Rental Success Podcast, Heather reconnects with long-time friend and returning guest, Lorraine Woodward, the unstoppable force behind Becoming rentABLE. Lorraine has been championing accessibility in the short-term rental industry for years, and this time, she’s back with big news - an exciting new partnership with Expedia Group through their Open World Accelerator Program. Together, Heather and Lorraine dive into what accessibility really means today (spoiler alert: it’s not just ramps and wide doors), and how simple, low-cost features like under-counter lighting, secondary locks, and hard surface driveways can dramatically open your property to a broader guest base - including families with children, seniors, people recovering from surgery, and neurodivergent travelers. Lorraine also shares her personal journey, building an inclusive rental to meet her family's needs, and the lightbulb moment that sparked the idea for a global platform. Her story is as inspiring as it is actionable

In this special replay episode in our Leadership Series, Heather reconnects with Rachel Alday, founder of Abode Luxury Rentals, for a powerful conversation on building a thriving business through intentional leadership and company culture. Rachel shares the real story behind how she and her husband grew their boutique vacation rental company from a few properties to a high-performing, values-driven team of nearly 60 people across three markets. What started as a “mom-and-pop” business became a case study in leadership - rooted in authenticity, driven by values, and centered around a deep commitment to both team and guest experience. Whether you’re managing five properties or five hundred, this episode offers practical insights on how to lead with purpose, build loyalty from the inside out, and create a culture that sustains long-term growth and excellence. Revolutionize Your Employee Onboarding with THRIVE Essentials: Faster Training, Stronger Teams, Better Results! Discover how THRIVE Essentials accelerates

In this landmark episode of the Vacation Rental Success Podcast, Heather Bayer is joined by Steve Schwab, the Founder and CEO of Casago, at a truly pivotal moment - not just in his personal journey, but in the history of the vacation rental industry. As Casago steps into a groundbreaking merger with Vacasa, Steve reflects on the path that led him here and the deeply held leadership values that have shaped the company’s evolution. From climbing rooftops in Rocky Point, Mexico, to becoming the driving force behind a national franchise brand, Steve’s story is anything but typical. In this conversation, he opens up about the early moments that launched his career, the foundation of the ORANGE Credo that anchors Casago’s culture, and what it means to scale a values-based business without losing its soul - especially in the wake of one of the industry’s biggest mergers to date. If you’re thinking about growth, culture, or the future of professional property management, this episode delivers both heart and strategy

In this powerful solo episode, Heather Bayer reflects on one of the most fundamental - and often overlooked - questions in the short-term rental space: What kind of leader are you? Through years of podcast interviews and her own journey managing STR properties, Heather unpacks the evolving nature of leadership and how it uniquely manifests in the vacation rental industry. From traditional leadership styles to emotionally intelligent approaches, she guides us through a wide spectrum of frameworks, weaving in personal stories and rich insights from some of the most inspiring voices in the business. This episode highlights the remarkable leadership archetypes shaping our space - from the spiritual and creative to the cultural and transformational. Whether you’re managing a team, growing a portfolio, or simply aiming to lead with more purpose, this episode is a must-listen. Revolutionize Your Employee Onboarding with THRIVE Essentials: Faster Training, Stronger Teams, Better Results! Discover how THRIVE Essentia

Most short-term rental operators didn’t plan on becoming leaders. They started as solopreneurs - cleaning toilets one day, managing a team the next. If you’ve ever found yourself in a leadership role and thought, “How did I get here?”, this episode is for you. In this powerful and relatable conversation, Heather is joined by leadership coach Ali Cammelletti, who has spent over 20 years helping hospitality professionals grow into confident, emotionally intelligent leaders - often without any formal training. Together, they explore the very real challenges of leadership in the short-term rental world and how to navigate them with grace, strategy, and self-awareness. Revolutionize Your Employee Onboarding with THRIVE Essentials: Faster Training, Stronger Teams, Better Results! Discover how THRIVE Essentials accelerates onboarding for new property management staff, boosting performance and reducing turnover. >> THRIVE Essentials Are you listening to this podcast on the move? Get to the show notes here: https://w

In this special episode, we kick off our brand-new Leadership Series with someone who’s been part of this journey from the very beginning - Matt Landau. Matt’s been on the show more than 20 times over the years, but this conversation feels different. It’s deeper, more reflective, and marks a shift in how we talk about leadership in the vacation rental industry. From managing boutique vacation rentals in Panama City’s historic Casco Viejo to founding The Vacation Rental Marketing Blog and The Inner Circle, Matt has always led by example. But over the last few years, he’s taken a big step back - literally and figuratively - to re-evaluate what leadership really means. His latest project, Here Goes Nothin’, is all about helping short-term rental professionals find clarity, reconnect with purpose, and lead from a place of authenticity. Revolutionize Your Employee Onboarding with THRIVE Essentials: Faster Training, Stronger Teams, Better Results! Discover how THRIVE Essentials accelerates onboarding for new prope

What happens when a vacation rental entrepreneur, his tech-savvy brothers, and a close-knit team of hospitality veterans come together with a mission to solve the biggest operational headaches in property management? You get Boom - the world’s first AI-powered property management system (AIPMS). In this episode, Heather sits down with Shahar Goldboim, the dynamic founder of Boom, to explore how artificial intelligence is reshaping the vacation rental industry - without sacrificing the personal, human-centered heart of hospitality. From automating time-consuming tasks to interpreting emotional cues in guest communication, Boom is more than a tool - it's a vision for the future of property management. Shahar shares how Boom was born out of real-world frustration, why AI isn’t replacing hospitality, but making room for more of it, and how his family-run team is scaling technology with soul. Revolutionize Your Employee Onboarding with THRIVE Essentials: Faster Training, Stronger Teams, Better Results! Discover h

In this episode of the Vacation Rental Success Podcast, host Heather Bayer sits down with Mark Simpson, the founder of Boostly, to discuss the practical applications of artificial intelligence (AI) for vacation rental hosts. Mark shares how AI can help streamline operations, enhance guest experiences, and optimize marketing efforts—without losing the personal touch that makes direct bookings successful. Mark Simpson is the founder of Boostly, a platform dedicated to helping short-term rental hosts and property managers increase their direct bookings. With years of experience in digital marketing and hospitality, Mark has become a leading advocate for independent hosts looking to take back control from OTAs.  Revolutionize Your Employee Onboarding with THRIVE Essentials: Faster Training, Stronger Teams, Better Results! Discover how THRIVE Essentials accelerates onboarding for new property management staff, boosting performance and reducing turnover. >> THRIVE Essentials Are you listening to this podcast on

This episode of the podcast is sponsored by Guesty, your all-in-one platform for hospitality businesses to automate and optimize every aspect of your operations. ***Use code SSTIRCRAZY for 50% off your first annual plan***  >> Discover more about Guesty in the Virtual Vendor Showcase We’re back with Part 2 of my chat with AI educator and vacation rental marketer, Nihal Salah - and trust me, if you thought the first conversation was packed, this one goes even deeper. In this episode, we tackle the challenge so many of us are facing right now: how do you choose the right AI tools without getting overwhelmed by the endless options? With over 32,000+ tools out there (yes, really), it’s easy to fall into analysis paralysis or end up subscribing to a dozen platforms you barely use. Nihal and I share our favorite go-to tools, what we’re using in our own businesses, and how to evaluate which platforms are truly worth your time and money. We also explore the difference between individual LLMs (like ChatGPT, Claud

This episode of the podcast is sponsored by Guesty, your all-in-one platform for hospitality businesses to automate and optimize every aspect of your operations. ***Use code SSTIRCRAZY for 50% off your first annual plan***  >> Discover more about Guesty in the Virtual Vendor Showcase AI-Powered Marketing for Vacation Rentals: What You Need to Know Wondering how AI can make your vacation rental marketing more efficient and impactful? From crafting compelling property descriptions to optimizing SEO and automating guest communication, AI is changing the game. But how do you use it effectively - without getting overwhelmed? In this episode, marketing expert Nihal Salah joins Heather Bayer to break down practical AI use cases for short-term rental marketing. You’ll discover how AI can help streamline content creation, enhance guest experiences, and drive more direct bookings - all while saving you time. Why AI Matters for Your Vacation Rental Marketing AI isn't just a trend - it’s a powerful tool that can hel

This episode of the podcast is sponsored by Guesty, your all-in-one platform for hospitality businesses to automate and optimize every aspect of your operations. ***Use code SSTIRCRAZY for 50% off your first annual plan***  >> Discover more about Guesty in the Virtual Vendor Showcase Brooke Pfautz is the innovative mind behind Vintory and Comparent and has been a trailblazer in the vacation rental industry for over 17 years. He’s also fully immersed in AI to not only streamline operations but also supercharge growth and efficiency, particularly in owner acquisition. In this episode Brooke shares the platforms he uses the most and offers advice and recommendations on their use. Revolutionize Your Employee Onboarding with THRIVE Essentials: Faster Training, Stronger Teams, Better Results! Discover how THRIVE Essentials accelerates onboarding for new property management staff, boosting performance and reducing turnover. >> THRIVE Essentials Are you listening to this podcast on the move? Get to the show

This episode of the podcast is sponsored by Guesty, your all-in-one platform for hospitality businesses to automate and optimize every aspect of your operations. ***Use code SSTIRCRAZY for 50% off your first annual plan***  >> Discover more about Guesty in the Virtual Vendor Showcase In a recent post on Linkedin, Amber Hurdle said: “Your ChatGPT Is Showing….and it’s stripping the authenticity out of your brand. ”Whether it’s an over-use of hyphens, emojis or particular sentence structures, most of us have used enough of them to be ‘seen’ as ChatGPT users, and the grammar police aren’t taking prisoners.   It’s time to take back our humanness and our attention to sharing personal brand in a way that makes us unique.If you have ever been in a room where Amber Hurdle is speaking, you’ll appreciate her passion for branding and marketing, and will have come away with a renewed enthusiasm for making your mark.   In this episode, Amber brings the zest she shares in her opening keynotes to the topic of strateg