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Vacation Rental Success

Heather Bayer aka @CottageGuru

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Heather Bayer, author of Renting Your Recreational Property for Profit, former CEO of a highly successful cottage rental agency, and a popular blogger, hosts the Vacation Rental Success podcast. With many years experience of owning and managing multiple vacation rental properties, Heather brings her knowledge and views on every aspect of the business, together with interviews with vacation homeowners and industry experts. Heather has appeared as a guest on CTV Canada, CBC Radio, Rogers TV, a ...
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Money in Halacha

Rabbi Eli Markowitz

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We each make thousands of financial decisions over the course of our lives. Learn how Halacha guides us in the world of money. How much charity should you give? Is your business compliant with the laws of kosher and Shabbos? The halachic considerations that must be discussed prior to any business venture.
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VILLA PARAISO VACATION RENTALS

VILLA PARAISO VACATION RENTALS

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Welcome to Villa Paraiso Vacation Rental, your premier destination for exquisite vacation experiences in the vibrant cities of Miami and Marathon, Florida. We are a leading vacation rental management company, dedicated to providing unparalleled luxury accommodations and personalized services for discerning travelers. At VPVR, we understand that your vacation is a time to unwind, indulge, and create lasting memories. That's why we handpick and manage an exclusive collection of exceptional pro ...
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Living Villa Cappelli

Paul Cappelli & Steven Crutchfield, discussing all things Italian: food, cu

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Direct from Italy! Follow the adventures of two Americans running a villa in Puglia, Italy, and learn all about Italian the culture, people, food and fun. Every week, we'll share our lives with you and what life in Italy is really like especially for two Americans. From Italian recipes to travel in Italy to interviews with others who share the same Italian spirit, we'll cover it all. So come along for the ride and discover that life is better when you put a little Italian into it.
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Discover the vibrant soul of the Dominican Republic with "The Simply Dominican Podcast" your weekly podcast escape hosted by Simply Dominican. Dive into a realm where the tropical rhythm of the Caribbean meets luxury, where every episode unfolds the island's hidden gems, breathtaking landscapes, and the exclusive luxury villas awaiting you. From the tranquil retreats in Punta Cana to the adventure-laced pathways of Jarabacoa, each week, we unveil destinations to ignite your wanderlust. Indul ...
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the no BS podcast

Mateo Bradford & John Stokinger

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An unfiltered look into the global hospitality and short-term rental industry with a focus on founder stories, current events, and culture. Co-Hosts Mateo Bradford and John Stokinger discuss current news and affairs surrounding the vacation rental, lodging, and accommodation industry. the no BS podcast brings the right people to the table at the right time giving their audience an inside view and real take like no other. https://thenoBSpodcast.co
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Dream of Italy

Kathy McCabe/Dream of Italy

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If you dream of Italy, host Kathy McCabe and her fascinating guests are here to make your Italian travel dreams come true whether you're seeking life transformation life with a move to Italy or simply want to make your Italian vacation as authentic as possible. McCabe is the host of the PBS TV travel series Dream of Italy and founded the award-winning travel publication Dream of Italy in 2002. Our episodes - mostly recorded on the road in Italy - cover everything from picking the best cookin ...
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show series
 
When disaster strikes - whether it's a fire, flood, or even a bat infestation - families are often left scrambling for safe, comfortable housing. That's where Jake Mast steps in. In this episode, Heather Bayer sits down with Jake, founder of Rapid Response AI Housing, to explore how his company is disrupting the traditional insurance housing model …
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📌In this power-packed episode, Heather Bayer is joined once again by vacation rental marketing guru Mark Simpson of Boostly. Mark returns for his fifth appearance on the podcast - and this time, he's bringing an urgent message for vacation rental professionals across North America: The FIFA World Cup 2026 doesn't start in June... it starts on Decem…
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This week I'm welcoming back one of my favourite guests, Neely Khan, founder of the storytelling agency Artwork Creative. This is her second time joining me in less than six months - and there's a good reason for that. Neely is at the forefront of one of the most important shifts we're seeing in vacation rental marketing: the rise of AI-powered sea…
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In this episode, Heather sits down with Dr. Rachel Gainsbrugh from Short Term Gems to explore how artificial intelligence is changing the way short-term rental businesses operate. Rachel shares how she moved from being a pharmacist to building a real estate education company focused on medical professionals, and how AI is now a core part of that mi…
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In this packed episode, Heather Bayer shares her biggest takeaways from the AI for Business Summit in Las Vegas - and how short-term rental hosts and property managers can take immediate, practical steps to adopt AI tools in their business. Heather reveals how she used a Plaud NotePin to record and summarize every session, giving her powerful insig…
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Dennis Goedheid is back on the show, and we dive deep into one of the most overlooked yet mission-critical aspects of running a property management company - identifying and saying no to the wrong owners. We also chat about his journey with Casiola's international expansion, his team's DEI award win at VRMA, and why scaling means getting crystal cl…
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Send us a text Cape Town, Safari, and Victoria Falls Adventure This eleven-day African luxury adventure itinerary curated by Dream Vacations, focusing on three major destinations: Cape Town, Kruger National Park's Sabi Sands, and Victoria Falls. The first four days detail an exploration of Cape Town's cultural, architectural, and natural beauty, in…
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While everyone's been playing around with AI tools like ChatGPT, few in the short-term rental industry have taken the next step - turning experimentation into strategy. In this episode, Heather shares a clear, step-by-step framework to help you move from random tinkering to thoughtful implementation, drawn straight from her AI Ambassador Program. W…
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In this episode, I'm joined by the brilliant Jenn Boyles, founder of the Direct Booking Success Summit and host of the Direct Booking Success Podcast. Jenn is a passionate advocate for empowering hosts and property managers to take back control from the OTAs - and she did it herself with an incredible 80% direct booking rate. We go deep into why di…
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In this penultimate episode in our series on Direct Booking, this is an episode you can't afford to miss. Heather is joined by long-time industry leader Chris Maughan, the founder of i-PRAC and a pioneer in the trust movement for short-term rentals. This conversation isn't about OTAs, algorithms, or the latest booking engine. It's about what really…
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In this solo episode, Heather shares her enthusiasm for Google's NotebookLM. If you've ever wished for a research assistant who knows your business inside and out - an assistant who can analyze guest reviews, SOPs, market data, and spit out insights without hallucinating - this one's for you. Heather walks through how NotebookLM works, why it's dif…
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In this bold and thought-provoking episode, Heather sits down with Humphrey Bowles, the founder of Truvi and who has adopted the term "digital sharecropping" within the short-term rental industry. Together, they explore the illusion of entrepreneurship in the short-term rental world - especially when you build your business entirely on platforms li…
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In this first episode of a special 5-part series on direct booking, Heather Bayer sits down with Louis Andrews, Director at OVO Network, to explore what it really takes to win the battle against OTAs and build a successful direct booking strategy. With OVO Network reaching 75-80% direct bookings, Louis shares the secrets behind their platform, the …
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Send us a text Greg and Laurie Shuss of Dream Vacations have earned "Best of the Gulfshore awards". Our expertise is demonstrated through the creation of a comprehensive 15-day Scottish and Irish tour designed to deliver "the ultimate vacation experiences". Their ability to provide unique travel experiences is highlighted by the diverse and immersi…
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I first met James Rubino at a VRMA conference in Orlando two years ago. He was there at the start of his journey in short term rentals, to learn and network and I mentioned to him then I would have him as a guest on the podcast down the road. So two years later here we are and what a story it is . At just 26, James launched Rubino Home Ventures and…
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Have you ever found yourself wondering why so many large-scale property management companies rise quickly… and then fall just as fast? In this episode, I'm joined by Ashley Ching, Founder and CEO of Inhaven, who brings a fresh - and deeply researched - perspective to this question. Ashley recently published an eye-opening report, "A 25-Year History…
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In this episode, Heather Bayer welcomes back a long-time friend and industry innovator, Bart Sobies, founder of iBooked.Online and the creative mind behind the Strive to Thrive events in Australia and beyond. Bart joins Heather (from tomorrow, no less - Australia time!) to share insights on: The power of in-person connections and how conferences ca…
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What does it really mean to run a tech-enabled hospitality business - and how do we do it without losing the human touch? In this episode, Heather sits down with Jessica Gillingham, founder of Abode Worldwide and author of Tech-Enabled Hospitality, to talk about how property managers can embrace technology to improve guest experiences, operations, …
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In this solo episode, Heather Bayer returns to the mic for an approachable explanation of the transformative power of AI in short-term rental operations. With over 600 episodes under her belt, Heather has seen just about every trend in this space - but few as game-changing as this. Whether you're a solo host or run a multi-property management compa…
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In this fun and super insightful episode, I'm joined once again by vacation rental marketing expert Jodi Bourne, and we're diving headfirst into something that's never been more important - your website. With all the recent changes to the big OTAs, more and more hosts are waking up to the power of direct bookings. And at the heart of that? Your web…
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In this episode of the Vacation Rental Success Podcast, host Heather Bayer sits down for a summer Sunday chat with Justin Ford from Breezeway, to discuss how prioritizing safety can transform your short-term rental business. Not just in protecting reputations, even boosting bookings, but in saving lives. Justin has been on the show just a few times…
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When change hits fast and hard, what keeps a company grounded? In this episode, Heather welcomes Jackie Norde, who shares her remarkable journey from vacation rental software onboarding to her current role helping Casago franchisees succeed - especially in the wake of Casago's rapid expansion via Vacasa acquisitions. Jackie offers rich insights int…
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