Vacation Rental Success

Heather Bayer aka @CottageGuru
  • 4.7 (210)
  • INVESTING
  • UPDATED WEEKLY
Vacation Rental Success

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, and Chex TV and is frequently interviewed on real estate and travel topics by magazines and daily newspapers.

  1. 2 DAYS AGO

    VRS599 - The Compliance Challenge: Strategies for Navigating New Regulations

    We’ve arrived at Week 4 of SSTIR Crazy 2025, and this might be the most critical challenge yet! Regulations Week is here, and the stakes have never been higher for StayWise Rentals. This episode of the podcast and SSTIR Crazy Month 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 >> Register today to attend SSTIR Crazy Month 2025 This week, we tackle one of the biggest challenges short-term rental operators face: regulations. With StayWise Rentals in crisis, our expert Dana Lubner from Rent Responsibly joins us to break down the strategies for compliance, advocacy, and overcoming regulatory hurdles. The StayWise Rentals Incident After weeks of dealing with trust issues, safety failures, and an insurance disaster, Sarah and Mike Chen at StayWise Rentals were blindsided by a notice from their local municipality. New short-term rental regulations had just been passed, and StayWise had only 60 days to comply with a long list of requirements: Mandatory fire safety upgrades across all properties. New occupancy limits based on square footage. A requirement to have a local representative available 24/7. A $1,500 licensing fee per property. Surprise city inspections—two properties even received cease and desist orders. With property owners panicked, guests caught in the crossfire, and mounting compliance costs, StayWise is at a crossroads. Can they navigate this storm without losing their business? 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/VRS599

    47 min

  2. FEB 12

    VRS598 - Lessons Learned from a Disaster Scenario with Nick Massey - Proper Insurance

    In this third week of SSTIR Crazy 2025, StayWise Rentals grapples with an insurance nightmare when a malicious pool party threatens to ruin their business. This episode of the podcast and SSTIR Crazy Month 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 Proper has developed a specialty short-term rental insurance policy that covers both commercial and personal use of your vacation rental.  >> Discover more about Proper Insurance >> Register today to attend SSTIR Crazy Month 2025 “It just makes sense to buy the best cover available," said a lone voice in a Facebook group in answer to the question “Where can I get the cheapest insurance?”.  Sadly many of the responses pointed to cut price options which is clearly the route Staywise Rentals went when they started out.  And now to their horror, an incident at one of their prime beachfront homes has brought home the folly of this choice. In this episode and third week of the SSTIR Crazy event where we follow the issues Stay Wise Rentals are facing, Nick Massey, a seasoned expert in vacation rental insurance and the director of sales at Proper Insurance, shares his thoughts on the direction they  need to take.   Nick has extensive experience in identifying coverage gaps and optimizing insurance strategies for property managers, and he brings a wealth of knowledge to one of the most daunting aspects of vacation rental management. He gets right into the complexities of insurance policies, highlighting common pitfalls and actionable strategies to protect rental properties effectively. 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/VRS598

    56 min

  3. FEB 5

    VRS597 - When Vacation Rental Safety Systems Fail: Lessons from the Field with Justin Ford

    In this second week of SSTIR Crazy 2025, StayWise Rentals grapples with a critical turning point: a safety crisis threatening their direct bookings. Easter Egg #7 [Justin] - >> SSTIR Crazy Registrants can enter this phrase in the gamification section on the app to earn big points towards the 2 VIP Tickets to VR Nation Conference, Austin, TX, April 27-28, 2025. This episode of the podcast and SSTIR Crazy Month 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 Join thousands of top operators using Breezeway to elevate their business—because better operations mean better guest experiences and stronger owner relationships.  >> Discover more about Breezeway >> Register today to attend SSTIR Crazy Month 2025 In this episode of the Vacation Rental Success Podcast, host Heather Bayer sits down with Justin Ford, the Director of Safety and Certification Programs at Breezeway, to discuss the crucial role of safety in vacation rentals and the ongoing SSTIR Crazy safety campaign." Justin is a recognized leader in property safety and certification. As the Director of Safety and Certification Programs, Justin brings a wealth of knowledge and experience to the forefront of vacation rental safety. His insights are not only valuable but essential for property managers and owners striving to maintain the highest standards of guest safety. Justin's work in developing comprehensive safety protocols and training programs has profoundly influenced industry standards, making him a pivotal figure in promoting safe and secure vacation experiences. 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/VRS597

    41 min

  4. JAN 29

    VRS596 - From Questionable to Trustworthy: A Trust Transformation - with Chris Maughan

    In this first week of SSTIR Crazy 2025, StayWise Rentals grapples with a critical turning point: a trust crisis threatening their direct bookings. Easter Egg #3 [Guest-Centric] - >> SSTIR Crazy Registrants can enter this phrase in the gamification section on the app to earn big points towards the 2 VIP Tickets to VR Nation Conference, Austin, TX, April 27-28, 2025. This episode of the podcast and SSTIR Crazy Month is sponsored by Guesty your all-in-one platform for hospitality businesses to automate and optimize every aspect of your operations. >> Discover more about Guesty in the Virtual Vendor Showcase Trust Week of SSTIR Crazy Month is also sponsored by I-Prac, your global verification and certification platform that ensures hosts and property managers are legitimate and trustworthy, thereby enhancing safety and confidence for travelers. >> Discover more about I-Prac >> Register today to attend SSTIR Crazy Month 2025 In this episode, Heather Bayer sits down with trust expert Chris Maughan from I-PRAC to explore how property managers can rebuild trust, enhance direct booking experiences, and transform skepticism into loyalty. Chris Maughan, founder of I-PRAC and a leader in trust certification for short-term rentals, joins Heather to share insights drawn from over two decades in the vacation rental industry. With a wealth of experience managing properties in the South of France, Chris has dedicated his career to understanding and building trust as the foundation for successful property management. His practical tips empower property owners to boost credibility, foster guest loyalty, and make their direct booking channels indispensable. 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/VRS596

    50 min

  5. JAN 22

    VRS595 - Navigating Change: Why, When and How to Switch Your PMS with David Angotti

    There comes a point in every property manager’s journey where they have to consider whether their chosen property management system is still the right fit.  For those who made a strong and well-researched choice early on, this may not be an issue, but for many, that tipping point arrives and needs to be addressed. This episode of the podcast and SSTIR Crazy Month is sponsored by Guesty your all-in-one platform for hospitality businesses to automate and optimize every aspect of your operations. >> Discover more about Guesty in the Virtual Vendor Showcase >> Register FREE for SSTIR Crazy Month So, as we kick off SSTIR Crazy Month, we’re discussing a hot topic that's especially relevant for our fictional company, Stay Wise Rentals.  Over the next five weeks, we'll follow Stay Wise as they tackle various challenges and consider switching their PMS to boost efficiency and growth." In this pivotal episode, I’m joined by David Angotti, Chief Evangelist at Guesty, who brings a wealth of knowledge about the evolution of property management systems. David’s expertise couldn’t come at a better time as we explore the critical role these systems play in scaling operations and enhancing profitability in the vacation rental industry. Today, we're setting the stage for a month-long exploration of how modern PMS can transform a business from surviving to thriving. 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/VRS595

    47 min

  6. JAN 15

    VRS594 - SSTIR Crazy 2025: Tackle the Tough Topics, Win the Grand Prize

    Around this time last year, we had an idea that grew out of a LinkedIn post by Justin Ford. He had expressed his disappointment at the limited attention given to some topics at the 2023 VRMA conference and questioned how we could get more interest in the foundational elements of our business. SSTIR Crazy Month is the perfect FREE online event for anyone in the short-term rental business. This is your opportunity to take advantage of a month of incredible content that will help protect, you, your guests and your business. >> Register FREE for SSTIR Crazy Month That was the spark for the first SSTIR Crazy month, and here we are now heading into year 2.   In this episode, the co-founders of the Vacation Rental Formula Business School share what you’ll experience in this new and enhanced SSTIR Crazy 2025. Joining your host Heather Bayer, is her son and business partner, Mike - both seasoned experts in the vacation rental industry. Together they bring their insights into the foundational aspects of running a successful vacation rental business - focusing on safety, sustainability, trust, insurance, and regulations.  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/VRS594

    42 min

  7. JAN 8

    VRS593 - AI at Work: Real-World Applications in the Vacation Rental Industry With Steve Trover

    If you’ve ever wondered how Artificial Intelligence (AI) is shaking things up in the vacation rental industry, you’re in for a treat. Steve Trover has been a driving force in our industry for over 28 years, and through his company, Better Talent, he’s helped over 300 property managers refine their recruitment strategies and operations. But here’s where it gets exciting - Steve and his team are harnessing AI to transform everything from how job ads are crafted to how talent is optimized. In this episode Heather and Steve explore how these innovations are not just streamlining operations, but also enhancing the guest and homeowner experience. It’s a conversation packed with insights, practical tips, and a glimpse into the future of AI in short-term rentals. 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/VRS593

    51 min

  8. JAN 1

    VRS592 - From Trends to Tactics with David Angotti

    Happy New Year! This special episode - our annual reflection on the last 12 months and a look at where we are going in 2025 - features none other than David Angotti.  David’s been in the short-term rental world for years and has done it all - co-founding tech startups, building a successful property management company in the Smoky Mountains, and now serving as Chief Evangelist at Guesty. He’s also an incredible storyteller and someone who just gets the ins and outs of this business like few others. Having him on the show is always a treat, and I couldn’t think of a better way to set the tone for the year ahead. In this episode, we take a look back at 2024 - what worked, what didn’t, and the lessons we can carry forward. From evolving guest expectations to AI tools that can transform your business, David shares his perspective on what’s next for the vacation rental industry and how you can thrive in 2025. What You'll Discover: Evolving Guest Expectations: Insights into how guest expectations are shifting and what property managers can do to meet these rising standards. Technological Advancements: Discussion on the critical role of technology in shaping the operations and efficiency of vacation rental businesses. Regulatory Challenges: Overview of the regulatory landscape in 2024 and how it might affect the industry moving forward. Market Dynamics: Analysis of market trends, including occupancy rates and average daily rates (ADRs), and their implications for property managers. Actionable Strategies for 2025: David shares practical strategies to help property managers and hosts thrive in the coming year, considering the ongoing industry transformations. You Will Learn: Adaptation to Market Changes: How to remain flexible and adaptable in a rapidly evolving industry to maintain competitiveness. Leveraging Technology: Ways to integrate and leverage new technologies to enhance operational efficiency and guest satisfaction. Navigating Regulations: Strategies to effectively manage and adapt to new and existing regulations within the vacation rental sector. Understanding and Setting Guest Expectations: Tips on managing guest expectations to ensure satisfaction and repeat business. Forecasting and Planning: How to use market data and trends from 2024 to better prepare for the opportunities and challenges of 2025. Connect with David Angotti: Listeners can connect with David through his LinkedIn profile or explore further insights and resources at Guesty's website. 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/VRS592

    54 min
See All (600)

4.7
out of 5
210 Ratings

About

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, and Chex TV and is frequently interviewed on real estate and travel topics by magazines and daily newspapers.

Information

  • Creator
    Heather Bayer aka @CottageGuru
  • Years Active
    2013 - 2025
  • Episodes
    600
  • Rating
    Clean
  • Copyright
    © MOSO Partnership Inc.
  • Show Website
    Vacation Rental Success

To listen to explicit episodes, sign in.

Stay up to date with this show

Sign in or sign up to follow shows, save episodes, and get the latest updates.
Select a country or region

Africa, Middle East, and India

Asia Pacific

Europe

Latin America and the Caribbean

The United States and Canada