The vacation rental industry has transformed from a scrappy alternative to hotels into a global powerhouse—but is the model starting to strain under its own weight?

In this episode, we explore how the ecosystem is evolving, and where fault lines are beginning to show. Can tech keep pace with rising guest expectations? Will hosts, managers, and platforms ever find equilibrium in their tug-of-war over economics, control, and trust? And what happens when regulators and communities push back against the very growth that made vacation rentals mainstream?

We look at the opportunities and tensions shaping the next phase of this category—where innovation collides with customer demands, and where the future may depend less on scale and more on who can truly deliver a consistent, high-quality experience.

Follows

Gilad Berenstein – host

Cara Whitehill - host

Annie Sloan — guest

Josh Kristoff — guest

Go Deeper

• Airbnb Lets You Add a Private Chef to Your Rental. Your Host Might Not Like It. - Wall Street Journal [$]
• **How much opportunity is there for STR ancillaries? Experts weigh in - PhocusWire**
• U.S. 2025 Mid-Year Short-Term Rental Outlook Report - AirDNA
• Short-Term Rental Headwinds: U.S. Supply Growth Is Slowing - Skift
• Perplexity Travel for Vacation Rentals: How AI Is Powering Trip Search - RentalScaleUp