The Check-In

On May 27th, a vacation rental was booked without a website, without an OTA, and without a human travel agent. Someone had a conversation with an AI, and the reservation landed directly in the property manager's PMS in seconds. It happened. It's real. And the person who made it happen is back on The Check-In. Boris Pavlov, CEO and founder of On Season, joins Leo and Sarah to walk through...

Should you allow pets in your short-term rental? Most operators treat it as a hassle question. The cleaning, the wear and tear, the risk. But when you look at the data across 317 US markets, it turns out to be a revenue question — and the answer is pretty one-sided. Sarah brings the numbers and Michael Goldin, co-founder of Nook and Good Morning Hospitality, brings the insights. What they find mig...

What does it actually take to run a vacation rental business at 100% direct bookings — no Airbnb, no OTAs, no exceptions? Francesca and Annie from Unique Homestays join Leo at Scale UK to answer exactly that. Unique Homestays is one of the UK's most quietly exceptional luxury vacation rental brands — a portfolio of around 190 handpicked properties, a sole founder still at the helm after a qua...

Airbnb just announced hotels, car rentals, grocery delivery, airport pickups and a clear signal that flights are coming. But what does all of that look like through the eyes of someone who's been running a family STR business since that's been operating since 1972? Tom Goodwin, CEO of Mountain Laurel Chalets in Gatlinburg, Tennessee, joins Leo and Sarah to react to Airbnb's 2026 sum...

 Anyone can build a vacation rental website in an hour with AI tools like Lovable or Replit. So what's the catch? Mark Simpson — founder of Boostly and one of the world's leading voices on direct bookings — joins Leo and Sarah to explain why a pretty AI-built site is like a Lamborghini with no engine. They get into what actually drives direct bookings, why the vibe-coded revolution is a...

 What’s the real difference between a multi-billion dollar "SPAC" failure like Vacasa and a scaling success like Hostaway? VC partner and industry expert Eugenia Dunaeva joins Sarah and Leo to pull back the curtain on short-term rental investments. We dive into "sticky" tech stacks, the shift from overvaluation to realism, and what operators need to show investors in 2026 to ge...

In this episode of The Check-In, Leo and Sarah sit down with two industry heavyweights, Jamie Lane, Chief Economist at AirDNA and PC Hamana CEO of Founder of Hospitable , to break down the data behind "Single-Channel Syndrome." Jamie reveals exclusive AirDNA research showing that a surprising amount of hosts aren't using a Property Management Software (PMS), and are listed on only o...

New York's 'own goal', the AI voice revolution and a preview of the latest Scale events:  What happens when a global event like the World Cup meets hyper-restrictive rental regulations? Leo is joined by Steve Taggert and Damian Sheridan to discuss why New York City is missing out on a massive tourism windfall, and why New Jersey is the one cheering from the sidelines. The trio dives...

The short-term rental industry is professionalizing at lightning speed. To stay ahead, operators must move beyond "heads in beds". In this episode, we sit down with Frank Bosi, a luxury hospitality veteran from The Ritz-Carlton and Four Seasons now at Hostfully, to see what can be learned from the rigorous systems of the world’s leading hotel brands. Frank breaks down the five core pilla...

Leo and Sarah continue the Short Stay Summit mini-series with special guest Andrew Evans, Director of Customer Success (EMEA) at Guesty. With the Short Stay Summit now only weeks away, the countdown is officially on! Andrew joins us to share why he is feeling so energised by this year’s show and why the "one-day energy" and the buzz of a London show floor is unbeatable. Andrew provides a...

Sarah and Leo are joined by Jessica Singer of BookingsCloud to discuss the secret to owning your demand in the STR industry with a strategy so powerful, it can cut your reliance on unpredictable OTAs and boost your margins.  If you're feeling the squeeze from algorithm tweaks, rising fees, or a flood of competition, this episode reveals how to future-proof your bookings and turn guests into l...

Leo and Sarah kick off the Short Stay Summit mini-series with special guest Martha Wilson from AirDNA.  Discover how industry leaders leverage AirDNA’s advanced tools to sharpen decision-making and optimize revenue. Martha dives into the power of AI-driven forecasting and explains how demand data—driven by massive events like the US World Cup—can be a game-changer for growth. Plus, hear what’s new...

Discover how to turn one-time guests into loyal advocates with a simple, scalable loyalty loop. In this episode, Steve Haase shares insights on why traditional loyalty programs fall short in the short-term rental world and how to leverage automation and personal touches to boost guest retention. Learn practical tactics like using SMS over emails and personalizing experiences effortlessly. Perfect...

Is the Great British seaside back? Chris Webb, MP for Blackpool South, joins us to discuss how his iconic hometown is spearheading a national tourism comeback. While many see coastal towns through a lens of nostalgia, Chris argues they are the key to unlocking millions in UK growth. In this episode, we explore: The Infrastructure Gap: Why broken transport links are the biggest hurdle to local econ...

In this episode of The Check-In, Charles Mullany, CEO of Host Genius, discusses the critical transition from viewing property management as a job to recognizing it as a business. He emphasizes the importance of outsourcing, particularly hiring an executive assistant, to reclaim time and focus on growth. The conversation explores the challenges of owner retention, operational scaling, and the neces...

This week, Leo and Sarah are joined by regular contributor Boris Pavlov to dissect the move that just changed the booking game: Ads have arrived on ChatGPT. Is this a new goldmine for the OTAs, or the ultimate direct booking shortcut for STR hosts? We dive into the "contextualized intent" driving conversion rates 8x higher than traditional Google ads, and the futuristic reality of guests...

Is your short-term rental strategy stuck in 2025? In this episode of The Check-In , hosts Sarah and Leo sit down with one of the STR industry's brightest stars, Hailie Maarie, who has built a staggering 70-property empire in just four years. Hailie breaks down her "2026 Host Checklist"—the essential moves that separate surviving hosts from those who scale. We dive into why "thr...

Join us as we delve into Kasa's acquisition of Mint House, a strategic move that positions them as one of the largest apartment hotel operator in the US. Discover what this deal could signify for the revenue share model in hospitality, and what it means for the future of urban hospitality specifically.

Join Leo and Damian as they delve into the vibrant world of France's short-term rental industry with Marie Pistinier, at Scale France. Discover how cultural nuances, expectations of international guests, regulatory challenges, and innovative solutions make France a truly unique (and challenging) market to operate in. This episode offers a comprehensive look at what makes France a standout des...

In this episode of The Check-In, Leo and Sarah discuss the evolving landscape of property management, emphasizing the importance of the human touch amidst the rise of AI. They explore how property managers can leverage local expertise, maintain strong relationships with cleaning teams, and focus on long-term property health to stand out in a competitive market. The conversation highlights the need...

Join Leo and Damian for this special episode recorded live at Scale France. They're joined on the sofa by Louis Andrews, CEO of OVO Network France, about the unique challenges and opportunities in the short-term rental industry. Discover how OVO Network has carved a niche in the French Alps, the importance of brand identity, and the evolving landscape of direct bookings. Whether you're i...

Airbnb was built on partnership, but is that era over?  This week, Sarah and Leo interview Steve Taggert of MyGetaways to dissect the platform’s aggressive pivot toward guest loyalty at the expense of host support.  We explore the financial impact of commission changes and the growing trend of hosts being sidelined in their own properties. If you’re a host feeling the squeeze, this episode offers...

In this episode, Sarah and Leo delve into the complex relationship between southern Europe and its tourism industry. Once a thriving love affair, the region's dependency on tourism is now facing unprecedented challenges. From economic strains to environmental concerns, we explore the factors driving this shift and what it means for the future of these beloved destinations. Join us for the sto...

In the latest episode of The Check-In Sarah and Leo discuss the significant changes happening at Airbnb, including the introduction of hotel inventory and new cancellation policies. They analyze the implications of these changes for hosts and the broader short-term rental industry, emphasizing the need for hosts to adapt to a more competitive landscape. The conversation also touches on Airbnb&apos...

In the latest episode of The Check-In, Sarah and Leo discuss the intricacies of managing short-term rental properties on your own, with Sarah interviewing James Kinnersly, who operates properties in the Canary Islands. They explore the challenges of remote management, the importance of local knowledge, the dynamics of online travel agencies (OTAs), and the impact of regulations on the short-term r...