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 exactly what occurred on May 27th — how the agentic booking flow works, what it means for operators right now, and why the single most important thing any property manager can do today has nothing to do with their website.

They get into what operators need to do to their listings to be discoverable by AI, and when Boris thinks agentic bookings will go mainstream. He predicted the first booking would happen by June. He was right. Listen to what he says is coming next.

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 might surprise you. Pet-friendly listings are about half the supply of non-pet listings — and yet they consistently outperform on almost every metric that matters. Revenue potential up nearly 15%. RevPAR up over 9%. Occupancy higher in 81% of markets. 

The conversation goes beyond the data too. Why are operators still saying no? What does a properly pet-friendly property actually need? Which markets see the biggest uplift — and which ones don't? And with 48% of Gen Z reporting no difference between their pet and a human child, is the pet-friendly STR about to become the most important amenity in the industry?

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 quarter century, and a waiting list of guests who come back year after year without ever needing a platform to find them.

In this conversation they get into what luxury really means (hint: it's often a whitewashed beach shack, not a chandelier), why curation beats scale every time, how the luxury guest is booking further in advance while the rest of the market is dealing with shortening book windows, and why AI is something a brand like theirs should welcome rather than fear.

If you've ever wondered whether building a truly independent, brand-led STR business is still possible — this episode is your answer.

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 summer release — and to offer a perspective most operators can't. MLC is in its 54th year, runs 75-80% direct bookings, and only joined Airbnb two and a half years ago.

Tom talks about why repeat guests are the real business model, why Airbnb's expansion into ancillary services should worry operators who've built their revenue around add-ons, and why the operators who came in hot in 2021 are now calling him every week with a problem. He also makes a case that the pendulum is swinging back — that travellers are tired of the plastic fantastic and craving something real.

A grounded, honest conversation about what the long game actually looks like in short-term rentals.

 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 challenge to certain third-party tools, and what the rise of AI search means for how guests discover properties. Mark also shares how he thinks about AI across his own team at Boostly, and why he's more optimistic about the direct booking movement than ever — even with Airbnb still in the picture. A wide-ranging, practical conversation for any host or property manager trying to figure out where to start. 

 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 get funded. 

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 one platform. PC Hamana explains how automation isn't just about saving time; it's about "technological dividends" that protect your business from platform volatility.

In this episode, we cover:

• The Data Drop: Why being on Airbnb alone could be costing you 50% of your potential revenue.
• The "Manual Tax": The hidden costs of refusing to automate your messaging and operations.
• Market Disparities: How different markets perform on each channel, with surprising insights. 

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 into the "boring" trajectory of Airbnb’s latest updates, the risk of "corporate homogenization" in hospitality, and a fascinating look at the future of guest communication. Steve shares how he is using a conversational AI layer to handle 92% of guest inquiries via WhatsApp and voice, proving that technology can actually make hospitality feel more human, not less.

And with Scale with AI and Scale UK just around the corner, Damian and Steve discuss what we will be treated to, at the events this June. 

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 pillars of hotel management that every STR owner should implement to increase ADR, owner and guest retention and more! 

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 an exclusive look at what the team has been building at Guesty, from advanced automation to the latest tools designed to help property managers scale with confidence in 2026. 

He explains why meeting clients face-to-face at Old Billingsgate is the highlight of his calendar. Plus, find out what Guesty has in store for the event and how their latest innovations are simplifying the day-to-day for hosts globally.