No Website. No OTA. No Problem. The Future of STR Bookings Is Here

No Website. No OTA. No Problem. The Future of STR Bookings Is Here

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.

Why Saying No to Pets Is Costing You Money

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?

The Secret to 100% Direct Bookings? Build a Brand Worth Talking About

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.

The Long Game — What 54 Years in STR Teaches You About Airbnb's Big Moves

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.

Direct Bookings in the Age of AI — with Mark Simpson, Boostly

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.