The Check-In
The real scoop on the deals, the data and the drama in short-term rentals.
The Check-In
No Website. No OTA. No Problem. The Future of STR Bookings Is Here
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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.
On May 27th, someone booked a vacation rental without a website, without an OTA, and without a human travel agent. They just had a conversation with an AI. The AI found the property, pulled a live price, collected the guest details, and injected the reservation directly into the property manager's PMS in under a minute. That happened. It's real. And the person who made it happen is with us today. Welcome back, Boris Pavlov.
SPEAKER_00Hi, thanks for having me again. Hi, Boris. Nice to see you, my friend. So for any of our regular fans, you'll know Boris comes on the show. So he's not, it's not an introduction. But anyone who's new here, this is Boris Pavlov. He's the CEO and founder of OnSeason. Boris, just give us a very quick introduction for those who've not met you before about what On Season does.
SPEAKER_02Sure. We've pivoted quite a number of times. So even if you've met me before, you probably don't know what exactly we're doing as of today. Essentially, we're building a distribution engine for location retors for the AI era. We are sort of a supply layer that sits in between the PMS and the future of location rental distribution, which most likely will be through ChatGPT, through Quad and all these AI agents. That's what we do in a nutshell. We build this infrastructure that will allow AI agents to book properties.
SPEAKER_00Amazing. And when we first had Boris on the show, he was a new dad. And he, let's be honest, he looked rubbish. He looked awful. But now look at you. You're looking back to your brilliant best. Are you sleeping through? More importantly, is your partner sleeping through? We are. Even our kid is. Congrats.
SPEAKER_02He's a sleeper.
SPEAKER_00Congrats. That's that's very exciting. And if we'd have told future you, Boris, that that would be happening all those months ago, would you have believed us? I would have hoped so. I would have hoped so.
SPEAKER_02But no, no. We're lucky. I guess we're lucky. Uh we have a very understanding kid because both myself and my wife were entrepreneurs. So uh we run our own businesses and we need to get enough sleep on a daily basis to be able to do so.
SPEAKER_00Love it. Well, look, if your child could come and teach my four-year-old and two-year-old how to sleep through, that'd also be fantastic. But let's not let's not set ourselves up for failure at the start of this episode by wishing for things that won't happen. Sarah, how are you doing? You look beachy. If anyone's just listening, Sarah looks very beachy at the moment. How's everything in Barcelona?
SPEAKER_01Oh, it is so hot. I woke up this morning, it was 28 degrees in my apartment. So for our listeners across the pond, that's like 93 Fahrenheit. It's hot. Yeah. It's real hot.
SPEAKER_00I suppose you don't need to go on holiday if you live in a holiday destination. Is that something, isn't it?
SPEAKER_01It's true. Yeah. Saturday, it was one of those days where it was like there's nothing else to do but go to the beach. Otherwise, you're gonna be miserable. So yeah, we gotta go to the beach.
SPEAKER_00And I think now I understand why your partner, the lovely male, is so upset with cold weather holidays. Because, you know, like you probably crave that after a summer of sick sitting in the oven, right?
SPEAKER_01He does. I actually I love summer. I always complain about it when I'm in the midst of summer, but I much prefer summer to winter. I get depressed in the winter, but he doesn't, he's a vampire.
SPEAKER_00So well guys, I'm just back from the great state of Idaho. Sarah, we've never spoken about Idaho in all our chats about America. What a state. Oh my God, for beauty alone. Like I was just completely captivated. Have you been?
SPEAKER_01I've never been, no.
SPEAKER_00There you go.
SPEAKER_01There you go.
SPEAKER_00Yeah, amazing. Amazing place.
SPEAKER_01The bucket list.
SPEAKER_00That's it. Yeah. An incredible place. Such lovely people. Yeah. So we were at a short-term rental conference in Cor Delaine, Idaho, which was, oh my God, it was magical. It was magical. If you've not been, if anyone's not never been to uh ever been to never been to that part of the world, please go. It's it's phenomenal. And this short-term rental conference was amazing. I'll put details of it on the FC description. It was a first go out of the gate from this these four hosts in the area, and they absolutely nailed it. Um filled the room, lots of great panels, lots of great conversations, good energy. It was great.
SPEAKER_01That's awesome, honey.
SPEAKER_00Yeah, gang. All right, let's get into it. We've got a big topic to talk about today. So, Boris, put some meat on the bones of what Sarah was talking about in the introduction in the introduction. What's happened here?
SPEAKER_02All right. So the big topic, I think is the big topic of the year, is agentic bookings. And actually, agentic everything is the big topic of 2026. If in 2025 we were talking a lot about how to interact with AI and how AI helps knowledge work with giving us information and helping us with a bunch of things. Now the topic is more on the agentic side of things, which means basically that AI is doing stuff for you on your behalf on its own. And a month ago, on May 27th, we managed to do something that I've been dreaming of uh for the past two years or so, pretty much ever since actually ChatGPT came out. I've been imagining bookings happening directly in an AI agent uh interface. So we did it, we made it happen a month ago. It was uh it was a test booking. So the user was making a test, it wasn't a real user. Although right now from my phone, I can go ahead and book one of 75,000 properties on my own ChatGPT app anywhere in the world, which is pretty much a big deal, and that booking would go into the property management system of the operator. So, what happens is there's a bunch of layers that get stuck for this to happen in the first place. So you have ChatGPT on one hand, and then you have the PMS on the other hand, right? So for a booking to occur, we need Rails in between. Well, let's start from this side, from the property management system. We need to get the information about the property, and this information needs to include everything from pictures, amenities, descriptions, rates, availability, and all that needs to be live information. So that needs to be connected to other property management systems because let's face it, there's no single property management system that operates allocation rentals, there's so many of them. That needs to go into a database that contains homogeneous information so that when we search across properties, we're always comparing apples to apples, not apples to oranges. And then we need a common API or a common gateway to this database, which would have to be wrapped in an MCP model context protocol. It's what AI reads. Uh and okay, I'm gonna stop here with the latest because uh we're getting too much into the details, but basically we stack all this uh together on top of each other, and that's how we make a gentic bookings happen. Now, disclaimer, you cannot go ahead and just download this on ChatGPT by yourself today and start making bookings for two main reasons. First of all, we haven't published it officially uh on ChatGPT or on Quad. Our goal here is not to become the next Airbnb, it's an infrastructure, so everyone needs to be able to use this infrastructure, whoever is going to be the distribution part, so if it's ChatGPT or Quad or Layla or some other new AI trip planners that are coming up, they will all need they all need to be uh using something like that, and we want to provide it to all of them. So that's one. And second thing is that payments are not yet fully configured between ChatGPT and Quad, so you cannot really pay for it. You'll be able to very, very soon with the help of some large financial companies that we're working with. So, long story short, this booking is now possible and it happened in literally seconds. By the time I checked if it was in the PMS, it was already in the PMS, so I don't know how long it took, but it was seconds. And I believe that's the future of how we're going to book travel in the in the yeah, in the coming years.
SPEAKER_01Let's talk a little bit about what that booking actually looks like on the side of the PMS, because I know, I think I know the answer to this because I know how much of a proponent you are for direct bookings, but what happens with that booking? Is it a direct booking only if the property manager or host has their own website? If not, it would go through one of the OTAs. Is there any logic in the algorithm itself that kind of prioritizes direct over not? How does it work?
SPEAKER_02Right. So right now it goes in as a direct booking, along with the user's name, email, phone number, how many guests are going to be at the properties. All of this information is collected during the booking process from ChatGPD itself and then it goes into the PMS. In the future, since this is an infrastructure product and it will be used by different distributors, we are looking to have uh the name of the distributor appear at the channel. It's not going to be direct exactly, but the the economy, the commercials will be very, very different because think about it. OTAs, their whole business model relies on the fact that they're aggregating commissions and then putting a bunch of this these commissions into Google and Meta to do advertising. Essentially, they're buying travelers. Whereas ChatGPT doesn't have to buy users, ChatGPT already has the users, right? So ChatGPT is not going to charge you 15% per booking. I don't know how much they're going to charge. They're going to charge something, it's probably going to be different if you're using ChatGPT or if you're using Cloud. It could be nothing. We don't know that yet. Nobody does, but they haven't made up their minds. And until we actually have the commercial partnerships in place with these companies, the bookings are going to be direct. So yeah, long story short, for now they're all direct. In the future, I'm not sure, but they're definitely not going to be OTA book.
SPEAKER_00When you say they're direct though, it doesn't actually, you don't need to have a direct booking website though, right? You just need to have a property on a PMS.
SPEAKER_02That's correct. You don't need a direct booking website.
SPEAKER_00Because the idea is it's pulling the data directly from the PMS, right? So it will show it will appear as direct. And you're quite right, there's no commercial relationship, right, in place yet with the LLMs. Who knows how they'll even look to monetize? So that's that's a whole wider that's a wider question. But that is what I think is really exciting. And where I was I was it excited by Sarah's initial question, because I was like, I can't wait for Boris to wow with this, right? Essentially, the dependency right now for a property manager, and I'm going to take words out of your mouth that you've said to me in the past, is making sure they're working with a PMS that's of a really good quality, because that is what's going to help the LLM read. Well, that's what's in in a nutshell the LLM is going to read to be able to suggest that property, right?
SPEAKER_02Exactly. In that whole like a stack of layers that I described earlier, the most important piece is the connectivity between the PMS and our infrastructure. Because the way we can extract data is via an API from the PMS. We cannot go ahead and extract data in different ways. Yes, we can maybe scrape Airbnb, but how accurate is that going to be? And besides, we need live rates and availability, and these lead in the PMS. So you don't need a website, you don't need anything except for a place that stores your data and transmits it via a machine readable format, which is the API today. So every single operator needs to be working with a PMS that has a very robust and complete API. Why do I say complete? Because all of PMS is out there, they can push rates and availability via their API, but they cannot push photos, they cannot push descriptions, they cannot push other essential information. Now, how am I going to explain to ChatGPT that I need a three-bedroom apartment and expect, you know, for ChatGPT to look at all the three-bedroom apartments possible in the given market if we don't have information passed from the API on whether the apartment has two, three, five bedrooms. So it's not just about rates and availability, it's also about rich content.
SPEAKER_01Yeah. Makes sense. Tell me a little bit more. I want I'm I want it to happen. I want it to be true, but I've always been a bit skeptical.
SPEAKER_00You're a cynic, Sarah. You always have been.
SPEAKER_01I'm a little bit of a cynic, mostly because I have massive SOMO. And so what I want to know is how are you 100% sure that this is the best property for me? What are the inputs that are going into that? Um, and then kind of on the back of that, if it's not perfect today, how long is it going to take, do you think, for it to be a perfect suggestion that I would feel confident trusting over my own criteria?
SPEAKER_02Right. No, that's a great question. So the advantage of using AI when making a booking is that the AI already has a lot of context about you. Sorry, like the AI knows what your preferences are. It knows whether you you're gonna tell the AI whether you're traveling for business at a short-term mental conference or whether you're traveling with your partner to a some cold destination to get to escape the heat in Barcelona. So it's gonna know all of this about you. It's gonna know the super hot in Barcelona. So it's going to suggest a place nice and cooler so that you can just go for a weekend. And no OTA, no marketplace, not even Google knows this about you when you start your search. So the discovery layer has completely shifted, is completely shifting because it's so much more personal about you. Now it knows your preferences, it needs to know the characteristics of all available properties in order to fit your preferences to uh you know, to match your preferences to the perfect property. It already has information from you and from a lot of people. We share a lot with uh with ChatGPT, but we need to make sure that it has enough information to make a decision on which property would fit you best. And that only happens if we as an infrastructure are able to obtain all information about the property. Now, one thing I need to point out here is that we don't just obtain if the PMS allows, we don't just obtain rates availability photos and descriptions. We can also get the reviews. So getting reviews and getting recent reviews would mean that we will have up-to-date information, which is a lot of times more the most up-to-date information about the property. Because you how often do you update your descriptions, right? Not that often, but uh we can read reviews from yesterday when suggesting properties for you. And if yesterday someone said this apartment was next to a construction site and it's too noisy, and apparently this construction site is gonna continue for like another two months or so, it's not gonna suggest it for you given that you're going somewhere to relax and escape the heat and just chill. Right? So that's the depth of information we can get in order to make sure that you're presented with the most suitable property for your preferences.
SPEAKER_01Do I get any kind of like multiple choice? So sometimes when I'm talking to AI, I'll say, like, hey, give me three different ideas and I'll tell you which one is closest to what I'm thinking of. How does how does it work on that end? Or is there like different levels of trust? If I were asking, I would probably ask more questions and my booking wouldn't happen in a minute. It might happen in 30 minutes, which is still a lot quicker than what it takes me now. But um yeah, just curious kind of what level of customization you've built into it.
SPEAKER_02That's entirely up to you, and that's the beauty of it. You can ask the AI to give you three, the top three or the top five recommendations or the top 10. Uh that that's up to you. We don't have a set user interface or even like a user experience journey right now. We have to create it ourselves. In my view, every user would create one for themselves. There's no such thing as a universal UI anymore. In the era of AI, there shouldn't be. So software needs to adapt to the user. We shouldn't adapt to software same way that AI needs to adapt to you, and we should you shouldn't adapt to the AI. So if you want three suggestions, fine that get three. If you want ten, get ten. If you want to spend two hours discussing different options, the AI is never ever going to get hyped. You know, a human travel agent will not spend two hours with you on the phone going over different vacation rentals. But uh, you know, the AI will spend as many hours as you need. That's the beauty of it.
SPEAKER_00That is great, isn't it? About about that way of doing it. It's just a it's a constant conversation that you can pick up and drop as you need to, uh, depending on how f how organized you're feeling at that particular moment for the trip. So I agree, I think it enhances it. Do you think the PMSs understand how big an opportunity this is for themselves? The smart ones do, right? That the the the O the OTAs could could potentially could potentially be being pushed to the back of the queue, right? And their and their inventory could be getting pushed forward.
SPEAKER_02Right. I don't think they do realize what's happening right now because we are connected to more than 40 property management systems, and only 11 support all of the information that we want to get for all of the properties. And some of them go as far as not allowing their users to get API keys. So keys are essentially, well, it's clear self-explanatory, it's what allows you access to your own data. So if you're using a PMS that has an API but would not give you the your own key, so that you can access your data via this API, it's like, why do you even have an API if you're not gonna let the user use it in any way? So it's a very, very wide spectrum. Uh some PMSs are at the forefront, some have even launched their own MCPs. So MCP stands for Model Contact Protocol is essentially an API for AI tools in agents. Uh what can you do with an MCP if your PMS has an MCP? Well, you can chat, you have to install it, and with ChatGPT you can tell your PMS to do things, or you can ask information that like a report on your occupancy for a given month, or something like that. And via the MCP, ChatGPT would pull this information from your PMS and it's going to get you the report. A few PMSs have already done that, or a few, I think, two have already done that and release their own MCPs. Now the problem is a PMS alone can't do much again at the OKAs. That's why we exist. We have to sort of work with all of the PMSs and come up with a unified MCP for all of them. But our job is very difficult given the fact that every API is different, it supports different data, and they even call it different ways. One property is called a one PMS beachfront, and the other one is seafront and then ocean front. It's the same property, just different conventions of naming ones and things. But I mean, just like with any new technology, it's a process, right? It would take time to establish standards, it would take time to uh roll this out. People often ask me, so when do you think OTAs are going to die? And my answer is well, die, it's not gonna happen for at least like five years or six years or something like that, and they're not even going to completely die. Maybe they're going to transform themselves somehow. It's not gonna happen overnight, even though a month ago we just made a technology that could kill them. Just like you know, when the internet appeared, travel agencies they didn't disappear overnight. It's a process. It's a process that accelerates with every new technology that surfaces. Um, that's for sure, but it's not gonna happen overnight.
SPEAKER_01Let's talk about if if I'm an operator, what are the things that I need to be conscious of when I'm publishing a listing, writing a description, all of these types of things, how much of what you've built is pulling from reviews versus something that the host or the property manager needs to be aware that they're gonna that they're gonna have to include? If they're like, do they have to write a description of every type of guest and why it would be great for them? How deep how in detail do they need to go?
SPEAKER_02Uh well, not that much in detail, but definitely highlight who are the perfect guests for the property because that's going to help. Yeah, it doesn't make sense if you just write all types of guests that are the perfect guests for the property. It's not gonna get picked up uh as the LMs get smarter and smarter. But detailed descriptions are important, very important, and is the main driver uh when we're doing search because reviews can be very biased, and a lot of times a review can be about something that is irrelevant to what the user is looking for. So reviews do play a role, but the most important parts are the structured amenities information and the actual description of the property, which are more static and the way it goes on to that. Now, keep in mind that right now we don't have a way of controlling what the LLM really puts emphasis on. The LLM decides on its own, we cannot really, as of today, influence its decision in any way. Which is also a good thing because I don't want to be the one who decides if property A or property B is better. Right? Uh we just need to relay the information with the infrastructure we trying to remain neutral and let the AI decide which one is best when we provide it with all the information. The models are smart enough to figure out the weights on their own, I think.
SPEAKER_00Boris, I know lots of small operators or single unit hosts, people or hosts who might be moving away from it who don't have a PMS. What's your advice there? Because you often hear about someone saying, Oh, you know, I'm gonna be vibe coding these things and that. And you know, it sounds to me like really this is your best bet. Having a really good PMS right now feels like your best bet. So, what would you say to people who, for one reason or another, Not have a PMS?
SPEAKER_02So the first thing I would say is don't vibe code your own PMS. That is not going to end well, especially if you try to sell it to other people. We don't need more PMSs out in the world. And you're gonna spend more money vibe coding and then supporting the PMS than you would on an actual established PMS. Now, if you don't have a PMS today, that's fine because by the time agentic bookings become more of a mainstream reality, not just you know testing space. By that time we would have developed a way for anyone to onboard with or without a PMS, but that would mean that the data will be added manually by the host. We need somewhere to get the data right. We don't want to get it from an LTA because the first thing that Airbnb, for example, is going to do is it's going to block us. And it's against obviously Airbnb to do so.
SPEAKER_00So it's really interesting. The the reason why I asked the question, I suppose, Boris, you kind of started to answer it there, is for so long, the marketing message has been from within the sector has been as quickly as you can get a direct booking website. Even if you get one booking to it a month, you're building your brand, you're growing a presence. Now, potentially with this, what we're saying is actually the first thing you should do is get your warehouse in order. Get your back office, get your back office of your listing. When I say warehouse, I mean the listing. Get your back the back office of your listing in order. Make sure it's optimized properly. That's that's the bet that's the first thing you can do. And the easiest place to do that is on a PMS.
SPEAKER_02Exactly. And you just touched upon something that that's been an ongoing debate at our team. You know, direct booking websites, we have this tool that lets you create a direct booking website with AI. It's very simple, it's very nice. Obviously, not something that is in any way vital to the vision of our company. So we were thinking, should we create a new product which is essentially create chat GPT apps for operators? And we've been debating about it because we have the technology, it's very easy for us to create a chat GPT app. Now, obviously, to publish a ChatGPT app, OpenAI needs to approve you. There's some sort of approval process for the time being, but uh the technology is there and we can do it very quickly. And we've been deliberating whether we should do that or whether we should encourage operators to create these chat GPT apps. And the problem with ChatGPT apps is pretty much the same as with direct booking websites. You still don't own the distribution, you still don't own demands, right? Because someone needs to install this ChatGPT app, just like someone needs to go on your website. Is it possible that you get a booking on there? Yes, it is possible. Will you get a booking? Probably by like a very, very early adopter of an AI that somehow happened to find your uh property management operation and downloaded your app and booked on there. It's possible, but it cannot happen at scale. So, direct booking websites are something that we have today. It works for your regular visitors. Most of them don't know what a ChatGPT app is, they live outside of this bubble of early adopters. So definitely keep a direct booking website, invest in SEO because SEO is quite important for your brand in general, to attract more homeowners and to to uh establish a property management brand and establish more trust. But having your back office in order, like you said, is becoming extremely important because once agentic bookings are enabled at scale, that's going to determine whether you get uh quoted and whether you get uh offered uh or not to to the travelers.
SPEAKER_01Let's talk a little bit about what this is gonna mean for if I'm a PMS or own a PMS or work for a PMS. You've mentioned already, like we don't need another PMS, there's too many out there. Do you think that this move towards a genetic booking is also going to lead to some consolidation in the PMS market, whereby the ones who are able to adapt to this change basically dominate the market, and the ones who are not slowly fade away because it becomes more and more important?
SPEAKER_02Yeah, I do believe some consolidation should happen. I don't know why it hasn't happened yet. Uh, there's too many PMS out there. And I the problem is it's become easier to develop new features and to even launch your own PMS now with AI coding tools. So I certainly hope that this is not going to be the case because we're gonna end up with a lot of zombie software stacks here and there that have managed to recruit a couple of operators and then struggling to scale. So for the PMSs out there, I would expect some sort of consolidation. I would expect them also to remain in the operations layer of AI. A lot of companies and startups are now trying to build AI agents for operations, which seemingly seems to sit on top of the PMS for now. But as these agents get better and better and better, soon they're gonna start trying to replace the PMS. So that's a threat I've personally identified for the PMS. The threat is no longer my user is going to build their own with AI. The threat is an AI-native startup is going to build AI agents for every single feature that I have and every single function that I have in the uh life cycle of a reservation, property managers operations in general, so that I'll be replaced by these new type of agentic systems that make my property management system well useless. Not useless, but just archaic, put it this way.
SPEAKER_01I think I think for me, like the million-dollar question here that I'd love to maybe leave the audience with is how long, Forest? You've done this before, and you told us a couple of months ago that this was gonna be possible, and I've kind of poo-fooed you. So I will listen this time. How long is it gonna be before this becomes mainstream? And and is there a certain segment of the population or generations that are gonna adopt this much more quickly than others?
SPEAKER_02Yes, so the early adopters of AI, which is about 1% of people, they're going to start making bookings within six to nine months using ChatGPT. And it's important to mention here without ever leaving ChatGPT or whatever AI agent they're using. It's all about discovery on ChatGPT, and then you go and you bookonbooking.com. No like proper ChatGPT bookings that's six to nine months away. But there's a lot of initiatives right now happening before the IPOs of the large labs. Commerce in general is one of the big initiatives. They need money, these labs, so they're gonna launch Commerce. In terms of mainstream adoption, it's gonna take a while. It's going to be five years until AI replaces OTAs as the dominant source of uh of bookings. So these are my current predictions as it stands now. Uh my previous one was correct. I was saying that in six months, that was I think back in January. I was saying that it's by by June and in six months' time, we're gonna have the first object booking. That was done. So, yeah, I think I think it's gonna be soon. One thing that's worth mentioning here is that there are a lot of AI travel planning startups out there that have been trying to penetrate the distribution layer, they've been trying to win the consumer. One that just launched a couple of weeks ago is by the founder of Sonder, a company that we know very well in the space. So he launched an AI travel planner. But unfortunately, if you want to book a vacation rental, it goes to Airbnb. So fortunately for Airbnb, unfortunately for operators out there. But I assume that as these companies mature, as all these startups uh start maturing, they gather some sort of a user base, they would look into margins, so they won't be able to afford bookings on Airbnb anymore if they want to keep their customer bases. So these ones I I can see them booking very, very soon. Like this is gonna be probably the first, maybe even before ChatGPT and caught.
unknownYeah.
SPEAKER_00Boris, I love it. Uh there you go. You've left us with another prediction, just very skillfully, so that Sarah's made sure you have to come back on there. Very good. Well done, Sarah. Boris, always so good to see you, my friend. Thanks for joining us.
SPEAKER_02It's a pleasure and thanks for having me. I I have a lot of fun with these uh every time.
SPEAKER_00Um it's always great to see you. Sarah, nice to see you. As always, my friend, my beach friend. Okay. So uh to you at home, if you enjoyed today's show, please hit like, share, subscribe in all the usual social places, and we'll see you again next week. Thank you. Thank you.
SPEAKER_02Bye bye.