What “AI-Bookable” Actually Means for Hotels and Short-Term Rentals

On this special holiday episode of Good Morning Hospitality, Brandy Canaley and Michael Goldin unpack one of the biggest shifts happening in travel right now: AI-powered booking. Joined by Jason Cincotta, founder of Kismet, the conversation breaks down Google’s new push into agentic hotel booking, what it means to become “AI-bookable,” and why independent hotels and vacation rentals may need to rethink how they show up online.

The episode also dives into Airbnb’s massive Summer Release, including boutique hotels, AI-powered review tools, airport pickups, grocery delivery, rental cars, and the company’s expanding push toward becoming a full trip platform. Michael and Brandy debate whether Airbnb’s latest features are meaningful product evolution or just great PR, while also exploring how AI could reshape direct bookings, loyalty, and the future of travel planning.

This episode is presented by ⁠⁠Cloudbeds⁠⁠, Bilt⁠⁠, and StayFi.

Watch This Episode

Good morning.

Happy Monday, but it’s not Monday for Brandy and I. We are off celebrating the holiday in our own unique ways.

Yes, yes. What are you doing, or what did you do for the holiday, Michael?

We are recording this on Thursday afternoon, taking the family down to Dolphin Island and doing some fishing for about a week. So excited to get down to the beach with the fam. And you’re exactly the opposite.

I literally could not be more.

I will be at the time of this airing, dancing somewhere in Detroit for Movement Music Festival.

So at 9 AM. Wow.

Yeah.

All right. Central time. Yeah.

Well, good for you, Brandy. Stay safe, have fun, stay hydrated.

Definitely. Got my water. But you know, there’s a lot, you know, when we can have two recordings in a week, sometimes like, okay, what are we, what could have just happened that we could talk about?

But there’s actually kind of a lot. So we had the Airbnb summer release and Jamie, our very own Jamie Lane was there. So when he gets back, we’ll have, you know, his whole take.

And then some interesting things from Google coming up. So very, very busy week.

Yeah, and we’ve got a special episode coming out with Dave Stevenson from Airbnb that Jamie interviewed at Airbnb offices earlier this week. So stay tuned for that. Well, it is out already actually.

Now that we’re talking. So we’re still live despite being Thursday afternoon. And the thing that we talk about a lot, Brandy, is AI.

So today’s discussion is going to be mostly around Google and their AI play, and the summer release of Airbnb, Brandy and my thoughts layered on top of what Jamie has already put out. So Brandy.

Yeah. Well, we have a special guest later in the episode, which I think is going to be very fun. But before we bring him on, we just want to give a quick shout out to our sponsor, Plusgrade.

Plusgrade helps travel companies unlock new revenue through upgrades, premium experiences and personalized offers across the traveler journey.

From airlines to hotels, they’re powering a lot of the stuff you’re seeing behind the scenes when it comes to monetization across travel today. So you can learn more about them at plusgrade.com and also the link in the show notes.

So do you want to bring on our special guest today, a good friend of yours?

4:09

Googleʼs AI Travel Play

So AI is very complex and you got to know your weaknesses.

And so Brandy and I know better than to dive deep on MCP layers of what Google is putting out and universal commercial protocols. So we have brought in the expert that’s solving this for both hotels and short term rentals.

So without further ado, Jason Cincotta from Kismet. All right. Well, Jason, I always oversimplify Kismet.

Let’s get a quick intro, but my oversimplification is turning the LLMs into direct booking channels. Sure. I know it’s a lot more.

Give us 30 seconds and then we’ll start hammering you with some Google questions.

We’re interested in helping accommodations providers reach guests who are searching with AI, wherever that might be. That’s going to mean a lot of things very soon.

We’re in the business of helping those providers, those suppliers, vacation rentals, short-term rentals, hotels serve the guests who arrive that way.

Beautiful. We’ve seen data earlier this year that we’ve talked about on the show, like 56 percent of search is now beginning on the LLMs. There’s the big two or three.

What Google put out this past week is different than what I might have guessed the route they go, and it’s different than where maybe we would have expected OpenAI or Chat GPT to go.

Can you tell us a little bit about Google’s plans now on monetizing travel?

Yeah. I’m curious. You said you’re surprised by it because it didn’t seem like the Google answer.

I understand why you’d say that. Google monetizes advertising and clicks historically, right? Historically, it was about getting you to go out to a bunch of different websites.

But they worked on this UCP protocol and they worked with Shopify on it.

Now, there’s a very supplier-friendly, supplier-aligned way for a guest, in our case, or a customer if you’re in e-commerce traditionally, to check out and buy things in Google’s surface without ever clicking out to a supplier’s website, which is

very different than the world we’ve lived in historically. I think it’s going to mean huge changes for how guests plan and book travel.

Yeah. I think it’s interesting because for a while, there was Google was getting into hotels and vacation rentals. I mean, we never really saw the promised land of Google vacation rentals.

Then when we’re talking about a lot of the LLMs and who is doing what, I mean, ChatGPT was supposed to have the in-app purchases and then that got sidelined for now.

I mean, Google just hasn’t been at least what we’re hearing in the news in the day-to-day as one of the leaders, but now I’m thinking and I was thinking for a little bit, is Google going to fall to the wayside if everybody’s just going to go on or

Yeah, and I think it’s a really good point.

But what’s interesting about UCP is the universal part. So Google helped to write the protocol, but this can be booked by an agent or operated by an agent, an AI, from any surface. So an anthropic clod agent could use UCP.

ChatGPT could choose to use UCP and they very well may. And anybody developing an AI could book your hotel or vacation rental from UCP. What Google announced is that a catalog will be put into Google via UCP.

And in this case, they announced six partners at launch. Two of them are the OTAs that we know well, Booking and Expedia. And then there’s four big branded hotels.

But UCP, it’s likely is going to power many catalogs and it’s likely that your hotel or vacation rental is gonna be in a lot of different catalogs in the long run.

So vacation rentals, you know, Google Vacation Rentals, which you mentioned, is a catalog that will likely become UCP enabled that Google will consume, but it’s possible for you to reach Google now via a variety of UCP catalogs that you could become

part of. So I think there really is an openness to this, that’s pretty exciting if you run accommodations.

Yeah, I’ve heard the naysayers say, well, people use GPT to get their inspiration, kind of like they did with socials and then moved to search. This is the polar opposite end of the spectrum where enabling agents to go book for you.

Yeah.

Where, what’s happening now and what’s happening because of this three or six months from now.

Yeah. I think one of the fair pushbacks that I often hear from people is, well, I like planning travel. I like, you know, considering all my options.

That’s part of the fun of putting a trip together. And also, it’s a really high intent, high cost purchase. I’m not going to trust some AI to go plan my whole trip and book it for me, which is like a really fair critique that people make.

But I think it shows a lack of imagination of what AI travel planning will look and feel like.

So I think what’s really important from our perspective at Kismet, and I talk about a lot with our partners, is that guests are going to want to plan in Chachi-PT or Claude, and they already do.

And they show up and they say, I’d like to come up with a great trip to Paris. Where should I stay? Where should I eat?

What should I see while I’m there? How do I get tickets to the Louvre or something more interesting? And already these AIs connect with so much of our life and can do a really good job planning the trip for us.

But what they can’t do is take action on our behalf. They can’t get pricing. They can’t put together the itinerary and they certainly can’t book it.

And that’s what UCP enables. So I think it’s very likely that you’ll still be very involved in the planning phase and you’ll work with your AI to build out that itinerary.

But what’s exciting about it is now it’s like a single buy button to go do the whole thing. And that’s what UCP really enables.

Yeah, you know, it’s interesting because I’m one of the people that loves the whole planning process. I mean, I’m using Claude for things, but I have my spreadsheets. I like to look around.

But then like with anything, we’re just in the baby phase of all of this. In a couple of years or whatever it may be, the people that are saying, I would never do that, are probably going to be doing just that. You know what I mean?

It’s going to be funny. I’ll have like, I mean, hours of clips of me being like, skeptical about things that I can go back and be like, I guess I was wrong.

But then it’s like, because it’s, you know, as these bits of technology get more ingrained into our everyday life, like it’s not going to be a switch.

Like one day you’re booking everything with a travel agent and the next day you’re using Claude to buy everything. Like it’s going to happen slowly over time and people become more used to it.

And it might be the like business travel that you start planning with it more. And then it worked up to like the big family house once you kind of like build that trust or that familiarity with the product.

Well it’s also about what is capable within the platforms. Six months ago on GPT, I couldn’t go and see tiles and scan through different properties, but that is now becoming available. So there’s the visual layer that’s worked its way into it.

Still, a lot of times, and I challenge any operator or brand today to search for their stuff on GPT, the majority of it’s probably a link out and not actually pulling in rates, availabilities, properties. So I think it’s already evolved quickly.

It’s going to evolve more quickly. And if you’re doing an entire planning session of hotel, flight, museum tickets and car rental, it would be nice to have it all in one spot.

And booking has talked about the connected trip forever, but turns out it might end up being Google that does the connected trip first.

Well, and Expedia kind of just announced two years later that they’re going to move things out of, I think it was called Romi, was there, like personal AI that they offered to consumers.

The reason that that’s happening is that the best travel planner that you could possibly have is already in your pocket. You know, Claude, ChatGPT, whatever, your favorite LLM or application of an LLM that you could use.

It’s already really good at knowing you. It connects to your calendar now. It connects to your email if you want to get exciting.

You can actually even connect it to your iMessage with Claude. I saw that the other day.

So it’s going to be really good at coordinating a lot of what is necessary for a trip and taking a lot of the parts that aren’t so much fun and the planning out of it.

One of those things is going to a million checkout screens and paying on your behalf. That’s going to be much better when you can allow the AI to handle that checkout part.

But the travel planning part of it is limited by what a hotel or a vacation rental can say to an AI and the information it can get from it. So I think that’s what’s changing really fast.

14:48

Becoming AI Bookable

Well, on that, Jason, people believe that AI is going to drive them more bookings and gives them the opportunity to get more direct bookings.

This is like, to me, it’s one of the most exciting eras that I’ve seen in hospitality, this shift that we can claw back more direct bookings from the OTAs. But what does it mean to actually be AI bookable? And how can you optimize for that right now?

I think what’s interesting is that Google just gave us one answer.

I fully expect that if your property is already in hotel center or Google vacation rentals, you’re now AI bookable whether you like it or not.

The launch partners that we mentioned for big brands to OTAs, their catalog, if you’re part of it, you’re going to be AI bookable when Google starts consuming UCP this summer. So it’s going to happen.

The question about direct bookings, so if you’re not part of a brand and you don’t want to only be booked through an OTA, is actually a very technical one. And chances are you’re not going to build that capability on your own.

You’re going to need to engage in some new specialized software. And I know no one got into hospitality because they love tech. And I hear you guys on a weekly basis making fun of AI and what’s doing in the industry.

And I didn’t get into hospitality because I love tech. But I do think that this is a really exciting moment if you’re an independent lodging provider to be able to get found, get your own brand out there, talk about what makes you special.

All of a sudden, these guests have an amazing travel agent in their pocket that is tireless and can read millions of words at a time and can find you.

But you’re going to have to have the technical ability for it to get a price quote, put it in the itinerary and book it if you want to actually drive direct bookings from this.

Sorry, Brandy. One question that I’ve heard you say before, Jason, of how to bring it down to earth, particularly in short-term rentals, is your Thanksgiving analogy. Can you walk us through that?

You like that one?

So I think every vacation rental or short-term rentals listing page has a lot of marketing speak. And it probably says, fully stocked kitchen. There’s probably some pictures of the kitchen.

But AI doesn’t want to rely on your marketing content because it’s kind of biased.

And it can’t look at pictures to answer and filter across thousands of potential renters and, you know, take the time and cost to look at all of them in order to answer a guest’s question of, I want to find a rental that’s, you know, big enough for

me to host Thanksgiving for 12. So what smart, you know, managers who are embracing tech will do is they’ll turn information into something that the AI can read.

And that can be review data, that can be pictures into the actual content that AI works with so that it can find your property when that guest is asking about it and pick you.

But that does require outputting, you know, different type of content than what’s already on your booking engine.

Yeah. And so I think we had this whole phase of, you know, SEO optimization. And now what is it?

A, E, O, optimizations, whatever, you know. And so, you know, there’s, you were talking about like the technical aspect. And before you and I have talked about how pricing is the big thing.

We had did a little test at one of our property in Florida. And even though we’re like a huge operator there, like this other operator that just had static pricing was coming up. Because that’s what the engine is looking for.

If someone is thinking like, okay, the technical aspect is terrifying, or just like from a workload and bandwidth perspective, is there a different, like, are there different things that people can be doing to rework their sites, just like on a basic

Yeah.

So good technical SEO applies to GEO, AEO, whatever you want to call it. And that means more than just like keyword stuffing into your website.

Back in the early days, you could just put like a bunch of white text on your page, and Google PageRank algorithm would help you find. You can’t do that anymore, and Google will penalize you.

But structured data, and that’s like a dollar in the swear jar word when I talk about it on calls. So I’m going to have to go through that afterward. But structured data is a real thing.

It’s part of actually what Google Vacation Rentals and Hotel Center runs off of. It’s pushing information up in a way that a machine can read it. But chances are you’re not going to do that on your own.

You’re going to need an SEO consultant or a web agency to help you with it. But moving beyond that, price checks, login, things like that, MCP servers, which is how we started this segment, right?

That’s probably beyond the purview of even your web agency. You really want to work with a technical specialist at the end of the day.

Awesome. Well, thank you so much for bringing actual expert advice onto this subject. It’s not just us talking out of the side of our mouths.

Pleasure chatting with you as always. I hope you come back and we need Jamie on here so we can have a proper fiery debate.

Yeah. I want Jamie to push back on all my optimism for the independent lodging providers and saying that everything’s going to be booked direct in the future. It’d be good to tussle with them a little bit on that one.

Beautiful.

We’ll have a link to your LinkedIn in the show notes if anyone wants to reach out and contact you.

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22:51

Airbnb Release Features

So tying in AI to AI.

Airbnb’s summer release just happened. And obviously, there’s a lot of talk about their new AI tools, but they also talks about some other new interesting features.

So instead of listing them all off, I was going to say, Michael, are there any of the releases that really called to you?

No. Honestly, one of the things that jumped out to me the most, I’ll say two things. One was the review highlighting.

And what jumped out to me is that Verbo, who’s not known as a technical forward company, they’re catching up fast, released this six plus months ago. So Airbnb is playing a bit of catch up mode from that standpoint.

They’re launching cars, which is a bit of a catch up point, and that one’s interesting. And the bell of the ball right now is the boutique and independent hotels. So I really do like the tie-in of boutique and independent hotels.

They like to play the angle that their hand selected, and I’m not sure to some extent that’s the case, and no big chains and all of that. But again, like you just said, the for now.

What I do find interesting is rate parity or price match guarantee coupled with the benefit of up to 15% of the value goes towards stays in the traditional short-term rental side of the fence. So they’re doing some interesting things.

They’re starting to look more like a traditional OTA, which I think all of the signs over the past six or 12 months have pointed that direction. But those are, I guess, the biggest jump outs to me. What about you?

Well, I thought it was interesting.

I think a couple episodes ago, when we were talking about Uber, I mentioned like, oh, the private car service is interesting. So I don’t think this is huge. Like this isn’t like, wow, I can’t believe they added this, but it is cool.

You can book your private car service and you get like a 20% discount and your driver can check your flights and meet you curbside. I think that like, that kind of depends on where you are.

Usually if you’re not in a big city where you have to like really coordinate some kind of, you know, more like chauffeur service kind of thing, that that’s interesting, but not wowing me.

And the car rentals, we talked about this previously, but like also, I mean, like rentals before flights, just doesn’t see, doesn’t totally make sense to me. But then I was comparing this to like Expedia and Uber, right?

And out of all of the OTAs, Airbnb has always been kind of like the cool art school kid.

And, you know, and then you have Expedia being the one that’s partnering with Uber, which like way, I mean, a quarter of people book a car rental, that’s fair, but like everybody’s using Uber, you know, at least, you know, most people.

It helps that Uber CEO was the head of Expedia.

Yeah, I mean, sure, sure, sure.

There’s some tie-ins there.

Of course, well, I always, okay, so not with Uber, but like, I feel like a natural pairing, even just like aesthetically, which is not what these companies are making decisions on, but would have been to have that kind of partnership with Lyft.

And, you know, I think about all of the, like, so with Lyft, like with my chase card, I get 10x points. And it’s like, wouldn’t there be cool ways to tie in with Airbnb?

Like you, if you book an Airbnb, and then you also, you know, connect your Lyft account, then that also somehow, like, it goes back to points somehow.

And like, I just, that would have made more sense to me, rather than car rentals, now that all of this is coming out.

One of the things that popped in my head, tying it back to the Google AI booking stuff, is in the future, I don’t have to figure out which credit card to use or which point system’s best. Like, I want to redeem this trip on points.

Pick one of my point pools and redeem it for me. Like, find the best and cheapest path, the best point value to reservation. I think that stuff’s going to be super cool.

It’s probably not too far away, especially as these bookings start coming online. But other things in there, release that are less interesting to me, luggage storage, Instacart deliveries.

Like, these things are good and helpful when I take my family to a new location and we flew there to not have to stop by the grocery store, at least for the basics of diapers and milk and snacks and stuff. I get it. It’s helpful.

I think it’s more of a show and a fun PR project than like actually drive any meaningful revenue.

That’s part of what, I guess the reason I’m more excited about the hotel side of things is because I do see it in the future being able to drive some level of meaningful revenue versus an Instacart API.

Yeah. Well, with hotels, when they eventually break down and add normal big box hotels because you got to get that never-ending search of TAM, nom, nom, nom, nom, nom. But the deliveries component, that’s just like my operator mind clicked in.

Let’s say we’ve all had experience doing deliveries at some point or another, and rarely does it go as planned.

I had left all the instructions to bring groceries inside my apartment building when I was coming back from a trip, and they just left it all outside. So then, and that’s just my apartment, right?

And I was thinking like, if you have a home, like what if there’s a back-to-back, and you can’t get in before 11, and like the cleaning crew is there, and they just like ignore the time, and they show up at 11, or at noon, or like I’m curious if

anyone in our audience has experience with people doing these deliveries, whether it’s through Airbnb or not. Like you can set up Instacart regardless, but like the operational side does put more work on the operator.

Like Airbnb just gets to be like, here’s our API connection, and the little thing we skim off the top, and you deal with it.

But does that surprise you, Brandy?

No, it doesn’t. But I also-

Brandy is famous for her Airbnb rants. Yeah.

And the thing is, I’m not even like so anti, like it makes a lot of sense. To your point, this is like kind of like a fun thing they get to add. It’s like definitely not for driving meaningful revenue.

It’s more to like for, I would say for PR. But it’s like, okay, how is this actually working in practice? And is it something that guests are really using in mass?

So like as they’re trying to add these new features, is it what people want?

Yeah.

30:11

World Cup Travel

And then to wrap up on their release, we’ve got the World Cup. They’re a big sponsor of it. They’re launching watch parties with celebrities and playing into the Airbnb experiences thing.

So right on cue, part for the course for them, doing big, fun, exciting PR-worthy partnerships. I’ve long said they’ve got by far the best. They create so much news around the brand that it’s super impressive.

They’re almost a PR company over anything.

Yeah. Well, and I was thinking, maybe for market research, I should do one of the experiences for the World Cup in Boston. And so, if I…

Jamie might know somebody.

Yeah, you know?

Cause that could be fun. And a quick little aside before we wrap, I saw this bit about the Scots that are… They’ve been collectively organizing to order, to bargain for hotel rates.

And they’re smart. They’re going to Providence, which is closer to Foxboro, which is where the stadium is. And they’ve also organized all these buses.

That is, as a nation, they have banded together to get the best deals possible for the World Cup. So yeah, shout out to all the Scots for being on top of it to come support your team.

They’re not taking the $180 train.

No, they’re not.

They’ve pulled together a $40 bus ride. So kudos to you. Make it more affordable.

I’m all for it. And the hell that’s going to be unleashed when those buses arrive. 40 buses of Scots.

I know.

Who knows how many beers or whiskeys deep it’s going to be a sight to see.

Providence Road Island is not ready.

It’ll be a good time.

Well, Brandy, a fun holiday episode, and we learned a little bit from Jason joining on. I’d imagine he might come on from time to time as big news in the AI space develops. But enjoy Detroit.

Excited to hear about the festival.

Yeah. Excited to hear about your fishing. Keep a tally.

We will.

We will.

All right, everyone, we will see you next Monday. Have a great week.