The Middle Class Short-Term Rentals Is Dying And Luxury Is Taking Over

On Monday’s Good Morning Hospitality, A Skift Podcast, Michael Goldin, Brandreth Canaley, Jamie Lane, and Wil Slickers are joined by Sean O’Neill, Senior Hospitality Editor at Skift, to break down a major strategic shift in the short-term rental space.

onefinestay is pulling back from hundreds of urban rentals to focus on ultra-luxury homes and high-end leisure destinations, signaling a broader move toward fewer, higher-quality listings as operators rethink where margins and demand are strongest.

The team also unpacks new data out of New York City showing that 27% of approved short-term rental listings are now operating illegally, highlighting the ongoing tension between regulation and enforcement even after strict laws were put in place. The episode wraps with a look at ChatGPT introducing cost-per-click ads, a shift that brings AI platforms directly into the same performance marketing model that powers Google and OTAs today, raising new questions about who controls travel discovery and demand.

This episode is brought to you by Vrbo. Learn how you can earn ⁠⁠⁠OneKeyCash⁠⁠⁠ today.

And for hotels with restaurants and restaurant owners, Bilt Hospitality is finally here. Go to biltdining.com/gmh to learn more.

Watch This Episode

Good morning.

Happy Monday.

We’re back. It’s been probably a month, right?

I know. I was thinking, yeah, we haven’t really had the gang together in a little while.

It’s honestly, it’s nice that there’s three of us to like, so with all of our crazy schedules that we can kind of like pop in and out a little bit, because we were chatting about this off stage, but all three of us are either in or about to enter

extremely crazy travel cycles. So it’s good that we can be flexible.

Millennial Brandy living out her best life.

Oh, okay. When I was in college, I was like, I don’t want to live in the United States. I want to be traveling everywhere and living in Europe and blah, blah, blah, blah, blah, and traveling all the time.

Now I’m in the middle of like three weeks of travel. None of it is to Europe and I’m really tired and I’m only halfway through. Just found out I have another trip.

I’m like, this is not as glamorous as 19-year-old Brandy thought it would be.

Well, I look forward to seeing you and executive producer, Wil Slickers, tomorrow.

Tomorrow. I know. In Denver.

You’re missed.

Yeah.

Speaking of travel, how was London? Getting over the jet lag?

Yeah. I wasn’t there long enough to get jet lagged. I just missed two entire days of sleep and so I slept really hard and I’m back to normal.

But yeah, I looked at my wife yesterday morning when we woke up in Virginia the week prior and I was like, how has it only been a week since the Virginia trip?

Now, I’m already home from London, leaving Monday night and returning home by lunch on Thursday. It was a quick one. But London was great.

The short stay summit, I haven’t been in three years, I think, and it’s doubled or tripled in size.

Lots of energy, not to knock many US shows, but the youthful energy that was in London was excellent, and I haven’t seen that at an industry conference in a while.

So kudos to the organizers and all the attendees, but really, really good group of people brought together.

Yeah, I guess tomorrow or this week, VR Nation, that’s my first conference of the year. And I’m curious to see how the spate of conferences in 2026 does energy-wise. I need the energy to be high to sustain all this travel.

Absolutely.

And we’ve got a fun little dinner plan tomorrow. So if anyone’s listening, message Brandeer Eye and we can add to the group. But Denver is a fun place to gather and there’s already a really solid group of folks coming.

So looking forward to that.

Awesome. Well, we have a really fun show for you guys today. We have a special guest who we’ll get to in a minute.

But before we jump in, giving another shout out to our April sponsor, Vrbo. You can find the link in the show notes to listed eligible property and you get one key cash back. It’s vrbo.com/goodmorning.

But you might have also seen that Michael and I did a very special interview with Tim Rosolio for Vrbo’s vacation rental of the year. We were in New Hampshire and got to sit down and chat with Tim. It’s so fun.

It just feels like a regular conversation. That was such a great time.

The quote of the year from a leader on the OTA landscape, the gold rush is over.

Yeah. I feel like that’s the clip out. That’s going around.

It’s true.

Part of the gold rush being over is why we’re bringing a special guest on today.

Yes.

Or maybe it’s the only gold that’s left over.

Yeah.

The gold rush that has now come remarkably full circle in many ways, which we’ll get into shortly.

Yes.

5:03

One Fine Stay Strategy

Please welcome to the show Sean O’Neill, Senior Hospitality Editor at Skift. Hey, Sean. How are you?

Good, Brandy.

How are you doing? Hi, everyone.

Doing well. Thank you for coming on the show with us. It’s always fun when we get someone from the inner skiffed circle to come and talk with us about the fun things they’re doing.

Why don’t you start us off, give us a little bit of an overview of what you’ve been working on.

Yeah. Well, One Fine Stay, the property management service that focuses on luxury vacation rentals, has pruned its listings from 3,000 to 1,000, so it’s quite the haircut.

This has come after Steve Case, AOL Steve Case has bought One Fine Stay as you and GMH were covering last year. He’s rolled the brand over into this group called Exclusive Collection, that includes also Inspirado and Exclusive Resorts.

They’re doing a couple of different things.

They’re tilting the portfolio mix, they’re moving out of European cities like London and Paris, the town homes that established the brand, and they’re tilting towards Mexico, the Caribbean, places like Lake Cuomo and Aspen.

Their belief is that the business model is better outside of cities, partly because you get bigger homes, you have larger transaction sizes, but also you avoid some of the European regulation that has really taken a bite in some of those cities with

London and Amsterdam having night caps, some cities in Paris having registration requirements. As part of that, they’ve taken about 200 of their listings that are in the UK and in France, and they’ve handed them to a company called Veev, which is

they’re outsourcing property management to this company that’s part of Under the Doormat group. That is significant from a milestone because back in 2010, One Fine Stay got its start really in the classic Belgravia, London district townhouse sale and

so now it has shifted. The one other big change is that they are sort of trying to go back up market in order to match Inspirato or be closer to Inspirato and exclusive resorts in terms of quality.

They believe that in a K-shaped economy, you can’t go high enough up. You want to be as up market as you can in order to make the economics work of sort of the orchestration of doing luxury property management.

So that’s what I’ve been reporting on First Gift.

Well, Sean, this is like a full circle moment because Travel Keys by Bobby Gibson and One Fine Stay were both acquired by Accor. Travel Keys CEO became CEO of One Fine Stay, sold off.

Now it basically sounds like it’s back to the Travel Keys portfolio. Super high end, very destination market. But that said, a strong brand in travel can survive.

Pivots, turns, different home types even. So kudos to the branding team at One Fine Stay originally, that has survived and advanced multiple transactions.

We’re somewhat back to where we started 10 plus years ago with the super high end destination market inventory.

Yeah, I’m not sure which musical reference is best, whether it’s like Elton John’s The Circle of Life, or whether it’s like Mel Brooks’ There’s No Freud, like Schade and Freud.

Both.

Keep singing, though. Keep singing.

Well, I’ll never invite me back if I keep doing that.

But I do think in terms of the economics, it’s interesting that when I talked to One Fine Stay back when it was originally on its own and then under Accor, one challenge they had was they kept having the high net worth individuals were very demanding

as guests and the property owners were very demanding on the supply side. You know, they didn’t want their artworks damaged by the guests. They didn’t want their prized mollusk collections to get damaged anyway.

And so problems would happen and service recovery was a big part of what they were doing. And that led to lots of heroic efforts, which gave them lots of great guest love and had a great brand halo.

As you were saying, Michael, great brand reputation. But it’s not good from a CFO’s perspective, because a lot of times there’s a temptation to throw money at problems.

And I’m not quite sure whether that tension still has been resolved necessarily just by the pruning and strategy that they’ve done. But I mean, you at Nook, you’re handling very demanding customers in the vacation rental section.

I’m not sure whether you or Brandy have sort of seen whether that operational tension, how you feel like One Fine Stay might deal with it.

Well, before we jump into that, the evolution of One Fine Stay, founded by Evan Frank, has now gone on to found a very, very successful agency called Fora. I think all of us have become aware of Fora through the years.

And I’ll let you speak to numbers because I read them but did not recall them. But the numbers that they’ve been putting out lately are astronomical. So sometimes your first startup goes well but not great.

And here we are doing big things over it for us. So congrats, Evan.

Yeah, I mean, it was a little bit of a One Fine Stay mafia, the way they talk about the PayPal mafia, because Greg Marsh has also gone on too. So it was like a household budget company that is doing well.

Another, the CTO went on another company that’s in sort of fintech doing well. So it was quite an inspiring crew of people there.

But to your point, Sean, about the kind of the little nuances of managing high-end luxury homes, and there’s this tension that I am learning now in my new life at Stay Terra, where you have these big homes and you can charge a chunky amount for them.

But then the owners are like, actually, no, we don’t really care if it gets booked. It’s like, well, we care. And they’re like, oh, we don’t want this channel, or we don’t want that channel, or this very specific things.

And you’re like, as a business, we are trying to make as much money as possible. But that’s kind of, I’ve said this many times, like dealing with the owner stuff is just not my cup of tea. But it is interesting.

We talk about this pretty frequently, like the luxury segment, like that’s the stable portion of travel. So it makes sense. There was this big boom for a while of like get as much inventory as possible.

It’s about units, it’s about these vanity metrics. And actually now it’s like, okay, why don’t we just get rid of what isn’t serving us?

And it’s interesting, like kind of outsourcing the property management, which is the hardest part of being a property manager is actually managing the house.

Just someone else kind of retaining the high margin, the sexy stuff that you can keep and just focusing, like kind of having your own niche and having that niche be ultra luxury. It makes a lot of sense.

It makes a lot of sense after this kind of like last decade that we’ve had and kind of where the industry is going this year.

That’s interesting.

Yeah. So Sean, this does seem to be like a page out of the luxury playbook of like, what happens when maybe you chase supply a bit, you delete your brand.

If you guys listen to the acquired podcast, but this last few weeks, they did Ferrari and they had this great example of during the 90s. They had expanded supply. They’re up to 4,000 cars a year.

Then they got a new CEO and they’re like, you know what, we’re going to cut production in half. We’re going to focus on the ultra luxury, high margin cars and we’re going to build this brand back.

Do you see it like crisis situation like that, where they feel like they need to bring it, build it back only for the ultra luxury? Or is this more of an operations play and protecting the brand?

Yeah, my sense is it’s the first. They were a little cagey when I was talking to them about it, but I would say that as you mentioned, in 2016, Accor bought it for $168 million, the one fine state brand, and then later had to write it down.

What it tried to do is it took it from about 2,500 units, then up to 5,000 at its peak, and then it sold at 3,000 units, and which is when Exclusive Collection has taken it on.

So it already had some attrition, and now this is more another two-thirds attrition. The argument is to have the inventory side match up with the ultra high net worth customer base.

They said that actually they were pleasantly surprised when they acquired One Fine Stay that the customer database actually was much more higher in income than they had sort of anticipated, and they pushed back on my asking, when I proposed, is this

a lead gen concept? Is it the idea that you’re trying to get some names to feed into your other brands?

And they said no, they thought that these brands were actually accretive to the 25,000 high net worth individuals that they said they already have in their database.

That’s interesting.

I would love to have access to that database.

I will push you off.

Yeah, dang. But I think that, so what do you think that this signals for the rest of the STR market? We kind of touched on this before, but the bulk of our industry is not the ultra luxury.

So what do you think, what is your kind of take on what this spells for the rest of the industry?

It’s hard for me to say. You have two smart minds. You have Aqours and you have Steve Case.

They both are walked away from what you might call the upper upscale segment of this space. I guess there’s an argument to pick a lane and don’t compete for the Kimpton customer. Just go for whatever your equivalent of a Waldorf Astoria type brand.

You prefer to see as comparable in the vacation rental space. So it may be more about market segmentation and just sort of like a focus in that way. But I’m not sure.

I mean, Jamie, you see the numbers and I don’t know whether like the operational efficiency level, like you just can’t make the math math.

And I’ll lead another question in for you, Jamie. Is the sole focus on uber luxury short-sided? Because is this going to last forever?

Because if you’re getting customer lists that are dumping the upper scale customer, are you going to miss out five years from now?

Yeah. No. And it’s the question, like what’s a better brand like Ferrari or Porsche?

Right. Like, there’s a lot of money to be made in selling Porsches. And it’s still a luxury brand.

It’s just not Ferrari. Right. And in this period where ultra luxury is doing really well, and the middle class, even upper middle class is maybe seeing a bit pinched.

And I think long-term, there’s a huge opportunity for it in the short-term middle space. I would push it more to do with urban than I would probably of these different tiers and how well they’re performing.

There’s, like you mentioned, Sean, these European cities and regulation is really hard. Supply has actually been very strong in London, in terms of growth as it has in Paris.

But there’s so much regulation if you’re actually trying to run a property management company with all these restrictions around these properties, it can make it very difficult.

So yeah, I think it’s more location and wanting to push into these great destination resort markets, which are incredible. You were listing, I was like, and that sounds like Michael’s vacation markets right there. But yeah.

On the private jet, of course.

Sorry, Delta.

Awesome. Well, Sean, thank you so much for coming on the pod. It’s always a pleasure to chat with you and keep doing fun articles.

We can bring you back. You can be our unofficial fourth host.

Thank you so much, Brandy. That’d be very cool.

Thanks, Sean.

Take care. All right. Well, before we get into our next topic, we’re very excited because we have another sponsor.

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18:48

New York City Rentals

And as we were kind of touching on previously a little bit of regulatory issues, our next topic is our good old friends in New York City.

But Jamie, you had a stat of the week. And what is our number that we get to guess?

Yeah, so the stat of the week is 21% and it has to do with the New York Airbnb market.

Well, it’s not the number of illegal listings because the article said 26%. So, Michael, I was left to guess this all by myself last week. So I’m going to put the pressure on you.

Well, let’s see, the increase in supply in the past six months.

No.

So what it is, is the share of reviews coming through Airbnb that are now hotels for Airbnb versus the ones…

No way.

So, 21% of reviews left in the last 12 months were for hotel properties.

Just in New York or…?

Just in New York.

Yeah. Wow.

Isn’t that incredible?

That is. Well, I guess it makes… If it’s just New York and they’ve reduced the supply so much, I guess it’s not like terribly surprising.

But still, I mean, that means that people are using Airbnb to book hotels. Absolutely. And if there is hotel supply on there.

So…

Yeah, I think it tells the story around one, how well hotels are doing in New York, but two, still how not well short-term rentals are doing in New York.

And what this article sort of calls out, and this is in that 26% put out by the city of New York.

I’m sorry, 27%.

27%. Get it right, guys. So, New York found that 27% of approved short-term rentals were now illegal.

So, what they called out that they think is happening is that after a host got their unit approved, with the extreme restrictions of two people max, no locks on doors, has to be a private room, not an entire home, that then the hosts were then

I love it.

I absolutely love it.

Add a lock on the bedroom door for the guests. It looks like Airbnb’s response was, well, there’s nothing in the law that said that they had to enforce it after the listing was improved. That’s up to the city.

Going through, and at the end, there’s one really funny quote.

They were like, another difficulty is that many operators see the fines, it’s just the cost of doing business. That’s true. At this point, it’s like, why don’t you just, the city has so many other things they could be spending resources on.

Why don’t you just make it like certain zones, this is where you can do short-term rentals, you have to get a license, here’s the requirements, you pay into this tax base, it goes to fund whatever, and just be done with it instead of really trying to

crack down on this, when there’s obviously such a demand from people that want to list, from hosts and from travelers. So just make some sensible rules, make some tax money, have it be a high tax. Who cares? People are coming to New York.

This seems so dumb that we are still talking about this.

Did you guys see the new Pettitare Tax in New York?

Yeah, I did.

So essentially Mondani’s, and they’re proposing this new tax for homes over $5 million, and where people are using-

That are your second homes.

Aren’t using them as their primary residence, that you’re gonna get a pretty big tax.

And that’s one of the things we were calling out when this local i-team was initially going into effect, was there was 300,000 homes that weren’t being used as short-term rentals. They’re essentially people’s second homes that were sitting empty.

Let’s solve affordable housing by going after the $5 million properties.

I don’t really have, I’m not shedding a tear for people that have pit-a-tears that are of $10 million homes and have to pay a little bit more money.

I want to rewind just a second. I was cracking up reading this article and listening to Jamie talk about how, anytime you put rules into place, people will find ways to get around them. Great, I’ll be compliant.

I only have one extra bedroom. Then boom, I can change my listing as soon as it’s live. Hey, that worked.

I’m going to go do this 10 more times. And Matt Curtis, a name that you guys might not even know, it was from way back when he ran government relations or policy for Expedia Homeway.

And he had a quote that I will always remember, but it was, onerous regulation drives black market activity.

Yeah.

And as soon as you come up with the craziest rules and regulations, people get confused. Some might be honest mistakes, others might be loophole finders.

And the more onerous the policy you put into place, the more likely people are to gain the system. And it’s not even profitable for New York to go after these bad actors. And so what are you going to do?

Like spend more money to go after people and lose money on this, or just make it a little bit more relaxed and let people do it and collect the tax.

Exactly, and it’s so, but New York is always just like the shiny example because it’s always in the news. But there’s, I mean, anyone, and I think anywhere that there’s a hot STR market is dealing with something like this.

I mean, in Miami and like the little fiefdoms of Florida, you have all these little municipalities, like the rules would be so crazy and you’d go and ask and you’d be like, can you clarify like what this rule is? And no one knows.

And so you’re like, okay, do I try to follow this to the T? So it gets approved and no one comes after me. Or is anyone even checking this?

Like, is it even possible to do this? So that you’re totally right. Then it creates more likely than not, people are like, I’m just going to like, beg for forgiveness, right?

Rather than ask for permission.

When I moved to Auburn and we put our property up for home games, I got a letter from the city saying we can’t do it. And so I called them and I asked, like, what’s the law? Point to it.

Tell me, like, educate me. And the law is you can’t rent your house for longer than two weeks. And I was like, great, I’m only going to do it on the weekends.

And he’s like, well, the spirit of the law is you can’t do it at all. And I was like, well, but the actual law says I can’t do it for two weeks.

The vibes of the law are that…

Here’s my number. You already have my address. If you change the law, let me know.

But until then, I’m going to keep doing this.

Yeah.

And again, we’ve talked about this before, like, for big events like the World Cup or a sporting event or concert, having relaxed regulations because, like, in Boston right now, they’re like, there aren’t enough hotel rooms at all to accommodate all

these people coming. So why not let people rent their homes out? I’m sure it’s happening anyways, but we’re approaching go time and that hasn’t been seen as a reasonable thing to do.

Yeah.

The other problem too in New York is, like, typically when you start to find these loopholes, it may be, I would go back to the quote from Jurassic Park, life will find a way. All right.

Are we going to see these short-term rentals come back in and, like, yes, it appears that some are sort of changing their listing after the fact, but it’s not like we’re seeing thousands of listings now coming in New York and saying that they are

abiding by the law and then changing it. So this is a relatively small percent of those existing listings, and it’s not changing the nature of what’s available in New York by any measure.

You know, the topic of, like, the shared room, I know that that was, like, the spirit of what Airbnb was founded on, and I just think that that is such, like, a nostalgic play, like, to the days of your, like, I mean, like, I just can’t, that’s not,

that’s not, like, what people want now. Now, when you, like, that’s, like, a crazy story that you’ll see someone that’ll go viral on Reddit or Instagram, like, I rented this, like, short-term rental, this Airbnb, and then the host was there.

You’re like, people aren’t excited about that anymore.

Well, real quick, before we move on to our next topic, I didn’t shout out Richard and Marilee from Under the Doormat. Congrats on the latest acquisition. Increase in the Unicounts in London and Paris, that’s huge.

Survive and advance, and you start becoming the vector to collect others’ inventory, so well done.

27:56

AI Advertising Future

And we have gone 26 minutes without mentioning AI, so let’s dive into it.

All right, no, I was like, God damn it.

ChatGPT introduces pricing model for travel ads to run on. I think this is great because it takes away a lot of the… It creates competition for Google, if nothing else.

And Google’s top clients are booking.com and Expedia. And so far, since the launch, Booking is significantly outspending the others on ChatGPT. But Airbnb is actually outspending Expedia.

And then you’ve got the hotel brands that are in the single digit percentages in spend. So the OTAs are heavily investing in this early wave. It makes sense.

They’ve kind of been handholding with the LLMs from the start of their discussions of travel and app integrations. But is this gonna be a significantly competitive channel to Google, Jamie, Brandy?

I think so. This has been part of the playbook we’ve been talking about for the past two years, right? That ChatGPT is gonna get the eyeballs.

They’re going after consumers. They’re making their product free. And then they’re gonna monetize it on the back end by selling ads.

And they launched, what, a few months ago on price per impression. And I’m sure a lot of the advertisers were like, really? Like Google got rid of that like 20 years ago.

Like, and now that they’ve moved to price per click, it gives them a much more comparable metric that they can use to deviate their ad spend across. They can track conversion and see what it actually relates to.

I think the biggest question for me is how this price is gonna evolve. Because Google charges so much for their clicks.

And I think it’s like the article talked about like five times the rate that Metta is able to charge just because you have such high intent that comes through Google. So where is ChatGPT gonna be within that realm?

Like is it gonna be really, maybe even more high intent than Google or much further down compared to like an Instagram ad?

Yeah, early data from the hotel that we managed was that intent was actually stronger coming from the LLMs than even Google search.

But probably much lower volume though, right?

Much lower volume. Yeah.

So just to add the doom and gloom aspect to this, I don’t know. I just like, so are we going to be able, like if you say I want to go to this hotel and in the article, the photo example is Santa Fe.

Like, are you going to just get your recommendations and your ads, just going to be whoever has paid the most for their ads to come?

Like, for you to see the recommendation, if you’re like, I want to go to a hotel that has all these features, are you actually going to get the best hotels that fit those things, or are you just going to be getting search results that are like

whoever is paying the most plus the ads of that same group? Like, I feel like the trustworthiness of the output is like, now I’m just like, I don’t know if I trust.

I mean, you should always verify ChatGPT stuff anyways, but now I’m like, oh, this is just whoever’s dumping the most into their ads.

Well, Google did a good job of delineating between paid and organic, right? So I’d imagine it evolves to somewhere where you’ve got your slider view and there’s five properties shown and then one of them is sponsored, right?

Well, or it’ll take the Google route and the entire first page is just sponsored ads.

It’s a highly competitive market, sure.

Right.

But then you also have how good the ads have gotten of the companies that are most willing to pay for your traffic is probably one of the best products out there because they want to convert you into the product.

I’m still constantly surprised by how good Instagram ads are of like, oh yeah, I do want those new shorts. Those are perfect for my lifestyle.

I hate how accurate it is.

But if ChatGPT can just serve those perfect ads to you at the perfect point, and you’re like, you know what? That resort would be the most incredible destination for my trip that I’m looking to do coming up. Thank you for serving that ad for me.

They could make it work.

As long as you don’t ask that one additional question of find me the property directly or find me the best price.

Before we wrap up, though, I do want to mention what Claude came out with last week, where they are now, and they’ve said publicly that they are not going to have ads. They are not going to have advertisement associated with their tears.

So really taking the opposite stance of ChatGPT of, and how can we fund this?

And they’re like, our results are so good that and our users are willing to pay, that if you’re willing to use our paid version, then you know you’re going to get the best result and not have to see an ad from any of that. I don’t like it.

I don’t like it. Never say never, Claude.

Yeah, that’s true. For the time, say, for this current moment.

The foreseeable future, we will never.

The foreseeable future, yes. Well, okay, so we’ve talked about a lot of our travel. What is on the docket for you guys this week?

Well, I’ll see you tomorrow in Denver for two days.

Yeah. Then my travels, my April non-stop gone every week is over, and then we hit into May. I’m excited to have the same old, but it’s been great seeing everybody, being a man of the people, getting back to shaking hands and giving out hugs.

Yeah.

Jamie, how about you?

I’ll be in town this week in Atlanta, and then I’ll miss the episode next week as I’ll be on the flight out to Denver, and then spend the week or a few days in our office, and then I’ll be in Grand Rapids, Michigan for the Michigan Short Terminal

Investment Conference. Looking forward to the back half of next week.

Well, yeah, I’m excited.

I’ll be seeing Michael and Will and a whole bunch of other people at VR Nation this week, and then I’m going to a con coming back and driving to the Adirondacks for another conference that is not work-related, but still a conference. Awesome.

Well, thank you everyone for tuning in. It’s always great to chat with you on Monday mornings. Again, thanks to Sean for chatting with us about One Fine Stay and to Vrbo & Bilt for being our sponsors this month.

We will see you all next week.