A guest checks out. Five-star review. They tell you they loved the place, they’ll definitely be back. Then silence. Not because they didn’t mean it. Not because they changed their mind about your property. But because six months later, when they’re planning their next trip, you’re not on their radar. Someone else is.
This is the default state for most short-term rental operators, and it’s costing them multiples of their initial booking revenue.
I heard an analogy years ago that’s stuck with me because it captures exactly where we are as an industry. Staying in a short-term rental is like doing a parachute jump. You go, you jump, you take photos, you talk about how brilliant it was. But no one remembers the company. No one remembers who organised the jump. They remember the experience, the location, the thrill. Not you.
That’s the fundamental problem. The guest had a great time. They’d happily return. But finding you again means digging through Airbnb history, hoping you’re still listed, hoping the property hasn’t changed hands. It’s an uphill battle to be a repeat guest even when someone wants to be one.
And that’s going through the platform that’s going to charge them an extra 20%.
Recently I spoke with Steve Haase, Chief Customer Officer at Yada, about why this gap exists and what operators can actually do about it. Steve came from HubSpot and Shopify before getting into short-term rentals, which gives him a useful perspective. He’s spent years thinking about customer retention and lifecycle marketing in industries that have figured this out. What struck him when he entered this space was how undeveloped the follow-up is. Millions of people travelling and staying in short-term rentals, and almost zero re-engagement afterwards.
The infrastructure for guest retention simply doesn’t exist in this industry the way it does everywhere else. That’s not an accident. It’s a design choice most operators don’t realize they’re making.
The Revenue You’re Not Tracking
In e-commerce, Steve points out, lifetime customer value is roughly 10 times that first purchase. The logic is straightforward: If someone likes a product, they become a loyal customer. The cost of acquiring that customer was the expensive part and everything after that is leverage.
In short-term rentals, we don’t think this way. We obsess over the lifetime value of a homeowner, the property we’re managing. The guest? Most operators couldn’t tell you. Steve estimates it’s roughly four times your initial booking revenue, and most of that is being left on the table.
Think about the economics. You’re relying on revenue coming through with a 20% OTA margin on top. That margin may well increase as time goes on. You’ve spent the most money getting that customer in the first place, and then you’re doing nothing to bring them back without paying that fee again.
This isn’t a small leak. It’s a structural problem with how the industry operates.
Most property management systems include a one-month post-checkout follow-up. Something generic about how their return journey went. Then nothing. Maybe the guest gets added to a Mailchimp list. Maybe they get a newsletter at some point.
Even this minimal follow-up isn’t standard. The infrastructure exists in the PMS to do it, but it’s not being used. Or it’s being used once, then abandoned because no one sees immediate results.
The opportunity is sitting there, the guests are willing, and the tools are available. But almost no one is actually doing it.
Why Simple Beats Perfect
Steve’s advice on this is counterintuitive: the best marketing is boring. Not boring for guests, of course: boring for you. It should just happen in the background without requiring constant attention or creative energy.
The pattern I see repeatedly is the opposite. Operators spend weeks building beautifully branded seven-part email series. They launch it. It runs for a few months. Then something else comes up and the whole thing gets abandoned. No more marketing. Nothing.
The problem isn’t the campaign. The problem is treating marketing like a project instead of a system. You don’t need elaborate sequences, just simple messages that actually go out consistently. Send an SMS three months after checkout. Six months on the anniversary of when they last booked. Whenever something interesting is happening in your area.
Not a full marketing campaign. Not a beautifully designed newsletter. Just a message.
The guest came to your destination for a reason. They had some experience they wanted. At the very least, there are good memories there. If you stay top of mind and they’re thinking “where should we go next?” you can get picked. The alternative is they open Airbnb and start searching around, and you’re competing with every other property in your market with no relationship advantage whatsoever.
For me and my wife with two kids and busy schedules, this is absolutely true. If we’ve had a nice time somewhere away from the kids for a weekend, I’m going to run back there if they’re reminding me about it. A seasonal reminder about a book festival happening in town makes me want to go back. Without that reminder, I’m probably just browsing Airbnb six months later with no particular destination in mind.
That’s where you as the local operator add value: You know what’s happening in your town and you know the appeal that brought people there in the first place. The common hesitation I hear is “if I’m reminding people once a quarter to come back, what am I actually saying to them?”
It has to draw on what drove them there originally. That’s how you drive them back. By telling them about something new, something seasonal, something happening. That’s where you as a human earn your money.
And it doesn’t have to be perfect. So many operators won’t use SMS because they worry about their brand, about expressing all its colours and glory in a text message. Your brand comes through in your warmth, in your voice. All you have to do is say “Hey, there’s an oyster festival coming up. You should come.” That simple invitation is what people want. They don’t want your brand colours. They don’t want the flash. They just want to be remembered.
Where AI Actually Helps
AI makes drafting communications trivial now. Point the bot at your website, tell it the season, tell it what you want, get an email. But that also means the value of generic AI-generated messages starts to diminish because people can tell when you don’t actually care.
Steve’s recommendation is to use AI and automation for scale, then bring in human attention where it actually matters. This is the hybrid approach that works.
Use automation to get the message in front of as many people as possible. If it’s the right message to the right person at the right time, it works. Steve sent a message recently and one response came back within minutes: “Do you have availability tonight?” That person was looking for somewhere to stay. Someone they’d stayed with previously sent a message. They’re going to book. You never know who’s looking at any given moment.
But what really differentiates you is what you do with the people who respond. The ones who click on your emails. The ones who reply positively to SMS campaigns. The ones who engage but don’t book immediately. That’s where you bring in the human dimension.
You’re not trying to call five thousand people on your email list. You’re calling the 50 who after a campaign clicked the link, browsed your availability, but didn’t book. Put that in front of your guest services team, someone with bandwidth between check-ins. Use intelligence to get the message in front of as many people as possible. Use human connection to enhance the experience for the people who actually want it.
This is the same principle we’ve explored before about AI’s role in property management. The technology should liberate you to do more of what actually creates value, not replace the human elements that matter.
What Actually Creates Loyalty
What makes a holiday memorable? It’s not the thread count of the sheets. It’s not whether you have a smart lock. It’s feeling like you’ve been welcomed by someone who knows the area.
The kind of host who tells you: don’t make that mistake, go to this restaurant instead. When you go, tell them I sent you – they’ll give you the best seat. That local knowledge, those specific recommendations, the ability to navigate someone away from tourist traps and toward the places that make your destination special. That’s what guests remember.
This is hyper-local knowledge. Your niche might be skiing, or it might just be your city that you know better than anybody else. Understanding what you’re offering and building that brand identity around it.
We used to have travel agents for this – someone you could talk to who would know all about you and give suggestions based on what they knew – but we replaced that with the algorithm. That’s why Airbnb is so popular. The algorithm knows who you are and what you like.
If you want to have any place in someone’s life outside of the OTAs, you’ve got to step up and be that person. It means creating real relationships. And it doesn’t have to be terrible. You can do it at scale.
One approach Steve particularly rates is creating a short video in response to an inquiry or for someone checking in. “Hey, I’m your host. Really looking forward to having you here. Let me know if there’s anything I can do for you.” You’re putting a face to a name. You’re letting them know they’re staying with a person, not just some faceless entity.
It amazes me how infrequently I receive that kind of message when I stay somewhere. When you go back to the roots of this industry, people finding accommodation in newspapers, in brochures, through word of mouth, you would be met by the owner or their contacts on the ground. “Oh yeah, you’re around the corner. Great. I’ll help you with the bags.”
Now we can’t help with bags because we’re trying to operate at scale. People don’t want to meet a human after a long-haul flight anyway. But replace that with “hey, how are you doing? I’m here if you need anything.” In very non-corporate language, in very personal language, it goes a long way.
The Information Gap
When someone stays with you, you should be learning as much about them as possible. Not in a creepy way. In a “this will make their next stay better” way.
If they mention they’re vegetarian in a message, note that. If they’re there for cycling, know it. If they ask about restaurants for a specific dietary requirement, remember it.
Steve went to Majorca for a cycling vacation last year and never got any messages afterwards. They never even asked if he was there to ride his bike. (Everyone goes to Majorca to ride their bike!) No follow-up about cycling at all.
The point isn’t to send a thousand personalised messages. The point is that once you have that data, the machine can use it. As intelligence in marketing builds out, having this information means it won’t go unused. What Steve describes as the loyalty loop works like this: market to past guests, get them to come back, learn about them during their stay, use that information to make the next message more relevant. The system can include something specific without you having to think about it. “Hey, come back to Majorca. The cycling is great this time of year.”
Elevating the guest experience like this is good business sense regardless of whether it brings them back. But it also creates the foundation for effective follow-up that doesn’t feel generic or automated.
This connects to how you think about professional infrastructure more broadly. When guest screening and damage protection are handled through proper systems rather than manual processes, you’re building operations that can scale without you being in every decision. The data you gather during stays becomes the foundation for everything that follows.
Making It Sustainable
We’ve talked before about how short-term rental operators are already spread thin running their businesses. Adding a loyalty programme sounds like one more thing to do. What’s the actual commitment?
Most of the time investment is in the beginning and in providing feedback to the system. Marketing can run automatically once campaigns are set up, but you need to review them. Same with AI messaging and guest experience tools. You need to print QR codes, put smart spaces in units. That takes some time, though you can delegate it to cleaners.
Once that’s in place, an hour or so every other week just to check in. Make sure the machine is doing what you want it to do. That’s the promise of automation and intelligence. It doesn’t eliminate the work. It makes the work sustainable at scale.
For the tech stack, you need tools that can send SMS, WhatsApp, email. Ideally all three. These things can be inexpensive. The barrier isn’t cost or complexity. It’s just doing it.
The next layer is the direct booking experience. If you want to save on OTA fees, if you want to own your destiny and build your own mailing list, you need a good direct booking site. Most PMS systems will have something you can use, but take it up one notch from what they give you. Steve’s observation here matches what I hear constantly: they’re not website people. There’s always something odd about out-of-the-box direct booking engines that makes the experience feel clunky.
Then comes collecting information while guests stay. Personalised guidebooks, guest books, QR codes guests can scan to access information and provide feedback. This is where you learn what you need to know to make the next interaction better.
How Loyalty Actually Works
Discounts work. “Be the Valentine’s Day hero. Book before the 14th and get fifty quid off your stay.” People respond to that kind of offer.
But you shouldn’t always use discounts. Sometimes what people want is just a nudge and an invitation. Not everyone is price sensitive, and training your audience that they should always wait for a discount creates its own problems.
What’s interesting with loyalty programmes, Steve points out, is the psychology around loss aversion. People don’t want to lose anything. With a loyalty program, you earn points, redeem points, but you can also set when they expire. That creates a natural opportunity to send a marketing message. “Hey, you’ve got 1,200 points. Use that to extend your stay by an extra night. Otherwise your points expire next month.” That causes action because no one wants to lose something they earned.
But honestly, a big part of loyalty is just being remembered. This idea of “I’ve been once and now I’m back again. I’m almost your friend or I’m on the inside of this.” You know the service is good. You know why you came back. That feeling of being recognised matters more than the specific mechanics of points and discounts.
If you have time, find those top 10 people who’ve engaged after a campaign and consider giving them a call. Or send them a text yourself. “Hey, how are things going? Got any travel plans coming up?” Create real relationships where it makes sense. It doesn’t have to be terrible. You can do it selectively at scale.
The One Thing
If you’re going to do one thing this quarter to improve loyalty, it’s simple. Reach out to your past guests.
You can’t have loyalty if people don’t even know who you are. The parachute jump problem exists because we let it exist. Guests want to remember you. They want an excuse to come back. They just need you to give them one.
Marketing should be part of the routine. It should just happen in the background. A text three months after checkout. An email about the oyster festival. A reminder that you exist and that you’d love to have them back.
Most of your competitors aren’t doing this. Most hosts are hoping guests remember them and track them down through Airbnb search six months later. That’s your opportunity.
Be in touch with your past guests. Start that relationship. Not everyone will want it. Some people will wonder why you’re emailing them. But most won’t be bothered at all, and a meaningful percentage will actually appreciate it and book again.
I think about some of my favourite stays, and it makes me sad that I haven’t heard from them. It actually made me sad when I wanted to rebook somewhere and didn’t even know who they were anymore.
That’s the default state. You can change it by doing something incredibly simple. Just reach out.
Want to hear the full conversation?
This article is based on an episode of The Check-In podcast, where Leo Walton and Sarah Nan DuPre talk with the people shaping the short-term rental industry.
Listen on YouTube, Spotify, or Apple Podcasts.
