2026 STR Predictions: What Smart Hosts Need to Prepare for Now

Welcome back to the Boostly podcast. And as we do every year, I like to come up with 2026 predictions for the for the year ahead. And it's not just my predictions. I wanted to reach out to those in the Slack community channel and ask anybody who would like to lend their predictions. And we've got seven amazing humans that have done so. So for those of you that are tuning in for the first time, my name is Mark Simpson, founder of Boostly and this podcast. And over the last 10 years we have worked with over 2000 hosts, AD Management companies all around the world and they have drove in over $1 billion in bookings, which is insane. And we like to give hosts the tools, the tactics, the training and the confidence to go ahead and grow their business, relying on Airbnb booking.com and VRBO. And like I said in this episode of the Boostly podcast, we wanna look ahead to 2026 and where we will be in 12 months time. My prediction is a super simple one, is I think going to be the year of the robots. I feel what we are going to see, whether it be driverless cars, whether it's actual robots that are going to be in your homes or in your business, I feel this is the year that we are going to see it happen. Whether it is the Neo, whatever Tesla have got cooking up or what any of these other companies are doing around the world, it is going to ramp up in 2026. How is that going to impact us and the hospitality businesses? Well, I feel like for number one having RO robots in and around any operation style of business, whether it is laundry etc is only going to be a good thing. It's going to help empower your members, your team, do twice as much work. And obviously the beauty of robots is that they never get tired, they never complain, they never get ill, they never have to finish early. So it is going to impact us whether it's going to be an instant thing. I do believe that the first round of these robots are going to be shocking. I feel like you're going to get social media posts of them breaking down, not working, just like we've seen with Waymos and the and the Tesla robot taxis. But once we get through that initial slump it is just going to go crazy. That is my prediction. So like I said, I threw up the questions to our slack community and if you would like to be part of the slack community please do let me know. It's totally free. All we ask is you just engage. And we've got some amazing people in there, seven people uploaded their video prediction before the cutoff point. And here is going to be Jan from guest away.

Hey, I'm Jeonsa Gun, founding account executive at Gasway and here are my 2026 STR predictions. I think that consolidation is going to keep accelerating in 2026. Property management companies will keep buying, merging and expanding through franchise models. And software companies will also keep acquiring and merging with others. On the tech side. Sorry Ben, I'll talk about AI. I think that AI won't be discussion anymore in 2026. It will be standard. So serious property management companies will be using it to automate guest communications, guest experiences, upsells and operational workflows. So the discussion won't be anymore. Do you use AI? It will be more like how well can you leverage it? On the guest experience side, I think that expectations from guests are rising fast. So AI is actually very huge opportunity on that end to actually deliver hyper customized experiences for guests, removing the friction so that humans can actually focus on delivering high touch memorable experiences on the ground as well. These impacts margins. I think that structure is a low margin business and so by automating as much as possible, you'll be able to lower your costs and by giving, you know, very personalized experiences, you will also be able to charge and price more aggressively. So for me, the property management companies that will win in the coming years will be the ones that master the balance between these two. And then bonus prediction for me will be that a NIO tech category will emerge. So it won't be any more a tool, software, ui, ux. It'll be more something like an orchestration engine. So not a system that only automates, but something that coordinates end to end real world work behind issues. Right. So like routing problems, scheduling tasks, coordinating teams, et cetera, following up. So yeah, I think that 2026 is going to be the year where property management starts being manually coordinating, but it starts running like a more tech enabled software type of business with higher margins. See ya.

Hi there, Alex here, co founder of MyEvent Concierge and we wanted to share our predictions for 2026 in the STR space. Now we've already seen a massive push for upselling. We know that that important. But specifically guest experiences. Throughout all this talk of AI, we know that people sell people, humans buy from humans. So how can we give our guests memorable experiences? And we feel the biggest shift in 2026 is going to be really placing a focus on creating memorable experiences for your guests that leave them wanting to come back again. And again from a people centered interaction.

My name is Jack Zappa, I'm with Haven Vacation Rentals and my prediction for the 2026 short term rent is that with the rise of AI, it's going to be table stakes that property managers will need to know how to use the tools, will need to be proficient with them and need to be able to scale them to provide high level of customer service across multiple properties. So the most important thing is going to become the human touch, dealing with guests, but also homeowners. So how well can you provide a service to homeowners and how good of a job can you do? Meeting their needs, educating them in the market, helping with their investment and everything that goes along with property management and working in short term rentals. So it really is returning back to a true service based business. How well can you perform your service and how good can you be at customer service to owners, to guests and using AI to be able to really focus on just that. And so I think we're going to see more and more companies be better and I think it's going to help people be better. And all across the board it'll be better guest days, it'll also be better service for owners. So that's my prediction.

Hello, my name is Alex Dawson and I am the co founder of company Offsites where we support venue owners across the UK to attract more midweek direct and repeat business by advertising their short term rentals to the corporates and the businesses that live within a couple of hours travel time of their venue. My predictions for 2026 are that companies and corporates are going to get completely bored of the hotel space with dark rooms, with meeting spaces, rubbish coffee and poor food. They're going to be looking to go to more creative places, better environment, UK and national parks. And there is a couple of things that venue owners need to get ahead of. They need to be designing their website to ensure that the information's there for corporates. Where's the closest train station? How do I get the team there together? If they're working remotely, Is there single occupancy rooms with bathrooms? Is there options for catering and team building activities that can come to the venue? My predictions are that venue owners are going to have to make some serious upgrades to their websites to make sure that they are appealing for these types of clients. And they also need to implement marketing strategies to make sure that they're going out and speaking to them. Thanks a lot.

Hi, I'm Ben, I'm an independent advisor and consultant within the short term rental space. And these are my three big predictions for 2026. And I'm going to try not to mention the AI in any of these predictions. So wish me luck. Right, first of all, Renters Rights Bill. I think this will really good thing for our industry basically because it will take traditional landlords and some of them will be forced to look at other options of which our industry is one of them. For example, right now they have an idea, most of them, when their property is going to come available and they try and keep it within certain good times of year, April, September mostly suddenly if one of our tenants decides to leave around now, around December, it's unlikely they're going to get a tenant until maybe February. Best case scenario, what short term rentals can do is basically move those properties into better times of year, stronger rental markets, so we might see more stuff come on sporadically. But I believe that will be an increased supply for our market this year. Second thing I believe is tourist tax. Now this has been widely reported that this is probably going to be introduced in various UK cities. The crucial point I want to point out here is actually the 90 day rule in London currently. Let's not lie, it's not being enforced at all. However then the tourist tax will allow the authorities to actually see, depending on how it's implicated, how many days are being used for tourism reasons within what properties. And I think that might be a bit of shock to some of the people working in the London space. So I think don't know how that's going to happen but let's see what happens. But I predict it will happen. Third point, I think we're going to see increased guest numbers. So I know that the general public are not actually feeling better off at this point. But if you look at the economic basics, real wages are rising and inflation is easing, meaning that people will have more disposable income. We saw a change come in in 2025 that this was going to happen and we're going to see it increase within 2026. More disposable income, more tourists, higher nightly rates, higher occupancy. All good things for our industry, all good things for the country. Those are my three predictions for 2026. I'd love to hear your thoughts on my pre. Please reach out if you have any. Thank you.

Hi, I'm Rose from youm Family's Place and hosting in the Motherhood and my prediction for 2026 is it's going to be about standardization and elevating guest experiences. Our guests are becoming more savvy and they have higher expectations. And so it's important for us across the industry to be raising our standards, setting those expectations appropriately for our guests that they have more consistent experiences across the product.

Hi, everyone, my name's Lucy from Breezeway and Here are my 2026 predictions. First, I think we're going to see even more consolidation of tools. Rising costs and fees mean that operators need less tools that do more, allowing them to maintain high standards for both guests and owners while protecting their bottom line. Second, I think we will see more regulations come in across Europe. We're already seeing it in Budapest, where short term rentals are being pushed out of the main tourist zones to protect the housing for locals. I used to live in Barcelona, so I totally get it. But for hosts, it does mean we'll need to stay flexible and pay very close attention to what's changing in our specific markets. And third, the increase of occupancy in shoulder and low seasons. In just a couple of years, the number of remote workers and digital nomads has jumped from around 35 million to over 50 million. Operators are mentioning this to me more and more that their occupancy is increasing in those periods. Guests are staying for longer, longer, and they're choosing the properties that have the amenities needed for working remotely. I think this will be an increasing win for hosts who can provide those suitable working conditions, especially in popular European cities where winter used to be really quiet. So, yeah, Those are my three predictions. I'm excited to see how 2026 shapes up against them.

Hey, everyone, it's Jessica Singer here at Bookings Cloud. I've got some pretty cool predictions for 2026. So as we kind of head into the. I just want to share those predictions for the vacation rental industry and what to expect. These are not guesses. I'm going to also caveat. These are really predictions based on trends that are already happening kind of beneath the surface that are about to accelerate in a super big way. So my first prediction, surprise, surprise. Direct bookings really kind of become a survival strategy. They're no longer a nice to have, they become survival. So for years the conversation around direct bookings has really been, oh, that would be really nice to have someday, or, you know, if we have more time, more staffing, more budget, like, then we can focus on it. Or I even hear, oh, I already have 85% direct bookings. I don't need more. But in 2026, the mindset shift really flips completely. Owners are becoming more sophisticated. We saw this A decade ago with revenue management we're going to see that, that as well with direct bookings and marketing. I'll get into those other predictions in a minute. But they're watching margins a lot more. They're, they're super educated. They're asking property managers the right questions like what is your direct booking strategy and how are you measuring it? What's your return on ad spend? What's your return? Next year I think we're going to see this major shift more from that passive marketing to kind of always on automated demand generation systems. So systems that take your listing content, pricing, availability and actually do something with that data every single day. So direct booking really is no longer a marketing project. It becomes an infrastructure for running a really, really profitable portfolio. Prediction two, you heard me mention revenue management. So revenue management and marketing finally merge for the first time. These two worlds will stop operating in silos. This is so critical for your bottom line. Booking windows tighten. Last minute demand is increasing. It's rising. Guests are discover days earlier in the funnel across meta and Google, YouTube, TikTok everywhere. So in 2026, property managers really start to rely on real time demand data to guide where the marketing dollars go. So this becomes less gut instinct. Not even last year's patterns can be repeatable in 2026. So much is changing so fast. So we're talking about property level scoring to identify which listings actually deserve ad spend because it's not always every property in the portfolio. We're talking about an intervention on the marketing side that is automated and not manual. So. No, no, more like, you know, manual creation of ads across a portfolio. You'd have to watch them 24, 7 to be effective. Dynamic budgets that move based on availability and revenue potential that can't be replicated by a human. You could be the most amazing marketer out there, but you're missing revenue potential when you don't have dynamic budgets that move your ad spend based on that availability and the revenue potential overall for each individual property. Automated campaigns that adjust to inventory the same way a revenue manager adjusts pricing. This is the year that marketing really becomes measurable, predictable and tied directly to revenue outcomes. So that's really, really exciting. We're already seeing this sh here at Bookings Cloud. My third and final prediction is that automation wins whether the industry is ready or not. Y', all. Automation is already winning. It is turning itself on its head. This next year we are going to see vacation rental marketing cross this threshold. Labor shortages, they're not going away. Guest expectations are getting higher. That's not going to change. And really the cost of doing nothing is becoming so real. Your competitors down the road are automating. If you're not, the owners are going to figure that out at some point and you become less competitive. So the managers that are winning next year are going to be the ones who embrace systems that build creatives automatically, no longer manually. Ones who are updating ads daily with real time PMS connected availability and pricing that is so critical it shifts constantly. We're shifting spend to properties with the most revenue potential and we're providing actual attribution, not guesswork. So we here at Bookings Cloud, I would be remiss if I didn't at least add this in here. We are already seeing an 8-18x return on AD spend for teams that are leaning into Bookings Cloud's ad automation. That performance gap between these early adopters and non adopters is widening like every day. It's wild to see this unfold this quickly. By the end of 2026, we think digital marketing and vacation rentals look a lot more like the hotel world or even the automotive space. Just always on ad spend. Data driven, automated and financially accountable. Which should make your your CFO jump for joy, quite honestly, and your revenue team. So Those are my three big predictions for 2026. Direct bookings become absolutely essential, Revenue management and marketing finally merge and then automation completely reshapes the entire landscape. And this is going to happen quickly. I know it because we're already seeing it at the end of 2025 here. So if you're watching this and thinking we're already feeling this shift, you are not alone. The industry is maturing really fast and the next year is really going to reward the managers who move really early on these adoptions. So thanks for watching and cheers to a smarter, more revenue profitable year for you in 2020.

Hello, my name is Tihana and I'm one of the founders of and Here are my three predictions for 2026. Firstly, off the back of the constant Airbnb changes, professional hosts will concentrate more on direct bookings. The two major players, booking.com and Airbnb, have created a huge gap in the market for one of the smaller booking platforms to take the business. So watch this space. Secondly, I think we'll see an increase in above and beyond services offered by professional hosts like extended check in or checkout hours and bonus add ons to stays like additional use of facilities. Guest behavior is shifting towards customization, so professional hosts need to respond to that to set themselves apart. Thirdly, we'll see an increase in properties marketed to and adapted for lengthier stays again in response to evolving consumer behavior and increase in digital nomads. Remote work is because becoming permanent for a growing proportion of people and for hosts it provides a more predictable income. And finally, as a bonus prediction, hosts will get more and more creative with check in instructions. Our attention spans are shorter than ever and expectations for a smooth guest experience are higher than ever. So expect to see more visual content like instruction videos and interactive guidebooks. The days of lengthy, confusing written instructions are open.

There you have it. What a 20 minutes. That was so good. I changed my T shirt and put a hat on. So we have our predictions in shock. There's a lot of chat about AI, but also guest expectations, communications and the leveling up. So again, thank you to all the amazing people who put their name down and submitted their video with their predictions. I'm looking forward to going back on it in a year's time and seeing what if it was was true, whether it is the robots, whether it is, you know, leveling up this industry as we talk about it, whether it is guest expectations or everything else that was mentioned in there. And yeah, it was lovely putting that together. And at no mean was it was it intentional to have boys first and girls second? It literally just how it felt. I did put our friend there at the end because her audio was shocking. It's amazing who's got good audio and who doesn't have good audio. But anyway, lessons learned for 2026 is predictions where I need to be making sure everybody's got good audio. Anyway, with all that being said, this is the end of it. Thank you so much for tuning in this year. We've definitely revamped and changed so much of our podcast this year and that will change in 2026 if you've made it this far. My my goal is to write a new book, the third in the Book Direct series. Let's see if that sticks to it because I have been putting this off for so long just because it's such a faff to put a book together. And this year just escaped me because there's so much that we're doing at Boostly and I have to be so much in the business. Hopefully with everything that I've done this year it means I can remove myself a little bit from the business to free up some time to write this book, which is something that I do want to do to complete the series. So let's see if I do it. You'll hear from me by the end of 2026 if that's the case. All right. Ta, ta.