How Short Term Rental Hosts Should Actually Use AI in 2026 artwork

How Short Term Rental Hosts Should Actually Use AI in 2026

The Boostly Podcast

June 22, 2026

In this episode of the Boostly Podcast, I joined the Stay Direct monthly meet-up to talk about where AI is really heading in the short-term rental industry, and what hosts, property managers and direct booking businesses should be paying attention to right now. Skool Group - https://www.skool.
Speakers: Alistair, Mark Simpson, Gareth
**Alistair** (0:00)
Okay, Mark, so I think probably the main cut and thrust of this session is just going to be picking your brain on AI, and specifically, I think, post-scale AI, which was a really fantastic conference last week. There's a lot of, I want to say, like disinformation in the market. There's a lot of people doing some really cool stuff in the market, and we heard from Graeme at Sykes last week, I should say, Forge last week, talking about 1,000 plus AI agents and 150 different tools that he's using, really, I'd say, innovating in the sector.
But for a lot of the businesses out here, the one-person band, so to speak, I think everyone wants to know what we should be using, where we should be spending our time, and what's the best use of the time and resource. Specifically, I think one of the things I want to fit your brain about is WordPress. It's definitely something I've got a ton of experience using. I think most people in the market use it.
Yeah, I'd love you just to start off with your WordPress journey, what you think is interesting in terms of developments there, and is it here to stay? Is anyone going to come and eat their lunch?

**Mark Simpson** (1:16)
Yeah, so WordPress is very interesting at the moment, and there's been a lot of cool discussions, and I've been on stage with Richard Vaughton at various events over the last couple of months, and we've been on podcasts and webinars talking about it, and obviously Boris from Onseason has joined in, and there's a lot of opinions at the moment. One of the things that caught my eye is, well, WordPress, for those who don't know, the CMS solution, content management solution for websites, it is the go-to. 43% of the entire market in January 2026, we're using WordPress websites. The reason being is the solutions like Wix and Squarespace or even for smaller operators who are using a PMS solution, it's very walled garden. So you've got a website, but you're very restricted in what you can and can't do. So WordPress is good because it's open source.
Search engines love it. It's like a blank canvas. It's like having literally the world is your oyster.
But what's really interesting over the last couple of months is that 43% has dropped down to 41%.
Why is that? Well, as you've mentioned, there are so many AI solutions now, Replit, Lovable, you name it. There are AI solutions out there. Obviously, Boris Onseason is creating his own AI solution, et cetera. So there has been a communication and discourse around this. But there's no way a company as big as WordPress and the overriding company that owns it is going to just give up their dominance on this. And they are doing a lot like you mentioned within the platform to be more AI ready, so to speak.
For us, I can't lie, we have had our heads sort of turned, especially when people do speak about it so openly. And I respect Richard Vaughton massively. And when he brings that bridge, that topic, that discussion, you have to pay attention to it. But of all the research that I've seen, of all the people that I've spoken to, including the likes of Gil, Khan from Crafted Stays and true experts on these topics, it is still the best option. I think where WordPress gets a bad rap is load speeds or potentially security. But for everybody that we've dealt with, and we've worked with over 2000 host websites now all over the world, you know, we generated a billion dollars in bookings over the last 10 years, when WordPress websites go wrong, it's not the solution, it's the human behind it. So, for example, you mentioned plugins. One of the reasons why WordPress websites could load so slowly is because it's very tempting to just dump and upload a ton of plugins to a website. When you do that, it naturally will just bulk up the site and slow it down. Security, again, humans get in the way, they maybe take down a couple of the barriers that make it secure, and then obviously things get in. You know, luckily at Boostly, we've got everything covered for that. That's why we do sort of take control of these WordPress sites for our clients. We give them full, you know, proximity to do what they want, but obviously this is like our bread and butter. But still, like WordPress, from all the research that I've seen, it is the best and it will continue to be in the best. And for us as a business, like one of the reasons why we got very popular over the last 10 years is because we've built these 27 integrations that go into the PMS. So your Guesty Host, Waylogify, et cetera. And we've been able to build a very good booking flow from landing on the home page, going to the listing and checking out, which is again, one of our USPs here. And going back to these AI websites, Lovable, whatnot, I've not seen a very good booking flow on these AI sites that have been spun up. They do get disjointed and broken for the prime reason being is they haven't got a very good integration that goes into said PMS.

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