I’ve been using Hospitable for years across multiple short-term rental properties, and in this episode I’m sharing my honest 2026 update on their AI features: what’s actually working in real operations, what’s created more problems than it solved, and how my approach has shifted since my first review a year and a half ago. If you’re a short-term rental investor trying to figure out where AI actually fits in your business, this one is for you.
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I’ve been using Hospitable for years now, not just testing it for a quick review video. And here’s what I think as a real estate investor with multiple short-term rentals on the platform. Now, if you’re new here, welcome. I love to share things that help real estate entrepreneurs break free of the grind and create bigger lives and bigger businesses and really live their dreams that they got to real estate for in the first place.
Now, let’s talk Hospitable. I did a full review of Hospitable about a year and a half ago. And if you haven’t seen that yet, I’ll link it in the description below, or if you’re on YouTube, we’ll link it here. Go check that out after this, because it’s going to go into more depth about the basic features of Hospitable. Now, since that first review, Hospitable has rolled out a lot more AI features. And so I want to talk about what actually works and what really doesn’t in real operations for short-term rentals.
Now, Hospitable, like so many other platforms, wants to get as much AI on their platform as possible. It looks great in demos and in marketing. But the reality is, does it work? Does it help? Automations and AI tools can help or hurt. And I think on Hospitable, there’s a little bit of both, which I’ll get into. Because while tools can look great on paper, when you’re dealing with real guests, real timing, and real conversations, that’s when you actually see what holds up versus what just makes a mess of things.
So let me share one of the AI features I consistently like every time I use it. And that is the improve message option in Hospitable when you’re messaging a guest. Why it works so well is because myself or my virtual assistant, somebody who knows the facts, is controlling the content first and then the AI is making it sound nicer, putting a little spin on it so it sounds really guest friendly and warm and welcoming.
So the specific way I use this improve with AI feature is myself or my property manager virtual assistant writes out the factual message first. Someone asks a question, do you accept pets or can I check in early or something like that? And we’ll write out the facts and then we click improve with AI. It improves the tone, the clarity, the professionalism. It just makes it really positive and friendly and warm. And I love it, it always works out well.
And I think this is a great example that AI is really good at refining something that’s already factually correct. But what I’ve seen is that AI is not great at creating the message from scratch, which gets me into the next AI tool within Hospitable that I do not love. And within guest messaging, there is also a suggest message option. So instead of getting in there and having a human being write the actual message or using a canned response or something like that, you can just click suggest message and the AI tool writes what it thinks the answer is. That answer has never been correct in my world. It has always been factually incorrect. It suggests things that are not how we do business, not our policies, not our procedures, nothing like that.
If somebody asks, can I get an early check-in? It’ll just be like, yeah, sure, whatever. Not quite. I might be exaggerating a little bit. You get the idea that that’s not how we handle early check-in. And so it’s never understood enough context about the situation, about the guest, about how we handle things to be correct.
And I have another example where the AI tools have broken down and not served me well. And that is the auto-reply tool. In my experience with Hospitable, this was one of the earlier AI tools that they rolled out. There’s a canned message option where you can save a template message for FAQs that you get a lot. Like I have one about early check-in. I have one about do you accept pets, all these things. When you get a question that is an FAQ, you can just select the canned message and it auto pops it in and you can send it.
What Hospitable did to level up their canned messages is they started this auto reply tool where you could have a templated response and say, hey, every time somebody asks about early check-in, just automatically send this response. And the AI tool in Hospitable was supposed to sense these keywords, recognize that somebody asked about early check-in, and then automatically send this response. So you get this really fast response time and have a happy guest because you replied right away. But it totally didn’t work well for me.
What would happen is that somebody might use a keyword or have a question and the AI tool would automatically send this auto response, but it wasn’t really what they were asking about. They just happened to use this phrase and the auto response was totally out of place. So I had this just happen. I had turned off all our auto responses, but I accidentally still had one on about early check-in. A guest asked for something that I couldn’t do, something about cleaning and linens, and I couldn’t say yes to them on that. And yet, I noticed that the night before they were scheduled to arrive hadn’t been booked yet. And so in order to have a good guest experience, I said, hey, odds are I’ll be able to get you early check-in. I’ll confirm the day of, but it looks like as of right now, we’ll probably be able to get you in at 2 p.m. instead of 4 p.m. So I wrote that in. Then they replied and they referenced that early check-in. So then this auto reply AI tool triggered and it sent the generic early check-in is case by case message that I have as my template response when people ask for early check-in.
It was completely inappropriate to the conversation because we’d already been having this conversation about early check-in. I already told the guy that odds were good that I could give it to him. And so this was really redundant and confusing. And just one of those grimace moments when you’re like, ooh, because you know, sending messages to a guest, it’s like pee in the pool. You can’t take it back, right? And so I immediately went in and made sure everything was turned off. Because that’s pretty much how it’s always gone for me. So I do not love this tool. I don’t think it’s a good example of AI and it doesn’t work for me.
Now, if you’re using this feature and it’s working well for you, I’d be really curious to hear how. Please put it in the comments below. If you are using this auto response AI tool in Hospitable, tell me how you have it set up and how it’s working, because it’s always been a hot mess for me.
Now let’s move on to a newer AI tool that Hospitable has rolled out, which is upsells. This is something brand new where they’re like, hey, you can put in these upsells and charge for them. They tout that you can do things like charge for early check-in, late checkout, things like that. And I saw this and I kind of rolled my eyes because I have been using an upsells tool for about a year and a half.
So before I ever set up this upsell option with Hospitable, I tried to find people who were using it to hear success stories and I couldn’t find anyone. Now, once I went to all the time and effort to set it up and it wasn’t leading to any sales, I did run across a few investors in my network who had also used it and said they had the same response, that they never sold anything with it. I was so excited about this because the HostCo already has vendors in their world. I didn’t have to deal with any of that. It was like, hey, if people want to rent baby equipment, if people want to schedule a massage, if people want grocery delivery, the HostCo already had vendors for that in the Myrtle Beach area as they do in multiple markets. So it was like the easiest possible way to do upsells and still nothing sold in a year and a half with three different properties.
And so I don’t really place much value on this upsells tool. Not necessarily because of the technology piece, it’s just that the upsells niche within short-term rentals hasn’t worked out for me and hasn’t worked out for anybody else that I have interacted with personally. So it’s not really a tech comment about Hospitable specifically. It’s just that the idea of upsells I think is better than the reality.
Personally, I’ve had it on my list for a few months now to have my property manager virtual assistant go in and shut down our upsells with the HostCo, get those messages out of our system, and just streamline our process more because it hasn’t led to anything. So there’s no reason to leave it in.
Now, another AI tool that Hospitable has had for a while now is the dynamic pricing tool. Now, many of us in the short-term rental space are using PriceLabs. It is the OG when it comes to dynamic pricing. You may also be using the built-in pricing with Airbnb. Now, PriceLabs is clunky. It is awkward. I don’t love it. And yet, it works. And I once more looked into Hospitable’s dynamic pricing and tested out their model to see what they would recommend for my properties. And it was not compelling. I have some weekday gaps over the next few weeks because my properties are in beach areas. People will come for a few nights over the weekend, so Monday, Tuesday, Wednesday nights are pretty much open, right?
And what the Hospitable dynamic pricing tool recommended for these weekday unbooked nights was actually to raise the prices. And it’s like, I’ve got these weekday nights over the next week or two, I don’t think increasing the prices is going to be what gets them booked. The fact that’s what they recommended just showed me that it’s really not there yet. As somebody who’s used dynamic pricing and used PriceLabs, I wasn’t convinced this was going to help me get more money or more bookings. So I don’t really see the dynamic pricing tool in Hospitable being there yet in terms of its quality.
Now, I know I’ve said a lot of things here that I don’t love about Hospitable. Again, if you go back and watch the first review, you’ll see I really like how Hospitable does the basics. I just think that a lot of their new AI tools, where they’re really trying to remove the need for a human being, isn’t working. So what is working? Well, their automation workflows are amazing for messaging guests. The check-in message, the checkout message, and all this standard guest communication works flawlessly in Hospitable. If guests don’t have one-off questions and just need the standard message of thank you for booking, get ready for your stay, here’s your welcome packet, here’s your reminder to take the trash out, and all your checkout messages, that works flawlessly 100% of the time. So I love their standard workflow for standard guest messaging.
Another thing I love in Hospitable that has worked flawlessly for me is the Smart Lock integration. I have Schlage and CodeLocks and I love the system that Hospitable has for setting up a unique code for every guest. We have very simple settings of when it starts to work, when it stops to work, and when we do things like early check-in or late checkout, it’s really easy to go into the system and modify the times for that code to work. So I love the Smart Lock integration.
Hospitable also works great for our team members. It’s really easy to connect with our cleaners’ system and their calendar. And for a few houses, we use a linen service. It does a great job of sending the linen service messages so that they can get things onto their calendar. We can also share a calendar link so they can see things on a calendar. So I love the integrations they have for collaborating with other team members. Hospitable is also really easy for my property manager virtual assistant to use as well. That’s all worked beautifully within Hospitable.
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Now, what do I do differently now than I did a year and a half ago when I made that first review? I have seen that with Hospitable, while we have these AI tools, at the end of the day, you need a human being behind the scenes who has the wisdom and the judgment that AI doesn’t always have yet, really controlling things. And then the AI just makes things faster, easier, and puts a prettier bow on it by making those messages read a little bit nicer when you use that improve with AI option.
What that means for me is I’ve really leaned into having that property manager virtual assistant, that real human being, and supporting them with AI so that they can do their job faster and easier. So in addition to things like the improve with AI, we have things that we’re using within ChatGPT that houses our information and helps the virtual assistant get the right answer and solve problems faster and easier. And she has that personal touch and that wisdom that connects the dots and doesn’t make it awkward.
So what is my final verdict on Hospitable in 2026 for short-term rental owners? I still recommend Hospitable with the right expectations. You do need a human being behind the scenes controlling things. You cannot have AI do everything here because the AI in Hospitable is going to embarrass you with some guest communication. It is great for supporting a team, and yet it’s not a fully automated system where you can remove humans from the process.
If you haven’t seen my original Hospitable review, I break down all the core features that I love there. Go watch or listen to that next. And I’d love to hear from other hosts in the comments, what’s been working for you and what hasn’t. Whether you’re using Hospitable or a different property management system, I’d love for you to share and add your voice to this conversation. And then join me again next week.