Welcome back to the Short-Term Rental Riches podcast. I’m happy you’re here again. Remember, way back when, over 10 years ago when Airbnb was easy, a lot of people didn’t even know what Airbnb was. If you’re considering getting into short-term rentals in 2026, well, things are way different than it was 10 years ago. So today we’re doing something a little bit fun. We’re taking a trip down memory lane, going all the way back to when I used to stay in Airbnb’s over a decade ago. The way things used to be and the reality the way things are today.

I also have one really counterintuitive reality that you have to follow today to do a good job with your short-term rentals. And it was much, much different back in the past, and actually it’s almost flipped a hundred percent. So stay tuned. Let’s dive in all that as we take a trip down memory lane.

10 years ago on Airbnb, it was all about connection and feeling how it would be to actually live in other people’s properties. So yeah, you saw their personal photos in there. They met you at the door, they gave you a guided tour of the property and their cell phone number, and they were messaging you constantly.

You became friends perhaps.

Having that personal connection with the host led to really great reviews. The reality is today most guests want the opposite.

Most guests are looking for a smart lock so they can check in and not have to talk to anyone. This is the reality. Maybe they’re coming from a long trip. They just want to check in. They want to know that everything is exactly how they imagine it. Everything is exactly how you portrayed. On your Airbnb listing, there is no more exchanging communication with your host 

Nope. Today guests are looking for much what they look for when they stay at a hotel. Now, yes, there’s a couple little caveats here. Maybe you have a extremely luxurious property and you’re acting as a concierge. Well, that is a little bit different, but I’m talking about the majority, the 90% of all short-term rentals out there.

Your guests are looking for some detailed check-in instructions. Timely check-in instructions, really quick responses, but only when they want to talk to you.

So a lot of that personal interaction today is gone. Why has this happened? Well, quite simply, it’s just been a cultural change with Airbnb and the industry.

Early Airbnb guests like myself were looking for adventures. We were looking for unique stays that we couldn’t find anywhere in hotels, and a lot of us were looking for some budget friendly options, 

which we know today is no longer true. There are thousands of Airbnbs out there that rival even the hotel industry’s most luxurious properties.

And yes, guests are now scrutinizing over every single little detail. The Expectation Bar has been raised because there’s way more competition than there used to be. and I’ve got some interesting, really mind blowing stats here for you in just a second.

So the overall culture has changed with Airbnb and along with these higher expectations. We have much more competitive pricing because there are literally millions more Airbnbs than they used to be. Now, of course, every market’s different, every property’s different. But if you’re not using dynamic pricing tools today, like Wheelhouse or price labs, you’re going to get left behind.

Not using dynamic pricing tools today is really not optional. You have to have access to all the data and price your properties accordingly. Imagine Marriott going back to not having dynamic pricing. And I know I’m sort of giggling here, but you just can’t imagine that, right? Or American Airlines charging the same static pricing or adjusting it once every week or two weeks.

That’s just not a reality. So yes, guest expectations are much higher, and for us to compete in the industry, we need to be using a dynamic pricing tool.

 Now let’s take a second and think about reviews. 10 years ago, yes, reviews mattered, but they weren’t this algorithmic gatekeeper the way they are today. If you have a 4.7. Average, for example, you literally can drop off of the search results

In the early days, guests were thinking of their stay more along this sharing economy type of setup. Right. That has definitely changed.

And don’t get me wrong, things are much harder than they were today, but short term rentals are an incredible opportunity. If we compare them to other real estate options around well, you’d be hard pressed to find better returns, assuming you’ve got yourself a good property and assuming that you have great reviews in today’s market, not what would be considered great 10 years ago.

So I went through some of my history, some trips that I’ve taken over the years. I gotta say, it was kind of nice to go back and reflect on these trips as well. I’ve stayed in dozens, I don’t know, at least a hundred or a couple hundred. Airbnbs over the years 

and the properties I stayed at in the early days, yes, I was in a little bit of a different financial position, so they were a little bit more budget friendly, but I left them good reviews and going back and looking at these same properties and seeing their average review scores today, years later.

Well, it’s a little sad. They haven’t kept up with the industry. They haven’t kept up with expectations, and they’ve fallen a little bit behind.

Looking at that Atlanta property, for example, a 4.28 review score. This gentleman happens to have over a thousand reviews on his profile as well, so we know that he’s been doing it for a long time. But if you’re at 4.28, you might as well just start over. I mean, that’s really, really low. If we look at Airbnb, we know that their first page of search results only has something like 18 listings.

Imagine you’re in a market with a thousand listings and you’ve got a 4.28 review score. Guess where you’re going to show up very, very, very far down if you even show up at all.

Okay, let’s just look at some stats today. Yes, we know the cultures change. We know that you need dynamic pricing. We know that reviews are more important than ever. Let’s look at some stats now to see why all this has changed. The reality is that people always chase higher returns.

We’re seeing lots of Wall Street money come in, venture capitalists chasing the short-term rental industry because they’re chasing better returns. And yes, you can still get much better returns with a short term rental in most cases than you can with a lot of other types of real estate assets.

In 2025, Airbnb was valued at almost $90 billion.

And if we go way back 10 years ago or a little more in 2015, they were accommodating around 72 million nights. Per year. Now that sounds like a lot. That is an awful lot. But if we fast forward to today, their latest annual report is not out yet, but 2026. It’s estimated that around 550 million nights will be occupied.

Via an Airbnb reservation that is well over a 600% increase in the last 10 years. So that helps us explain why these guest expectations are higher and a lot of the reason why these things have changed.

But does it still make sense to be investing in short-term rentals in 2026? I absolutely a hundred percent would say yes, but like many things in life. It depends. So I get asked this question all the time. I just spoke with a gentleman yesterday that said, me and my wife are making around $750,000 per year, but we pay a lot of taxes.

And so they’re looking at the tax side. The tax benefits of a short-term rental. We’ve talked about bonus depreciation on this channel before. If you’re new to the show, you can go to st riches.com. You can find all of our prior episodes. We talk about everything from operations to taxes, so find us there.

You’ll also find a lot of free guidebooks and if you are enjoying the content and if you’re finding it helpful, I’d really appreciate a like or a follow on Spotify or Apple, wherever you happen to be tuning in.

So is it still worth it? Yes. And let’s just compare a short-term rental to a long-term rental. When I first got started in real estate over 16 years ago, it was long-term rentals. They made sense. Prices were lower, interest rates were lower, and your cash flow was higher. But a lot of that has disappeared.

I don’t want to say it’s not available because there’s lots of people doing a good job and finding really good opportunities. But in general, short-term rentals, if you choose your property right, have the opportunity to far exceed what you could do with a long-term rental. All right. I promised I’d give you one really important counterintuitive takeaway that’s changed from 10 years ago to where we’re at today, and that is that the hosts that are really excelling and doing well in earning great reviews. Are actually sending fewer messages today. So back in the past, yeah.

You had your, your host cell phone and you guys were chatting and he was following up all the time. Not that following up is not important, but what we want to accomplish today is to set the perfect expectations And answer all of our guest questions before they actually ask them.

So in the past, great hospitality really kind of equaled more communication, but that’s not what our guests are looking for today. And actually, if there’s more communication going on between you and your guests, it probably signals that there’s some sort of issue or something that has gone wrong. Now there are some caveats.

Yes, if you’re acting as a concierge. On behalf of your guests staying at your ultra luxury property, that’s a totally different story, but I’m talking about the majority of properties today. If you have more messages going out, it signals that you either didn’t set the right expectations or your guests were left with a lot of questions requiring them to reach out.

And when our guests are on vacation or taking some time off, they don’t want to have to be searching for answers.

So the Airbnb landscape has changed dramatically over the last 10 years. But tons of opportunity available. You just wanna make sure that you’re taking advantage of the latest technology, dynamic pricing, understanding what guests are looking for today, and where their expectations are at. I hope that gave you a little bit more insight, 

And if you have some awesome stories from staying in Airbnb’s over a decade ago and how that changed for you and your life, we’d love to know. Leave us some comments, shoot us an email. Until next time, I hope you have a fab this week.