If you have ever wondered how investors find Airbnb deals that reliably net fifty to a hundred thousand dollars a year, this episode is for you!
Tune in to Episode 113 of the Host Coach Airbnb Investing Podcast to learn the exact formula of a guy who has helped over 400 investors find their cash-flowing dream Airbnbs! — from choosing the right market, to spotting the characteristics of high-performing properties, to how to underwrite deals so you know exactly what a place can earn before you make an offer.
If you want a clear, realistic roadmap for finding your first — or next — high-cash-flow Airbnb deal, buckle up! We're going to guide you through it!
Topics discussed in this episode:
- How to choose the right Airbnb market to invest in
- The characteristics of high-performing properties to look for
- How to underwrite a potential Airbnb investment BEFORE buying
- The biggest red flags to avoid when selecting a property
- Creative upgrades that can turn an average Airbnb into a top performer
- How STR Insights can help you skip the stress and pick a winner
Host Coach Airbnb Podcast Episode 113 Show Notes:
Kenny, how do you find Airbnb deals that net $50,000 to $100,000 every year?
There's three things that I do when I'm searching for Airbnb deals. Number one, I look in markets that fit my budget. So if I can't afford to be in a market, then I shouldn't even be looking at market. Number two, I have to clearly define my return on investment (ROI) goals. So 50k -100k is a pretty big difference. I like to narrow that a little bit, and that also helps me know where to look. And then finally, the third and most important one that a lot of people underate, it's their personal preferences - meaning proximity to where they live, regulation preferences, natural disaster preferences, or even if they want to vacation in that market preferences. All of those things combined really helped me identify and know where to invest. And that works for yourself and looking for others.
How many short term rental properties do you own and what's their annual cash flow like?
So right now I'm at six properties. I own all across the United States: New York, North Carolina, Texas, Kentucky, Arizona, and I have a hotel in New Orleans. The cash flow ranges from $80,000 to $175,000.
Cashflow aside, what is your favorite location?
The Bourbon Trail one is awesome. It's huge. It's almost 10,000 square feet with a heated pool, two hot tubs, and a three car garage we converted into a massive game room with a golf simulator. There's Frisbee golf, there's a theater room, there's a gym, there's a yoga studio. There's a little mini pup putt - bourbon themed golf thing on there. The Airbnb has a pond that you can fish on. It's like a little private mini resort. I love that property.
I love how you've packed the amenities into that one!
All the properties that I own and run as short-term rentals - they are loaded with amenities. We have to be willing to invest into our properties. Now, you don't need to spend $300,000 into amenities or furnishings to have success, but you do need to be willing to invest into the property. You have to be willing to invest in furnishings, amenities, and updates. So your budget isn't just your down payment amount. That's a piece of the pie. When you're looking where you can invest, don't max out your budget based on what the bank says you can afford. Instead, base your budget based on what you're prepared to invest into the property.
Where New Airbnb Investors Should Invest
It sounds like you are invested all across country. But for a first time investor, do you have any thoughts on proximity to their home residence?
Not really. It's a preference. It all centers around why are we investing? Why are we doing this? Some people are doing it to simply make money. Maybe they want to leave their W2 job. If that's the case, and if they live in Southern California, it might not make sense for them to invest in Southern California based on their ROI goals. It might be more affordable to invest in a market that's a flight away. Are they comfortable doing that? If not, then we kinda look at, alright, well you know, these markets near you, these are what they're kind of yielding in terms of returns, and these are the expectations.
So for me, it's not like you need to be within four hours of where you live for your first one, because it comes down to why are you buying this? And if you're trying to maximize returns, then you need to be comfortable with a plane ride away for most.
I had a Host Coach client recently who was in Southern California, and we ended up finding her a property in North Carolina.
Wow! There you go. That's the beauty of it.
One thing I love about short term rentals is you can be successful anywhere. It's all about your local team and boots on the ground. You guys know that probably best. You guys aren't cleaning your Airbnbs, you're not doing the maintenance, and really shouldn't expect investors to do that if they want to do this the right way. So in my opinion, further away, it's scarier, but it's actually a lot less time than closer in my experience. Distance forces you not to run down there.
Yeah, exactly. It makes you have a really good team. So in case something happens, you're not having to sweat too much.
Key Characteristics of a Strong Airbnb Market
So talking about these different markets, what. What do you think the characteristics are of a good market?
Right now there's a lot of uncertainty, especially in the economy and on the macroeconomic side. We have seen short-term rentals this year dip across markets 10% year over year compared to 2024. And so really you kinda have to take a step back and go, "Okay. Well, what markets are getting hit more than other markets?" And what we found in the data is that the markets that are fly-in markets, meaning your big cities like Nashville, Miami, Orlando, places like that, those markets saw a bigger hit in revenue year over year.
Whereas you're drive-in markets within a maximum drive of three to four hours of a major city - those markets seem to be strong and thriving. So one of the characteristics I'm looking for, especially in 2026, in markets is are people driving into these destinations? They tend to be more affordable too. Obviously you want to have some sort of traffic driver there. You just don't want it to be in the middle of nowhere. Also what's regulation like? And then finally, what type of revenue are properties doing in those markets? So when I combine those things together, that gives me a good idea of the health and wellbeing of that market.
Summarizing that a little bit, what I'm hearing is. It should be a drivable market, but it doesn't have to be drivable for you.
Correct. It's where people in DC might drive to or people in Raleigh might drive to, but I could be the investor in Southern California.
I love it. I tell people all the time, there are over 12,000 potential markets in the United States. That's a lot. You can pick a major metropolitan area. And then just draw a little radius around four hours of that metropolitan area and look at all the attractions and things within that radius. Pick some really cool markets without having insider access to secret data and stuff behind the scenes - you don't need that to find success in the short term rental space.
There's a lot of common sense in Airbnb investing. I wish it was relayed that way on social media. People tend to chase what others are doing. Like the popular markets... we hear about the Smokies, we hear about Orlando, we hear about Lake Tahoe and Colorado, you know, sexy markets. But, the reality is the markets that are just drivable - they have high amounts of tourism, because of demand, and maybe they are really cool markets, just no one's talking about them. Those tend to be the best ones.
You're describing the location of all 15 of our properties, so I feel good!
What Makes a Strong Airbnb Investment Property?
Let's move from market to property just. What do you think is essential to look for in a potential investment property?
The biggest thing I look for is something called a moat. The moat is something that separates you from the competition. One thing that I've learned in the space of doing this for eight years is that people love to copy success. There's nothing wrong with that, but the problem with that is they'll look at your property if you're having success and try to replicate it. If it's easy to replicate, what happens is your property that's at the top starts to go down because everybody else is doing the same thing.
So, when I'm looking for successful properties, I'm looking for properties that have unique attributes. They could be location, could be property type. Could be the type of amenities in design, could be doing A-frames or unique types of properties in and around areas or the space of what it offers, the types of views it might have. Those are limiting factors that not everybody can replicate. So finding a moat is one of the most key pieces in finding a good deal in today's market.
I completely agree. Is there anything that you would tell our listeners, if you see this runaway from this property? What should they avoid when they're looking for an investment property?
One thing I tell people to avoid is don't buy in communities where all the properties are exactly the same. Just don't do that. Run away. What would you be competing on? Right. That's the opposite of the moat. Avoid cookie cutter.
How to Make Your Airbnb Exceptional
All right, so if you already have a property. What are some creative strategies for turning that average short term rental into an exceptional?
Number one niche down. Find out who your guest avatar is, their demographic, where they're coming from, and why they're coming to that market, and go all in on that. It really does seem like, "why wouldn't I just market to everybody?" But, what I've learned in this space is when you market to everyone, you market to, no one. In a sense, you become washed out or vanilla, essentially like you look like all the other listings.
The listings that do well on Airbnb have something unique about them that stands out, that calls to the guest avatar. So if you already have a property, really think about who your guest avatar is and how you can better market through amenities or your photos to that particular guest avatar - and you'll make more money.
Makes total sense. No more vanilla. I hate vanilla! None of our places are vanilla.
How to Calculate Return on Investment
Once you've identified a market and a target property that isn't a cookie cutter, how do you evaluate the potential performance or a return on investment for that property?
Really, it comes down to what are current properties in that market doing? I know that's kind of a cop out answer, but we need data, right? Whether we actually have hard data, where we know what other properties are literally doing, because when we talk to property managers or we know owners in the area, or we use data platforms like STR Insights or AirDNA or Pricelabs to know how properties are performing.
But heres the thing, I don't look at averages. I look at the types of properties. So for example, let's take my Kentucky property. It's a nine bedrooms, seven bath, right? So when we're looking at the data, we're not just looking in that tiny little zip code or the tiny city, we're actually looking across the region.
So number one, who's coming there and why they're coming there? They're coming there for the bourbon distilleries. They could stay anywhere. It's a drive-in markets destination. They could stay anywhere between Lexington and Louisville. Okay? So if that's the case, my market. And where I'm comparing my comps against are between Lexington and Louisville. So I need understand my market boundaries. And then I'm looking at what nine bedrooms are doing in the market, the nine bedrooms with pools, how are they doing? And kind of getting a base idea of revenue from there. And then when I go into underwriting, I underwrite it in three scenarios. I call it my good, better, best. But worst case to best case scenario for revenue, and that helps me understand my risk levels. You know, not just like, "oh, I'm going to make $150,000." Instead I look at this is what it will make in the worst case, and what it can do to the best case.
How to Make Airbnb Investing Easier
For our listeners that think this process for finding and underwriting a winning short term rental sounds kind of time consuming, what does your company, STR Insights, do to streamline that process?
Well, we do it for them. People pay my company or pay me (essentially) to help them find deals, underwrite deals, and essentially coach them through that acquisition process and knowing what they need to do to have a moat. So it's like, cool, you found a property with a moat? How do you expound upon it? How do you target your guest avatar? What things do you need to add based on your budget and your goals? That's basically what we do at SDR Insights. We got creative with a name, it's called Property Finder, done for you.
How much does something like that cost? So our total cost of the program, it's not commission based. We're not realtors. We charge a flat fee. It's $14K. We charge half upfront and half upon close of the property. So $7K upfront. $7K upon close of the property.
How many investors have you helped find their perfect, not vanilla, amazingly moated property?
This year we hit 176, but altogether since I started this, it's about a little over 300.
Congratulations. That's awesome.
Airbnb Tax Advice
With tax season creeping up, how would you advise investors to use their Airbnb to offset their taxes?
You got the STR Tax Loophole, I'm sure you guys have had people on here talk about, but I just love short-term rentals because it's considered active income. There's a lot of things you can write off, not just from the depreciation standpoint, but as an active business. Deducting expenses and if it's a place you vacation to, you can use some of your write off from the vacation. So I love that about my short-term rentals compared to a long-term rental where you can't really do that.
The Airbnb Investor Wealth Divide Trend
What trends are you seeing in the short-term rental market? Show us your crystal ball. What do you see happening in 2026? What are the Kenny predictions?
Because I have access to a lot of good data, and I've seen enough in the last few years to kind of know where things are headed. I don't have a crystal ball, but I'm like 90% sure this is going to happen. When I'm about to tell you this current year, what we saw and what we've seen for the past three to four years is actually what I call a wealth divide amongst short term rental hosts. Meaning that properties that are performing in the average, they're making less and less every single year. I alluded that to beginning. I said 10% year over year decline. Well, the year before that was also 10%, so we're looking at 20% delta between 2025 and 2023, but that is for the average properties.
Whereas if you flip it, and you look at the top 10% of performing properties based on revenue, they're actually up in 2025, year over year by 10%. So while the average is down, the top 10% is up. And we're seeing this widening of how much money the top 10% is making versus what the average is making. And so what that means, number one, is that the industry is maturing. People are making more money, but also there's a higher level of professionalism and hospitality and amenities that guests expect and those properties that are offering that. They're finding a lot of success in today's market.
Whereas everyone else who's got the "Gilmore Girls House" or "Grandma's Closet" - I like to call it (meaning the average or the cookie cutter houses.) They're getting hurt every single year and they're going down. So in 2026 we're going to continue to see the top making more and the bottom making less. And so what I ask everyone is, "which one do you want to be?" And if you want to be in the top, you need to be willing to invest in your property and look for properties that have a moat because those are the ones who are doing well.
Why Being a Professional Airbnb Host Matters
You become the more professional host by being more educated, not just taking the actions of adding more amenities, but by understanding the new tools and trends and things out there. By listening to expert advice from amazing people. I love having guests on that have multiple properties. It's nice to talk to experts.
There are tons of people sharing about their ideas about Airbnb, but they have never actually put their own skin in the game. You know what we're talking about. You've lived the life, you've unpacked a million boxes, you've made some mistakes, and you care. You've almost gotten a divorce once or twice from setting up a property... we've all been there.
How to Connect With Kenny
We're about to release the top markets for 2026 on my website, strinsights.com. It's free, and it has over 80 different markets across the country that are top investible markets for 2026.
So there you have it. You now know the biggest red flags to avoid when selecting a property, the creative upgrades that can turn an average Airbnb into a top tier performer, and how tools like STR Insights can streamline the whole process. If you don't want to spend hours digging through the data, keep listening to the Host Coach Show.
We're here every Tuesday sharing actionable expert advice systems and software to help you fast hack the success of your Airbnb and maximize the cash flow so you can live a life that you love. Do you feel like you need some guidance to make sure you're making the right decisions for your Airbnb investment.
Should you need an Airbnb coach to help you find the right market, property, and help you set yourself up for success - feel free to book a free 30 minute coaching call with us. We LOVE helping new investors avoid pitfalls and find financial freedom through Airbnb investing!
