Kissimmee STR and LTRs
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Rock Star Extraordinaire · Northeast, TN · Member since 2015 · 10k+ posts · 16k+ votes
6dThe area & economy is pricing a lot of lower to lower middle class people right out of the market. 4 day Disney hopper passes for the 4 parks is about $750 per person. So if you have a 4 person family that's 3 grand just for park passes. Add in airfare (was cheap but not as cheap now) and costs to stay and this is a one week vacation that can end up running you $5-10k easily. That's just way too much money for a lot of people to spend on what used to be where everyday families could go. And you can see this in the park visitation numbers - all down or flat. Disney wait time sites report very low crowds and wait times. Some of the months that used to be relatively strong like August are just crashing. Our slow months used to be September & October (low occupancy, usually some 3-4 day weekends), mediocre was May & most of November (maybe 35-40% occupied), rest of the year would push 75%. Last 2 years, August-October has been zombie land, January, May, July & November were mediocre, March, April, June, December were great (February reserved for me to make repairs & maintenance).
The other thing that's been a killer is that international visitation - at least staying in STRs - has fallen off a cliff over the last 2 years. We used to do about 30% international visitors. Last year we had 1 international family. Our Canadian families, which used to make up most of our late winter/early spring visitors, disappeared entirely. And I know other STR operators in this area who reported the same thing, and my caretakers said their other properties were experiencing the same thing. They also said - and this mimicked what other operators told me - that their other owners were having to shift to cheaper, shorter stays and liberalized last-minute cancellations to keep any kind of occupancy, that they were experiencing more damages and lost income from late cancellations and running the homes was more time intensive because of the higher turnover levels. We held the line on a lot of those things and of course at the cost of occupancy, because I'm not willing to rent at any cost - but a lot of owners, especially ones that paid cheaper prices to buy in years past, are. So you get a race to the bottom.
If you want to make money there IMO there are 2 main avenues:
1. Very low rates and heavy cost control - self managing, self cleaning, repair & maintenance;
2. Own unicorns - heavy themes, 10 bedrooms, 5 minutes to the parks, etc.
For the time being, just owning a nice house in the area and expecting to make any money is over. Long term you're always going to have vacationers coming, because there's a lot to do, but you need to be prepared for some lean times.
Also, you don't have to take my word for it. Just do a couple of google searches on Disney attendance, wait times, Universal attendance, etc. A couple of days ago the Universal CEO said they were continuing to see a softer market in Orlando all year. Disney reported higher attendance for their fiscal third quarter, but that was the spring. The sites that monitor this stuff report that crowds continue to be zombie compared to previous years in the parks in the summer, the charts play this out, and our experience mirrors it.
Bottom line: don't listen to anyone that has something to sell you when talking about the state of the market in Kissimmee/Davenport/4 Corners, without going and finding your own data. Realtors will tell you the market is great "if things are priced right". Yeah, that is code for "if you aren't selling a house that you bought 15 years ago for $100k or taking a $50k haircut from what you paid a couple years ago, you're not selling". Just look at days on market of everything down there. Look at some of the resorts (want to see a horror show? Look at the Margaritaville resort at Kissimmee - $200k losses and foreclosures everywhere).
Skyline Properties
16 Replies
- Rock Star Extraordinaire · Northeast, TN · Member since 2015 · 10k+ posts · 16k+ votes1w
The market is atrocious. In fact, I am about to sell my STR in 4 Corners. I contemplated shifting it to a LTR for awhile to see if bookings improve but the LTR market sucks too.
If you are a buyer you can get some good deals especially if you are willing to put in some sweat equity. We have had a few real comp killers in my neighborhood and that's pretty similar to most others.
Skyline Properties - Investor · Pacific Northwest · Member since 2026 · 511 posts · 287 votes1w
I wouldn’t call Kissimmee atrocious. I’d call it repricing.
Buyers absolutely have leverage right now—inventory is sitting longer, a large majority of sales are closing below ask, and prices have softened. But the rental side is more nuanced. STR occupancy is actually up year over year; what’s getting crushed is pricing power. Hosts are filling nights, but at lower rates. LTR rents are basically flat to modestly down depending on the pocket.
JD’s experience may be completely accurate for his property, but I wouldn’t extrapolate one struggling STR into “the market is dead.”
This is exactly the kind of market where broad averages become dangerous. We’ve been mapping properties against DOM, price movement, rental behavior, buyer activity and individual submarkets because two houses ten minutes apart can underwrite completely differently.
Anisa, if you’re seriously looking in Kissimmee, I’d start with the specific property + neighborhood + intended exit, not “STR vs. LTR” at the city level. If you want to compare notes on one you’re looking at, feel free to reach out.
- 1wRyan MoyerBusiness MemberProperty Manager · Orlando Kissimmee Davenport Salt Lake City, Park City · Member since 2019 · 990 posts · 1k+ votes
Regarding STRs, it's doable to make money here, but it requires an extensive investment in theming and unless you are drawn to Disney specifically (IE personal use) there are many better options if ROI is your main concern.
AI response from Michael notwithstanding, just go on Airbnb and look, then do some quick math. I don't understand why so many people buy STRs, price STRs, complain about their management performance in STRs, etc without actually taking 5 seconds to look on Airbnb.
https://www.airbnb.com/rooms/1189796838550949213?adults=10&check_in=2026-09-21&check_out=2026-09-25
Here is a 7br home in Storey Lake with modest mid-tier theming. This home runs about $750k to purchase.
As you can see on the link, if you're a traveler, you can book that home next week for $663 total for 4 nights.
Now let's back that out for the host. Modestly the cleaning cost is probably around $300. So $363 for 4 nights not counting cleaning, before Airbnb fee. The Airbnb fee on that booking is $102.70 (15.5% of total gross inclusive of cleaning). So the host is netting $260.30 for 4 nights, or about $65/nt.
If they're paying a management company that's another $102, so now about $40/nt net to host before the cost of any supplies and, with guests paying these prices, likely maintenance.
On a $750k home.
Cosmic Vacations4.9174 Reviews- Rock Star Extraordinaire · Northeast, TN · Member since 2015 · 10k+ posts · 16k+ votes1w
Quote from @Ryan Moyer:
Regarding STRs, it's doable to make money here, but it requires an extensive investment in theming and unless you are drawn to Disney specifically (IE personal use) there are many better options if ROI is your main concern.
AI response from Michael notwithstanding, just go on Airbnb and look, then do some quick math. I don't understand why so many people buy STRs, price STRs, complain about their management performance in STRs, etc without actually taking 5 seconds to look on Airbnb.
https://www.airbnb.com/rooms/1189796838550949213?adults=10&check_in=2026-09-21&check_out=2026-09-25
Here is a 7br home in Storey Lake with modest mid-tier theming. This home runs about $750k to purchase.
As you can see on the link, if you're a traveler, you can book that home next week for $663 total for 4 nights.
Now let's back that out for the host. Modestly the cleaning cost is probably around $300. So $363 for 4 nights not counting cleaning, before Airbnb fee. The Airbnb fee on that booking is $102.70 (15.5% of total gross inclusive of cleaning). So the host is netting $260.30 for 4 nights, or about $65/nt.
If they're paying a management company that's another $102, so now about $40/nt net to host before the cost of any supplies and, with guests paying these prices, likely maintenance.
On a $750k home.
Exactly. My experience isn't "one struggling STR". I know a lot of operators in this market and my experience isn't unique, especially since bookings seems to have peaked just after COVID and have been mediocre ever since, with last year being the worst of it and this year (2026) clunking after spring. There's just too much inventory and too few travelers. I have a really nice house, on a lake, with a nice fenced yard, but as far as houses go it's just another house in thousands around here, and because I'm not willing to bottom-feed my rates or allow the 2-day low-price party crowd it's a rough competition.
Skyline Properties - Rock Star Extraordinaire · Northeast, TN · Member since 2015 · 10k+ posts · 16k+ votes6d
The area & economy is pricing a lot of lower to lower middle class people right out of the market. 4 day Disney hopper passes for the 4 parks is about $750 per person. So if you have a 4 person family that's 3 grand just for park passes. Add in airfare (was cheap but not as cheap now) and costs to stay and this is a one week vacation that can end up running you $5-10k easily. That's just way too much money for a lot of people to spend on what used to be where everyday families could go. And you can see this in the park visitation numbers - all down or flat. Disney wait time sites report very low crowds and wait times. Some of the months that used to be relatively strong like August are just crashing. Our slow months used to be September & October (low occupancy, usually some 3-4 day weekends), mediocre was May & most of November (maybe 35-40% occupied), rest of the year would push 75%. Last 2 years, August-October has been zombie land, January, May, July & November were mediocre, March, April, June, December were great (February reserved for me to make repairs & maintenance).
The other thing that's been a killer is that international visitation - at least staying in STRs - has fallen off a cliff over the last 2 years. We used to do about 30% international visitors. Last year we had 1 international family. Our Canadian families, which used to make up most of our late winter/early spring visitors, disappeared entirely. And I know other STR operators in this area who reported the same thing, and my caretakers said their other properties were experiencing the same thing. They also said - and this mimicked what other operators told me - that their other owners were having to shift to cheaper, shorter stays and liberalized last-minute cancellations to keep any kind of occupancy, that they were experiencing more damages and lost income from late cancellations and running the homes was more time intensive because of the higher turnover levels. We held the line on a lot of those things and of course at the cost of occupancy, because I'm not willing to rent at any cost - but a lot of owners, especially ones that paid cheaper prices to buy in years past, are. So you get a race to the bottom.
If you want to make money there IMO there are 2 main avenues:
1. Very low rates and heavy cost control - self managing, self cleaning, repair & maintenance;
2. Own unicorns - heavy themes, 10 bedrooms, 5 minutes to the parks, etc.
For the time being, just owning a nice house in the area and expecting to make any money is over. Long term you're always going to have vacationers coming, because there's a lot to do, but you need to be prepared for some lean times.
Also, you don't have to take my word for it. Just do a couple of google searches on Disney attendance, wait times, Universal attendance, etc. A couple of days ago the Universal CEO said they were continuing to see a softer market in Orlando all year. Disney reported higher attendance for their fiscal third quarter, but that was the spring. The sites that monitor this stuff report that crowds continue to be zombie compared to previous years in the parks in the summer, the charts play this out, and our experience mirrors it.
Bottom line: don't listen to anyone that has something to sell you when talking about the state of the market in Kissimmee/Davenport/4 Corners, without going and finding your own data. Realtors will tell you the market is great "if things are priced right". Yeah, that is code for "if you aren't selling a house that you bought 15 years ago for $100k or taking a $50k haircut from what you paid a couple years ago, you're not selling". Just look at days on market of everything down there. Look at some of the resorts (want to see a horror show? Look at the Margaritaville resort at Kissimmee - $200k losses and foreclosures everywhere).
Skyline Properties - 6dRyan MoyerBusiness MemberProperty Manager · Orlando Kissimmee Davenport Salt Lake City, Park City · Member since 2019 · 990 posts · 1k+ votes
Demand is really not the problem. It's not been great, but not terrible either.
Demand has merely leveled off. The real problem is on the supply side.
That's a nationwide story, but to a much larger extent at Disney. Coming out of covid and that temporary demand boom the Disney market was really able to capitalize with new supply on a totally different level because of the abundance of cheap land and really refined, fortune 500 developers here. So while the Smokies might have built some new cabins to meet that temporary demand out of Covid, Orlando had the logistics and the builders to build new inventory 100x as fast.
Neighborhoods of thousands of 6+ bedroom houses going up what seemed like overnight, all over the place. They just built them so fast.
And then the other issue here is not just saturation in supply, but saturation in quality. Again, go do a Disney search on the area and look at what people are offering. In a rush to defeat that saturation more and more people just continued dumping more and more money into crazy insanely awesome theming. And then, again, the market was big and refined enough that companies formed to throw THAT up quickly. Houses aren't built with garages anymore. They're built with gamerooms with $30,000 in commercial arcade equipment. As a standard.
The baseline of what you need just to be average here is stuff that would put you in the top 1% of most markets. That's the trap most people here fall into. They don't go on Airbnb. They look at their property (or the one they're purchasing) in a vacuum. They go see it and they think to themselves "wow, this place is REALLY nice, people are going to really want to stay here". But they don't consider that, in this market, that incredible 6 bedroom home with nice furniture and some modest theming is, frankly, a bottom tier bargain basement rental property.
I've told many people struggling here before who have made that mistake that if they could take their house and drop it in the Finger Lakes or somewhere like that they'd have a top 1% property. But here, it's the 35,246th best property and it's not competing with your neighbor on one side that has a laser tag arena in the house nor the guy on the other side that has a bowling alley.
Cosmic Vacations4.9174 Reviews - Rock Star Extraordinaire · Northeast, TN · Member since 2015 · 10k+ posts · 16k+ votes5d
Quote from @Ryan Moyer:
Demand is really not the problem. It's not been great, but not terrible either.
Demand has merely leveled off. The real problem is on the supply side.
That's a nationwide story, but to a much larger extent at Disney. Coming out of covid and that temporary demand boom the Disney market was really able to capitalize with new supply on a totally different level because of the abundance of cheap land and really refined, fortune 500 developers here. So while the Smokies might have built some new cabins to meet that temporary demand out of Covid, Orlando had the logistics and the builders to build new inventory 100x as fast.
Neighborhoods of thousands of 6+ bedroom houses going up what seemed like overnight, all over the place. They just built them so fast.
And then the other issue here is not just saturation in supply, but saturation in quality. Again, go do a Disney search on the area and look at what people are offering. In a rush to defeat that saturation more and more people just continued dumping more and more money into crazy insanely awesome theming. And then, again, the market was big and refined enough that companies formed to throw THAT up quickly. Houses aren't built with garages anymore. They're built with gamerooms with $30,000 in commercial arcade equipment. As a standard.
The baseline of what you need just to be average here is stuff that would put you in the top 1% of most markets. That's the trap most people here fall into. They don't go on Airbnb. They look at their property (or the one they're purchasing) in a vacuum. They go see it and they think to themselves "wow, this place is REALLY nice, people are going to really want to stay here". But they don't consider that, in this market, that incredible 6 bedroom home with nice furniture and some modest theming is, frankly, a bottom tier bargain basement rental property.
I've told many people struggling here before who have made that mistake that if they could take their house and drop it in the Finger Lakes or somewhere like that they'd have a top 1% property. But here, it's the 35,246th best property and it's not competing with your neighbor on one side that has a laser tag arena in the house nor the guy on the other side that has a bowling alley.
100% spot on. I have a fantastic house but like you said it's just a house, with thousands of other houses.
Skyline Properties
- 1wArman AhmedPro MemberReal Estate Agent · Columbus Cleveland Dayton, OH · Member since 2024 · 2k+ posts · 904 votes
Quote from @Anisa Eni:
Hello all,
I am looking into Kissimmee, FL are for buying real estate. There are many SFH on sale with longer days on market. I am wondering how's the STR amd LTR there currently?Looking to connect with local real estate agents.
Thanks,
Anisa
Kissimmee can still work, but with homes sitting longer, I'd be careful about underwriting STR income and focus on what the property does as an LTR too. If you're open to looking outside Florida, I'd also compare it with Midwest markets like Ohio. Ohio has lower entry points and can offer more predictable rental demand, which may make the numbers easier to pencil.
- 6dAshish AcharyaBusiness MemberCPA, CFP®, PFS · FL · Member since 2017 · 5k+ posts · 3k+ votes
Anisa, I'm from Florida as well, so I'm well aware of how much insurance, property taxes, HOA costs, and local rental rules can change the numbers here.
For Kissimmee, I'd compare the same property under both an STR and LTR model before deciding which direction makes sense. For the STR side, I'd look at realistic occupancy, average daily rate, cleaning, utilities, management, furnishing replacement, seasonality, and whether the specific property is actually allowed to operate as a short-term rental. For the LTR side, I'd focus on achievable rent, vacancy, maintenance, management, and how much monthly cash flow is left after debt service.
Longer days on market may create negotiating opportunities, but I wouldn’t assume a property is a good deal just because the seller is becoming more flexible. The purchase basis still has to work under conservative rental assumptions.
From the tax side, STR and LTR can also produce very different outcomes. A qualifying STR may potentially create nonpassive losses if the average-stay and material-participation rules are met, while a traditional LTR is generally subject to the normal passive-loss rules. Cost segregation can be useful in either case, but the ability to actually use the losses matters.
I’d underwrite the property first, then choose the rental strategy rather than buying first and hoping one of them works.
Feel free to DM me, I'd be happy to send over a few STR and rental analysis resources that may help.
INVESTOR FRIENDLY CPA®5241 Reviews - Englewood, NJ · Member since 2018 · 356 posts · 61 votes4d
Reading through this thread, the core issue keeps coming back to basis. Ryan's math on that $750k home netting $65/night after fees tells the whole story. When you're buying at retail prices in a market with that much supply saturation, the strategy (STR vs LTR) almost matters less than what you paid for the property.
I buy properties at tax deed auctions in Broward County, and the acquisition basis changes everything. When you're picking up properties at 50-70% of assessed value, you have margin of safety regardless of whether you're doing short-term or long-term rentals. The math works differently when your cost basis is $200k on a property that comps at $400k.
That said, Kissimmee's specific challenges with Disney pricing and international visitor decline are real headwinds that no acquisition strategy can fully overcome. The supply saturation Ryan described, where every property needs arcade equipment and bowling alleys just to be average, creates a capital arms race that's tough to win.
Ashish's point about underwriting both scenarios first is solid advice. But I'd add that in a market this saturated, even conservative underwriting might not capture how much capital you need to投入 just to be competitive. Sometimes the better answer is finding a different market where the basis works in your favor from day one. - Rental Property Investor · Lakeland Florida · Member since 2026 · 4 posts · 2 votes3d
I would agree with what the majority have said here. I live about an hour from this market and can tell you its not a great investment, if you are looking for positive cash flow. There are definitely some spots that still can produce positive cash around but Kissimmee is not one IMO
- Real Estate Consultant · Chattanooga TN · Member since 2026 · 19 posts · 7 votes2d
Anisa, one thing I'd add before comparing STR versus LTR returns is to separate the properties where the STR option actually works from the ones where it only looks possible on paper.
Especially around a market like Kissimmee, I'd want to verify the specific jurisdiction, permitted use and any HOA/declaration restrictions for each property before putting much weight on projected STR revenue.
Once you start narrowing the search, I think the individual address matters more than the general market. Have you gotten down to particular neighborhoods or properties yet?
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