I Think Most Investors Are Looking at Orlando the Wrong Way

Orlando, Florida

Short-Term & Vacation Rental Discussions

I Think Most Investors Are Looking at Orlando the Wrong Way

Andres Rodriguez

Member since 2025 · 27 posts · 4 votes

I might be completely off here—but I’ve been thinking about this a lot lately.

It feels like most investors analyzing Orlando are asking the wrong question.

The common approach is still:
“Does this deal make sense as a rental?”

But what if that’s not the right lens anymore?

Because when I look at what’s actually happening on the ground, Orlando doesn’t behave like a typical rental market. It behaves more like a demand-driven ecosystem.

You have:

Constant tourism flow
Convention-driven weekday demand
Massive infrastructure and entertainment expansion
New developments being designed specifically for short-term use

That combination doesn’t just support rentals—it creates velocity.

People coming in, people leaving, units constantly turning over, revenue fluctuating based on how well something is operated—not just what it is.

Which makes me wonder…

Are we underestimating how much execution matters in this market?

Because if two investors buy similar units, but one treats it like passive real estate and the other treats it like a business—those outcomes won’t even be close.

So maybe the question isn’t:
“Is Orlando a good rental market?”

Maybe it’s:
“Are you set up to operate in a market like Orlando?”

Curious if anyone else has seen this disconnect—especially from out-of-state investors underwriting deals from a distance.

300 views

Investor-friendly agents in Orlando, FL

See the agents BiggerPockets members work with in Orlando, FL.

Most Popular Reply

John UnderwoodPro Member

Investor · Greer, SC · Member since 2014 · 13k+ posts · 17k+ votes

I personally always stay on a disney owned property for the convenience of the Disney transportation system.

See this reply in the discussion

15 Replies

Jump to latestLatest

Sort by

Andrew SteffensBusiness Member
Tampa, FL · Member since 2022 · 4k+ posts · 3k+ votes
6mo
About once per week I get a call from a buyer who thinks they have a wonderful and novel idea - to buy a STR in Orlando. Basically for all of the reasons you mention, and likely they also have children so it would be a great vacation house for them too from time to time. The problem is, too many people had that same idea and supply exceeds demand. There is also a ton of hotels there as well.
[email protected]813-563-0877
Vacation Rentals of Florida53 Reviews
Website View Page
2 Reply
- JD MartinBusiness Member
  Moderator
  Rock Star Extraordinaire · Northeast, TN · Member since 2015 · 10k+ posts · 17k+ votes
  6mo
  Quote from @Andrew Steffens:
  
  About once per week I get a call from a buyer who thinks they have a wonderful and novel idea - to buy a STR in Orlando. Basically for all of the reasons you mention, and likely they also have children so it would be a great vacation house for them too from time to time. The problem is, too many people had that same idea and supply exceeds demand. There is also a ton of hotels there as well.
  
  The area is deathsville right now when it comes to STR. Too much supply, not enough demand. Nothing fancy or complicated about it. Our occupancy has fallen every year for the past 4 years, and I've got all the fancy STR doodads (premier host, (had) a perfect 10.0 review score over many reviews, great location, etc). Disney's attendance has been declining or flat for the last 3 years and we've seen the correlation in our occupancy numbers. There's too many bottom feeders and a lot of visitors just want a place to drop their bags. If you have something really unique you have a little better chance.
  Podcast Guest on Show #243
  Skyline Properties
  View Page
  1 Reply
- Hannah McDonald
  Property Manager · Orlando, FL · Member since 2021 · 22 posts · 17 votes
  6mo
  Quote from @JD Martin:
  
  Quote from @Andrew Steffens:
  
  About once per week I get a call from a buyer who thinks they have a wonderful and novel idea - to buy a STR in Orlando. Basically for all of the reasons you mention, and likely they also have children so it would be a great vacation house for them too from time to time. The problem is, too many people had that same idea and supply exceeds demand. There is also a ton of hotels there as well.
  
  The area is deathsville right now when it comes to STR. Too much supply, not enough demand. Nothing fancy or complicated about it. Our occupancy has fallen every year for the past 4 years, and I've got all the fancy STR doodads (premier host, (had) a perfect 10.0 review score over many reviews, great location, etc). Disney's attendance has been declining or flat for the last 3 years and we've seen the correlation in our occupancy numbers. There's too many bottom feeders and a lot of visitors just want a place to drop their bags. If you have something really unique you have a little better chance.
  I live in the Davenport/Four Corners area and we're seeing a massive wave of owners shifting from STR to LTR because the consistent demand just isn't there like it was 5-10 years ago. Unless you have a top-tier, highly unique property, the race to the bottom on pricing makes LTR a much more attractive play right now.
  1 Reply
- JD MartinBusiness Member
  Moderator
  Rock Star Extraordinaire · Northeast, TN · Member since 2015 · 10k+ posts · 17k+ votes
  6mo
  Quote from @Hannah McDonald:
  
  Quote from @JD Martin:
  
  Quote from @Andrew Steffens:
  
  About once per week I get a call from a buyer who thinks they have a wonderful and novel idea - to buy a STR in Orlando. Basically for all of the reasons you mention, and likely they also have children so it would be a great vacation house for them too from time to time. The problem is, too many people had that same idea and supply exceeds demand. There is also a ton of hotels there as well.
  
  The area is deathsville right now when it comes to STR. Too much supply, not enough demand. Nothing fancy or complicated about it. Our occupancy has fallen every year for the past 4 years, and I've got all the fancy STR doodads (premier host, (had) a perfect 10.0 review score over many reviews, great location, etc). Disney's attendance has been declining or flat for the last 3 years and we've seen the correlation in our occupancy numbers. There's too many bottom feeders and a lot of visitors just want a place to drop their bags. If you have something really unique you have a little better chance.
  I live in the Davenport/Four Corners area and we're seeing a massive wave of owners shifting from STR to LTR because the consistent demand just isn't there like it was 5-10 years ago. Unless you have a top-tier, highly unique property, the race to the bottom on pricing makes LTR a much more attractive play right now.
  
  I'm in 4 Corners and I might have considered that except the LTRs in the community where I am are lousy, both in the quality of the tenants and the way the properties are managed. And the price point sucks - $450k houses are getting $2300-2500 in rent. If you bought when the market crashed in 2008 you can make that work but if you bought in the last 7 or 8 years like me the prices are too low to make sense; in my own market I can pull that kind of rent on 275-300k houses. And given the way the renters beat the hell out of the houses there's no way I'd turn mine into a LTR. But the race to the bottom on STRs around here is very real.
  Podcast Guest on Show #243
  Skyline Properties
  View Page
  1 Reply
Shawn McCormickPro Member
Realtor · Central Florida-Orlando · Member since 2014 · 1k+ posts · 894 votes
6mo
@Andres Rodriguez
I agree with what you are saying. I specialize in STR as a Realtor and have a youtube channel to address much of this. And each time I have a call with an investor that wants to get in that space, I literally tell them you have to treat it like a business. That is essentially what they are buying, a turn key business and one of the biggest reasons we have so many for sale here are that people don't treat it that way.
Most buyers want a p&l to see how its performing and most sellers don't have one or don't provide it because it shows terrible numbers. There is plenty of opportunity here, but noone wants to put in the work and/or money to make their unit attractive and stand out. With around 40,000 units here, it's easy to get lost in the algorithm, and get no bookings.
Educating a buyer is key for me, I'm not here to sell a dream, I want them to be successful and sometimes they just don't want to hear it or don't realize how much work it can be.
2 Reply
John UnderwoodPro Member
Investor · Greer, SC · Member since 2014 · 13k+ posts · 17k+ votes
6mo
I personally always stay on a disney owned property for the convenience of the Disney transportation system.
2 Reply
- Andres Rodriguez
  OP
  Member since 2025 · 27 posts · 4 votes
  6mo
  Quote from @John Underwood:
  
  I personally always stay on a disney owned property for the convenience of the Disney transportation system.
  
  Funny you say that! The projects I have both will be part of the Disney programs, like Disney resort and vilas as well as the Disney Good neighbor hotel. Allowing us to have the same benefits of staying at a Disney Property.
  1 Reply
- John UnderwoodPro Member
  Investor · Greer, SC · Member since 2014 · 13k+ posts · 17k+ votes
  6mo
  Quote from @Andres Rodriguez:
  
  Quote from @John Underwood:
  
  I personally always stay on a disney owned property for the convenience of the Disney transportation system.
  
  Funny you say that! The projects I have both will be part of the Disney programs, like Disney resort and vilas as well as the Disney Good neighbor hotel. Allowing us to have the same benefits of staying at a Disney Property.
  
  That's awesome.
  0 Reply
Rafael RodriguezBusiness Member
Member since 2025 · 10 posts · 3 votes
6mo
I fully agree with Andre’s perspective. I’ve seen firsthand how quickly it evolves compared to most others markets. The pace of change here continuously reshapes both opportunities and the strategies needed to capture them. Many investors enter with goals that would have worked flawlessly three to five years ago, yet those same approaches often clash with today’s realities, leading to misaligned analysis, missed opportunities and frustration.
Orlando is a market that rewards operators, not spectators. Successful analysis here should go beyond the numbers and account for operational capability, team systems, automation, and guest experience design. Without those elements, distant investors can find themselves puzzled by performance gaps that their P&L can’t explain.
0 Reply
John RacinePro Member
Rental Property Investor · Casselberry, FL · Member since 2008 · 130 posts · 76 votes
6mo
I love the Orlando market and you are spot on here. I know people who look at the market that way and then the true operators, who ARE running it like a business, are executing at a high level.
When I look at a property here, I look at it from every sense I can:
1. Can it be a long term rental and if so, what rent could I get compared to expenses
2. Can it be a mid-term rental and if so, is there demand for it and what could I make vs expenses
3. Can it be a short term rental and if so, is it zoned for it and what does my comp set look like and what is my upside vs the expenses
4. Could I do an lease option to an end buyer and if so, what structure and pricing would I need to do that
I think opportunity here is MASSIVE but too few look at the options myopically instead of globally.
1 Reply
Ryan MoyerBusiness Member
Property Manager · Orlando Kissimmee Davenport Salt Lake City, Park City · Member since 2019 · 996 posts · 1k+ votes
6mo
I made a post about this recently on my personal page. At my Kissimmee property we are still within shouting distance of our 2022 numbers.
But it takes more work, and a different approach.
When I have a 2 night orphan gap on a 9br property, I fill it, even at a discounted price. I take same day bookings. When someone asks for a discount, I consider it if I think I will have trouble filling those dates at full price anyway. When the roof leaks right before Christmas, I send a handyman out to crudely patch that thing up for $150 so I can postpone the real roof work to January, and not have to cancel expensive holiday bookings.
On the flipside, I have clients I manage for that want to run their place like it's 2010. Longer minimum stays, less aggressive discounting, less aggressive orphan day fills, old school rental agreements,s etc.
And that's fine, but those folks just have to understand (and I tell them up front) that it is going to impact returns, and that my property that is run differently is not a comp for them.
Unfortunately, I don't meet most of these people until after they make the purchase. But pre-purchase, it's important to define your main goal (is it ROI, or personal use, or long term appreciation, or tax advantages, etc) and how you want to run the property, and underwrite in line with that.
If you want to run it in a style where you can keep your sentimental grandmmother's lamp in the home and not have as much maintenance that's totally fine, but you need to underwrite more conservatively because many of the comps you're underwriting against probably aren't operating the same way.
Cosmic Vacations4.9175 Reviews
Website View Page
1 Reply
- JD MartinBusiness Member
  Moderator
  Rock Star Extraordinaire · Northeast, TN · Member since 2015 · 10k+ posts · 17k+ votes
  6mo
  Quote from @Ryan Moyer:
  
  I made a post about this recently on my personal page. At my Kissimmee property we are still within shouting distance of our 2022 numbers.
  But it takes more work, and a different approach.
  When I have a 2 night orphan gap on a 9br property, I fill it, even at a discounted price. I take same day bookings. When someone asks for a discount, I consider it if I think I will have trouble filling those dates at full price anyway. When the roof leaks right before Christmas, I send a handyman out to crudely patch that thing up for $150 so I can postpone the real roof work to January, and not have to cancel expensive holiday bookings.
  On the flipside, I have clients I manage for that want to run their place like it's 2010. Longer minimum stays, less aggressive discounting, less aggressive orphan day fills, old school rental agreements,s etc.
  And that's fine, but those folks just have to understand (and I tell them up front) that it is going to impact returns, and that my property that is run differently is not a comp for them.
  Unfortunately, I don't meet most of these people until after they make the purchase. But pre-purchase, it's important to define your main goal (is it ROI, or personal use, or long term appreciation, or tax advantages, etc) and how you want to run the property, and underwrite in line with that.
  If you want to run it in a style where you can keep your sentimental grandmmother's lamp in the home and not have as much maintenance that's totally fine, but you need to underwrite more conservatively because many of the comps you're underwriting against probably aren't operating the same way.
  
  All good points. One thing I would add is that in this market you really need to either have unicorns or low prices. 9br homes are unicorns - yes, there's more than one out there but relatively speaking to the market it's a low supply commodity. Anyone who is in my bandwidth - 3/2s to 5/3s - either has to accept lower nightly prices and higher levels of accommodating things or accept lower levels of occupancy, because the market is completely oversaturated in this demographic. Because mine is also "my house" there are things I won't countenance that pushes my occupancy lower, such as no pets (I have a dog so I don't want anyone else's pet in my house), no 2 night weekend only stays (to discourage partyers that would disturb my neighbors), etc. No question I could increase my occupancy if I dropped my prices much lower, or let people bring pets, etc. but it's not worth it to me - and of course the point is that before things got really saturated like it is now you didn't have to run a place like a flophouse just to keep it occupied.
  In my case, I don't need to rent my house out, so it's hard to consider it a pure investment but more of a "cost offset" investment. For me, it's just got to the point that as Jay says "the juice isn't worth the squeeze", and if I'm not going to rent it out then I don't need to be in the location I'm in. Assuming I sell this year I'm going to probably look more towards Lake Wales, Avon Park, Frostproof, etc. I don't want to get too far south away from my father (my principal concern on location) but just far enough south that the park traffic & visitors are non-existent.
  Podcast Guest on Show #243
  Skyline Properties
  View Page
  0 Reply
Jorge VazquezBusiness Member
Real Estate Broker · Tampa, FL · Member since 2017 · 1k+ posts · 700 votes
6mo
I’ve owned short term and long term rentals for over 20 years and I’ve seen this in Orlando just like in Tampa. I’ve always focused more on stable demand instead of chasing pure tourism like the beach or Busch Gardens areas. Corporate rentals and workforce housing hold up better because that demand comes from jobs, not seasons. Same with location, I don’t chase the flashy areas where the numbers barely work, I stick to the “salmon,” not the big fish. Some of my best short term rentals were affordable spots near Ybor, not South Beach type areas. Less hype, more consistency, and way less stress when things shift. I’m not saying don’t go after tourism, just stress test your deal using corporate rental numbers as your worst case so you’re covered, and always look to build equity into the property with an extra room, office, or flexible layout so you’ve got multiple ways to win.
Graystone Investment Group519 Reviews
Website View Page
0 Reply
Adrian Lammersdorf-SciollBusiness Member
Realtor · FL · Member since 2020 · 234 posts · 101 votes
5mo
I do agree with you here. I think most investors looking to invest in Orlando just want an easy rental, but don't realize you have to really dig for the right deal, and you have to be more proactive as well and look into doing creative financing, pad split, or other adding value/units to increase rent. I have been able to find plenty of cash flowing deals over the past 5 years, it just takes a little more work. I do think that people expectations are wayyy to high for the amount of work they want to put in, and that is the real issue.
[email protected]561-305-2404
Thomas Lynne Realty528 Reviews
Website View Page
1 Reply

Join the conversationCreate a free account to reply, vote on answers and follow this thread.

Log In Join for Free