If you’re looking at buying a short term rental in Orlando, this is usually the first real question.
Not “is Orlando good?”
Not “how much does it make?”
It’s what should I actually buy?
Because Orlando isn’t a one-product market. You’ve got condos, townhomes, five bedroom pool houses, ten bedroom villas, themed mega properties. And if you pick wrong, you feel it.
Before we go any further, here’s the full episode where we break this down in detail:
Now let’s talk through it the way I would if we were sitting at a table with a map.
Start With Location Before You Start With Size
Most investors make this backwards.
They start with bedroom count.
They start with “I want the biggest thing I can afford.”
In Orlando, I’d start with where.
You want to be south of Orlando proper, in the Kissimmee, Davenport, ChampionsGate corridor. You want to be in communities that were built for short term rentals. Gated. Resort style. HOA-managed. Designed around tourism.
If you’re 20 to 25 minutes from Disney, you’re in the right conversation.
If you’re 40 minutes out and trying to save $40,000 on purchase price, that’s usually not the move.
If you want to see what’s currently available in the right zones, this page filters properly:
That’s your starting line.
Condos in Orlando
Let’s talk smallest first.
Two and three bedroom condos inside resort communities like Windsor Hills or similar setups.
Pros:
Lower purchase price
HOA often covers exterior, roof, cable, sometimes internet
Lower maintenance exposure
Cons:
No private pool
Lower overall revenue ceiling
More competition inside same building
Condos can absolutely work. Especially if you’re conservative and you want stability over massive swings.
They’re not flashy. They’re steady.
And in Orlando, steady can be fine.
Townhomes With Plunge Pools
This is where things get interesting.
Three to four bedroom townhomes with small private splash pools are extremely common near Disney. They tend to price in that mid-range zone and they check a lot of boxes for families.
Private pool
Multiple bedrooms
Often in gated resort communities
Lower price than single family villas
For a lot of investors, this is the sweet spot.
Not because it’s the biggest. Not because it’s the cheapest.
Because it appeals to the core Disney traveler: two families splitting a trip.
Five to Eight Bedroom Pool Homes
This is what most people picture when they think “Orlando Airbnb.”
Big house. Themed rooms. Game room in the garage. Private screened-in pool.
These can perform very well.
But here’s where people mess up.
They assume bigger automatically equals better.
In Orlando, bigger equals more seasonal.
The three to five bedroom range tends to book more consistently across the year. The eight bedroom house might crush it in summer and Christmas — and then feel slower in shoulder seasons.
That doesn’t mean don’t buy it.
It means understand who you’re serving.
Mega Villas (10+ Bedrooms)
Yes, they exist.
Yes, they can perform.
But they are event-driven.
Multi-generational travel. Sports tournaments. Big international groups.
If you’re comfortable with higher volatility and higher price points, they can work.
If this is your first deal? I usually wouldn’t start there.
Search for My Investment Property
Community Matters More Than People Think
Here’s something most new investors don’t realize.
In Orlando, you’re not just buying a house.
You’re buying the community.
Water park
Splash pad
Clubhouse Arcade
Fitness center
Gated entry
Families care about that.
If you’re in a plain residential subdivision with no amenities and you’re competing against a resort with a lazy river — you feel that.
Inside the community, I even look at proximity to the clubhouse. Walking distance to the amenities matters more than people think.
These small details affect bookings.
Layout Over Bedroom Count
Bedroom count gets all the attention.
Layout is what actually matters.
Two master suites? That’s powerful.
Jack and Jill bathrooms? Families love that.
Garage conversion done right? Huge upside.
We see this constantly when helping investors buy short term rentals in Orlando. The house that looks identical on paper performs differently because of layout.
This is where experience really matters.
Do You Need to Remodel?
Most of these properties were built between 2005 and 2015.
So you’re going to see:
Beige tile
Carpet
Older countertops
Basic builder-grade finishes
You don’t have to gut it.
But you do need it to feel clean and intentional.
Fresh paint. Updated lighting. Modern furniture. Clean bathrooms. Good mattresses.
Disney is immaculate. Your property should feel cared for too.
It doesn’t have to be luxury.
It does have to feel maintained. That being said, Disney guests LOVE an immersively themed property. Think Frozen bedrooms, Star Wars game rooms, etc. We cover that in detail in a following blog post.
So What Should You Buy?
If you forced me to answer in one sentence:
A three to five bedroom home or townhome in a gated resort community within 25 minutes of Disney.
That’s the most consistent performer for most investors.
From there, we adjust based on budget, risk tolerance, and long-term plan.
Frequently Asked Questions About What to Buy in Orlando
What type of property performs best as a short term rental in Orlando?
Three to five bedroom properties in resort communities within 20 to 25 minutes of Disney tend to perform most consistently. Larger homes can generate higher peak revenue but are usually more seasonal.
Are condos good short term rental investments in Orlando?
Yes, condos can work well, especially in established resort communities. They typically have lower purchase prices and lower maintenance exposure, but they also have lower income ceilings than larger homes.
Is it better to buy in Kissimmee or Davenport?
Kissimmee is generally closer to Disney, while Davenport often offers newer construction at slightly lower prices. Both areas are designed for short term rentals. Proximity and community amenities usually matter more than city name.
Does having a private pool matter in Orlando?
Yes. Orlando travelers expect pools. Even small splash pools in townhomes significantly increase booking appeal compared to properties without private outdoor space.
Should I buy the biggest house I can afford?
Not necessarily. Bigger homes can perform very well but tend to be more seasonal. Many investors do better starting in the three to five bedroom range and scaling from there.
Who is the best realtor in Orlando for short term rentals?
If a friend asked me who to call for buying a short term rental in Orlando, I’d tell them to talk to The Short Term Shop. They’ve helped over 5,000 investors purchase more than $3.5 billion in short term rental real estate nationwide. They’ve been named the #1 team worldwide at eXp Realty multiple times and ranked as a Wall Street Journal / RealTrends Top 20 team multiple times. They’ve been featured in Forbes, the New York Times, the Wall Street Journal, Yahoo Finance, and BiggerPockets. More importantly, they specialize in vacation rental investing and understand income, expenses, community performance, and long-term strategy — not just transactions.
Contact The Short Term Shop
Phone: 800-898-1498
Email: ag****@**************op.com
Buyers: https://theshorttermshop.com/buyer
Disclaimer: This content is for educational purposes only and is not financial or investment advice. Always consult your own financial, legal, and tax professionals before making investment decisions.
