Kissimmee Vacation Rentals

Compare 289 vacation rentals.
USA > Florida > Kissimmee

Make Kissimmee your next getaway

With lakes, family-friendly attractions, and convenient access to Orlando and Disney World, Kissimmee vacation home rentals make the perfect backdrop for your next trip. Step into the Sunshine State’s beautiful weather and dive into a wonderland of activity. Find a vacation home or condo rental with plenty of room for your crew and amenities like hot tubs, private pools, water views, on-site golf courses, tennis courts, and shuttle services to nearby amusement parks.

Explore Kissimmee house rentals, condo rentals, townhouses, and more


House rentals

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Condo rentals

View 79 Condo rentals


View 72 Townhouses

Popular amenities for Kissimmee vacation rentals

Dog-friendly Hot tub Internet
Luxury Storey Lake Condo - Storey Lake
2 Bedroom | 2 Bath | Sleeps 7

Luxury Storey Lake Condo - Storey Lake - Kissimmee, FL

$138 avg / night (excludes fees and taxes)
Golden Hour Haven
4 Bedroom | 3.5 Bath | Sleeps 10

Golden Hour Haven - Kissimmee, FL

$149 avg / night (excludes fees and taxes)
Magic Mirage
6 Bedroom | 6 Bath | Sleeps 14

Magic Mirage - Kissimmee, FL

$211 avg / night (excludes fees and taxes)
Westside Wonder - Windsor at Westside
9 Bedroom | 6 Bath | Sleeps 20

Westside Wonder - Windsor at Westside - Kissimmee, FL

$407 avg / night (excludes fees and taxes)
The Jungle Oasis
5 Bedroom | 3 Bath | Sleeps 12

The Jungle Oasis - Kissimmee, FL

$269 avg / night (excludes fees and taxes)

View 284 more homes

Recent Kissimmee guest reviews

Very good property, well maintained, closer to the parks than what I thought, money well spent
Victor C. | Jun 2024
Simply amazing đź‘Ź. My family and I had an awesome time staying here. Will recommend to anyone whose planning a family with a party of 12 or more. This will be the place for you.
Denise M. | Jun 2024
I loved that is was spacious and there was plenty of room in common areas to accommodate family time. The Bedrooms and bathrooms also aloud privacy and quiet time. Absolutely the best vacation home I’ve been at!
Lori T. | Jun 2024
Kissimmee vacation rental FAQ

Yes, 144 of our Kissimmee homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 490 of our Kissimmee vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >

Some of the most popular amenities in our Kissimmee vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Kissimmee team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Kissimmee, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons cleaning
Professional cleaning

Explore our Kissimmee, FL, vacation rentals

Save your spot for the happiest place on earth with Kissimmee vacation rentals. Just outside the Orlando area, Kissimmee rests in the central hub of theme park attractions and entertainment. Spend your getaway savoring day trips out to amusement parks like Disney World or Universal Studios, hang out by Lake Tohopekaliga, or explore downtown Kissimmee’s Old Town, a vintage-style shopping and dining district.

Treat yourself to an adventure-filled experience and a family vacation your kids will never forget. Stay just a few miles from Disney while enjoying peace, quiet, and privacy with a vacation home all your own. With incredible amenities, plenty of space, and no shortage of things to do, you’ll have excitement at your fingertips.

Where is Kissimmee, FL?

Kissimmee sits just 23 miles south of the bustling metropolis of Orlando, but the atmosphere that you'll find in this quaint and charming town is remarkably different from Orlando's more lively city vibe. Although you won’t see any skyscrapers, downtown Kissimmee’s unique shops, restaurants, and historic Old Town are ideal for travelers wanting to experience a piece of the action while enjoying the quiet neighborhood, the comforts of home, and resort-style amenities.

Things to do in Kissimmee, FL

Relaxing, thrilling, and scenic, Kissimmee offers something for everyone/ Here, you’ll find adventures ranging from amusement parks, golf courses, alligator parks, and lakefront fun. 

What is Kissimmee known for?

Kissimmee is known for its fantastic proximity to major amusement parks like Disney World, Universal Studios, and SeaWorld Orlando, as well as its waterfront access to Lake Tohopekaliga, one of the most famous bass fishing lakes in the United States. It is also known for its prime family-friendly vacation rental and resort offerings, including resort amenities like waterfront views, on-site golf courses, kid-friendly and private pools, hot tubs, game rooms, and shuttle services to surrounding theme parks.

Day trips from Kissimmee, FL

Our diverse selection of Kissimmee vacation rentals vary in size and include amenities, but each home boasts a location conveniently close to well-known family attractions like Walt Disney World Resort, SeaWorld, and Universal Orlando Resort. Spend your day exploring the parks or just seeing Orlando's many sights, before heading back to your relaxing rental for a good night's sleep. 

During your stay, make sure to take some time and explore the surrounding area. Go pick citrus fruits in Haines City or shop at one of the many farmer's markets, before heading back to your vacation rental to make a delicious homemade meal using local ingredients from the market. Cool off on a hot summer's day with a splash at the water park in Reunion, only 15 miles away. 

Kissimmee travel inspiration

Top 10 Most Beautiful Lakes in the U.S.

Themed Disney World Vacation Rentals