Kissimmee Vacation Rentals

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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

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House rentals

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Condo rentals

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Townhouses

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Kissimmee vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Paradise Dream Vacation
5 Bed | 5.5 Bath | Sleeps 12

Paradise Dream Vacation - Kissimmee, FL

$299 avg / night
Magic Views Villa
4 Bed | 4.5 Bath | Sleeps 8

Magic Views Villa - Kissimmee, FL

$211 avg / night
4.21 (19)
Fantasy Family Escape - Encore at Reunion Resort
8 Bed | 7 Bath | Sleeps 19

Fantasy Family Escape - Encore at Reunion Resort - Kissimmee, FL

$507 avg / night
4.36 (33)
Luxury Storey Lake Condo - Storey Lake
2 Bed | 2 Bath | Sleeps 7

Luxury Storey Lake Condo - Storey Lake - Kissimmee, FL

$187 avg / night
4.49 (67)
The Cozy Cove
3 Bed | 3 Bath | Sleeps 8

The Cozy Cove - Kissimmee, FL

$248 avg / night

View 219 more homes

Recent Kissimmee vacation rental reviews

Close to Disney. Beds were comfy. Nice large clean condo.
Dee C. | May 2025
We were a family of 12 on a Disney/Universal vacation: 9 adults and 3 children. The configuration of rooms was perfect for our group - there was even room for more kids. We especially liked the common area on the second floor because it served as a place for the kids to hang out that was close to the parents. The bedrooms were large and the beds were comfortable. There were plenty of bathrooms and all were clean and well stocked with towels and toiletries. The kitchen was big and had lots of pantry space for our food. We didn't cook there much so we didn't need a lot of kitchen equipment but it seemed like there was a lot available. The pool was nice. It was heated per our request. We enjoyed the spa and were thankful for the child barrier. One nice addition would be some pool toys. The game room was fun and our younger kids especially enjoyed it. We stopped at the clubhouse when we checked in and the man at the desk was very friendly. There are mini golf courses, a pool, and snack bar. They looked nice but we didn't have time to take advantage of them. The house is close (10-15 minutes) to a lot of restaurants, retail, and grocery stores. And it's close to the main highway (192) that takes you to all things Disney. We drove 20-30 minutes to the parks each day (which included some traffic) so getting to and from was easy. Universal is farther, around 40 minutes. I only had email interactions with Vacasa but they were all professional, responsive, and helpful. Two minor complaints: The driveway is said to hold 4 cars which technically it does, but it's a tight fit. And there was a problem with an animal getting into the garbage at the houses around the cul-de-sac during the night. A better system for keeping the animals out (besides the elastic cords) would be helpful. Picking up the garbage more frequently would help, too. Overall this house was perfect for our use and I would highly recommend it!
Roni F. | May 2025
Love! Love! Love the house! ❤️❤️❤️
Sean K. | Apr 2025
Kissimmee Frequently Asked Questions

Yes, 133 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. 430 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.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional 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

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