Kissimmee Vacation Rentals

Compare 308 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

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Kissimmee vacation rentals for every getaway

Dog-friendly Hot tub Internet
Golden Hour Haven
4 Bed | 3.5 Bath | Sleeps 10

Golden Hour Haven - Kissimmee, FL

$158 avg / night
Westside Wonder - Windsor at Westside
9 Bed | 6 Bath | Sleeps 20

Westside Wonder - Windsor at Westside - Kissimmee, FL

$506 avg / night
SunKissed Retreat
3 Bed | 2 Bath | Sleeps 8

SunKissed Retreat - Kissimmee, FL

$175 avg / night
Target Acquired
9 Bed | 5 Bath | Sleeps 24

Target Acquired - Kissimmee, FL

$462 avg / night
Luxury Storey Lake Condo - Storey Lake
2 Bed | 2 Bath | Sleeps 7

Luxury Storey Lake Condo - Storey Lake - Kissimmee, FL

$158 avg / night

View 303 more homes

Recent Kissimmee vacation rental reviews

Absolutely loved the home, the amenities like heated pool, the friendly ppl we met there. Would recommend to anyone.
Donna M. | Mar 2024
This rental was a delightful find. With an arcade room and a pool, it offered great entertainment. What stood out was its comfortable accommodation, easily sleeping 4+ adults. Ideal for families or groups seeking both relaxation and recreation.
Roman F. | Feb 2024
Very near Disney theme parks, ideal stays for families planning to go to Orlando area. Thank you for an excellent experience.
Huy H. | Feb 2024
Kissimmee Frequently Asked Questions

Yes, 160 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. 537 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

Top 10 Most Beautiful Lakes in the U.S.

Themed Disney World Vacation Rentals