Kissimmee Vacation Rentals

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USA > Florida > Kissimmee

Make Kissimmee your next getaway—choose from 349 great vacation rentals

With geography unlike any other, the Sunshine State combines emerald-green waters, swamplands, and inland cities. If you’re looking for a blend of both world-class tourist attractions and small-town charm, our Kissimmee vacation rentals are the perfect choice for you! Whether you're planning a relaxing retreat or an adventure-filled experience, our vacation homes serve as the perfect home base as you explore all that the eventful Central Florida region has to offer. 

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

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House rentals

View 148 House rentals
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Condo rentals

View 102 Condo rentals
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Townhouses

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Kissimmee vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Remington View Retreat
4 Bedroom | 3 Bath | Sleeps 10

Remington View Retreat - Kissimmee, FL

$166 avg / night
Bright and Cozy Escape - The Hamlets
5 Bedroom | 3 Bath | Sleeps 10

Bright and Cozy Escape - The Hamlets - Kissimmee, FL

$206 avg / night
Tropical Oasis - Trafalgar Village Resort
4 Bedroom | 3 Bath | Sleeps 8

Tropical Oasis - Trafalgar Village Resort - Kissimmee, FL

$179 avg / night
House of Mouse
4 Bedroom | 2.5 Bath | Sleeps 8

House of Mouse - Kissimmee, FL

$177 avg / night
Sunrise Magic - Emerald Island Resort
6 Bedroom | 4.5 Bath | Sleeps 14

Sunrise Magic - Emerald Island Resort - Kissimmee, FL

$259 avg / night

View 344 more homes

Recent Kissimmee vacation rental reviews

A little bit pricey!! but safety is a must, also close to everything!!! Traffic is a bummer in Orlando but plan to leave early.
Paul L. | Nov 2022
Room for the family to rest, relax and play games.
Deanna E. | Nov 2022
Home is large and very clean and convenient to stores and the parks. The amenities were great at the resort
Cathy B. | Nov 2022
Kissimmee Frequently Asked Questions

Yes, 26 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. 103 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

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 and the comforts of home! 

Old Town Kissimmee

Arts, culture, and entertainment come alive in Old Town! The outdoor shopping mall and amusement park offer 18 amusement rides (including both a merry-go-round and roller coasters), 10 restaurants, and upwards of 75 specialty boutiques. The brick streets come alive every weekend with a parade of hundreds of hot rods and classic cars during the Nite Car Cruise. 

Old Town is home to an arcade, laser tag, and even a shooter alley so you try your luck at some classic arcade games! Brave travelers can visit the haunted house and ghost tours at the Legends Dark Amusements, while those hoping for a more family-friendly experience can crash into each other at Happy Days Extreme Bumper Cars. With something for everyone, Old Town Kissimmee offers fun - with a little flair - for the whole family! 

Day trips from Kissimmee, FL

Our diverse selection of Kissimmee vacation rentals vary in size and included amenities, but each home boasts a location that is 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. 

Outdoor adventures in Kissimmee, FL

If you're looking for an outdoor adventure or hoping for a bit of an adrenaline rush during your stay, you're in luck! Tee off at Kissimmee golf courses, including the Remington Golf Club, or view the city by sky in a hot air balloon with Thompson Aire. Discover the Florida Everglades and alligators on an airboat ride with Boggy Creek Airboat Rides, an unforgettable experience that is guaranteed to amaze guests of all ages! 

Invite your friends, pack your bags, and leave your worries behind when you come to one of our Kissimmee vacation homes. This charming town promises an exciting getaway full of adventure and family-friendly fun that you'll remember for years to come.

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Photo credit: Henry Hazboun via Shutterstock