Kissimmee Vacation Rentals

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USA > Florida > Kissimmee

Make Kissimmee your next getaway—choose from 193 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 condo rentals, house rentals, townhouses, and more

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Condo rentals

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House rentals

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Townhouses

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Kissimmee vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Villa Winny 3D Tour
5 Bedroom | 5 Bath | Sleeps 12

Villa Winny - Kissimmee, FL

From $139
Caribe Cove Resort 50204 3D Tour
3 Bedroom | 2 Bath | Sleeps 8

Caribe Cove Resort 50204 - Kissimmee, FL

From $74
Caribe Cove Resort 50503 3D Tour
3 Bedroom | 2 Bath | Sleeps 6

Caribe Cove Resort 50503 - Kissimmee, FL

From $74
Mickey's Magic at Windsor Hills Resort 3D Tour
3 Bedroom | 3 Bath | Sleeps 8

Mickey's Magic at Windsor Hills Resort - Kissimmee, FL

From $99
A Kiss of Sunshine 3D Tour
9 Bedroom | 6 Bath | Sleeps 22

A Kiss of Sunshine - Kissimmee, FL

From $239

View 188 more homes

Recent Kissimmee vacation rental reviews

Very satisfied, great value. Vacasa was easy to use.
William M. | Sep 2021
Todo muy hermoso, muy amable la atención recibida.
Maria Salome F. | Sep 2021
Beautiful just like the pictures even better spaceus comfortable!!!
Audrey B. | Sep 2021

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.

Discover Kissimmee

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Photo credit: Henry Hazboun via Shutterstock