Kissimmee Vacation Rentals

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USA > Florida > Kissimmee

Make Kissimmee your next getaway—choose from 282 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


House rentals

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Condo rentals

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Kissimmee vacation rentals for every getaway

Dog-friendly Hot tub Internet
Dream in Paradise Palm 3D Tour
4 Bedroom | 3 Bath | Sleeps 8

Dream in Paradise Palm - Kissimmee, FL

From $114
Pembridge Charm Villa 3D Tour
4 Bedroom | 2.5 Bath | Sleeps 11

Pembridge Charm Villa - Kissimmee, FL

From $160
Caribe Cove Condominiums 10102 3D Tour
2 Bedroom | 2 Bath | Sleeps 5

Caribe Cove Condominiums 10102 - Kissimmee, FL

From $85
Caribe Cove Condominiums 30307 3D Tour
2 Bedroom | 2 Bath | Sleeps 6

Caribe Cove Condominiums 30307 - Kissimmee, FL

From $64
Mouse House 3D Tour
5 Bedroom | 4 Bath | Sleeps 12

Mouse House - Kissimmee, FL

From $132

View 277 more homes

Recent Kissimmee vacation rental reviews

ERIKA C. | May 2022
Everything but the neighbors were noisy 2 nights in a row. Although not a fault of the home or Lakeside community
Gina S. | May 2022
This condo located at Caribe Cove was absolutely amazing. I cannot even begin to describe how beautiful it is. Flooring was stunning and the furniture was top notch and so comfortable. I slept so well at night. The home was sparkling clean and a real tribute to housekeeping and maintenance. They really know what they are doing at Caribe Cove. Everyone I saw was extremely friendly from my checkin with the desk to anyone of the staff that I encountered along the way. Checkout was top notch as well. I cannot recommend Caribe Cove enough and this home was amazing as well. Beautiful is all I can say! Be sure to stop and spend some time at Caribe Cove and be sure to stay in 3104.
Susan V. | May 2022

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.

Kissimmee travel inspiration

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Photo credit: Henry Hazboun via Shutterstock