Kissimmee Vacation Rentals

Compare 209 vacation rentals. Enter your trip dates to get started.
USA > Florida > Kissimmee

Make Kissimmee your next getaway—choose from 209 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


Condo rentals

View 92 Condo rentals

House rentals

View 78 House rentals


View 32 Townhouses

Kissimmee vacation rentals for every getaway

Dog-friendly Hot tub Internet
Pembridge Charm Villa 3D Tour
4 Bedroom | 2.5 Bath | Sleeps 11

Pembridge Charm Villa - Kissimmee, FL

From $114
Caribe Cove Resort 40405 3D Tour
3 Bedroom | 2 Bath | Sleeps 6

Caribe Cove Resort 40405 - Kissimmee, FL

From $74
Bright & Breezy 3D Tour
3 Bedroom | 2.5 Bath | Sleeps 6

Bright & Breezy - Kissimmee, FL

From $96
Caribe Cove Resort 30108 3D Tour
2 Bedroom | 2 Bath | Sleeps 6

Caribe Cove Resort 30108 - Kissimmee, FL

From $93
Caribe Cove Resort 50204 3D Tour
3 Bedroom | 2 Bath | Sleeps 8

Caribe Cove Resort 50204 - Kissimmee, FL

From $74

View 204 more homes

Recent Kissimmee vacation rental reviews

We really enjoyed staying at this home. The pictures matched the home, all rooms were big and comfortable, we were expecting tight spaces. It does have normal wear and tear on some items, like some ripped chairs, the pool cues for the pool table were missing tips so was very hard to play with, one of the refrigerators struggled to keep cold, we used it as our drink fridge but the second one was perfect. Some information would have been nice, like what the garbage process was, and the schedule of the pool heater. We will definitely stay at this home again. Thanks!
WILL T. | Nov 2021
We loved this condo. It was clean and nicely furnished!! We loved that it was so close to Disney World.
Cynthia Anne S. | Nov 2021
We had a great time! My only issue was that the tv in the small room doesn't work and didn't have a remote. But everything was great! We will stay again.
Melissa B. | Nov 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.

Kissimmee travel inspiration

Top 10 Most Beautiful Lakes in the U.S.

Themed Disney World Vacation Rentals

Photo credit: Henry Hazboun via Shutterstock