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Kissimmee Vacation Rentals

1 - 42 of 54 rentals
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Winter Escape - Kissimmee, FL Vacation Rental

Winter Escape

Kissimmee, FL
4 Bed 3.5 Bath Sleeps 10
- - - - - - - - 130 180 180 135 135 135 135 130 -
Legacy Dunes 9102 - Kissimmee, FL Vacation Rental

Legacy Dunes 9102

Kissimmee, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Winter Hideaway - Kissimmee, FL Vacation Rental

Winter Hideaway

Kissimmee, FL
4 Bed 3.5 Bath Sleeps 8
- - - - - - - - - 170 180 135 135 130 - - -
Sunshine Daydream Villa - Kissimmee, FL Vacation Rental

Sunshine Daydream Villa

Kissimmee, FL
5 Bed 3 Bath Sleeps 12
- - - - - - - - - - - - - - - - -
Emerald Oasis - Kissimmee, FL Vacation Rental

Emerald Oasis

Kissimmee, FL
4 Bed 3 Bath Sleeps 10
- - - - - - - - - - - - - 115 115 115 135
Lucaya Village Luxury - Kissimmee, FL Vacation Rental

Lucaya Village Luxury

Kissimmee, FL
4 Bed 3.5 Bath Sleeps 10
- - 99 - - - - - - - - - - - 99 99 -
Polynesian Hideaway - Kissimmee, FL Vacation Rental

Polynesian Hideaway

Kissimmee, FL
1 Bed 1 Bath Sleeps 2
- - - - - - - 70 - - - - - - - - -
Golden Villa - Kissimmee, FL Vacation Rental

Golden Villa

Kissimmee, FL
4 Bed 3 Bath Sleeps 8
- - - - - - - - - - - - 115 115 115 - -
Snow White's Dream - Kissimmee, FL Vacation Rental

Snow White's Dream

Kissimmee, FL
3 Bed 2 Bath Sleeps 7 (6 Adults Max)
- - - - - - 99 160 160 195 195 160 160 155 - - -
Windsor Palms (#2374) - Kissimmee, FL Vacation Rental

Windsor Palms (#2374)

Kissimmee, FL
3 Bed 2.5 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Encantada Resort (#3146) - Kissimmee, FL Vacation Rental

Encantada Resort (#3146)

Kissimmee, FL
3 Bed 2.5 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Family Ridge Villa - Davenport, FL Vacation Rental

Family Ridge Villa

Davenport, FL
4 Bed 3 Bath Sleeps 8
- - - - - - - 115 120 155 155 120 120 115 - - -
Vista Villa - Davenport, FL Vacation Rental

Vista Villa

Davenport, FL
5 Bed 4.5 Bath Sleeps 10
- 140 140 - - - - - - - - - - - - - -
Forest View Chateau - Davenport, FL Vacation Rental

Forest View Chateau

Davenport, FL
7 Bed 4.5 Bath Sleeps 14
- - - - - - - - - - - - - - - - -
Reunion  Sunset - Reunion, FL Vacation Rental

Reunion Sunset

Reunion, FL
3 Bed 3 Bath Sleeps 8
- 90 - - - 90 99 99 - - - 99 - - - - -
557 Miramar Villa - Davenport, FL Vacation Rental

557 Miramar Villa

Davenport, FL
4 Bed 3.5 Bath Sleeps 9
- - - 120 90 90 90 99 99 135 135 99 - - - - 135
Esprit Palm Villa - Davenport, FL Vacation Rental

Esprit Palm Villa

Davenport, FL
4 Bed 2 Bath Sleeps 8
- - - - - - - - - - - - - - - - -
Windstar Villa - Davenport, FL Vacation Rental

Windstar Villa

Davenport, FL
4 Bed 3 Bath Sleeps 8
- - - - - - - - - - - - - - - - -
4 Corners Getaway  - Davenport, FL Vacation Rental

4 Corners Getaway

Davenport, FL
4 Bed 3.5 Bath Sleeps 8
- - - - - - - - - - 115 115 115 115 115 115 135
Sunshine Grove - Clermont, FL Vacation Rental

Sunshine Grove

Clermont, FL
4 Bed 2 Bath Sleeps 8
- - - - - - - - - - - - - - - - -
The Terraces On The Green - Reunion, FL Vacation Rental

The Terraces On The Green

Reunion, FL
3 Bed 2 Bath Sleeps 8
- 70 - - - - - - - - - - - - - - -
Sunset Terrace Villa - Davenport, FL Vacation Rental

Sunset Terrace Villa

Davenport, FL
6 Bed 5.5 Bath Sleeps 12
- - - - - - 200 200 200 200 200 200 200 200 - - -
Welcoming Palms - Davenport, FL Vacation Rental

Welcoming Palms

Davenport, FL
4 Bed 3 Bath Sleeps 8
- - - - - - - - - - - - - - - - -
Villa Palama - Davenport, FL Vacation Rental

Villa Palama

Davenport, FL
5 Bed 4.5 Bath Sleeps 10
- - - - - - - - - - - - - - - - -
Serene Splendor - Davenport, FL Vacation Rental

Serene Splendor

Davenport, FL
4 Bed 3.5 Bath Sleeps 7
- - - - - - - - - - - - - - - - -
Coral Days - Davenport, FL Vacation Rental

Coral Days

Davenport, FL
4 Bed 3 Bath Sleeps 8
- - - 115 - - - - - - - - - - - - -
Solterra (#5120) - Davenport, FL Vacation Rental

Solterra (#5120)

Davenport, FL
5 Bed 4.5 Bath Sleeps 10
- - 145 - - - - - - - - - - - - 145 -
Sundrop Villa - Davenport, FL Vacation Rental

Sundrop Villa

Davenport, FL
4 Bed 3 Bath Sleeps 8
- - - - - - - - - - - - - - - - -
Turtle Paradise - Clermont, FL Vacation Rental

Turtle Paradise

Clermont, FL
4 Bed 3 Bath Sleeps 8
- - - - - - 115 - - 120 - - - - - - -
Sunshine's Happy Pool Home  - Davenport, FL Vacation Rental
- - - - - - 99 140 140 165 165 140 140 140 135 - -
Florida Ridge Villa - Davenport, FL Vacation Rental

Florida Ridge Villa

Davenport, FL
4 Bed 3.5 Bath Sleeps 10
- - - - - - - - - - 125 115 115 115 115 115 125
Willow Lodge - Davenport, FL Vacation Rental

Willow Lodge

Davenport, FL
4 Bed 3 Bath Sleeps 8
- - - - - - - - - - - - - - - - -
Davenport Decadence - Davenport, FL Vacation Rental

Davenport Decadence

Davenport, FL
4 Bed 2 Bath Sleeps 8
- - - - - - - - - - - - - - - - -
Sun Seeker Villa - Davenport, FL Vacation Rental

Sun Seeker Villa

Davenport, FL
4 Bed 3.5 Bath Sleeps 8
115 - - - - - - - - - - - - - - 115 160
Silver Cove - Clermont, FL Vacation Rental

Silver Cove

Clermont, FL
4 Bed 3.5 Bath Sleeps 8
- - - - - 115 115 115 115 150 140 - - - - - -
Reunion Grande Retreat - Reunion, FL Vacation Rental

Reunion Grande Retreat

Reunion, FL
2 Bed 2 Bath Sleeps 6
- - - - 135 140 140 135 - - - 150 160 160 160 160 160
Sunburst Villa - Davenport, FL Vacation Rental

Sunburst Villa

Davenport, FL
5 Bed 4 Bath Sleeps 12
- - - - 125 - - - - 140 140 - - - - - -
Mermaid Villa - Davenport, FL Vacation Rental

Mermaid Villa

Davenport, FL
4 Bed 3 Bath Sleeps 8
- - - - - - - - - - - - - - - - -
Sunrise Vista Sanctuary - Clermont, FL Vacation Rental

Sunrise Vista Sanctuary

Clermont, FL
6 Bed 3.5 Bath Sleeps 12
- - - - 150 - - - - - - - - - - - -
Tuscana Hideaway  - Champions Gate, FL Vacation Rental

Tuscana Hideaway

Champions Gate, FL
3 Bed 2.5 Bath Sleeps 8 (6 Adults Max)
- - - - - - 120 120 120 120 - - - - - - -
Dolphin Key Villa  - Davenport, FL Vacation Rental

Dolphin Key Villa

Davenport, FL
4 Bed 2.5 Bath Sleeps 8
- - - - - - - - - - - - - 125 125 125 -
Windsor Villa - Davenport, FL Vacation Rental

Windsor Villa

Davenport, FL
5 Bed 4 Bath Sleeps 10
- - - - - - - - - - - - - - - - -
Page 1 of 2

About Kissimmee

Kissimmee rated 4.5 out of 5 based on 111 reviews Kissimmee, FL

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, Kissimmee is the perfect choice for you! Whether you're planning a relaxing retreat or an adventure-filled experience, our vacation rentals serve as the perfect home base as you explore all that the eventful Central Florida region has to offer. 

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

Our diverse selection of vacation rentals in Kissimmee 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

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! 

For an activity that is more suitable for younger guests, stop by the Green Meadows Petting Farm. Families can enjoy the petting zoo, train, and pony rides or sample tasty treats at the Chocolate Kingdom Factory Adventure Tour. 

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

Photo credit: Henry Hazboun via Shutterstock

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