We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Kissimmee Vacation Rentals

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
Distance from
1 km
Price per night
C$0
C$1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
Neighbourhood
Show more
3435 rentals in Kissimmee.
Sort by:
Tripadvisor Sort
Belle's Cove, Family-Friendly Villa with Gameroom and Hot Tub
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Disney 5 Star Vacations / The Osprey Villa
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Themed rooms, lots of space no crowds!
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Villa Linton - Beautiful Florida Home with Themed Bedrooms
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Family-Friendly Large Villa with a Pool, Jacuzzi,
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Disney Family Villa pool/spa/games room, 5 bds 4 bathrooms, 15 Mins to Disney
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Roughtallys Villa
7 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Amazing Disney Condo, Pool & Hot tub Onsite
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Palm Tree Villa Florida, 5 Star Review Rating with Pool Lift & Wheel in Shower.
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
villanirvana
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Save time - get the best Kissimmee rentals sent straight to your email!
Debbie's Florida Retreat a Luxury Vacation Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Superb 4 Bedroom Home, just 3 minutes from Disney
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Disney Vacation Villa with Lake View
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
DISNEY WORLD! LOW $'S! ENTIRE NEW Home! Harry Potter Theme, Sleeps 8!
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Star Lake Villa, close to Disney with pool
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Fantasy Pool Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Disney Dream Villa At CLC Encantada Resort
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
The Charming Mickey's Tree House,
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
DISNEY DREAM LUXURY HOME PRIVATE WATERPARK POOL SPA
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
New Opening 9 Br/6 Ba luxurious Pool House from $300/nt, Close To Disney
9 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Sonshines Florida Villa, Peaceful Getaway and Pool
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
⭐Spacious 7 Bedrooms w/ Private Pool - Great Location!⭐
7 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Stunning 6 Bed Pool Home Close to Disney Parks.
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Luxury 4 Bedroom Villa with Private Pool, 2 Miles from Disney
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
New Upgraded Luxury Villa w/ Frozen & Star Wars Rooms at Encore!
6 bedrooms
7 bathrooms
Sleeps 16
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
New 9br/6ba pool villa from $280/nt,Close to Disney
9 bedrooms
6 bathrooms
Sleeps 20
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Bargain Vacation Home near Disney
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Spacious 4-bed lakeside pool villa near Disney
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
(9110-CAL) Calabria 5 Bed South Face Pool, GAMES ROOM
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Charming Townhouse with Pool and Tennis Court in Gated Community
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Near Disney, 5 Star Princess Themed Home and Resort
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Villa di Lusso
6 bedrooms
10 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Luxury Home with Exceptional Games Room. 610
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Magical Manor, Beautiful Emerald Island Lake View Villa
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
BRUSONS RETREAT, 5 Bed Villa, South Facing Pool & Terrace.
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
⭐Good Location for Theme Parks - Spacious 8 Bedrooms Villa w/ Private Pool⭐
8 bedrooms
6 bathrooms
Sleeps 20
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
A perfect Holiday House Waitting U at Windsor Palms Resort 10mins to Disney
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
VP_1801R Veranda Jewel
13 bedrooms
11 bathrooms
Sleeps 25
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Stunning Lake View House 2mls to Disney,games room
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
SweetDreamsRUs - 4miles to Disney, Free WiFi, Free Pool Heat, South Facing Pool
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
New 9Br/6Ba luxurious Pool House from $300/nt, Close To Disney
9 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Luxury Lakeside House with private solar heated pool & spa
5 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Kissimmee Windsor at Westside's 'The Second Star to the Right' vacation home
7 bedrooms
6 bathrooms
Sleeps 17
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Ultimate luxury 15 bedroom suites for 30 guests
15 bedrooms
15 bathrooms
Sleeps 30
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Mickeys Clubhouse Windsor Palm Frozen & New Minion themed rooms
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Golden Palms Resort 8 Bedroom Vacation Home with Pool (1904)
8 bedrooms
7 bathrooms
Sleeps 18
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
New 8br/6ba pool villa from $260/nt , Close to Disney
8 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Fantastic Orange Blossom Villa includes a Gameroom and Private Pool
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Florida Villa Dreams Come True
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Seasons Villa,5 Bedrooms, Pool with Spa, Gameroom Sleeps 10
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
PreviousNext
12345669
About Kissimmee
Kissimmee, Florida is a budget-lover's dream with easy access to Disney parks for a fraction of the cost. Smart vacationers know that searching for a vacation rental in Kissimmee, Florida often gets you space, luxury and a great rate. This area also boasts plenty of natural beauty with a number of public parks. Kissimmee is an active community with bike trails and abundant golf courses. Baseball fans can enjoy a spring training game as Kissimmee is the (February) home of the Houston Astros.
More
About Kissimmee
Kissimmee, Florida is a budget-lover's dream with easy access to Disney parks for a fraction of the cost. Smart vacationers know that searching for a vacation rental in Kissimmee, Florida often gets you space, luxury and a great rate. This area also boasts plenty of natural beauty with a number of public parks. Kissimmee is an active community with bike trails and abundant golf courses. Baseball fans can enjoy a spring training game as Kissimmee is the (February) home of the Houston Astros.
Kissimmee Vacation Rentals
Whether you’re interested in a one-bedroom condo rental in Kissimmee or a seven-bedroom luxury villa, booking a vacation rental on TripAdvisor makes your selection easy. Families that do the math will realize renting a condo or villa with multiple bedrooms in Kissimmee will be much, much cheaper than staying at a theme park or resort. The rentals often come with special amenities like a pool, hot tub, movie theater, arcade, or patio with grill for cookouts. Since the theme parks come with extreme costs, you can save a ton by cooking meals in your full kitchen at home, rather than wasting it all at a restaurant three meals a day. You’ll even save money on baggage fees with a rental—when you’ve got your own washer and dryer, you can do a few loads of laundry and pack much less clothing.
Things to do in Kissimmee
Don’t forget, there’s more to this part of Florida than Mickey and Donald and friends. From go-kart racing and miniature golf to water parks and adventure sports, Kissimmee offers family-oriented activities to suit any taste. Animal lovers will want to spend a day at Sea World, or take a day trip to the Everglades. Shoppers should save time (and suitcase space) for bargain-hunting at outlets in Kissimmee and the nearby Orlando Premium Outlets. Every Saturday night in Old Town Kissimmee, there is a classic car cruise through the city streets, accompanied by a live band. This downtown area also has plenty of shopping and restaurants for the entire family. Named after Florida's most famous reptile, Gatorland is a giant animal theme park with lots of wildlife. Bring the kids to Kissimmee Lakefront Park which is perfect for family picnics and exploring the lighthouse. Travel back in time at Oscaloosa County Pioneer Village and experience what life was like for early settlers.