Kissimmee Vacation Homes

A pathway through a park with Spanish moss hanging from trees and a body of water in the background.

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Our top choices for Kissimmee holiday homes

A swimming pool with a white fence, surrounded by palm trees and a sunset in the background.

1. Maple Leaf Inn & Suites

Kissimmee

Alex

HK$525 total

includes taxes & fees

16 Nov - 17 Nov

A bedroom with a large bed, a mural of a castle, a chandelier, and a window with blinds.

2. 7BR Near Disney with Private Pool, Games and 4 King Suites

Kissimmee

HK$4,664 total

includes taxes & fees

16 Nov - 17 Nov

A children's room with two beds, a white desk, and a mural of Disney characters.

3. 3BR townhouse at Fiesta Key in kissimmee

Kissimmee

HK$2,752 total

includes taxes & fees

29 Nov - 30 Nov

A modern kitchen with a large island, double sinks, and a view to the outside.

4. Sunset Greens Villa

Reunion

Richard

HK$4,356 total

includes taxes & fees

20 Nov - 21 Nov

A modern kitchen with wooden cabinets, a white countertop, and a backsplash.

5. Charming 2BR/2BA Townhome with Patio near Disney

Kissimmee

michael h.

HK$1,948 total

includes taxes & fees

17 Nov - 18 Nov

A large outdoor swimming pool with multiple lanes, surrounded by lounge chairs and palm trees.

6. 4732 Lakeview Townhome Near Disney Gym Access

Kissimmee

norris f.

HK$3,322 total

includes taxes & fees

16 Nov - 17 Nov

A modern kitchen with white cabinetry, stainless steel appliances, and a large window.

7. Freshly Updated~Near Disney~Private Pool~Resort

Crystal Cove

Dijaun B.

HK$3,715 total

includes taxes & fees

17 Nov - 18 Nov

A covered swimming pool area with lounge chairs and a basketball hoop.

8. Modern 4BR/2BA with pool in gated community

Kissimmee

HK$3,254 total

includes taxes & fees

23 Nov - 24 Nov

A modern two-story building with a balcony, number 10, and a well-maintained garden area.

9. 6 MINS TO Disney

Kissimmee

Sharlene B.

HK$2,959 total

includes taxes & fees

22 Nov - 23 Nov

A covered outdoor swimming pool with lounge chairs and a flamingo float.

10. Heated Pool~Game Room~Modern~Resort~Disney Magic

Lake Berkley

Kelly F.

HK$3,885 total

includes taxes & fees

26 Nov - 27 Nov

A staircase with carpeted steps, white railings, and a view into a room with a gray sofa and a dining table.

11. 10 mins to parks in Orlando,Kissimmee, with gated community and pool

Cumbrian Lakes

Corey C.

HK$3,292 total

includes taxes & fees

16 Nov - 17 Nov

12. Fully renovated 3-bedroom townhome Kissimmee - Close to theme parks and airport

Buena Ventura Lakes

Franks

HK$2,420 total

includes taxes & fees

16 Nov - 17 Nov

A covered outdoor patio with a sofa, chairs, a table, a hot tub, and a view of the forest.

13. Corvette Cove

Kissimmee

HK$5,163 total

includes taxes & fees

27 Nov - 28 Nov

A residential street with colorful houses, a stop sign, and a delivery truck.

14. Shake Shack Heated Pool & Hot Tub

Kissimmee

Keith

HK$3,130 total

includes taxes & fees

8 Dec - 9 Dec

An outdoor patio with wicker furniture, a glass table, and a hammock.

15. -A Sweet Home Near Theme Parks!-

Kissimmee

Natalie V.

HK$2,616 total

includes taxes & fees

16 Nov - 17 Nov

A swimming pool with a concrete edge, lounge chairs, and a covered area with a blue umbrella.

16. It’s only 15 minutes drive to Disney World and the amazing outlets in Orlando

Kissimmee

Donald B.

HK$2,456 total

includes taxes & fees

17 Nov - 18 Nov

A modern building with a glass-enclosed swimming pool, a sun terrace, and a covered outdoor seating area.

17. Resort-Style Villa | Pool, Spa & Game Room!

Kissimmee

HK$4,490 total

includes taxes & fees

9 Dec - 10 Dec

An outdoor swimming pool with a covered seating area, surrounded by a metal frame structure.

18. Luxury Lake Resort ✨

Cumbrian Lakes

Shannon B.

HK$3,192 total

includes taxes & fees

16 Nov - 17 Nov

An indoor swimming pool with clear blue water, surrounded by a metal fence, and a grassy area visible through the fence.

19. Private pool~Lazy River~Near Disney~Resort~Pool Table

Kissimmee

Camille

HK$5,248 total

includes taxes & fees

16 Nov - 17 Nov

A beachside lounge area with chairs and a view of a lake, surrounded by palm trees and a clear sky.

20. Family-Friendly 4 Bedroom 3 Bath Pool Home 271

Kissimmee

Jennifer

HK$4,154 total

includes taxes & fees

8 Dec - 9 Dec

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Top Kissimmee Hotel Reviews

Legacy Vacation Resorts - Kissimmee/Orlando

8/10 Good

"The room itself could use some updating. The shower had no door and the jetted tub just shot water everywhere."

Palazzo Lakeside Hotel

10/10 Excellent

"This was very clean, breakfast was decent, and pool looked clean. Only problem in room was a lip in the floor, very bad for walking in night to bathroom hit it every time back and forth and shower was a little strange no opening to turn on without getting soaked. But nothing terrible, we were very impressed for price and would stay again!"

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