Kissimmee Vacation Homes

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Our top choices for Kissimmee holiday homes

A decorative stone fountain with a twisted base, surrounded by vibrant red flowers and tropical foliage, set against a backdrop of a pool and palm trees.

1. Maple Leaf Inn & Suites

Kissimmee

Alex

HK$525 total

includes taxes & fees

8 Nov - 9 Nov

A modern bedroom with a large bed, a ceiling fan, and a view of a pool and building.

2. Private Resort Access~King Bed~Hot Tub~Balcony

Kissimmee

paul m.

HK$2,921 total

includes taxes & fees

1 Dec - 2 Dec

A modern kitchen with a central island, built-in appliances, and a large window providing natural light.

3. Resort Stay~Near Disney~Bright~Gym~Hot Tub

Kissimmee

John

A living room with two brown leather sofas, a beige throw blanket, and a coffee table with a decorative item. A painting of a beach landscape hangs on the wall, and a wooden clock is visible.

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

Kissimmee

michael h.

HK$2,181 total

includes taxes & fees

6 Dec - 7 Dec

A modern kitchen with white cabinets, stainless steel appliances, and a marble island with bar stools.

5. Charming 2-bedroom Florida Getaway! Sleeps 6

Kissimmee

Jack Francis G.

HK$2,399 total

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with dark cabinets, stainless steel appliances, a black refrigerator, a microwave, and a bar area with white bar stools.

6. 3BR townhouse near Disney with themed rooms

Kissimmee

A building with a pink facade, white columns, and a brown door.

7. Coral Cay 4BR Vacation Home,Close to Disney

Kissimmee

A bedroom with a large bed, a wooden headboard, two bedside tables with lamps, a view of a swimming pool, and a sliding door.

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

Lake Berkley

Kelly F.

HK$3,542 total

includes taxes & fees

1 Dec - 2 Dec

A modern kitchen with white cabinetry, a large island with two decorative bowls, and a pendant light with multiple bulbs.

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

Crystal Cove

Dijaun B.

HK$3,767 total

includes taxes & fees

17 Nov - 18 Nov

A restaurant with a wine cellar, a chandelier, and a television screen on the wall.

10. 6 MINS TO Disney

Kissimmee

Sharlene B.

HK$3,051 total

includes taxes & fees

22 Nov - 23 Nov

A swimming pool with lounge chairs and gazebos, surrounded by palm trees and buildings with red-tiled roofs.

11. Plunge Pool Oasis~Bella Vida Resort~Close to Parks

Bellavida

Marjorie S.

HK$3,340 total

includes taxes & fees

17 Nov - 18 Nov

A spacious living room with a grey sofa, a teal rug, a grand piano, and a ceiling fan.

12. Escape to Paradise!Luxury Waterfront Heated Pool House with Game Room and Piano!

Buena Ventura Lakes

Bridget H.

13. Shake Shack Heated Pool & Hot Tub

Kissimmee

Keith

HK$3,130 total

includes taxes & fees

15 Nov - 16 Nov

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

Buena Ventura Lakes

Franks

HK$2,522 total

includes taxes & fees

9 Nov - 10 Nov

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

15. -A Sweet Home Near Theme Parks!-

Kissimmee

Natalie V.

HK$3,074 total

includes taxes & fees

6 Dec - 7 Dec

A large rectangular pool with a central island, surrounded by palm trees and lounge chairs.

16. NBA Dream Mansion 15br Luxury Villa w Pool

Kissimmee

HK$11,911 total

includes taxes & fees

18 Nov - 19 Nov

A modern living room with a round dining table, grey sofas, and a TV mounted on the wall.

17. Disney Getaway w/ Splash Pool + Kids’ Theme Rooms

Kissimmee

"This property was excellent and the host was amazing in every respect. The property was very clean and had all the necessary amenities. We had a huge disappointment with our original rental which was deplorable and with this property it was bliss! We will definitely stay here again when we return to Florida. If you’re looking for a 5 Star property this one is sure to please. The property also has plenty of nice cookware and dishes so can work for family gatherings as well. For Disney fans there...

Wanda O.

HK$4,491 total

includes taxes & fees

1 Dec - 2 Dec

A spacious living room with a large sectional sofa, a wooden coffee table, and a flat-screen TV mounted on the wall.

18. 10 mins to parks in Orlando,Kissimmee, with gated community and pool

Cumbrian Lakes

Corey C.

HK$3,433 total

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

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

Kissimmee

A poolside area with lounge chairs, a table, and an umbrella.

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

Kissimmee

Donald B.

HK$2,558 total

includes taxes & fees

8 Nov - 9 Nov

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Top Kissimmee Hotel Reviews

Palazzo Lakeside Hotel

10/10 Excellent

"Great stay and breakfast was very good"

Vacation Village Orlando, Celebration

10/10 Excellent

"Me and my three children stayed here at the end of October. We came to go to Disney world the location was excellent and the room was very accommodating for what we needed and more . It was super clean which is the most important to us and the bonus was it had a washer dryer which was a little wonky but we made it work lol . The pool and hot tub was very nice my kids loved it and it stayed open until 11 pm and felt great after a long day after the parks . Would definitely recommend this hotel for a family and we will be visiting again hopefully soon."

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