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

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

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

Maple Leaf Inn & Suites
2.5 star property
Kissimmee
6.8 out of 10, (72 reviews)
"The room was clean and the staff was okay "
United States
Shaneka
The price is HK$463
HK$526 total
includes taxes & fees
11 Oct - 12 Oct
Maple Leaf Inn & Suites
Interior

2. Sunset Greens Villa

Sunset Greens Villa
2.0 star property
Reunion
10.0 out of 10, Exceptional, (1 review)
"Very nice property"
United States
Richard
The price is HK$815
HK$3,402 total
includes taxes & fees
15 Oct - 16 Oct
Sunset Greens Villa
Outdoor dining

3. SPACIOUS 2 BEDROOM HOUSE IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 2772 W

SPACIOUS 2 BEDROOM HOUSE IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 2772 W
Kissimmee
9.8 out of 10, Exceptional, (17 reviews)
"Great place. Was clean and cozy. "
United States
Casey W.
The price is HK$699
HK$1,889 total
includes taxes & fees
11 Oct - 12 Oct
SPACIOUS 2 BEDROOM HOUSE IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 2772 W
A modern bedroom with a large bed, a ceiling fan, and a view of a pool and building.

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

Private Resort Access~King Bed~Hot Tub~Balcony
Kissimmee
10.0 out of 10, Exceptional, (3 reviews)
"Great host and fantastic pool"
United States
paul m.
The price is HK$360
HK$2,940 total
includes taxes & fees
2 Nov - 3 Nov
Private Resort Access~King Bed~Hot Tub~Balcony
A modern kitchen with a central island, built-in appliances, and a large window providing natural light.

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

Resort Stay~Near Disney~Bright~Gym~Hot Tub
Kissimmee
10.0 out of 10, Exceptional, (10 reviews)
"Property was very clean and convenient and host communication was excellent"
United States
John
The price is HK$288
HK$2,872 total
includes taxes & fees
12 Oct - 13 Oct
Resort Stay~Near Disney~Bright~Gym~Hot Tub
A restaurant with a wine cellar, a chandelier, and a television screen on the wall.

6. 6 MINS TO Disney

6 MINS TO Disney
Kissimmee
10.0 out of 10, Exceptional, (31 reviews)
"Great stay for big family!"
United States
Sharlene B.
The price is HK$890
HK$3,285 total
includes taxes & fees
16 Oct - 17 Oct
6 MINS TO Disney
A modern kitchen with white cabinets, stainless steel appliances, and a marble island with bar stools.

7. Charming 2-bedroom Florida Getaway! Sleeps 6

Charming 2-bedroom Florida Getaway! Sleeps 6
Kissimmee
9.8 out of 10, Exceptional, (21 reviews)
"Great little place. We would book it again."
United States
Jack Francis G.
The price is HK$722
HK$2,407 total
includes taxes & fees
14 Oct - 15 Oct
Charming 2-bedroom Florida Getaway! Sleeps 6
Exterior

8. Shake Shack Heated Pool & Hot Tub

Shake Shack Heated Pool & Hot Tub
3.5 star property
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"We had a great time. The location was amazing and the convenience of a home is unmeasurable. Cheers! "
United States
Keith
The price is HK$1,005
HK$2,913 total
includes taxes & fees
27 Oct - 28 Oct
Shake Shack Heated Pool & Hot Tub
A swimming pool with people swimming and lounging, surrounded by palm trees and a building with a tiled roof.

9. Superb Townhouse Newly Renovated 1.5 miles to Disney

Superb Townhouse Newly Renovated 1.5 miles to Disney
Kissimmee
9.8 out of 10, Exceptional, (141 reviews)
"Great spot, close to Disney parks"
United States
Sandy T.
Superb Townhouse Newly Renovated 1.5 miles to Disney
Relax by the tropical-themed lazy river with cascading waterfalls surrounded by palm trees.

10. 2BR family retreat w/ resort access

2BR family retreat w/ resort access
Kissimmee
10.0 out of 10, Exceptional, (2 reviews)
"Very nice stay! I strongly recommend the stay"
United States
dwayne
2BR family retreat w/ resort access
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.

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

Charming 2BR/2BA Townhome with Patio near Disney
Kissimmee
8.6 out of 10, Excellent, (23 reviews)
"Very nice stay"
United States
michael h.
The price is HK$388
HK$1,787 total
includes taxes & fees
12 Oct - 13 Oct
Charming 2BR/2BA Townhome with Patio near Disney
A bedroom with a large bed, a wooden headboard, two bedside tables with lamps, a view of a swimming pool, and a sliding door.

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

Heated Pool~Game Room~Modern~Resort~Disney Magic
Lake Berkley
10.0 out of 10, Exceptional, (3 reviews)
"We absolutely loved our stay in this home. The host's were extremely kind and responsive. The home was squeaky clean and the beds were super comfy. We cannot wait to book again. Thank you Derek & Lauren!!!"
United States
Kelly F.
The price is HK$492
HK$3,674 total
includes taxes & fees
13 Oct - 14 Oct
Heated Pool~Game Room~Modern~Resort~Disney Magic
A residential complex with multiple two-story houses, a central swimming pool, and well-maintained lawns.

13. Disney Themed Single Family Home, Private Pool, 15 Mins From Disney & Sleeps 10

Disney Themed Single Family Home, Private Pool, 15 Mins From Disney & Sleeps 10
Lake Berkley
9.2 out of 10, Wonderful, (32 reviews)
"Love lake Berkley. Perfect location. Great facilities. Easy check in. Great value for money. We had a brilliant time and would defo recommend!"
United Kingdom
Lauren
The price is HK$981
HK$3,510 total
includes taxes & fees
23 Oct - 24 Oct
Disney Themed Single Family Home, Private Pool, 15 Mins From Disney & Sleeps 10
A poolside area with lounge chairs, a table, and an umbrella.

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

It’s only 15 minutes drive to Disney World and the amazing outlets in Orlando
Kissimmee
9.8 out of 10, Exceptional, (38 reviews)
"Great location and condo."
United States
Lonnie M.
It’s only 15 minutes drive to Disney World and the amazing outlets in Orlando
1.jpg

15. 4 BD/ 4 BA/ Bella Vida (440 LF)

4 BD/ 4 BA/ Bella Vida (440 LF)
Bellavida
9.0 out of 10, Wonderful, (28 reviews)
"This was a great property conveniently located to everything. The pool was great the accommodations were perfect for our family of 6."
United States
Eric H.
4 BD/ 4 BA/ Bella Vida (440 LF)
3205 Tranquil Trail 2.jpg

16. 3 Bedrooms/ 3 Baths/ The Hub At Westside (3205TT)

3 Bedrooms/ 3 Baths/ The Hub At Westside (3205TT)
Kissimmee
9.8 out of 10, Exceptional, (34 reviews)
"Yes we were in great condition, thanks again for the stay."
United States
Ernestine M.
3 Bedrooms/ 3 Baths/ The Hub At Westside (3205TT)
Pool

17. Family 5-Bedroom Villa w/ Private Pool & BBQ – Windsor at Westside Near Disney!

Family 5-Bedroom Villa w/ Private Pool & BBQ – Windsor at Westside Near Disney!
Four Corners
9.4 out of 10, Exceptional, (26 reviews)
"Great location to Disney World! Very quiet, gated location. This is our 2nd time staying and would stay again. Plenty of room! "
United States
Brian H.
The price is HK$950
HK$4,984 total
includes taxes & fees
9 Nov - 10 Nov
Family 5-Bedroom Villa w/ Private Pool & BBQ – Windsor at Westside Near Disney!
A resort with a large pool, water slides, and palm trees.

18. Amazing Home Near Disney, Amazing Amenities Renovated.Free Shuttle to the Parks!

Amazing Home Near Disney, Amazing Amenities Renovated.Free Shuttle to the Parks!
Kissimmee
9.2 out of 10, Wonderful, (104 reviews)
"Great place to stay. Especially for families!"
United States
Heather C.
The price is HK$542
HK$1,880 total
includes taxes & fees
12 Oct - 13 Oct
Amazing Home Near Disney, Amazing Amenities Renovated.Free Shuttle to the Parks!
A modern kitchen with a central island, stainless steel appliances, and a view of a body of water through large windows.

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

Escape to Paradise!Luxury Waterfront Heated Pool House with Game Room and Piano!
Buena Ventura Lakes
10.0 out of 10, Exceptional, (45 reviews)
"Comfortable & close to Orlando attractions."
United States
Bridget H.
The price is HK$1,123
HK$2,730 total
includes taxes & fees
12 Oct - 13 Oct
Escape to Paradise!Luxury Waterfront Heated Pool House with Game Room and Piano!
A modern kitchen with a stainless steel refrigerator, a built-in dishwasher, and a large island with a sink.

20. Family 5BR Villa w Pool Theatre Reunion Village

Family 5BR Villa w Pool Theatre Reunion Village
2.5 star property
Reunion
The price is HK$1,239
HK$3,548 total
includes taxes & fees
15 Oct - 16 Oct
Family 5BR Villa w Pool Theatre Reunion Village
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Kissimmee Hotel Reviews

Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent
"Our 2 room/2 bath condo was excellent. We were on the 6th floor and had a great view. The lazy river was very relaxing. We thoroughly enjoyed our stay."
Natalie 4-night trip
Posted 8 hours ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Find out more about Kissimmee

Kissimmee Vacation Homes information

Number of reviews
534
Accommodation
15585 Vacation Homes
Lowest Price
HK$526
Highest Price
HK$4,984

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