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

Holiday Homes in Kissimmee

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

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, (71 reviews)
"The room was clean and the staff was okay "
United States
Shaneka
The price is AU$93
includes taxes & fees
30 Aug - 31 Aug
Maple Leaf Inn & Suites
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

Private Resort Access~King Bed~Hot Tub~Balcony
Kissimmee
10.0 out of 10, Exceptional, (2 reviews)
"Great host and fantastic pool"
United States
paul m.
The price is AU$500
includes taxes & fees
31 Aug - 1 Sept
Private Resort Access~King Bed~Hot Tub~Balcony
A modern kitchen with white cabinets, stainless steel appliances, and a marble island with bar stools.

3. 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 AU$401
includes taxes & fees
9 Sept - 10 Sept
Charming 2-bedroom Florida Getaway! Sleeps 6
A modern kitchen with a central island, built-in appliances, and a large window providing natural light.

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

Resort Stay~Near Disney~Bright~Gym~Hot Tub
Kissimmee
10.0 out of 10, Exceptional, (7 reviews)
"The place was great & convenient if going to the parks. It had everything we needed & was clean and nicely updated."
United States
Sadie H.
The price is AU$460
includes taxes & fees
30 Aug - 31 Aug
Resort Stay~Near Disney~Bright~Gym~Hot Tub

5. 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
The price is AU$452
includes taxes & fees
30 Aug - 31 Aug
2BR family retreat w/ resort access
A modern living room with a round dining table, grey sofas, and a TV mounted on the wall.

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

Disney Getaway w/ Splash Pool + Kids’ Theme Rooms
Kissimmee
9.6 out of 10, Exceptional, (25 reviews)
"Great stay nice and clean "
United States
Vanna C.
The price is AU$764
includes taxes & fees
28 Aug - 29 Aug
Disney Getaway w/ Splash Pool + Kids’ Theme Rooms

7. "Pequod Lakeview" - 4BD/3BA Townhome near Disney

"Pequod Lakeview" - 4BD/3BA Townhome near Disney
Kissimmee
9.4 out of 10, Exceptional, (21 reviews)
"Simple check in and out. Clean home in safe gated neighborhood. Close to the parks."
United States
Trey J.
The price is AU$544
includes taxes & fees
9 Sept - 10 Sept
"Pequod Lakeview" - 4BD/3BA Townhome near Disney
A modern living room with a curved sectional sofa, a flat-screen TV mounted on the wall, and a large window providing natural light.

8. 5Bd Home, Storey Lake with Private Pool 14 Guests - Private Pool - 2773 BD

5Bd Home, Storey Lake with Private Pool 14 Guests - Private Pool - 2773 BD
Kissimmee
9.2 out of 10, Wonderful, (33 reviews)
"Worked great for our trip!"
United States
Jennifer
The price is AU$798
includes taxes & fees
31 Aug - 1 Sept
5Bd Home, Storey Lake with Private Pool 14 Guests - Private Pool - 2773 BD
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

Freshly Updated~Near Disney~Private Pool~Resort
Crystal Cove
10.0 out of 10, Exceptional, (3 reviews)
"Everything was amazing would love to rent more properties in the future!!"
United States
Dijaun B.
The price is AU$738
includes taxes & fees
10 Sept - 11 Sept
Freshly Updated~Near Disney~Private Pool~Resort

10. "Brier's Storey" - 4BD/3BA townhome near Disney #18

"Brier's Storey" - 4BD/3BA townhome near Disney #18
Kissimmee
9.4 out of 10, Exceptional, (23 reviews)
"We had a lovely stay and would stay here again in a heartbeat."
United States
Terra and Matthew L.
The price is AU$547
includes taxes & fees
29 Aug - 30 Aug
"Brier's Storey" - 4BD/3BA townhome near Disney #18

11. Cozy Lakeview 4BED Townhouse close to Major Parks

Cozy Lakeview 4BED Townhouse close to Major Parks
Kissimmee
9.4 out of 10, Exceptional, (59 reviews)
"Pool was enjoyable. Stay was great! "
United States
Michael M.
The price is AU$545
includes taxes & fees
4 Sept - 5 Sept
Cozy Lakeview 4BED Townhouse close to Major Parks
A residential complex with multiple two-story houses, a central swimming pool, and well-maintained lawns.

12. 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, (31 reviews)
"Awesome place and location. "
United States
Montigo W.
The price is AU$612
includes taxes & fees
2 Sept - 3 Sept
Disney Themed Single Family Home, Private Pool, 15 Mins From Disney & Sleeps 10
An aerial view of a resort with a winding pool, multiple lounge areas, and a separate building with a pool.

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

Family-Friendly 4 Bedroom 3 Bath Pool Home 271
Kissimmee
8.4 out of 10, Very good, (27 reviews)
"First of all we entered and everything was off and with the broken wall and the sofa, the refrigerator was broken, the food was ruined and the pool was dirty with hair, the grill didn't work either, we didn't repeat it"
United States
Jennifer
The price is AU$715
includes taxes & fees
14 Sept - 15 Sept
Family-Friendly 4 Bedroom 3 Bath Pool Home 271
A golf cart parked in front of a house with a porch and a fenced yard.

14. 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 AU$334
includes taxes & fees
9 Sept - 10 Sept
SPACIOUS 2 BEDROOM HOUSE IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 2772 W
A swimming pool with blue chairs and tables, surrounded by palm trees and a building with a red roof.

15. Magical Family Townhome Retreat – Comfort & Convenience Near Top Attractions!

Magical Family Townhome Retreat – Comfort & Convenience Near Top Attractions!
Kissimmee
9.4 out of 10, Exceptional, (57 reviews)
"Very clean family friendly stay. I will definitely come stay again and recommend to friends and family to book their stay here."
United States
Elain S.
Magical Family Townhome Retreat – Comfort & Convenience Near Top Attractions!

16. Beautiful 4/3 TH w/ private pool in gated resort w/ clubhouse (10' to WDW)

Beautiful 4/3 TH w/ private pool in gated resort w/ clubhouse (10' to WDW)
Kissimmee
9.4 out of 10, Exceptional, (56 reviews)
"This home was such a wonderful space for our stay! It was clean, welcoming & in a great location! Would definitely stay here again!"
United States
Kathleen C.
The price is AU$547
includes taxes & fees
30 Aug - 31 Aug
Beautiful 4/3 TH w/ private pool in gated resort w/ clubhouse (10' to WDW)
A resort with a large swimming pool, palm trees, and a covered area with lounge chairs.

17. Discover Opulence: 4-Bedroom Villa with Pool, and Magical Themed Rooms! 2901 SS

Discover Opulence: 4-Bedroom Villa with Pool, and Magical Themed Rooms! 2901 SS
Kissimmee
9.8 out of 10, Exceptional, (13 reviews)
"We had so much fun and the place was exactly as listed."
United States
Annaliese B.
The price is AU$714
includes taxes & fees
6 Sept - 7 Sept
Discover Opulence: 4-Bedroom Villa with Pool, and Magical Themed Rooms! 2901 SS

18. 5BD/4BA Grand Townhome w/pool close to Disney

5BD/4BA Grand Townhome w/pool close to Disney
Kissimmee
9.8 out of 10, Exceptional, (15 reviews)
"Everything was great pool property cleanliness"
United States
Frank V.
The price is AU$644
includes taxes & fees
9 Sept - 10 Sept
5BD/4BA Grand Townhome w/pool close to Disney
A spacious outdoor bar area with high ceilings and large windows, featuring multiple seating arrangements and a television screen.

19. 5BD Private Pool Villa - Storey Lake Resort - 4810 LL

5BD Private Pool Villa - Storey Lake Resort - 4810 LL
Kissimmee
9.0 out of 10, Wonderful, (32 reviews)
"No complaints, house was very spacious and clean"
United States
Michael G.
The price is AU$718
includes taxes & fees
27 Sept - 28 Sept
5BD Private Pool Villa - Storey Lake Resort - 4810 LL
A pool area with lounge chairs and a fountain.

20. Mandalorian Retreat – Private Pool Near Disney

Mandalorian Retreat – Private Pool Near Disney
Bellavida
9.8 out of 10, Exceptional, (38 reviews)
"My family and I thoroughly enjoyed our time stay at the Mandalorian Retreat, we got speedy and clear communication, the amenities did what they were supposed to do and the location was the amazing and I plan on referring anyone I know to book with you all "
United States
Patrick D.
Mandalorian Retreat – Private Pool Near Disney
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

Delta Hotels by Marriott Orlando Celebration

Delta Hotels by Marriott Orlando Celebration

10/10 Excellent
"Beautiful property, maintained with a friendly staff. Highly recommended!"
Dawana 2-night trip
Posted 9 hours ago
Delta Hotels by Marriott Orlando Celebration

Find out more about Kissimmee

Kissimmee Holiday Homes information

Number of reviews
362
Accommodation
15406 Holiday Homes
Lowest Price
AU$93
Highest Price
AU$798

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