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
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 AU$96
includes taxes & fees
12 Oct - 13 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 AU$621
includes taxes & fees
15 Oct - 16 Oct
Sunset Greens Villa
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

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 AU$532
includes taxes & fees
2 Nov - 3 Nov
Resort Stay~Near Disney~Bright~Gym~Hot Tub
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 AU$533
includes taxes & fees
2 Nov - 3 Nov
Private Resort Access~King Bed~Hot Tub~Balcony
A modern kitchen with white cabinets, stainless steel appliances, and a marble island with bar stools.

5. 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$439
includes taxes & fees
14 Oct - 15 Oct
Charming 2-bedroom Florida Getaway! Sleeps 6
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.

6. 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 AU$326
includes taxes & fees
13 Oct - 14 Oct
Charming 2BR/2BA Townhome with Patio near Disney
Exterior

7. 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 AU$532
includes taxes & fees
27 Oct - 28 Oct
Shake Shack Heated Pool & Hot Tub
A resort with a large pool, water slides, and palm trees.

8. 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 AU$368
includes taxes & fees
19 Oct - 20 Oct
Amazing Home Near Disney, Amazing Amenities Renovated.Free Shuttle to the Parks!
A modern kitchen with a stainless steel refrigerator, a built-in dishwasher, and a large island with a sink.

9. Family 5BR Villa w Pool Theatre Reunion Village

Family 5BR Villa w Pool Theatre Reunion Village
2.5 star property
Reunion
The price is AU$654
includes taxes & fees
15 Oct - 16 Oct
Family 5BR Villa w Pool Theatre Reunion Village
Outdoor dining

10. 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$348
includes taxes & fees
12 Oct - 13 Oct
SPACIOUS 2 BEDROOM HOUSE IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 2772 W
A bedroom with a large bed, a wooden headboard, two bedside tables with lamps, a view of a swimming pool, and a sliding door.

11. 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 AU$667
includes taxes & fees
13 Oct - 14 Oct
Heated Pool~Game Room~Modern~Resort~Disney Magic
A modern kitchen with white cabinets, stainless steel appliances, and a dining area set for a meal.

12. Stylish Family Retreat in Kissimmee

Stylish Family Retreat in Kissimmee
Trafalgar Village
10.0 out of 10, Exceptional, (2 reviews)
"Great communication, the one little thing that was wrong was fixed right away. House had everything you need and even a few starter items. The only suggesstion is to get better fluffier pillows. "
United States
Keshia E.
Stylish Family Retreat in Kissimmee
A modern living room with a round dining table, grey sofas, and a TV mounted on the wall.

13. 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.
Disney Getaway w/ Splash Pool + Kids’ Theme Rooms
A modern kitchen with granite countertops, stainless steel appliances, and a dining area with a table and chairs.

14. 3-bedroom Disney Townhome Retreat

3-bedroom Disney Townhome Retreat
Kissimmee
10.0 out of 10, Exceptional, (9 reviews)
"Great stay nice home "
United States
julia t.
The price is AU$500
includes taxes & fees
13 Oct - 14 Oct
3-bedroom Disney Townhome Retreat
Exterior detail

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

Fully renovated 3-bedroom townhome Kissimmee - Close to theme parks and airport
Buena Ventura Lakes
9.6 out of 10, Exceptional, (7 reviews)
"Excellent house"
United States
Franks
The price is AU$465
includes taxes & fees
25 Oct - 26 Oct
Fully renovated 3-bedroom townhome Kissimmee - Close to theme parks and airport
An aerial view of a residential area with houses, roads, and a body of water.

16. 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 AU$594
includes taxes & fees
17 Oct - 18 Oct
Disney Themed Single Family Home, Private Pool, 15 Mins From Disney & Sleeps 10
An outdoor patio with wicker furniture, a glass table, and a hammock.

17. -A Sweet Home Near Theme Parks!-

-A Sweet Home Near Theme Parks!-
Kissimmee
10.0 out of 10, Exceptional, (5 reviews)
"This place is SO cozy and comfortable! I was amazed at all of the touches the hosts have added to make it a true “home away from home”. I am local and had a small get together with some family - it was so great for a gathering - plenty of seating and the outdoor spot is lovely!"
United States
Natalie V.
The price is AU$510
includes taxes & fees
24 Oct - 25 Oct
-A Sweet Home Near Theme Parks!-
A modern kitchen with white cabinetry, a large island with two decorative bowls, and a pendant light with multiple bulbs.

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

Freshly Updated~Near Disney~Private Pool~Resort
Crystal Cove
10.0 out of 10, Exceptional, (4 reviews)
"Everything was amazing would love to rent more properties in the future!!"
United States
Dijaun B.
The price is AU$849
includes taxes & fees
24 Oct - 25 Oct
Freshly Updated~Near Disney~Private Pool~Resort
A large rectangular pool with a central island, surrounded by palm trees and lounge chairs.

19. NBA Dream Mansion 15br Luxury Villa w Pool

NBA Dream Mansion 15br Luxury Villa w Pool
2.0 star property
Kissimmee
The price is AU$2,127
includes taxes & fees
13 Oct - 14 Oct
NBA Dream Mansion 15br Luxury Villa w Pool
1.jpg

20. 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.
The price is AU$739
includes taxes & fees
20 Oct - 21 Oct
4 BD/ 4 BA/ Bella Vida (440 LF)
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

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

10/10 Excellent
"Los recomiendo al 100"
Rafael 3-night trip
Posted 1 hour ago
Palazzo Lakeside Hotel

Find out more about Kissimmee

Kissimmee Holiday Homes information

Number of reviews
269
Accommodation
15675 Holiday Homes
Lowest Price
AU$96
Highest Price
AU$2,127

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