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

Kissimmee Vacation Rentals

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Check prices for these dates

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

Our top choices for Kissimmee vacation 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 CA $84
CA $95 total
includes taxes & fees
Oct 12 - Oct 13
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 CA $148
CA $616 total
includes taxes & fees
Oct 12 - Oct 13
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 CA $70
CA $542 total
includes taxes & fees
Nov 1 - Nov 2
Resort Stay~Near Disney~Bright~Gym~Hot Tub
A modern kitchen with white cabinets, stainless steel appliances, and a marble island with bar stools.

4. 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 CA $115
CA $421 total
includes taxes & fees
Oct 9 - Oct 10
Charming 2-bedroom Florida Getaway! Sleeps 6
A modern bedroom with a large bed, a ceiling fan, and a view of a pool and building.

5. 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 CA $65
CA $537 total
includes taxes & fees
Nov 4 - Nov 5
Private Resort Access~King Bed~Hot Tub~Balcony
A modern living room with a sofa, ottoman, and glass dining table. There is a kitchen area with a microwave and cabinets.

6. Enchanting Newly Renovated 1.5miles to Disney and Near Tons of Restaurants 760

Enchanting Newly Renovated 1.5miles to Disney and Near Tons of Restaurants 760
Kissimmee
9.0 out of 10, Wonderful, (59 reviews)
"The property was cozy and comfortable. It was perfect for myself and my husband. The beds were comfortable, shower was a good size, water was hot."
United States
Mari L.
Enchanting Newly Renovated 1.5miles to Disney and Near Tons of Restaurants 760
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.

7. 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 CA $70
CA $326 total
includes taxes & fees
Oct 18 - Oct 19
Charming 2BR/2BA Townhome with Patio near Disney
A living room with two sofas, a coffee table, and two lamps. There is a painting on the wall and a window with plants.

8. Sunny Private Pool & Spa & Fenced Yard. Nr Parks

Sunny Private Pool & Spa & Fenced Yard. Nr Parks
4.5 star property
Indian Point
Sunny Private Pool & Spa & Fenced Yard. Nr Parks
Resort pool area with water slides, lazy river, and shaded lounge chairs

9. 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 CA $116
CA $477 total
includes taxes & fees
Oct 18 - Oct 19
2BR family retreat w/ resort access
Exterior

10. 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 CA $183
CA $529 total
includes taxes & fees
Oct 27 - Oct 28
Shake Shack Heated Pool & Hot Tub
A pool area with a water feature, lounge chairs, and a pergola.

11. Pond Access & Grill! Group Escape, 19 Mi to WDW

Pond Access & Grill! Group Escape, 19 Mi to WDW
Kissimmee
Pond Access & Grill! Group Escape, 19 Mi to WDW
A shuffleboard table in a room with a mural depicting a theme park.

12. 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 CA $127
CA $344 total
includes taxes & fees
Oct 9 - Oct 10
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.

13. 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 CA $89
CA $665 total
includes taxes & fees
Oct 13 - Oct 14
Heated Pool~Game Room~Modern~Resort~Disney Magic
A resort with a large pool, water slides, and palm trees.

14. 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 CA $98
CA $344 total
includes taxes & fees
Oct 12 - Oct 13
Amazing Home Near Disney, Amazing Amenities Renovated.Free Shuttle to the Parks!
A modern kitchen with white cabinets, stainless steel appliances, and a dining area set for a meal.

15. 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.
The price is CA $114
CA $606 total
includes taxes & fees
Oct 11 - Oct 12
Stylish Family Retreat in Kissimmee
1.jpg

16. 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 CA $157
CA $756 total
includes taxes & fees
Oct 12 - Oct 13
4 BD/ 4 BA/ Bella Vida (440 LF)
Exterior detail

17. 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 CA $191
CA $468 total
includes taxes & fees
Oct 11 - Oct 12
Fully renovated 3-bedroom townhome Kissimmee - Close to theme parks and airport
A modern kitchen with granite countertops, stainless steel appliances, and a dining area with a table and chairs.

18. 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 CA $144
CA $497 total
includes taxes & fees
Oct 13 - Oct 14
3-bedroom Disney Townhome Retreat
A modern kitchen with white cabinetry, a large island with two decorative bowls, and a pendant light with multiple bulbs.

19. 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 CA $114
CA $790 total
includes taxes & fees
Oct 12 - Oct 13
Freshly Updated~Near Disney~Private Pool~Resort
An aerial view of a hotel with a large swimming pool, multiple water slides, and a parking lot.

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

Private pool~Lazy River~Near Disney~Resort~Pool Table
Kissimmee
9.4 out of 10, Exceptional, (10 reviews)
"It was amazing!! Host Derek was so responsive - beautiful house!!"
Canada
Camille
The price is CA $153
CA $1,016 total
includes taxes & fees
Oct 20 - Oct 21
Private pool~Lazy River~Near Disney~Resort~Pool Table
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

Embassy Suites by Hilton Orlando Lake Buena Vista South

Embassy Suites by Hilton Orlando Lake Buena Vista South

10/10 Excellent
"Cleaning"
Mohamed 1-night trip
Posted 2 hours ago
Embassy Suites by Hilton Orlando Lake Buena Vista South

Price trends for Vacation Homes in Kissimmee

Less expensive
More expensive
This month
Next month
November
March
CA $168
CA $160
Month
Price
January
CA $175
February
CA $180
March
CA $231
April
CA $161
May
CA $161
June
CA $183
July
CA $192
August
CA $165
September
CA $168
October
CA $168
November
CA $160
December
CA $217
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed Vacation Homes in Kissimmee. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Kissimmee

Kissimmee Vacation Homes information

Number of reviews
278
Accommodation
15617 Vacation Homes
Lowest Price
CA $95
Highest Price
CA $1,016

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