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 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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 18 - Oct 19
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
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 $64
CA $529 total
includes taxes & fees
Nov 2 - Nov 3
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 $131
CA $436 total
includes taxes & fees
Oct 27 - Oct 28
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.

5. 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 $322 total
includes taxes & fees
Oct 17 - Oct 18
Charming 2BR/2BA Townhome with Patio near Disney
Outdoor dining

6. 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 $339 total
includes taxes & fees
Oct 16 - Oct 17
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.

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

Heated Pool~Game Room~Modern~Resort~Disney Magic
Lake Berkley
10.0 out of 10, Exceptional, (4 reviews)
"Property was very clean and so well cared for. Communication was very easy and excellent. Exceeded our expectations"
United Kingdom
Julie S.
The price is CA $91
CA $667 total
includes taxes & fees
Nov 2 - Nov 3
Heated Pool~Game Room~Modern~Resort~Disney Magic
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 CA $182
CA $528 total
includes taxes & fees
Oct 27 - Oct 28
Shake Shack Heated Pool & Hot Tub
A modern living room with a round dining table, grey sofas, and a TV mounted on the wall.

9. 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 CA $120
CA $779 total
includes taxes & fees
Oct 19 - Oct 20
Disney Getaway w/ Splash Pool + Kids’ Theme Rooms
A residential complex with multiple two-story houses, a central swimming pool, and well-maintained lawns.

10. 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)
"We enjoyed our stay!"
United States
Kelly F.
The price is CA $151
CA $603 total
includes taxes & fees
Oct 17 - Oct 18
Disney Themed Single Family Home, Private Pool, 15 Mins From Disney & Sleeps 10
A resort with a large pool, water slides, and palm trees.

11. 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 $112
CA $360 total
includes taxes & fees
Oct 19 - Oct 20
Amazing Home Near Disney, Amazing Amenities Renovated.Free Shuttle to the Parks!
A modern kitchen with granite countertops, stainless steel appliances, and a dining area with a table and chairs.

12. 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 $146
CA $501 total
includes taxes & fees
Oct 19 - Oct 20
3-bedroom Disney Townhome Retreat
A modern kitchen with white cabinets, stainless steel appliances, and a dining area set for a meal.

13. 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 $610 total
includes taxes & fees
Oct 16 - Oct 17
Stylish Family Retreat in Kissimmee
An outdoor patio with wicker furniture, a glass table, and a hammock.

14. -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 CA $199
CA $518 total
includes taxes & fees
Oct 18 - Oct 19
-A Sweet Home Near Theme Parks!-
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, (8 reviews)
"Excellent house"
United States
Franks
The price is CA $191
CA $467 total
includes taxes & fees
Oct 19 - Oct 20
Fully renovated 3-bedroom townhome Kissimmee - Close to theme parks and airport
A modern kitchen with white cabinetry, a large island with two decorative bowls, and a pendant light with multiple bulbs.

16. 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 $124
CA $799 total
includes taxes & fees
Oct 25 - Oct 26
Freshly Updated~Near Disney~Private Pool~Resort
A swimming pool with lounge chairs and gazebos, surrounded by palm trees and buildings with red-tiled roofs.

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

Plunge Pool Oasis~Bella Vida Resort~Close to Parks
Bellavida
10.0 out of 10, Exceptional, (12 reviews)
"Excellent customer service from booking to checkout. Maintenance was very quick to respond and address any concerns. Quiet neighborhood & great location"
United States
Marjorie S.
The price is CA $92
CA $674 total
includes taxes & fees
Oct 18 - Oct 19
Plunge Pool Oasis~Bella Vida Resort~Close to Parks
A modern kitchen with a stainless steel refrigerator, a built-in dishwasher, and a large island with a sink.

18. Family 5BR Villa w Pool Theatre Reunion Village

Family 5BR Villa w Pool Theatre Reunion Village
2.5 star property
Reunion
Family 5BR Villa w Pool Theatre Reunion Village
1.jpg

19. 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 $156
CA $754 total
includes taxes & fees
Oct 20 - Oct 21
4 BD/ 4 BA/ Bella Vida (440 LF)
A modern kitchen with a central island, stainless steel appliances, and a view of a body of water through large windows.

20. 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, (46 reviews)
"Comfortable & close to Orlando attractions."
United States
Bridget H.
The price is CA $283
CA $596 total
includes taxes & fees
Nov 8 - Nov 9
Escape to Paradise!Luxury Waterfront Heated Pool House with Game Room and Piano!
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

Galleria Palms Hotel

Galleria Palms Hotel

10/10 Excellent
"Todo"
Mariano 1-night trip
Posted 1 hour ago
Galleria Palms Hotel

Price trends for Vacation Homes in Kissimmee

Less expensive
More expensive
Next month
November
March
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
321
Accommodation
15617 Vacation Homes
Lowest Price
CA $95
Highest Price
CA $799

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