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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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 $83
CA $94 total
includes taxes & fees
Oct 26 - Oct 27
Maple Leaf Inn & Suites
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.

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

Charming 2BR/2BA Townhome with Patio near Disney
Kissimmee
8.6 out of 10, Excellent, (25 reviews)
"Very nice stay"
United States
michael h.
The price is CA $69
CA $322 total
includes taxes & fees
Oct 31 - Nov 1
Charming 2BR/2BA Townhome with Patio near Disney
A modern bedroom with a large bed, a ceiling fan, and a view of a pool and building.

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

Private Resort Access~King Bed~Hot Tub~Balcony
Kissimmee
10.0 out of 10, Exceptional, (4 reviews)
"Great host and fantastic pool"
United States
paul m.
The price is CA $64
CA $527 total
includes taxes & fees
Oct 27 - Oct 28
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.

4. 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 $111
CA $584 total
includes taxes & fees
Nov 7 - Nov 8
Resort Stay~Near Disney~Bright~Gym~Hot Tub
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, (23 reviews)
"Great little place. We would book it again."
United States
Jack Francis G.
The price is CA $129
CA $434 total
includes taxes & fees
Oct 27 - Oct 28
Charming 2-bedroom Florida Getaway! Sleeps 6
A poolside area with lounge chairs, a table, and an umbrella.

6. 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, (39 reviews)
"Nice view! Very quiet."
United States
Donald B.
The price is CA $164
CA $473 total
includes taxes & fees
Oct 26 - Oct 27
It’s only 15 minutes drive to Disney World and the amazing outlets in Orlando
Outdoor dining

7. 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, (18 reviews)
"Great place. Was clean and cozy. "
United States
Casey W.
The price is CA $125
CA $338 total
includes taxes & fees
Oct 28 - Oct 29
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.

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

Heated Pool~Game Room~Modern~Resort~Disney Magic
Lake Berkley
10.0 out of 10, Exceptional, (5 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 $82
CA $654 total
includes taxes & fees
Nov 18 - Nov 19
Heated Pool~Game Room~Modern~Resort~Disney Magic
Exterior

9. 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 $179
CA $520 total
includes taxes & fees
Oct 27 - Oct 28
Shake Shack Heated Pool & Hot Tub
Exterior detail

10. 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, (9 reviews)
"Excellent house"
United States
Franks
The price is CA $151
CA $467 total
includes taxes & fees
Oct 26 - Oct 27
Fully renovated 3-bedroom townhome Kissimmee - Close to theme parks and airport
A swimming pool with lounge chairs and gazebos, surrounded by palm trees and buildings with red-tiled roofs.

11. 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 $69
CA $631 total
includes taxes & fees
Oct 26 - Oct 27
Plunge Pool Oasis~Bella Vida Resort~Close to Parks
A modern kitchen with white cabinetry, a large island with two decorative bowls, and a pendant light with multiple bulbs.

12. 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 $95
CA $755 total
includes taxes & fees
Nov 17 - Nov 18
Freshly Updated~Near Disney~Private Pool~Resort
A spacious living room with a large sectional sofa, a wooden coffee table, and a flat-screen TV mounted on the wall.

13. 10 mins to parks in Orlando,Kissimmee, with gated community and pool

10 mins to parks in Orlando,Kissimmee, with gated community and pool
Cumbrian Lakes
9.8 out of 10, Exceptional, (123 reviews)
"Great house, easy to get t o all the parks . Would definitely stay there again "
United States
Corey C.
The price is CA $144
CA $625 total
includes taxes & fees
Oct 26 - Oct 27
10 mins to parks in Orlando,Kissimmee, with gated community and pool
A swimming pool with lounge chairs and a tiled deck.

14. Fabulous 3 Bedrooms 3 bath Townhouse in a Resort 15 min to Disney

Fabulous 3 Bedrooms 3 bath Townhouse in a Resort 15 min to Disney
Kissimmee
9.2 out of 10, Wonderful, (15 reviews)
"Over all a great stay!! I was able to Walmart order my groceries and super close to all the parks. Comfortable stay for my big family and will probably book again in the future !"
United States
Edith V.
The price is CA $125
CA $428 total
includes taxes & fees
Nov 17 - Nov 18
Fabulous 3 Bedrooms 3 bath Townhouse in a Resort 15 min to Disney
A large rectangular pool with a central island, surrounded by palm trees and lounge chairs.

15. NBA Dream Mansion 15br Luxury Villa w Pool

NBA Dream Mansion 15br Luxury Villa w Pool
2.0 star property
Kissimmee
The price is CA $408
CA $1,976 total
includes taxes & fees
Oct 26 - Oct 27
NBA Dream Mansion 15br Luxury Villa w Pool
An outdoor patio with wicker furniture, a glass table, and a hammock.

16. -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 $196
CA $506 total
includes taxes & fees
Oct 26 - Oct 27
-A Sweet Home Near Theme Parks!-
A modern kitchen with a central island, stainless steel appliances, and a view of a body of water through large windows.

17. 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 $279
CA $587 total
includes taxes & fees
Nov 8 - Nov 9
Escape to Paradise!Luxury Waterfront Heated Pool House with Game Room and Piano!
A modern kitchen with white cabinets, stainless steel appliances, and a dining area set for a meal.

18. 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 $112
CA $557 total
includes taxes & fees
Oct 27 - Oct 28
Stylish Family Retreat in Kissimmee
A swimming pool with a glass enclosure, outdoor seating, and a covered patio area.

19. Lake Breeze 6 Bedrooms

Lake Breeze 6 Bedrooms
4.0 star property
Kissimmee
The price is CA $380
CA $1,065 total
includes taxes & fees
Nov 19 - Nov 20
Lake Breeze 6 Bedrooms
A resort with a large pool, water slides, and lounge areas.

20. Incredible Fantasy World Nr Disney, Amazing Amenities.Free Shuttle to the Parks

Incredible Fantasy World Nr Disney, Amazing Amenities.Free Shuttle to the Parks
Kissimmee
9.4 out of 10, Exceptional, (83 reviews)
"Clean spacious place. Fantastic pool area with slides. Family loved it."
United States
Thomas K.
The price is CA $97
CA $338 total
includes taxes & fees
Nov 2 - Nov 3
Incredible Fantasy World Nr Disney, Amazing Amenities.Free Shuttle to the Parks
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

Legacy Vacation Resorts - Kissimmee/Orlando

Legacy Vacation Resorts - Kissimmee/Orlando

8/10 Good
"overall ok , the water pressure sucks but ok"
Tamra 2-night trip
Posted 1 hour ago
Legacy Vacation Resorts - Kissimmee/Orlando

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
301
Accommodation
15616 Vacation Homes
Lowest Price
CA $94
Highest Price
CA $1,976

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