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 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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 28 - Oct 29
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, (27 reviews)
"Very nice stay"
United States
michael h.
The price is CA $69
CA $320 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 28 - Oct 29
Private Resort Access~King Bed~Hot Tub~Balcony
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, (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 28 - Oct 29
Charming 2-bedroom Florida Getaway! Sleeps 6
A modern kitchen with a central island, built-in appliances, and a large window providing natural light.

5. 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 building with a pink facade, white columns, and a brown door.

6. Coral Cay 4BR Vacation Home,Close to Disney

Coral Cay 4BR Vacation Home,Close to Disney
Kissimmee
The price is CA $78
CA $436 total
includes taxes & fees
Oct 28 - Oct 29
Coral Cay 4BR Vacation Home,Close to Disney
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, (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 $75
CA $645 total
includes taxes & fees
Nov 18 - Nov 19
Heated Pool~Game Room~Modern~Resort~Disney Magic
A modern living room with a sofa set, a dining area with chairs, and a kitchen with wooden cabinets.

8. 6 MINS TO Disney

6 MINS TO Disney
Kissimmee
9.8 out of 10, Exceptional, (36 reviews)
"Great stay for big family!"
United States
Sharlene B.
The price is CA $153
CA $578 total
includes taxes & fees
Nov 22 - Nov 23
6 MINS TO Disney
A two-story house with a porch, a staircase, and a covered carport.

9. 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 modern kitchen with white cabinetry, a large island with two decorative bowls, and a pendant light with multiple bulbs.

10. 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 $94
CA $747 total
includes taxes & fees
Nov 17 - Nov 18
Freshly Updated~Near Disney~Private Pool~Resort
Exterior detail

11. 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 $471 total
includes taxes & fees
Nov 2 - Nov 3
Fully renovated 3-bedroom townhome Kissimmee - Close to theme parks and airport
Exterior

12. 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 28 - Oct 29
Shake Shack Heated Pool & Hot Tub
A swimming pool with lounge chairs and a tiled deck.

13. 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)
"Place was clean"
United States
Kayla C.
The price is CA $125
CA $425 total
includes taxes & fees
Nov 17 - Nov 18
Fabulous 3 Bedrooms 3 bath Townhouse in a Resort 15 min to Disney
A modern kitchen with white cabinets, stainless steel appliances, and a dining area set for a meal.

14. 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 30 - Oct 31
Stylish Family Retreat in Kissimmee
A modern kitchen with a central island, stainless steel appliances, and a view of a body of water through large windows.

15. 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 $251
CA $551 total
includes taxes & fees
Nov 1 - Nov 2
Escape to Paradise!Luxury Waterfront Heated Pool House with Game Room and Piano!
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 $510 total
includes taxes & fees
Nov 2 - Nov 3
-A Sweet Home Near Theme Parks!-
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 $69
CA $637 total
includes taxes & fees
Oct 28 - Oct 29
Plunge Pool Oasis~Bella Vida Resort~Close to Parks
An aerial view of a resort with a central pool area, multiple swimming pools, and a water park.

18. Perfect Home Near Disney, Amazing Amenities Renovated.Free Shuttle to the Parks!

Perfect Home Near Disney, Amazing Amenities Renovated.Free Shuttle to the Parks!
Kissimmee
9.4 out of 10, Exceptional, (43 reviews)
"Exactly what we needed for a quick summer trip. Amenities are great and the unit is just perfect."
United States
Ellen M.
Perfect Home Near Disney, Amazing Amenities Renovated.Free Shuttle to the Parks!
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

Embassy Suites by Hilton Orlando Lake Buena Vista South

Embassy Suites by Hilton Orlando Lake Buena Vista South

10/10 Excellent
"Everything was great. 5 stars"
Pablo 3-night trip
Posted less than an hour ago
Embassy Suites by Hilton Orlando Lake Buena Vista South

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
343
Accommodation
15616 Vacation Homes
Lowest Price
CA $94
Highest Price
CA $1,065

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