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

Kissimmee Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Kissimmee vacation homes

A modern kitchen with a central island, built-in appliances, and a large window providing natural light.

1. Resort Stay~Near Disney~Bright~Gym~Hot Tub

Resort Stay~Near Disney~Bright~Gym~Hot Tub
Kissimmee
10.0 out of 10, Exceptional, (8 reviews)
"The place was great & convenient if going to the parks. It had everything we needed & was clean and nicely updated."
United States
Sadie H.
The price is CA $55
CA $457 total
includes taxes & fees
Sep 20 - Sep 21
Resort Stay~Near Disney~Bright~Gym~Hot Tub
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.

2. Maple Leaf Inn & Suites

Maple Leaf Inn & Suites
2.5 star property
Kissimmee
6.8 out of 10, (71 reviews)
"The room was clean and the staff was okay "
United States
Shaneka
The price is CA $82
CA $93 total
includes taxes & fees
Sep 14 - Sep 15
Maple Leaf Inn & Suites
A modern kitchen with white cabinets, stainless steel appliances, and a marble island with bar stools.

3. 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 $109
CA $405 total
includes taxes & fees
Sep 19 - Sep 20
Charming 2-bedroom Florida Getaway! Sleeps 6
A bedroom with a large bed, a wooden headboard, two bedside tables with lamps, a view of a swimming pool, and a sliding door.

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

Heated Pool~Game Room~Modern~Resort~Disney Magic
Lake Berkley
10.0 out of 10, Exceptional, (1 review)
"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 $83
CA $649 total
includes taxes & fees
Sep 24 - Sep 25
Heated Pool~Game Room~Modern~Resort~Disney Magic
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 $58
CA $513 total
includes taxes & fees
Sep 17 - Sep 18
Private Resort Access~King Bed~Hot Tub~Balcony
A residential complex with multiple two-story houses, a central swimming pool, and well-maintained lawns.

6. 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, (31 reviews)
"Awesome place and location. "
United States
Montigo W.
The price is CA $118
CA $550 total
includes taxes & fees
Sep 14 - Sep 15
Disney Themed Single Family Home, Private Pool, 15 Mins From Disney & Sleeps 10

7. 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 $137
CA $593 total
includes taxes & fees
Sep 14 - Sep 15
Sunset Greens Villa
A modern living room with a curved sectional sofa, a flat-screen TV mounted on the wall, and a large window providing natural light.

8. 5Bd Home, Storey Lake with Private Pool 14 Guests - Private Pool - 2773 BD

5Bd Home, Storey Lake with Private Pool 14 Guests - Private Pool - 2773 BD
Kissimmee
9.2 out of 10, Wonderful, (34 reviews)
"Worked great for our trip!"
United States
Jennifer
The price is CA $123
CA $770 total
includes taxes & fees
Sep 16 - Sep 17
5Bd Home, Storey Lake with Private Pool 14 Guests - Private Pool - 2773 BD

9. Awesome 5BR Townhouse Near Disney - Private Pool!

Awesome 5BR Townhouse Near Disney - Private Pool!
Kissimmee
9.8 out of 10, Exceptional, (10 reviews)
"House is gorgeous and plenty of room, I will highly recommend this place, our family loved it "
United States
Sky K.
The price is CA $151
CA $873 total
includes taxes & fees
Sep 25 - Sep 26
Awesome 5BR Townhouse Near Disney - Private Pool!
A modern kitchen with a central island, bar stools, pendant lighting, and a coffee station.

10. Near Disney: Private Heated Pool, BBQ Included & Sleeps 10

Near Disney: Private Heated Pool, BBQ Included & Sleeps 10
Kissimmee
9.0 out of 10, Wonderful, (25 reviews)
"Great communication with host - great location "
United States
Ana H.
The price is CA $159
CA $557 total
includes taxes & fees
Sep 14 - Sep 15
Near Disney: Private Heated Pool, BBQ Included & Sleeps 10
A swimming pool with blue chairs and tables, surrounded by palm trees and a building with a red roof.

11. Magical Family Townhome Retreat – Comfort & Convenience Near Top Attractions!

Magical Family Townhome Retreat – Comfort & Convenience Near Top Attractions!
Kissimmee
9.4 out of 10, Exceptional, (59 reviews)
"Very clean family friendly stay. I will definitely come stay again and recommend to friends and family to book their stay here."
United States
Elain S.
The price is CA $136
CA $493 total
includes taxes & fees
Sep 15 - Sep 16
Magical Family Townhome Retreat – Comfort & Convenience Near Top Attractions!
A modern living room with a round dining table, grey sofas, and a TV mounted on the wall.

12. 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 $117
CA $766 total
includes taxes & fees
Sep 14 - Sep 15
Disney Getaway w/ Splash Pool + Kids’ Theme Rooms

13. 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 $124
CA $334 total
includes taxes & fees
Sep 14 - Sep 15
SPACIOUS 2 BEDROOM HOUSE IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 2772 W

14. "Pequod Lakeview" - 4BD/3BA Townhome near Disney

"Pequod Lakeview" - 4BD/3BA Townhome near Disney
Kissimmee
9.4 out of 10, Exceptional, (21 reviews)
"Simple check in and out. Clean home in safe gated neighborhood. Close to the parks."
United States
Trey J.
The price is CA $111
CA $558 total
includes taxes & fees
Sep 14 - Sep 15
"Pequod Lakeview" - 4BD/3BA Townhome near Disney

15. 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 $120
CA $474 total
includes taxes & fees
Oct 5 - Oct 6
2BR family retreat w/ resort access
A hot tub with a glass ceiling and a view of the outdoors.

16. Luxury Lake Resort ✨

Luxury Lake Resort ✨
Cumbrian Lakes
9.8 out of 10, Exceptional, (65 reviews)
"My family and I really enjoyed our stay. This house offers everything needed to have a comfortable stay."
United States
Shannon B.
The price is CA $136
CA $582 total
includes taxes & fees
Sep 14 - Sep 15
Luxury Lake Resort ✨
A modern living room with a sofa, ottoman, and glass dining table. There is a kitchen area with a microwave and cabinets.

17. 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, (58 reviews)
"Loved our beautiful stay and appreciated the extra details to amenities during our stay! "
United States
Jennifer D.
The price is CA $69
CA $236 total
includes taxes & fees
Oct 7 - Oct 8
Enchanting Newly Renovated 1.5miles to Disney and Near Tons of Restaurants 760

18. 4BD/3BA Family Townhome near Disney

4BD/3BA Family Townhome near Disney
Kissimmee
9.8 out of 10, Exceptional, (51 reviews)
"The home was warm, welcoming and very clean."
United States
Jonathan L.
The price is CA $132
CA $586 total
includes taxes & fees
Sep 14 - Sep 15
4BD/3BA Family Townhome near Disney
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 $195
CA $832 total
includes taxes & fees
Oct 11 - Oct 12
Freshly Updated~Near Disney~Private Pool~Resort
A spacious outdoor bar area with high ceilings and large windows, featuring multiple seating arrangements and a television screen.

20. 5BD Private Pool Villa - Storey Lake Resort - 4810 LL

5BD Private Pool Villa - Storey Lake Resort - 4810 LL
Kissimmee
9.0 out of 10, Wonderful, (32 reviews)
"No complaints, house was very spacious and clean"
United States
Michael G.
The price is CA $105
CA $713 total
includes taxes & fees
Sep 21 - Sep 22
5BD Private Pool Villa - Storey Lake Resort - 4810 LL
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Kissimmee Hotel Reviews

Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent
"We absolutely loved our stay here. The staff were all very friendly and helpful. The River Island section made for a fun pool day and we spent over 6 hours there with the pool, lazy river, slides and mini golf. Our room was clean and well maintained. There was a full kitchen and Publix less than 5 minutes away. We will absolutely be staying here again."
Shannon 2-night trip
Posted less than an hour ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Price trends for Vacation Homes in Kissimmee

Less expensive
More expensive
This month
Next month
November
March
CA $168
CA $168
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
17
Accommodation
15566 Vacation Homes
Lowest Price
CA $93
Highest Price
CA $2,139

Explore a world of travel with Expedia