Holiday Homes in Kissimmee

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Our top choices for Kissimmee holiday homes

1. Maple Leaf Inn & Suites

Maple Leaf Inn & Suites
2.5 star property
Kissimmee
7.0 out of 10, Good, (73 reviews)
"Yes recomende"
United States
Alex
The price is €60
includes taxes & fees
8 Nov - 9 Nov
Maple Leaf Inn & Suites

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 €235
includes taxes & fees
9 Nov - 10 Nov
Charming 2BR/2BA Townhome with Patio near Disney

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

Resort Stay~Near Disney~Bright~Gym~Hot Tub
Kissimmee
10.0 out of 10, Exceptional, (11 reviews)
"Property was very clean and convenient and host communication was excellent"
United States
John
The price is €369
includes taxes & fees
7 Nov - 8 Nov
Resort Stay~Near Disney~Bright~Gym~Hot Tub

4. Charming 2-bedroom Florida Getaway! Sleeps 6

Charming 2-bedroom Florida Getaway! Sleeps 6
Kissimmee
9.8 out of 10, Exceptional, (24 reviews)
"Great little place. We would book it again."
United States
Jack Francis G.
The price is €274
includes taxes & fees
9 Nov - 10 Nov
Charming 2-bedroom Florida Getaway! Sleeps 6

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

Coral Cay 4BR Vacation Home,Close to Disney
Kissimmee
The price is €274
includes taxes & fees
10 Nov - 11 Nov
Coral Cay 4BR Vacation Home,Close to Disney

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

Heated Pool~Game Room~Modern~Resort~Disney Magic
Lake Berkley
10.0 out of 10, Exceptional, (6 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 €412
includes taxes & fees
1 Dec - 2 Dec
Heated Pool~Game Room~Modern~Resort~Disney Magic

7. 3BR townhouse near Disney with themed rooms

3BR townhouse near Disney with themed rooms
Kissimmee
The price is €315
includes taxes & fees
9 Nov - 10 Nov
3BR townhouse near Disney with themed rooms

8. 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 €432
includes taxes & fees
17 Nov - 18 Nov
Freshly Updated~Near Disney~Private Pool~Resort

9. 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 €351
includes taxes & fees
22 Nov - 23 Nov
6 MINS TO Disney

10. 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, (47 reviews)
"Comfortable & close to Orlando attractions."
United States
Bridget H.
The price is €351
includes taxes & fees
8 Nov - 9 Nov
Escape to Paradise!Luxury Waterfront Heated Pool House with Game Room and Piano!

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 €378
includes taxes & fees
8 Nov - 9 Nov
Plunge Pool Oasis~Bella Vida Resort~Close to Parks

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 €356
includes taxes & fees
11 Nov - 12 Nov
Shake Shack Heated Pool & Hot Tub

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 €330
includes taxes & fees
8 Nov - 9 Nov
Stylish Family Retreat in Kissimmee

14. 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 €289
includes taxes & fees
9 Nov - 10 Nov
Fully renovated 3-bedroom townhome Kissimmee - Close to theme parks and airport

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 €1,355
includes taxes & fees
18 Nov - 19 Nov
NBA Dream Mansion 15br Luxury Villa w Pool

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 €303
includes taxes & fees
9 Nov - 10 Nov
-A Sweet Home Near Theme Parks!-

17. 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.
Incredible Fantasy World Nr Disney, Amazing Amenities.Free Shuttle to the Parks

18. ☆☆☆☆☆Price Drop! OCT-NOV • 5BR • Pool • Themed Rooms!☆☆☆☆☆

☆☆☆☆☆Price Drop! OCT-NOV • 5BR • Pool • Themed Rooms!☆☆☆☆☆
Kissimmee
9.8 out of 10, Exceptional, (10 reviews)
"Place was great!"
United States
melissa m.
The price is €619
includes taxes & fees
27 Nov - 28 Nov
☆☆☆☆☆Price Drop! OCT-NOV • 5BR • Pool • Themed Rooms!☆☆☆☆☆

19. 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 €293
includes taxes & fees
8 Nov - 9 Nov
It’s only 15 minutes drive to Disney World and the amazing outlets in Orlando

20. Resort-Style Villa | Pool, Spa & Game Room!

Resort-Style Villa | Pool, Spa & Game Room!
4.0 star property
Kissimmee
8.0 out of 10, Very good, (1 review)
The price is €522
includes taxes & fees
19 Nov - 20 Nov
Resort-Style Villa | Pool, Spa & Game Room!
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.

Learn more about Kissimmee

Just minutes from Orlando's theme parks, this sunny gateway offers airboat tours where gators glide beneath your feet. Spend mornings paddling through natural springs and evenings exploring Old Town's vintage car shows and family-friendly restaurants.

A large, historic building with a tower, reflecting on a calm lake with lily pads, surrounded by trees and a sunset sky.

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