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Our top choices for Kissimmee holiday homes
1. Maple Leaf Inn & Suites
Maple Leaf Inn & SuitesKissimmee
7.0 out of 10, Good, (73 reviews)
"Yes recomende"
Alex
The price is NZ$119
includes taxes & fees
11 Nov - 12 Nov
2. Charming 2BR/2BA Townhome with Patio near Disney
Charming 2BR/2BA Townhome with Patio near DisneyKissimmee
8.6 out of 10, Excellent, (27 reviews)
"Very nice stay"
michael h.
The price is NZ$455
includes taxes & fees
11 Nov - 12 Nov
3. Charming 2-bedroom Florida Getaway! Sleeps 6
Charming 2-bedroom Florida Getaway! Sleeps 6Kissimmee
9.8 out of 10, Exceptional, (24 reviews)
"Great little place. We would book it again."
Jack Francis G.
The price is NZ$510
includes taxes & fees
11 Nov - 12 Nov
5. Coral Cay 4BR Vacation Home,Close to Disney
Coral Cay 4BR Vacation Home,Close to DisneyKissimmee
The price is NZ$546
includes taxes & fees
11 Nov - 12 Nov
6. Heated Pool~Game Room~Modern~Resort~Disney Magic
Heated Pool~Game Room~Modern~Resort~Disney MagicLake 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!!!"
Kelly F.
The price is NZ$811
includes taxes & fees
30 Nov - 1 Dec
7. Freshly Updated~Near Disney~Private Pool~Resort
Freshly Updated~Near Disney~Private Pool~ResortCrystal Cove
10.0 out of 10, Exceptional, (4 reviews)
"Everything was amazing would love to rent more properties in the future!!"
Dijaun B.
The price is NZ$843
includes taxes & fees
17 Nov - 18 Nov
8. 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."
Bridget H.
9. Fully renovated 3-bedroom townhome Kissimmee - Close to theme parks and airport
Fully renovated 3-bedroom townhome Kissimmee - Close to theme parks and airportBuena Ventura Lakes
9.6 out of 10, Exceptional, (9 reviews)
"Excellent house"
Franks
The price is NZ$565
includes taxes & fees
11 Nov - 12 Nov
10. Shake Shack Heated Pool & Hot Tub
Shake Shack Heated Pool & Hot TubKissimmee
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! "
Keith
The price is NZ$708
includes taxes & fees
11 Nov - 12 Nov
11. 6 MINS TO Disney
6 MINS TO DisneyKissimmee
9.8 out of 10, Exceptional, (36 reviews)
"Great stay for big family!"
Sharlene B.
The price is NZ$659
includes taxes & fees
22 Nov - 23 Nov
12. 10 mins to parks in Orlando,Kissimmee, with gated community and pool
10 mins to parks in Orlando,Kissimmee, with gated community and poolCumbrian Lakes
9.6 out of 10, Exceptional, (124 reviews)
"Great house, easy to get t o all the parks . Would definitely stay there again "
Corey C.
The price is NZ$759
includes taxes & fees
15 Nov - 16 Nov
13. -A Sweet Home Near Theme Parks!-
-A Sweet Home Near Theme Parks!-Kissimmee
10.0 out of 10, Exceptional, (6 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!"
Natalie V.
The price is NZ$611
includes taxes & fees
11 Nov - 12 Nov
14. Disney Getaway w/ Splash Pool + Kids’ Theme Rooms
Disney Getaway w/ Splash Pool + Kids’ Theme RoomsKissimmee
9.6 out of 10, Exceptional, (25 reviews)
"This property was excellent and the host was amazing in every respect. The property was very clean and had all the necessary amenities. We had a huge disappointment with our original rental which was deplorable and with this property it was bliss! We will definitely stay here again when we return to Florida. If you’re looking for a 5 Star property this one is sure to please. The property also has plenty of nice cookware and dishes so can work for family gatherings as well. For Disney fans there...
Wanda O.
15. NBA Dream Mansion 15br Luxury Villa w Pool
NBA Dream Mansion 15br Luxury Villa w PoolKissimmee
The price is NZ$2,609
includes taxes & fees
9 Dec - 10 Dec
16. Plunge Pool Oasis~Bella Vida Resort~Close to Parks
Plunge Pool Oasis~Bella Vida Resort~Close to ParksBellavida
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"
Marjorie S.
17. 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 OrlandoKissimmee
9.8 out of 10, Exceptional, (39 reviews)
"Nice view! Very quiet."
Donald B.
18. Resort-Style Villa | Pool, Spa & Game Room!
Resort-Style Villa | Pool, Spa & Game Room!Kissimmee
8.0 out of 10, Very good, (1 review)
The price is NZ$1,068
includes taxes & fees
9 Dec - 10 Dec
19. Private pool~Lazy River~Near Disney~Resort~Pool Table
Private pool~Lazy River~Near Disney~Resort~Pool TableKissimmee
9.4 out of 10, Exceptional, (10 reviews)
"It was amazing!! Host Derek was so responsive - beautiful house!!"
Camille
The price is NZ$1,157
includes taxes & fees
11 Nov - 12 Nov
20. Superb Townhouse Newly Renovated 1.5 miles to Disney
Superb Townhouse Newly Renovated 1.5 miles to DisneyKissimmee
9.8 out of 10, Exceptional, (146 reviews)
"This is a beautiful townhome,secure and also close to alot of places. Loved it and definitely plan on coming back!"
Rachel M.
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.
