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Our top choices for Kissimmee vacation homes
1. Maple Leaf Inn & Suites
Maple Leaf Inn & SuitesKissimmee
6.8 out of 10, (74 reviews)
"Yes recomende"
Alex
The price is CA $84
CA $96 total
includes taxes & fees
Nov 16 - Nov 17
2. 7BR Near Disney with Private Pool, Games and 4 King Suites
7BR Near Disney with Private Pool, Games and 4 King SuitesKissimmee
The price is CA $225
CA $848 total
includes taxes & fees
Nov 16 - Nov 17
3. 3BR townhouse at Fiesta Key in kissimmee
3BR townhouse at Fiesta Key in kissimmeeKissimmee
The price is CA $160
CA $501 total
includes taxes & fees
Nov 29 - Nov 30
4. Sunset Greens Villa
Sunset Greens VillaReunion
10.0 out of 10, Exceptional, (1 review)
"Very nice property"
Richard
The price is CA $177
CA $653 total
includes taxes & fees
Nov 19 - Nov 20
5. Charming 2BR/2BA Townhome with Patio near Disney
Charming 2BR/2BA Townhome with Patio near DisneyKissimmee
8.6 out of 10, Excellent, (28 reviews)
"Very nice stay"
michael h.
The price is CA $81
CA $347 total
includes taxes & fees
Nov 16 - Nov 17
6. 4732 Lakeview Townhome Near Disney Gym Access
4732 Lakeview Townhome Near Disney Gym AccessKissimmee
9.8 out of 10, Exceptional, (19 reviews)
"I would like to have had a mop the toilets was too low the door and one in the bedroom closet was off the furniture need upgrade"
norris f.
The price is CA $100
CA $604 total
includes taxes & fees
Nov 16 - Nov 17
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 CA $74
CA $676 total
includes taxes & fees
Nov 17 - Nov 18
8. Modern 4BR/2BA with pool in gated community
Modern 4BR/2BA with pool in gated communityKissimmee
The price is CA $197
CA $575 total
includes taxes & fees
Nov 23 - Nov 24
9. 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 CA $128
CA $529 total
includes taxes & fees
Nov 22 - Nov 23
10. 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 CA $119
CA $676 total
includes taxes & fees
Nov 30 - Dec 1
11. 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 CA $139
CA $599 total
includes taxes & fees
Nov 16 - Nov 17
12. 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 CA $154
CA $440 total
includes taxes & fees
Nov 16 - Nov 17
13. Corvette Cove
Corvette CoveKissimmee
The price is CA $535
CA $934 total
includes taxes & fees
Nov 27 - Nov 28
14. 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 CA $218
CA $569 total
includes taxes & fees
Dec 8 - Dec 9
15. -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 CA $200
CA $476 total
includes taxes & fees
Nov 16 - Nov 17
16. 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, (40 reviews)
"Nice view! Very quiet."
Donald B.
The price is CA $167
CA $447 total
includes taxes & fees
Nov 16 - Nov 17
17. 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 CA $232
CA $795 total
includes taxes & fees
Dec 9 - Dec 10
18. Luxury Lake Resort ✨
Luxury Lake Resort ✨Cumbrian Lakes
9.8 out of 10, Exceptional, (66 reviews)
"My family and I really enjoyed our stay. This house offers everything needed to have a comfortable stay."
Shannon B.
The price is CA $167
CA $581 total
includes taxes & fees
Nov 16 - Nov 17
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 CA $134
CA $950 total
includes taxes & fees
Nov 16 - Nov 17
20. Family-Friendly 4 Bedroom 3 Bath Pool Home 271
Family-Friendly 4 Bedroom 3 Bath Pool Home 271Kissimmee
8.4 out of 10, Very good, (28 reviews)
"First of all we entered and everything was off and with the broken wall and the sofa, the refrigerator was broken, the food was ruined and the pool was dirty with hair, the grill didn't work either, we didn't repeat it"
Jennifer
The price is CA $145
CA $756 total
includes taxes & fees
Dec 8 - Dec 9
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.
