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Our top choices for Kissimmee vacation homes
1. Maple Leaf Inn & Suites
Maple Leaf Inn & SuitesKissimmee
7.0 out of 10, Good, (73 reviews)
"Yes recomende"
Alex
The price is CA $84
CA $96 total
includes taxes & fees
Nov 15 - Nov 16
2. Sunset Greens Villa
Sunset Greens VillaReunion
10.0 out of 10, Exceptional, (1 review)
"Very nice property"
Richard
The price is CA $157
CA $629 total
includes taxes & fees
Nov 18 - Nov 19
3. Corvette Cove
Corvette CoveKissimmee
The price is CA $473
CA $860 total
includes taxes & fees
Nov 27 - Nov 28
4. 3BR townhouse near Disney with themed rooms
3BR townhouse near Disney with themed roomsKissimmee
The price is CA $160
CA $500 total
includes taxes & fees
Nov 29 - Nov 30
5. Charming 2-bedroom Florida Getaway! Sleeps 6
Charming 2-bedroom Florida Getaway! Sleeps 6Kissimmee
9.8 out of 10, Exceptional, (25 reviews)
"Great little place. We would book it again."
Jack Francis G.
6. 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 $88
CA $354 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 $675 total
includes taxes & fees
Nov 17 - Nov 18
8. 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 $120
CA $677 total
includes taxes & fees
Nov 30 - Dec 1
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 CA $154
CA $440 total
includes taxes & fees
Nov 16 - Nov 17
10. 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 $135
CA $538 total
includes taxes & fees
Nov 22 - Nov 23
11. 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 $207
CA $557 total
includes taxes & fees
Dec 8 - Dec 9
12. -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
13. 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 $624 total
includes taxes & fees
Nov 15 - Nov 16
14. Beautiful 4/3 TH w/ private pool in gated resort w/ clubhouse (10' to WDW)
Beautiful 4/3 TH w/ private pool in gated resort w/ clubhouse (10' to WDW)Kissimmee
9.4 out of 10, Exceptional, (56 reviews)
"This home was such a wonderful space for our stay! It was clean, welcoming & in a great location! Would definitely stay here again!"
Kathleen C.
The price is CA $115
CA $549 total
includes taxes & fees
Nov 18 - Nov 19
15. 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.
The price is CA $167
CA $465 total
includes taxes & fees
Nov 15 - Nov 16
16. 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 10Lake Berkley
9.2 out of 10, Wonderful, (34 reviews)
"We enjoyed our stay!"
Kelly F.
The price is CA $155
CA $582 total
includes taxes & fees
Nov 20 - Nov 21
17. 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.
The price is CA $91
CA $614 total
includes taxes & fees
Nov 17 - Nov 18
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 CA $261
CA $830 total
includes taxes & fees
Dec 9 - Dec 10
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 $755 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.
