Vacation Rentals in Kissimmee, Florida

50 Properties Available

Solara Resort - 5 Bed 4.5 Baths Townhouse Private vacation home
Solara Resort - 5 Bed 4.5 Baths Townhouse
$8414 / night
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Solara Resort - 9 Bed 6 Baths Villa Villa
Solara Resort - 9 Bed 6 Baths Villa
$8411 / night
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New Listing! Windsor At Westside Resort, 7mi to Disney & 15mi to Universal - FS362035 Private vacation home
New Listing! Windsor At Westside Resort, 7mi to Disney & 15mi to Universal - FS362035
$7707 / night
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SUPER STAR mansion w\/ pool & spa close to Disney! Private vacation home
SUPER STAR mansion w\/ pool & spa close to Disney!
$6177 / night
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Spacious 15BR 14 Bath Vernada Palms Resort-2477RD Private vacation home
Spacious 15BR 14 Bath Vernada Palms Resort-2477RD
$5527 / night
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Beautiful Story Lake Resort 3 BR 2 Bath Condo-4741-208CTD Private vacation home
Beautiful Story Lake Resort 3 BR 2 Bath Condo-4741-208CTD
$5462 / night
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New 8Bd Pool Spa Gm Hm Encore Club at Reunion-7708FD Villa
New 8Bd Pool Spa Gm Hm Encore Club at Reunion-7708FD
$5250 / night
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The Grove At Reunion-TT485 Villa
The Grove At Reunion-TT485
$4826 / night
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SAFARI SPORTS WONDER TRIPLE LISTING, sleeps 120 Private vacation home
SAFARI SPORTS WONDER TRIPLE LISTING, sleeps 120
$3889 / night
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Amazing Mansion on Toho Private vacation home
Amazing Mansion on Toho
$3827 / night
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THE STUNNER Private vacation home
THE STUNNER
$3800 / night
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The Coastal Hideaway-TT472 Villa
The Coastal Hideaway-TT472
$3596 / night
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42 bedrooms, SAFARI SPORTS WONDER SIDE-BY-SIDE BOWLING VILLAS, sleep 120 Private vacation home
42 bedrooms, SAFARI SPORTS WONDER SIDE-BY-SIDE BOWLING VILLAS, sleep 120
$3431 / night
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Luxury Modern Mansion with Basketball Court at Reunion Private vacation home
Luxury Modern Mansion with Basketball Court at Reunion
$3414 / night
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Charming townhome in Kissimmee, furnished, in a wonderful location, 3 +1 bd. Private vacation home
Charming townhome in Kissimmee, furnished, in a wonderful location, 3 +1 bd.
$3348 / night
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NEW FURNITURE Aug 2026 | Movie Theater & Games Room | Golf Course Views Private vacation home
NEW FURNITURE Aug 2026 | Movie Theater & Games Room | Golf Course Views
$3225 / night
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The Palm House at Reunion-TT484 Private vacation home
The Palm House at Reunion-TT484
$3141 / night
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The Palace | 13BR Luxury Villa w/ Private Pool, Theater, Themed Rooms, and Game Lounge Near Disney Villa
The Palace | 13BR Luxury Villa w/ Private Pool, Theater, Themed Rooms, and Game Lounge Near Disney
$2768 / night
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21 BR\/20 Bath Two Pools Large Yard Luxe Getaway Private vacation home
21 BR\/20 Bath Two Pools Large Yard Luxe Getaway
$2676 / night
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2 Side-by-side homes w Bowling, 1GB wifi, videowall TVs, ensuites, sleep 80 Private vacation home
2 Side-by-side homes w Bowling, 1GB wifi, videowall TVs, ensuites, sleep 80
$2665 / night
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Multiple Family Homes - 23 Rooms \/ Pools&Spas Villa
Multiple Family Homes - 23 Rooms \/ Pools&Spas
$2499 / night
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Orlando | Couples Safari Escape | Pool + Hot Tub Hotel resort
Orlando | Couples Safari Escape | Pool + Hot Tub
$2476 / night
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Luxury Home w/ Pool, Hot Tub | Gated Resort Villa
Luxury Home w/ Pool, Hot Tub | Gated Resort
$2412 / night
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Three-Bedroom Villa - Orange Lake Resort Villa
Three-Bedroom Villa - Orange Lake Resort
$2356 / night
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The Regal Manor-TT486 Villa
The Regal Manor-TT486
$2283 / night
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The Most Fun House with tons of room, huge pool, pickleball and an amazing view. Private vacation home
The Most Fun House with tons of room, huge pool, pickleball and an amazing view.
$2274 / night
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It is a very nice suit Hotel resort
It is a very nice suit
$2172 / night
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Brand New 6 BR, Solara Resort Home w\/Pool & Theater Near Disney Private vacation home
Brand New 6 BR, Solara Resort Home w\/Pool & Theater Near Disney
$1952 / night
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Relax in Ultimate Comfort with Pool & BBQ Area Private vacation home
Relax in Ultimate Comfort with Pool & BBQ Area
$1922 / night
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15 Bedrooms / 16.5 Bathrooms / Sonoma (4171SB) Private vacation home
15 Bedrooms / 16.5 Bathrooms / Sonoma (4171SB)
$1917 / night
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Near Disney Pool Home with Harry Potter Game Room Private vacation home
Near Disney Pool Home with Harry Potter Game Room
$1909 / night
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Aurea Cove at Reunion-TB033 Private vacation home
Aurea Cove at Reunion-TB033
$1847 / night
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24-bedroom house in Kissimmee near Disney 17/25 Private vacation home
24-bedroom house in Kissimmee near Disney 17/25
$1818 / night
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Vacationer's Paradise | 9,021 Sq. Ft. Private Pool Home, Basketball Court, Games Rooms, Theater Room Villa
Vacationer's Paradise | 9,021 Sq. Ft. Private Pool Home, Basketball Court, Games Rooms, Theater Room
$1788 / night
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Stunning Mansion- Lake View- Theater-Gym-Near Disney-2713 Private vacation home
Stunning Mansion- Lake View- Theater-Gym-Near Disney-2713
$1746 / night
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2614 Veranda Palms Private vacation home
2614 Veranda Palms
$1729 / night
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Breathtaking Mansion with Indoor Spa at Reunion Private vacation home
Breathtaking Mansion with Indoor Spa at Reunion
$1656 / night
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1 Bedroom at WESTGATE TOWN CENTER RESORT Private vacation home
1 Bedroom at WESTGATE TOWN CENTER RESORT
$1645 / night
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?Spacious Home?Beautiful Resort - Fabulous Amenities Villa
?Spacious Home?Beautiful Resort - Fabulous Amenities
$1604 / night
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Every Amenity! 2 Theaters, Private Gym, Pool, Baby Equip FREE, Outdoor Grill Private vacation home
Every Amenity! 2 Theaters, Private Gym, Pool, Baby Equip FREE, Outdoor Grill
$1600 / night
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A beautiful Resort 1 mile from Disney. Hotel resort
A beautiful Resort 1 mile from Disney.
$1581 / night
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Epic Mansion Near Disney w/ Sports Arcade, Theater, Game Loft, Huge Pool & Patio Private vacation home
Epic Mansion Near Disney w/ Sports Arcade, Theater, Game Loft, Huge Pool & Patio
$1529 / night
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Theater Room | Games Room | Themed Kids Bedrooms | Private Pool Private vacation home
Theater Room | Games Room | Themed Kids Bedrooms | Private Pool
$1516 / night
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HI SPEED INTERNET,POOL/SPA EXT/DECKING,GAMESROOM,THEMED BEDROOMS,FREE USA CALLS Private vacation home
HI SPEED INTERNET,POOL/SPA EXT/DECKING,GAMESROOM,THEMED BEDROOMS,FREE USA CALLS
$1506 / night
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Luxury 15Bd Pool Home with Game Room-2489SD Villa
Luxury 15Bd Pool Home with Game Room-2489SD
$1470 / night
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Regal Royale at Reunion | Sleeps 30 | Pool, Theater & Game Room Villa
Regal Royale at Reunion | Sleeps 30 | Pool, Theater & Game Room
$1411 / night
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Spacious Kissimmee Villa, 14BR, Sleeps 30 Villa
Spacious Kissimmee Villa, 14BR, Sleeps 30
$1401 / night
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Two Luxury Homes, One Unforgettable Vacation Private vacation home
Two Luxury Homes, One Unforgettable Vacation
$1396 / night
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Family Friendly 15 Bed Game Pool Home in Veranda Palms-2489SD Private vacation home
Family Friendly 15 Bed Game Pool Home in Veranda Palms-2489SD
$1393 / night
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Reunion Mansion with Infinity Pool & Game Room Private vacation home
Reunion Mansion with Infinity Pool & Game Room
$1389 / night
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