Kissimmee vacation rentals
We found 35,111 vacation rentals — enter your dates for availability
Discover a selection of vacation rentals near Kissimmee, FL (ISM-Kissimmee Gateway) that can be your home away from home. Whether you're traveling with a group or just with your pet, vacation homes have the best amenities for hanging out with the people that matter most, which might include WiFi and a washer and dryer, You'll be able to choose a rental for everyone's needs, including places that are non-smoking or accessible.
Vacation rentals with weekly discounts - Kissimmee, FL (ISM-Kissimmee Gateway)
Showing deals for:Aug 1 - Aug 8
Image gallery for Super Fun House with Amazing Views
1010 out of 10 rating
Exceptional
(37 reviews)
Super Fun House with Amazing Views
Kissimmee, FL
10% off
Price is $2,066
$2,066
$16,829 total
$16,829 total
Image gallery for Big Pool&Spa/Themed rooms/Private yard/ CLOSE TO EVERYTHING, Lakeview,Playground
1010 out of 10 rating
Exceptional
(149 reviews)
Big Pool&Spa/Themed rooms/Private yard/ CLOSE TO EVERYTHING, Lakeview,Playground
Kissimmee, FL
10% off
Price is $297
$297
$2,608 total
$2,608 total
Image gallery for Welcome To Magnolia Blossom Villa! South Facing Pool in Prime Location.
9.89.8 out of 10 rating
Exceptional
(49 reviews)
Welcome To Magnolia Blossom Villa! South Facing Pool in Prime Location.
Kissimmee, FL
5% off
Price is $230
$230
$2,114 total
$2,114 total
Image gallery for RATED#1 BEST HOME Near Disney! LUXURY 5BEDROOM 5Bath VILLA ,GATED RESORT ,POOL
9.49.4 out of 10 rating
Exceptional
(116 reviews)
RATED#1 BEST HOME Near Disney! LUXURY 5BEDROOM 5Bath VILLA ,GATED RESORT ,POOL
Kissimmee, FL
10% off
Price is $293
$293
$2,611 total
$2,611 total
Image gallery for STUNNING 2 BEDROOM AT THE TOWN CENTER RESORT NEAR DISNEY
8.68.6 out of 10 rating
Excellent
(45 reviews)
STUNNING 2 BEDROOM AT THE TOWN CENTER RESORT NEAR DISNEY
Kissimmee, FL
5% off
Price is $227
$227
$1,780 total
$1,780 total
Image gallery for Margaritaville Resort Cottage - 4 BR - Minutes from Disney
9.89.8 out of 10 rating
Exceptional
(43 reviews)
Margaritaville Resort Cottage - 4 BR - Minutes from Disney
Kissimmee, FL
5% off
Price is $277
$277
$2,405 total
$2,405 total
Image gallery for SUMMER SALE! Hogwarts Haven - Universal Epic! Windsor Hills 3BR, near Disney!
1010 out of 10 rating
Exceptional
(42 reviews)
SUMMER SALE! Hogwarts Haven - Universal Epic! Windsor Hills 3BR, near Disney!
Kissimmee, FL
10% off
Price is $154
$154
$1,373 total
$1,373 total
Image gallery for 3BR/2B condo with views of Disney FIREWORKS!!!!
9.89.8 out of 10 rating
Exceptional
(27 reviews)
3BR/2B condo with views of Disney FIREWORKS!!!!
Kissimmee, FL
5% off
Price is $119
$119
$1,062 total
$1,062 total
Image gallery for 5 MINS to DISNEY! Themed! Costumes, Toys, HEATED POOL/SPA, PS4, Grill.
1010 out of 10 rating
Exceptional
(208 reviews)
5 MINS to DISNEY! Themed! Costumes, Toys, HEATED POOL/SPA, PS4, Grill.
Kissimmee, FL
5% off
Price is $303
$303
$2,637 total
$2,637 total
Image gallery for Regal Palms Resort Dream Vacation-8 miles to Disney
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Regal Palms Resort Dream Vacation-8 miles to Disney
Davenport, FL
10% off
Price is $126
$126
$1,328 total
$1,328 total
Image gallery for 2 Bedroom Resort Condo at Highrise Walking distance to UNIVERSAL
9.49.4 out of 10 rating
Exceptional
(102 reviews)
2 Bedroom Resort Condo at Highrise Walking distance to UNIVERSAL
Orlando, FL
5% off
Price is $227
$227
$1,757 total
$1,757 total
Image gallery for Newly Updated Tropical Villa 3.5 miles from Disney, Specious,Clean,Quite,Private
9.49.4 out of 10 rating
Exceptional
(53 reviews)
Newly Updated Tropical Villa 3.5 miles from Disney, Specious,Clean,Quite,Private
Kissimmee, FL
5% off
Price is $278
$278
$2,394 total
$2,394 total
Image gallery for Steps from clubhouse. "Be Our Guest" in Windsor Hills-Pool Heat
1010 out of 10 rating
Exceptional
(101 reviews)
Steps from clubhouse. "Be Our Guest" in Windsor Hills-Pool Heat
Kissimmee, FL
10% off
Price is $192
$192
$1,668 total
$1,668 total
Image gallery for NEWThemed Rooms, Lake pool+spa, Resort + Gameroom!
9.49.4 out of 10 rating
Exceptional
(19 reviews)
NEWThemed Rooms, Lake pool+spa, Resort + Gameroom!
Davenport, FL
5% off
Price is $257
$257
$2,348 total
$2,348 total
Image gallery for BEAUTIFUL RESORT STUDIO CLOSE TO DISNEY ATTRACTIONS
8.68.6 out of 10 rating
Excellent
(36 reviews)
BEAUTIFUL RESORT STUDIO CLOSE TO DISNEY ATTRACTIONS
Kissimmee, FL
5% off
Price is $142
$142
$1,114 total
$1,114 total
Image gallery for Reunion BRAND NEW Fancy Vacation Home
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Reunion BRAND NEW Fancy Vacation Home
Kissimmee, FL
10% off
Price is $334
$334
$3,212 total
$3,212 total
Image gallery for Luxurious 5 Bed/5 Bath 3500sf Villa With Private Pool In Highlands Reserve
1010 out of 10 rating
Exceptional
(147 reviews)
Luxurious 5 Bed/5 Bath 3500sf Villa With Private Pool In Highlands Reserve
Davenport, FL
10% off
Price is $198
$198
$1,732 total
$1,732 total
Image gallery for Wyndham Bonnet Creek Resort | 2BR/2BA King Bed
1010 out of 10 rating
Exceptional
(5 reviews)
Wyndham Bonnet Creek Resort | 2BR/2BA King Bed
Orlando, Florida
15% off
Price is $252
$252
$1,979 total
$1,979 total
Image gallery for Summer Kitchen, Pvt Pool & Themed Bedrooms, on Int. Drive near Universal Studios
9.69.6 out of 10 rating
Exceptional
(10 reviews)
Summer Kitchen, Pvt Pool & Themed Bedrooms, on Int. Drive near Universal Studios
Orlando, FL
8% off
Price is $503
$503
$4,321 total
$4,321 total
Image gallery for Our Retro Mod Pod-Disney & Old Town Minutes Away!
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Our Retro Mod Pod-Disney & Old Town Minutes Away!
Kissimmee, FL
15% off
Price is $74
$74
$718 total
$718 total
Image gallery for Superb 3 bed pool home, games room, Disney 8 miles!
1010 out of 10 rating
Exceptional
(35 reviews)
Superb 3 bed pool home, games room, Disney 8 miles!
Davenport, FL
5% off
Price is $166
$166
$1,466 total
$1,466 total
Image gallery for 3 miles Disney, New Renovated 4 BR/3Ba Pool,Hot tub, Super Speed Wi-Fi,game room
9.49.4 out of 10 rating
Exceptional
(118 reviews)
3 miles Disney, New Renovated 4 BR/3Ba Pool,Hot tub, Super Speed Wi-Fi,game room
Kissimmee, FL
10% off
Price is $153
$153
$1,357 total
$1,357 total
Image gallery for Special Discount Spacious 3BR in Vista Cay Isles near Universal & Disney World
9.49.4 out of 10 rating
Exceptional
(36 reviews)
Special Discount Spacious 3BR in Vista Cay Isles near Universal & Disney World
Orlando, FL
10% off
Price is $211
$211
$1,949 total
$1,949 total
Image gallery for There's space for everyone in this gorgeous 3-Story Townhome near the theme park
9.89.8 out of 10 rating
Exceptional
(96 reviews)
There's space for everyone in this gorgeous 3-Story Townhome near the theme park
Orlando, FL
10% off
Price is $269
$269
$2,297 total
$2,297 total
Find spaces that suit your style
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Chalet
Find the best place to stay - Kissimmee
Vacation USA LTD
Sleeps 7 · 3 bedrooms
6.86.8 out of 10
155 reviews(155 reviews)
Eclectic Estate with Location Themed Bedrooms at Reunion
Sleeps 28 · 14 bedrooms · 15+ bathrooms
8.68.6 out of 10
Excellentexcellent
9 reviews(9 reviews)
FLASH SALE! Lovely Condo Just 1 Mile From Disney w/ Resort Pool, WiFi & More
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.29.2 out of 10
Wonderfulwonderful
616 reviews(616 reviews)
Modern Luxury Villa with Everything
Sleeps 19 · 8 bedrooms · 5 bathrooms
9.89.8 out of 10
Exceptionalexceptional
404 reviews(404 reviews)
Encore Resort
Sleeps 12 · 6 bedrooms
6.46.4 out of 10
116 reviews(116 reviews)
Karaoke Room, Themed Bedrooms, Pool Table, Foosball, Air Hockey: The Gallery House
Sleeps 42 · 14 bedrooms · 11 bathrooms
Top rated rentals - Kissimmee
Didn’t vacation 2025
1010 out of 10
Exceptionalexceptional
1 review(1 review)
The Best Week at the Best Nest!
1010 out of 10
Exceptionalexceptional
74 reviews(74 reviews)
Great stay for our vacation!!
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
As advertised
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Quiet Family Stay
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Perfect for family reunion
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
Great place to stay
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Two Family Vacation
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
More for lessMore space, more privacy, more amenities — more value
