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Vacation Homes in Osceola

Osceola
Wed, 18 Nov 2026 - Thu, 19 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 2.000+ Vacation Homes in Osceola
Sport & Beauty

Windsor Grand Retreat 11ppl!

Vacation Home

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Osceola
Windsor Grand Retreat 11ppl! Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, within a 10-minute drive of Flamingo Crossings Town Center and ChampionsGate Golf Club. This golf vacation home is 7.9 mi (12.7 km) from Walt Disney World® Resort and 9.5 mi (15.3 km) from Disney's Animal Kingdom® Theme Park.

Windsor Grand Retreat 11ppl! Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center.

Windsor Grand Retreat 11ppl! Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool and a flat-screen TV. There's a private furnished lanai. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Digital television is provided for your entertainment.

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Exterior & Views

Nottingham Home with Pool in Terra Verde

Vacation Home

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Osceola
Nottingham Home with Pool in Terra Verde Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 8.9 mi (14.3 km) from Disney Springs™ and 9.2 mi (14.7 km) from Walt Disney World® Resort.

Nottingham Home with Pool in Terra Verde Facility and Service
Take in the views from a garden and make use of amenities such as complimentary wireless internet access.

Nottingham Home with Pool in Terra Verde Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool and a flat-screen TV. There's a private furnished patio. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Cable programming and a DVD player are provided for your entertainment, while complimentary wireless internet access keeps you connected.

Restaurant and Cafe
Wrap up your day with a drink at the poolside bar.

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Others

4 Bed Townhome With Private Pool Near Disney! 4 Bedroom Townhouse by Redawning

Vacation Home

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Osceola
4 Bed Townhome With Private Pool Near Disney! 4 Bedroom Townhouse by Redawning Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 5.5 mi (8.8 km) from Disney Springs™ and 6 mi (9.7 km) from ESPN Wide World of Sports Complex.

4 Bed Townhome With Private Pool Near Disney! 4 Bedroom Townhouse by Redawning Rooms
Make yourself comfortable in this air-conditioned vacation home, which has a kitchen. Complimentary wireless internet access is available to keep you connected.

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Room

Sunlit Serenity Oasis House in Kissimmee With Private Pool, Pool Table, Tennis

Vacation Home

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Osceola
Sunlit Serenity Oasis House in Kissimmee With Private Pool, Pool Table, Tennis Location
With a stay at this vacation home in Kissimmee (Crescent Lakes), you'll be within a 10-minute drive of Green Meadows Petting Farm and Shingle Creek Regional Park. This vacation home is 11.6 mi (18.7 km) from Old Town and 13.8 mi (22.3 km) from Orlando Vineland Premium Outlets.

Sunlit Serenity Oasis House in Kissimmee With Private Pool, Pool Table, Tennis Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Sunlit Serenity Oasis House in Kissimmee With Private Pool, Pool Table, Tennis Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Exterior & Views

4 Bd Sleeps 10 w/ GameRoom Close to Disney 5147

Vacation Home

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Osceola
4 Bd Sleeps 10 w/ GameRoom Close to Disney 5147 Location
When you stay at this vacation home in Kissimmee, you'll be on a lake, a 5-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This family-friendly vacation home is 5.3 mi (8.5 km) from Disney Springs™ and 6 mi (9.6 km) from Walt Disney World® Resort.

4 Bd Sleeps 10 w/ GameRoom Close to Disney 5147 Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

4 Bd Sleeps 10 w/ GameRoom Close to Disney 5147 Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private hot tub and a Smart TV. There's a private balcony or patio. A kitchen is outfitted with a full-sized refrigerator/freezer, an oven, and a stovetop. Wired and wireless internet access is complimentary, while a DVD player and cable programming provide entertainment.

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4.1/5
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Game room

Brand New Modern State of the Art Home! Sleeps 31

Vacation Home

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Osceola
Brand New Modern State of the Art Home! Sleeps 31 Location
With a stay at this vacation home in Kissimmee, you'll be near the beach, within a 15-minute drive of Old Town and 192 Flea Market. This vacation home is 9.8 mi (15.9 km) from Orlando Vineland Premium Outlets and 10 mi (16.2 km) from Disney Springs™.

Brand New Modern State of the Art Home! Sleeps 31 Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center. This vacation home also features an arcade/game room and barbecue grills.

Brand New Modern State of the Art Home! Sleeps 31 Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Bedroom

UpstaySleeps26PrivatePoolHotTubCinemaG

Vacation Home

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Osceola
UpstaySleeps26PrivatePoolHotTubCinemaG Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 7.1 mi (11.4 km) from Disney Springs™ and 7.7 mi (12.4 km) from Walt Disney World® Resort.

UpstaySleeps26PrivatePoolHotTubCinemaG Facility and Service
Take advantage of recreation opportunities including an outdoor pool and an indoor pool.

UpstaySleeps26PrivatePoolHotTubCinemaG Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected. Conveniences include an electric kettle and a washer/dryer.

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Room

Family Friendly 4 Bedroom close to Disney in Orlando Area 5126A

Vacation Home

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Osceola
Family Friendly 4 Bedroom close to Disney in Orlando Area 5126A Location
With a stay at this vacation home in Kissimmee, you'll be a 5-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This family-friendly vacation home is 5.4 mi (8.6 km) from Disney Springs™ and 6 mi (9.7 km) from Walt Disney World® Resort.

Family Friendly 4 Bedroom close to Disney in Orlando Area 5126A Facility and Service
Take advantage of recreation opportunities such as an outdoor pool or take in the view from a terrace and a garden. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Family Friendly 4 Bedroom close to Disney in Orlando Area 5126A Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool and a private hot tub. There's a private balcony or patio. A kitchen is outfitted with a full-sized refrigerator/freezer, an oven, and a stovetop. Wired and wireless internet access is complimentary, while a 60-inch Smart television with cable programming provides entertainment.

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3.7/5
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Living area

Wonderfull 4Bd W/ Pool @ Champions Gate Resort 8945

Vacation Home

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Osceola
Wonderfull 4Bd W/ Pool @ Champions Gate Resort 8945 Location
With a stay at this vacation home in Four Corners, you'll be within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This vacation home is 12.3 mi (19.9 km) from Old Town and 12.4 mi (19.9 km) from Walt Disney World® Resort.

Wonderfull 4Bd W/ Pool @ Champions Gate Resort 8945 Rooms
Make yourself comfortable in your vacation home.

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2.5/5
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Others

Champions Gate Resort

Vacation Home

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Osceola
Champions Gate Resort Location
With a stay at this vacation home in Four Corners (Champions Gate), you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This family-friendly vacation home is 11.4 mi (18.3 km) from Old Town and 12.2 mi (19.6 km) from ESPN Wide World of Sports Complex.

Champions Gate Resort Facility and Service
Don't miss out on the many recreational opportunities, including a complimentary water park, an outdoor pool, and a lazy river. Additional amenities at this vacation home include complimentary wireless internet access and a vending machine.

Champions Gate Resort Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a refrigerator and an oven. A flat-screen television with cable programming provides entertainment, while complimentary wireless internet access keeps you connected. Conveniences include a microwave and a washer/dryer, and housekeeping is provided on a limited basis.

Restaurant and Cafe
Quench your thirst with your favorite drink at the poolside bar.

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2.8/5
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Bedroom

1569 SD - Modern Champions Gate Escape

Vacation Home

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Osceola
1569 SD - Modern Champions Gate Escape Location
With a stay at this vacation home in Four Corners (Champions Gate), you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This golf vacation home is 11.4 mi (18.3 km) from Old Town and 12.2 mi (19.6 km) from ESPN Wide World of Sports Complex.

1569 SD - Modern Champions Gate Escape Facility and Service
Enjoy recreational amenities such as an outdoor tennis court and a fitness center.

1569 SD - Modern Champions Gate Escape Rooms
Make yourself comfortable in your vacation home.

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Luxurious Home Private Pool + Spa

Vacation Home

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Osceola
Luxurious Home Private Pool + Spa Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be a 4-minute drive from Reunion Resort Golf Course and 9 minutes from Mystic Dunes Golf Club. This vacation home is 7.5 mi (12.1 km) from Walt Disney World® Resort and 9.5 mi (15.3 km) from Old Town.

Luxurious Home Private Pool + Spa Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Luxurious Home Private Pool + Spa Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Fully Booked
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Brand New AAA 4-diamond Home w/ Premium Resort Amenities, Close to Theme Parks

Vacation Home

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Osceola
Brand New AAA 4-diamond Home w/ Premium Resort Amenities, Close to Theme Parks Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be a 3-minute drive from Reunion Resort Golf Course and 8 minutes from ChampionsGate Golf Club. This vacation home is 6.7 mi (10.8 km) from Walt Disney World® Resort and 8.7 mi (14 km) from ESPN Wide World of Sports Complex.

Brand New AAA 4-diamond Home w/ Premium Resort Amenities, Close to Theme Parks Facility and Service
Take advantage of recreation opportunities such as a sauna, or other amenities including complimentary wireless internet access and an arcade/game room.

Brand New AAA 4-diamond Home w/ Premium Resort Amenities, Close to Theme Parks Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Fully Booked
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Windsor Palms Townhome With Wifi, AC, Screened Patio, Pool, hot Tub, & Tennis

Vacation Home

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Osceola
Windsor Palms Townhome With Wifi, AC, Screened Patio, Pool, hot Tub, & Tennis Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, a 4-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort. This vacation home is 6.1 mi (9.8 km) from Old Town and 6.1 mi (9.8 km) from ESPN Wide World of Sports Complex.

Windsor Palms Townhome With Wifi, AC, Screened Patio, Pool, hot Tub, & Tennis Facility and Service
Take advantage of recreation opportunities including a hot tub and an outdoor tennis court. Additional amenities at this vacation home include complimentary wireless internet access and barbecue grills.

Windsor Palms Townhome With Wifi, AC, Screened Patio, Pool, hot Tub, & Tennis Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Room

Resort Home With Private Pool, Patio, Foosball & 2 Living Areas - Near Disney

Vacation Home

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Osceola
Resort Home With Private Pool, Patio, Foosball & 2 Living Areas - Near Disney Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 15-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This vacation home is 8.6 mi (13.8 km) from Walt Disney World® Resort and 10.4 mi (16.7 km) from Disney's Animal Kingdom® Theme Park.

Resort Home With Private Pool, Patio, Foosball & 2 Living Areas - Near Disney Facility and Service
Take advantage of recreation opportunities such as an outdoor pool, or other amenities including complimentary wireless internet access and an arcade/game room.

Resort Home With Private Pool, Patio, Foosball & 2 Living Areas - Near Disney Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Others

Modern House 4 Bedrooms 15 Minutes From Disney

Vacation Home

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Osceola
Modern House 4 Bedrooms 15 Minutes From Disney Location
When you stay at this villa in Four Corners, you'll be in the suburbs, within a 15-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center. This villa is 9.3 mi (14.9 km) from Disney's Animal Kingdom® Theme Park and 10.5 mi (16.8 km) from ESPN Wide World of Sports Complex.

Modern House 4 Bedrooms 15 Minutes From Disney Facility and Service
Take advantage of recreation opportunities such as an outdoor pool or take in the view from a terrace and a garden. Additional features at this villa include complimentary wireless internet access and barbecue grills.

Modern House 4 Bedrooms 15 Minutes From Disney Rooms
Make yourself comfortable in your villa. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. The bathroom has a bathtub or shower and complimentary toiletries. Conveniences include a desk and a washer/dryer, and you can also request a crib/infant bed (complimentary).

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Spacious Townhouse With Resort Style Amenities, Waterview and Fitness Center

Vacation Home

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Osceola
Spacious Townhouse With Resort Style Amenities, Waterview and Fitness Center Location
With a stay at this vacation home in Kissimmee (Venetian Bay Villages), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 9.8 mi (15.8 km) from Disney Springs™ and 10.8 mi (17.4 km) from Walt Disney World® Resort.

Spacious Townhouse With Resort Style Amenities, Waterview and Fitness Center Facility and Service
Take advantage of recreation opportunities such as a fitness center, or other amenities including complimentary wireless internet access and an arcade/game room.

Spacious Townhouse With Resort Style Amenities, Waterview and Fitness Center Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

See details
Fully Booked
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Others

Bv528 - 6BR House With Pool Near Disney

Vacation Home

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Osceola
Bv528 - 6BR House With Pool Near Disney Location
Located in Kissimmee, this cottage is within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This cottage is 9.1 mi (14.6 km) from Disney Springs™ and 10 mi (16.2 km) from Walt Disney World® Resort.

Bv528 - 6BR House With Pool Near Disney Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Bv528 - 6BR House With Pool Near Disney Rooms
Make yourself comfortable in this individually decorated cottage, featuring a kitchen with an oven and a stovetop. There's a private patio. Conveniences include a microwave and a washer/dryer.

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Colorful 10br at Encore, 10 Min to Disney

Vacation Home

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Osceola
Colorful 10br at Encore, 10 Min to Disney Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 10-minute drive of Mystic Dunes Golf Club and Reunion Resort Golf Course. This vacation home is 5.5 mi (8.9 km) from Walt Disney World® Resort and 7.8 mi (12.5 km) from ESPN Wide World of Sports Complex.

Colorful 10br at Encore, 10 Min to Disney Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including an arcade/game room.

Colorful 10br at Encore, 10 Min to Disney Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Fully Booked
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Paradise Palms-6 bedrooms House w-pool-3509PP 6 Home by RedAwning

Vacation Home

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Osceola
Paradise Palms-6 bedrooms House w-pool-3509PP 6 Home by RedAwning Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 8.2 mi (13.2 km) from ESPN Wide World of Sports Complex and 8.4 mi (13.6 km) from Disney's Animal Kingdom® Theme Park.

Paradise Palms-6 bedrooms House w-pool-3509PP 6 Home by RedAwning Facility and Service
Enjoy the recreation opportunities such as an outdoor tennis court or make use of other amenities including barbecue grills.

Paradise Palms-6 bedrooms House w-pool-3509PP 6 Home by RedAwning Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with a refrigerator and an oven. Complimentary wireless internet access is available to keep you connected. Conveniences include a coffee/tea maker and a washing machine.

See details
Fully Booked
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Vacation Homes in Osceola

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