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Vacation Homes in Osceola

Osceola
Mon, 16 Nov 2026 - Tue, 17 Nov 2026 (1 night)
1 Adult, 0 Children
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Showing 1.000+ Vacation Homes in Osceola

Luxury 4 BDR House near Disney 11105

Vacation Home

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Osceola
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5-bedroom House With Pool and spa Near Disney

Vacation Home

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Osceola
5-bedroom House With Pool and spa Near Disney Location
With a stay at this villa in Kissimmee, you'll be within a 10-minute drive of Mystic Dunes Golf Club and Reunion Resort Golf Course. This villa is 5.4 mi (8.7 km) from Walt Disney World® Resort and 7.6 mi (12.3 km) from ESPN Wide World of Sports Complex.

5-bedroom House With Pool and spa Near Disney Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a hot tub. Additional features at this villa include complimentary wireless internet access and barbecue grills.

5-bedroom House With Pool and spa Near Disney Rooms
Make yourself comfortable in this villa, which features a private pool and a Smart TV. There's a private furnished patio. A kitchen is outfitted with a full-sized refrigerator/freezer and a stovetop. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment.

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Spacious Modern Townhouse With Resort Pool Access and Elegant Open Living Spaces

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Osceola
Spacious Modern Townhouse With Resort Pool Access and Elegant Open Living Spaces Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, a 5-minute drive from Walt Disney World® Resort and 8 minutes from Old Town. This vacation home is 5.3 mi (8.5 km) from ESPN Wide World of Sports Complex and 5.8 mi (9.3 km) from Disney's Hollywood Studios®.

Spacious Modern Townhouse With Resort Pool Access and Elegant Open Living Spaces Facility and Service
Take advantage of recreation opportunities such as a hot tub, or other amenities including complimentary wireless internet access and an arcade/game room.

Spacious Modern Townhouse With Resort Pool Access and Elegant Open Living Spaces Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Ov3781 - Windsor Hills Resort - 3 Bed 2 Baths Townhome

Vacation Home

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Osceola
Ov3781 - Windsor Hills Resort - 3 Bed 2 Baths Townhome Location
Located in Kissimmee (Windsor Hills), this vacation home is within a 10-minute drive of Walt Disney World® Resort and Old Town. This golf vacation home is 5.6 mi (9 km) from ESPN Wide World of Sports Complex and 6 mi (9.7 km) from Disney's Hollywood Studios®.

Ov3781 - Windsor Hills Resort - 3 Bed 2 Baths Townhome Facility and Service
While the golfer in the family is out on the course, try one of the other recreational amenities offered, such as a hot tub or an outdoor tennis court. Additional features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Ov3781 - Windsor Hills Resort - 3 Bed 2 Baths Townhome Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private plunge pool and a flat-screen TV. There's a private balcony or patio. A kitchen is outfitted with a refrigerator, an oven, and a microwave. Cable television is provided for your entertainment.

Restaurant and Cafe
Enjoy a meal at the restaurant or snacks in the vacation home's coffee shop/cafe. Wrap up your day with a drink at the bar/lounge.

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Exterior & Views

Themed Bedrooms & Private Pool Gated in Fun Resort 4 Townhouse

Vacation Home

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Osceola
Themed Bedrooms & Private Pool Gated in Fun Resort 4 Townhouse Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This vacation home is 10.2 mi (16.4 km) from Disney's Animal Kingdom® Theme Park and 10.9 mi (17.5 km) from ESPN Wide World of Sports Complex.

Themed Bedrooms & Private Pool Gated in Fun Resort 4 Townhouse Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Windsor at Westside Resort 9-Bedroom Pool/Spa Home 9 Home

Vacation Home

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Osceola
Windsor at Westside Resort 9-Bedroom Pool/Spa Home 9 Home Location
Located in Kissimmee, this vacation home is within a 15-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This vacation home is 9 mi (14.5 km) from Walt Disney World® Resort and 10.7 mi (17.2 km) from Disney's Animal Kingdom® Theme Park.

Windsor at Westside Resort 9-Bedroom Pool/Spa Home 9 Home Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with a refrigerator and an oven. Complimentary wireless internet access keeps you connected, and a Smart television is provided for your entertainment. Conveniences include a coffee/tea maker and a washing machine.

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1505mb- Non-renting 5-31-2022 The Retreat at Championsgate

Vacation Home

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Osceola
1505mb- Non-renting 5-31-2022 The Retreat at Championsgate 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 11.3 mi (18.1 km) from Old Town and 12 mi (19.4 km) from ESPN Wide World of Sports Complex.

1505mb- Non-renting 5-31-2022 The Retreat at Championsgate Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

1505mb- Non-renting 5-31-2022 The Retreat at Championsgate Rooms
Make yourself comfortable in your vacation home.

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Exterior & Views

4885romeo

Vacation Home

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Osceola
4885romeo 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 (8.9 km) from Disney Springs™ and 6.5 mi (10.5 km) from Walt Disney World® Resort.

4885romeo Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

4885romeo Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and a microwave. Complimentary wireless internet access keeps you connected, and a flat-screen television is provided for your entertainment.

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Sport & Beauty

Grhbch3031 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse

Vacation Home

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Osceola
Grhbch3031 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse 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 family-friendly vacation home is 8.3 mi (13.4 km) from Disney's Animal Kingdom® Theme Park and 9.2 mi (14.8 km) from ESPN Wide World of Sports Complex.

Grhbch3031 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse Facility and Service
Practice your swing on the golf course or dip into one of the 2 hot tubs. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Grhbch3031 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private plunge pool and a flat-screen TV. There's a private balcony or patio. A kitchen is outfitted with a refrigerator, an oven, and a microwave. Cable television is provided for your entertainment.

Restaurant and Cafe
Satisfy your appetite at the vacation home's coffee shop/cafe, or stop in at the grocery/convenience store. Relax with your favorite drink at the bar/lounge or the poolside bar.

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Exterior & Views

"boutique" Style Home Near Disney! 5 Bedroom Home by RedAwning

Vacation Home

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Osceola
"boutique" Style Home Near Disney! 5 Bedroom Home by RedAwning Location
With a stay at this vacation home in Kissimmee, you'll be a 5-minute drive from Old Town and 8 minutes from Orlando Vineland Premium Outlets. This vacation home is 5.9 mi (9.5 km) from Disney Springs™ and 6.7 mi (10.8 km) from ESPN Wide World of Sports Complex.

"boutique" Style Home Near Disney! 5 Bedroom Home by RedAwning Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected. Conveniences include a coffee/tea maker and a washing machine.

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Updated Townhome With an Enclosed Pool, Five Bedrooms, W/D - Close to Everything

Vacation Home

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Osceola
Updated Townhome With an Enclosed Pool, Five Bedrooms, W/D - Close to Everything Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 7.2 mi (11.6 km) from Disney Springs™ and 8.2 mi (13.2 km) from Walt Disney World® Resort.

Updated Townhome With an Enclosed Pool, Five Bedrooms, W/D - Close to Everything Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Updated Townhome With an Enclosed Pool, Five Bedrooms, W/D - Close to Everything Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Fun, Dog-friendly Home With Private Pool, High-speed Wifi, W/d, & Game Rooms

Vacation Home

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Osceola
Fun, Dog-friendly Home With Private Pool, High-speed Wifi, W/d, & Game Rooms 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 9.1 mi (14.6 km) from Walt Disney World® Resort and 10.9 mi (17.5 km) from Disney's Animal Kingdom® Theme Park.

Fun, Dog-friendly Home With Private Pool, High-speed Wifi, W/d, & Game Rooms 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.

Fun, Dog-friendly Home With Private Pool, High-speed Wifi, W/d, & Game Rooms Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Windsor Westside Resort Townhouse w/ Pool & Fast Wifi

Vacation Home

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Osceola
Windsor Westside Resort Townhouse w/ Pool & Fast Wifi Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This vacation home is 10.1 mi (16.3 km) from Disney's Animal Kingdom® Theme Park and 11.3 mi (18.2 km) from ESPN Wide World of Sports Complex.

Windsor Westside Resort Townhouse w/ Pool & Fast Wifi Facility and Service
Take advantage of recreation opportunities such as an outdoor tennis court, or other amenities including complimentary wireless internet access and an arcade/game room.

Windsor Westside Resort Townhouse w/ Pool & Fast Wifi Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Grhsgd8979 - Champions Gate Resort - 5 Bed 4 Baths Townhouse

Vacation Home

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Osceola
Grhsgd8979 - Champions Gate Resort - 5 Bed 4 Baths Townhouse 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 11.3 mi (18.2 km) from Old Town and 12.1 mi (19.5 km) from ESPN Wide World of Sports Complex.

Grhsgd8979 - Champions Gate Resort - 5 Bed 4 Baths Townhouse Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Grhsgd8979 - Champions Gate Resort - 5 Bed 4 Baths Townhouse Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private plunge pool and a flat-screen TV. There's a private balcony or patio. A kitchen is outfitted with a refrigerator, an oven, and a microwave. Cable television is provided for your entertainment.

Restaurant and Cafe
Enjoy a meal at the restaurant or snacks in the vacation home's coffee shop/cafe. Relax with your favorite drink at the bar/lounge or the poolside bar.

See details
Fully Booked
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Solara Resort 4 Bedroom Townhome- Private Pool 4 Townhouse

Vacation Home

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Osceola
Solara Resort 4 Bedroom Townhome- Private Pool 4 Townhouse Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This vacation home is 10.1 mi (16.3 km) from Disney's Animal Kingdom® Theme Park and 11.3 mi (18.2 km) from ESPN Wide World of Sports Complex.

Solara Resort 4 Bedroom Townhome- Private Pool 4 Townhouse 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.

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Sonoma Resort, Private Pool, and Much More!!

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Osceola
Sonoma Resort, Private Pool, and Much More!! 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 9.7 mi (15.6 km) from Disney Springs™ and 10.7 mi (17.3 km) from Walt Disney World® Resort.

Sonoma Resort, Private Pool, and Much More!! Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center.

Sonoma Resort, Private Pool, and Much More!! Rooms
Make yourself comfortable in this vacation home, which features a private pool. Complimentary wireless internet access is available to keep you connected.

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1585pd-the Retreat at Championsgate

Vacation Home

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Osceola
1585pd-the Retreat at Championsgate 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 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.

1585pd-the Retreat at Championsgate Rooms
Make yourself comfortable in this vacation home, which has a kitchen.

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Comfy Modern House w Pool Perfect Location

Vacation Home

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Osceola
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Exterior & Views

Solara Resort by Nova VH

Vacation Home

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Osceola
Solara Resort by Nova VH Location
Located in Kissimmee, Solara Resort by Nova VH is within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This luxury vacation home is 10.2 mi (16.4 km) from Disney's Animal Kingdom® Theme Park and 11.1 mi (17.8 km) from ESPN Wide World of Sports Complex.

Solara Resort by Nova VH Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

Solara Resort by Nova VH Rooms
Treat yourself to a stay in one of the 2 individually decorated guestrooms, featuring private pools and flat-screen televisions. Rooms have private patios. Kitchens are outfitted with refrigerators, ovens, and stovetops. Cable programming and video-game consoles are provided for your entertainment, while complimentary wireless internet access keeps you connected.

Important Information
This property is closed from June 6 2025 to June 5 2027 (dates subject to change).

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4.5/5
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Stylish Family Home Private Pool/spa 10min to Theme Park Sleeps 22 En101

Vacation Home

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Osceola
Stylish Family Home Private Pool/spa 10min to Theme Park Sleeps 22 En101 Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, within a 10-minute drive of Mystic Dunes Golf Club and ChampionsGate Golf Club. This golf vacation home is 5.4 mi (8.8 km) from Walt Disney World® Resort and 7.2 mi (11.5 km) from ESPN Wide World of Sports Complex.

Stylish Family Home Private Pool/spa 10min to Theme Park Sleeps 22 En101 Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Stylish Family Home Private Pool/spa 10min to Theme Park Sleeps 22 En101 Rooms
Make yourself comfortable in your vacation home. The bathroom has a bathtub or shower.

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Vacation Homes in Osceola

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