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Vacation Homes in Osceola

Osceola
Fri, 06 Nov 2026 - Sat, 07 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 1.000+ Vacation Homes in Osceola
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Grhmyr1466 - Champions Gate Resort - 8 Bed 5 Baths House

Vacation Home

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Osceola
Grhmyr1466 - Champions Gate Resort - 8 Bed 5 Baths House 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 11.8 mi (19 km) from Old Town and 12.6 mi (20.3 km) from ESPN Wide World of Sports Complex.

Grhmyr1466 - Champions Gate Resort - 8 Bed 5 Baths House Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools or 2 hot tubs. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Grhmyr1466 - Champions Gate Resort - 8 Bed 5 Baths House Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private plunge pool and a private hot tub. There's a private balcony or patio. A kitchen is outfitted with a refrigerator, an oven, and a microwave. A flat-screen 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. Unwind at the end of the day with a drink at the bar/lounge or the poolside bar.

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Stunning 4 Bd W/ Pool @ Storey Lake Resort 2613

Vacation Home

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Osceola
Stunning 4 Bd W/ Pool @ Storey Lake Resort 2613 Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 7.5 mi (12.1 km) from Disney Springs™ and 8.5 mi (13.8 km) from Walt Disney World® Resort.

Stunning 4 Bd W/ Pool @ Storey Lake Resort 2613 Rooms
Make yourself comfortable in your vacation home.

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5.0/5
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Others

Non-renting - 1586pd - The Retreat at Championsgate

Vacation Home

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Osceola
Non-renting - 1586pd - The Retreat at Championsgate Location
With a stay at this villa in Four Corners (Champions Gate), you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This golf villa is 11.4 mi (18.3 km) from Old Town and 12.2 mi (19.6 km) from ESPN Wide World of Sports Complex.

Non-renting - 1586pd - The Retreat at Championsgate Facility and Service
Don't miss out on the many recreational opportunities, including an outdoor pool, an outdoor tennis court, and a fitness center.

Non-renting - 1586pd - The Retreat at Championsgate Rooms
Make yourself comfortable in this air-conditioned villa, featuring a kitchen with a refrigerator and a stovetop. A flat-screen television is provided for your entertainment. Conveniences include a microwave and an iron/ironing board.

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Others

Advantage Vacation Homes

Vacation Home

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Osceola
Advantage Vacation Homes Location
Located in Kissimmee, this vacation home is in the suburbs, a 3-minute drive from Orange Lake Golf and 8 minutes from Northeast Regional Park. This vacation home is 5.9 mi (9.4 km) from Highland Reserve Golf Club and 7 mi (11.2 km) from Disney's Animal Kingdom® Theme Park.

Advantage Vacation Homes Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. This vacation home also features complimentary wireless internet access and tour/ticket assistance.

Advantage Vacation Homes Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with a full-sized refrigerator/freezer and a stovetop. Complimentary wired and wireless internet access keeps you connected, and cable programming provides entertainment. Conveniences include a separate sitting area and a microwave.

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3.8/5(100 Reviews)
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1300bw- Non Renting 5/1/2022 The Retreat at Championsgate

Vacation Home

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Osceola
1300bw- Non Renting 5/1/2022 The Retreat at Championsgate Location
With a stay at this vacation home in Four Corners (Champions Gate), you'll be within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This golf vacation home is 12.7 mi (20.5 km) from Old Town and 13.3 mi (21.4 km) from Walt Disney World® Resort.

1300bw- Non Renting 5/1/2022 The Retreat at Championsgate Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

1300bw- Non Renting 5/1/2022 The Retreat at Championsgate Rooms
Make yourself comfortable in this vacation home, which has a kitchen.

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Pool

Family 5Bd Pool, Spa, Themed Rooms & GameRoom 7832

Vacation Home

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Osceola
Family 5Bd Pool, Spa, Themed Rooms & GameRoom 7832 Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be a 3-minute drive from Reunion Resort Golf Course and 7 minutes from ChampionsGate Golf Club. This vacation home is 9.9 mi (15.9 km) from Old Town and 10.7 mi (17.2 km) from ESPN Wide World of Sports Complex.

Family 5Bd Pool, Spa, Themed Rooms & GameRoom 7832 Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with an oven and a stovetop.

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3.0/5
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Private kitchen

Paradise Palms Resort 5 Bedroom Home with Spa 5 Home

Vacation Home

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Osceola
Paradise Palms Resort 5 Bedroom Home with Spa 5 Home 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 8.4 mi (13.5 km) from Disney's Animal Kingdom® Theme Park and 9.3 mi (14.9 km) from ESPN Wide World of Sports Complex.

Paradise Palms Resort 5 Bedroom Home with Spa 5 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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Exterior & Views

Luxurious Family-Friendly 5 Bd w/ Screened Pool & Close to Disney 2905

Private Vacation Home

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Osceola
Luxurious Family-Friendly 5 Bd w/ Screened Pool & Close to Disney 2905 Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This family-friendly vacation home is 6.9 mi (11.2 km) from Disney Springs™ and 8 mi (12.9 km) from Walt Disney World® Resort.

Luxurious Family-Friendly 5 Bd w/ Screened Pool & Close to Disney 2905 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 features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Luxurious Family-Friendly 5 Bd w/ Screened Pool & Close to Disney 2905 Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool and a Smart TV. 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. Conveniences include a safe and a desk, and you can also request a crib/infant bed (surcharge).

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5.0/5
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Others

1559fd - The Retreat at Championsgate

Vacation Home

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Osceola
1559fd - 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 (18.2 km) from Old Town and 12.1 mi (19.4 km) from ESPN Wide World of Sports Complex.

1559fd - The Retreat at Championsgate Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

1559fd - The Retreat at Championsgate Rooms
Make yourself comfortable in your air-conditioned vacation home, which features a flat-screen TV. The bathroom features complimentary toiletries and a hair dryer.

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Exterior & Views

Spectacular Champions Gate Vacation Home

Private Vacation Home

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Osceola
Spectacular Champions Gate Vacation Home Location
Located in Four Corners, this cottage is within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This cottage is 11.8 mi (19 km) from Old Town and 12.6 mi (20.3 km) from ESPN Wide World of Sports Complex.

Spectacular Champions Gate Vacation Home Rooms
Make yourself comfortable in this air-conditioned cottage, which has a kitchen. Satellite television is provided for your entertainment.

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Sport & Beauty

Luxury Vacation Home in Kissimmee, Perfect for Families and Golfers

Vacation Home

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Osceola
Luxury Vacation Home in Kissimmee, Perfect for Families and Golfers Location
With a stay at this vacation home in Kissimmee, you'll be steps from Remington Golf Club and a 3-minute drive from Osceola Center for the Arts. This vacation home is 14.3 mi (23.1 km) from Old Town and 17.1 mi (27.5 km) from Walt Disney World® Resort.

Luxury Vacation Home in Kissimmee, Perfect for Families and Golfers 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.

Luxury Vacation Home in Kissimmee, Perfect for Families and Golfers 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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Bedroom

4562 Seven Dwarfs

Vacation Home

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Osceola
4562 Seven Dwarfs 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 6.3 mi (10.1 km) from Disney Springs™ and 7.2 mi (11.6 km) from ESPN Wide World of Sports Complex.

4562 Seven Dwarfs Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

4562 Seven Dwarfs Rooms
Make yourself comfortable in this vacation home, which features a private hot tub. There's a private patio. A kitchen is outfitted with a refrigerator. Conveniences include a dryer and an iron/ironing board.

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Others

C'est Banana! 2341

Vacation Home

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Osceola
C'est Banana! 2341 Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This vacation home is 7.9 mi (12.8 km) from Walt Disney World® Resort and 9.7 mi (15.6 km) from Disney's Animal Kingdom® Theme Park.

C'est Banana! 2341 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.

C'est Banana! 2341 Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower and designer toiletries. Conveniences include a coffee/tea maker and a washer/dryer.

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Exterior & Views

Windsor At Westside 7bd Hm Pool-2112mw 7 Bedroom Home by RedAwning

Vacation Home

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Osceola
Windsor At Westside 7bd Hm Pool-2112mw 7 Bedroom Home by RedAwning 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 10.3 mi (16.6 km) from Disney's Animal Kingdom® Theme Park and 11.2 mi (18 km) from ESPN Wide World of Sports Complex.

Windsor At Westside 7bd Hm Pool-2112mw 7 Bedroom Home by RedAwning Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Airy House With Private Pool in Encore

Vacation Home

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Osceola
Airy House With Private Pool in Encore Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This vacation home is 7.6 mi (12.3 km) from ESPN Wide World of Sports Complex and 8.1 mi (13.1 km) from Disney's Hollywood Studios®.

Airy House With Private Pool in Encore Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a hot tub.

Airy House With Private Pool in Encore Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Kissimmee Retreat 6BR House Sleeps 14

Vacation Home

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Osceola
Kissimmee Retreat 6BR House Sleeps 14 Location
With a stay at this villa in Kissimmee, you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This villa is 5.9 mi (9.6 km) from Disney Springs™ and 6.8 mi (11 km) from Walt Disney World® Resort.

Kissimmee Retreat 6BR House Sleeps 14 Rooms
Make yourself comfortable in your villa. Complimentary wireless internet access is available to keep you connected. Conveniences include a washing machine and an iron/ironing board.

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Cg9025 - 5BR House With Pool Near Disney

Vacation Home

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Osceola
Cg9025 - 5BR House With Pool Near Disney Location
With a stay at this cottage in Four Corners (Champions Gate), you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This cottage is 11.3 mi (18.2 km) from Old Town and 12.1 mi (19.5 km) from ESPN Wide World of Sports Complex.

Cg9025 - 5BR 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.

Cg9025 - 5BR House With Pool Near Disney Rooms
Make yourself comfortable in this air-conditioned 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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Sport & Beauty

Villa Telles - Storey Lake

Vacation Home

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Osceola
Villa Telles - Storey Lake 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 5.8 mi (9.3 km) from Disney Springs™ and 6.7 mi (10.7 km) from ESPN Wide World of Sports Complex.

Villa Telles - Storey Lake Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with an oven and a stovetop. Complimentary wireless internet access is available to keep you connected. Housekeeping is provided once per stay, and a rollaway/extra bed can be requested.

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Room

Stylish Sleek Home With Full Kitchen at Encore

Vacation Home

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Osceola
Stylish Sleek Home With Full Kitchen at Encore 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 (8.8 km) from Walt Disney World® Resort and 7.7 mi (12.4 km) from ESPN Wide World of Sports Complex.

Stylish Sleek Home With Full Kitchen at Encore 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.

Stylish Sleek Home With Full Kitchen at Encore Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Bedroom

Hunky Dory II Margaritaville Resort!

Vacation Home

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Osceola
Hunky Dory II Margaritaville Resort! Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, a 4-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort. This golf vacation home is 5.8 mi (9.3 km) from Old Town and 5.8 mi (9.4 km) from ESPN Wide World of Sports Complex.

Hunky Dory II Margaritaville Resort! Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Hunky Dory II Margaritaville Resort! 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. Digital television is provided for your entertainment.

See details
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Vacation Homes in Osceola

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