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Vacation Homes in Osceola

Osceola
Sun, 15 Nov 2026 - Mon, 16 Nov 2026 (1 night)
1 Adult, 0 Children
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Showing 1.000+ Vacation Homes in Osceola
Interior

Special Offer Great House w Pvt Pool at Champions Gate

Vacation Home

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Osceola
Special Offer Great House w Pvt Pool at Champions Gate 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 villa is 11.4 mi (18.3 km) from Old Town and 12.1 mi (19.5 km) from ESPN Wide World of Sports Complex.

Special Offer Great House w Pvt Pool at Champions Gate Rooms
Make yourself comfortable in this air-conditioned villa, which has a kitchen. Cable television is provided for your entertainment. Conveniences include a dryer and an iron/ironing board.

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Room

Sunny Private Pool & Spa & Fenced Yard. Nr Parks

Vacation Home

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Osceola
Sunny Private Pool & Spa & Fenced Yard. Nr Parks Location
With a stay at this vacation home in Kissimmee (Indian Point), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This luxury vacation home is 9.5 mi (15.3 km) from Disney Springs™ and 9.8 mi (15.7 km) from Walt Disney World® Resort.

Sunny Private Pool & Spa & Fenced Yard. Nr Parks Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a hot tub.

Sunny Private Pool & Spa & Fenced Yard. Nr Parks Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and an outdoor private hot tub. There's a private patio. A kitchen is outfitted with a full-sized refrigerator/freezer, an oven, and a stovetop. A 55-inch Smart television with digital programming provides entertainment, while complimentary wireless internet access keeps you connected.

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Beautiful & Spacious Resort Home in the Heart of Central FL

Vacation Home

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Osceola
Beautiful & Spacious Resort Home in the Heart of Central FL Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 15-minute drive of Walt Disney World® Resort and Disney Springs™. This vacation home is 8.6 mi (13.8 km) from ESPN Wide World of Sports Complex and 9 mi (14.4 km) from Disney's Hollywood Studios®.

Beautiful & Spacious Resort Home in the Heart of Central FL 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.

Beautiful & Spacious Resort Home in the Heart of Central FL Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Private Pool, Home Theater & Dog-friendly Retreat Near Disney

Vacation Home

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Osceola
Private Pool, Home Theater & Dog-friendly Retreat Near Disney Location
Located in Kissimmee (Indian Ridge), this vacation home is within a 10-minute drive of Mystic Dunes Golf Club and Flamingo Crossings Town Center. This vacation home is 5.2 mi (8.3 km) from Walt Disney World® Resort and 7.4 mi (11.9 km) from ESPN Wide World of Sports Complex.

Private Pool, Home Theater & Dog-friendly Retreat 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.

Private Pool, Home Theater & Dog-friendly Retreat Near Disney Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Exterior & Views

5BR Pool Home in Storey Lake by SHV-4817

Private Vacation Home

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Osceola
5BR Pool Home in Storey Lake by SHV-4817 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 mi (9.7 km) from Disney Springs��� and 6.8 mi (11 km) from ESPN Wide World of Sports Complex.

5BR Pool Home in Storey Lake by SHV-4817 Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a terrace.

5BR Pool Home in Storey Lake by SHV-4817 Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a private hot tub. There's a private furnished balcony. A kitchen is outfitted with a full-sized refrigerator/freezer, an oven, and a stovetop. A flat-screen television and a DVD player are provided for your entertainment, while complimentary wireless internet access keeps you connected.

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Disney Dream Vacation Home by Disney

Vacation Home

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Osceola
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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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Exterior & Views

1094ssp-the Retreat At Championsgate 4 Bedroom Home by RedAwning

Vacation Home

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Osceola
1094ssp-the Retreat At Championsgate 4 Bedroom Home by RedAwning Location
With a stay at this vacation home in Four Corners, you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This vacation home is 12 mi (19.4 km) from Old Town and 12.8 mi (20.6 km) from ESPN Wide World of Sports Complex.

1094ssp-the Retreat At Championsgate 4 Bedroom Home by RedAwning Rooms
Make yourself comfortable in your vacation home, which features a refrigerator. Complimentary wireless internet access is available to keep you connected. The bathroom has a bathtub or shower.Conveniences include a coffee/tea maker and a washing machine.

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Outdoor pool

Gorgeous 4 Bd w/ Pool Close to Disney @ Storey Lake 2963

Vacation Home

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Osceola
Gorgeous 4 Bd w/ Pool Close to Disney @ Storey Lake 2963 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 7.5 mi (12.1 km) from Disney Springs™ and 8.6 mi (13.9 km) from Walt Disney World® Resort.

Gorgeous 4 Bd w/ Pool Close to Disney @ Storey Lake 2963 Facility and Service
Be sure to enjoy recreational amenities, including a complimentary water park, an outdoor pool, and a lazy river. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Gorgeous 4 Bd w/ Pool Close to Disney @ Storey Lake 2963 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 rollaway/extra bed (surcharge).

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4.8/5
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Room

Wilmington Grand Escape

Vacation Home

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Osceola
Wilmington Grand Escape Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Mystic Dunes Golf Club and Reunion Resort Golf Course. This family-friendly 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.

Wilmington Grand Escape Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a hot tub. Additional features at this vacation home include an arcade/game room and gas grills.

Wilmington Grand Escape 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 washer/dryer.

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Windsor Palms Resort 5 Bedroom Home with Game Room 5 Home

Vacation Home

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Osceola
Windsor Palms Resort 5 Bedroom Home with Game Room 5 Home Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 8.2 mi (13.2 km) from Disney's Hollywood Studios® and 9.2 mi (14.9 km) from Disney's Animal Kingdom® Theme Park.

Windsor Palms Resort 5 Bedroom Home with Game Room 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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Family-friendly Townhouse w/ Private Pool & Clubhouse

Vacation Home

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Osceola
Family-friendly Townhouse w/ Private Pool & Clubhouse 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 6.5 mi (10.5 km) from Walt Disney World® Resort.

Family-friendly Townhouse w/ Private Pool & Clubhouse Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including complimentary wireless internet access.

Family-friendly Townhouse w/ Private Pool & Clubhouse Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Bedroom

Championsgate 6BR Luxury Home Pool Spa Near Disney

Vacation Home

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Osceola
Championsgate 6BR Luxury Home Pool Spa Near Disney Location
With a stay at this vacation home in Four Corners, you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This vacation home is 12.1 mi (19.4 km) from Old Town and 12.8 mi (20.7 km) from ESPN Wide World of Sports Complex.

Championsgate 6BR Luxury Home Pool Spa 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.

Championsgate 6BR Luxury Home Pool Spa Near Disney Rooms
Make yourself comfortable in your individually decorated vacation home. There's a private patio. The bathroom has a bathtub or shower and designer toiletries.

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Others

Sl4807 - 5BR House Near Disney Parks Modern Home

Vacation Home

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Osceola
Sl4807 - 5BR House Near Disney Parks Modern Home Location
With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This cottage is 6.1 mi (9.7 km) from Disney Springs™ and 7 mi (11.2 km) from Walt Disney World® Resort.

Sl4807 - 5BR House Near Disney Parks Modern Home Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Sl4807 - 5BR House Near Disney Parks Modern Home Rooms
Make yourself comfortable in this individually decorated cottage, featuring a kitchen with an oven and a stovetop. Conveniences include a microwave and a washer/dryer.

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Windsor Hills Resort 5 Bedroom Home with Game Room 5 Home

Vacation Home

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Osceola
Windsor Hills Resort 5 Bedroom Home with Game Room 5 Home Location
With a stay at this vacation home in Kissimmee (Windsor Hills), you'll be within a 10-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 5.2 mi (8.4 km) from ESPN Wide World of Sports Complex and 6.1 mi (9.8 km) from Disney's Hollywood Studios®.

Windsor Hills Resort 5 Bedroom Home with Game Room 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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Solara Resort 7 Bedroom Private Pool+Spa Movie Room Home 7 Home

Vacation Home

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Osceola
Solara Resort 7 Bedroom Private Pool+Spa Movie Room Home 7 Home Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This golf vacation home is 10.1 mi (16.2 km) from Disney's Animal Kingdom® Theme Park and 11.3 mi (18.1 km) from ESPN Wide World of Sports Complex.

Solara Resort 7 Bedroom Private Pool+Spa Movie Room Home 7 Home 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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Others

1575mvd-the Retreat At Championsgate 4 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
1575mvd-the Retreat At Championsgate 4 Bedroom Townhouse by RedAwning 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 11.5 mi (18.5 km) from Old Town and 12.3 mi (19.8 km) from ESPN Wide World of Sports Complex.

1575mvd-the Retreat At Championsgate 4 Bedroom Townhouse by RedAwning Facility and Service
Don't miss out on recreational opportunities including an outdoor tennis court and a fitness center.

1575mvd-the Retreat At Championsgate 4 Bedroom Townhouse by RedAwning Rooms
Make yourself comfortable in your vacation home, featuring a refrigerator and a DVD player. There's a private patio. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. The bathroom has a bathtub or shower and complimentary toiletries.

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Bedroom

1543 CP - Opulent 4BR Townhome: Private Pool, Solara Resort

Vacation Home

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Osceola
1543 CP - Opulent 4BR Townhome: Private Pool, Solara Resort Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This vacation home is 8.7 mi (13.9 km) from Walt Disney World® Resort and 10.4 mi (16.8 km) from Disney's Animal Kingdom® Theme Park.

1543 CP - Opulent 4BR Townhome: Private Pool, Solara Resort Rooms
Make yourself comfortable in your vacation home.

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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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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.

See details
4.1/5
Fully Booked
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Vacation Homes in Osceola

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