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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
Room amenity

Family Friendly 5 Bedrooms Home Close to Disney 4849

Vacation Home

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Osceola
Family Friendly 5 Bedrooms Home Close to Disney 4849 Location
When you stay at this vacation home in Kissimmee, you'll be on a lake, within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This family-friendly vacation home is 5.8 mi (9.4 km) from Disney Springs™ and 6.8 mi (11 km) from Walt Disney World® Resort.

Family Friendly 5 Bedrooms Home Close to Disney 4849 Facility and Service
Don't miss out on the many recreational opportunities, including a complimentary water park, an outdoor pool, and an indoor pool. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Family Friendly 5 Bedrooms Home Close to Disney 4849 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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4.5/5
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Room

9089-Hazard

Vacation Home

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Osceola
9089-Hazard 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 11.6 mi (18.6 km) from Old Town and 12.3 mi (19.9 km) from ESPN Wide World of Sports Complex.

9089-Hazard Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Sl3111 - 4BR House With Pool Near Disney Parks

Vacation Home

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Osceola
Sl3111 - 4BR House With Pool Near Disney Parks 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 mi (9.7 km) from Disney Springs™ and 7 mi (11.2 km) from Walt Disney World® Resort.

Sl3111 - 4BR House With Pool Near Disney Parks Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Sl3111 - 4BR House With Pool Near Disney Parks Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with an oven and a stovetop. Conveniences include a microwave and a washer/dryer.

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Others

Family-friendly House w/ Resort Pool & Splash Park

Vacation Home

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Osceola
Family-friendly House w/ Resort Pool & Splash Park Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Flamingo Crossings Town Center and Mystic Dunes Golf Club. This vacation home is 6.8 mi (11 km) from Walt Disney World® Resort and 8.3 mi (13.4 km) from Old Town.

Family-friendly House w/ Resort Pool & Splash Park Facility and Service
Take advantage of recreational opportunities offered, including an outdoor pool, an outdoor tennis court, and a fitness center. Additional features at this vacation home include complimentary wireless internet access and an arcade/game room.

Family-friendly House w/ Resort Pool & Splash Park Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Sl4926 - 4BR House With Pool Near Disney Area

Vacation Home

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Osceola
Sl4926 - 4BR House With Pool Near Disney Area Location
With a stay at this cottage in Kissimmee, you'll be a 5-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This cottage is 5.2 mi (8.4 km) from Disney Springs™ and 6.2 mi (10 km) from Walt Disney World® Resort.

Sl4926 - 4BR House With Pool Near Disney Area Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Sl4926 - 4BR House With Pool Near Disney Area 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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Bedroom

Spacious Family Reunion 15br Home Pool Spa Game Rm

Vacation Home

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Osceola
Spacious Family Reunion 15br Home Pool Spa Game Rm 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 7.6 mi (12.2 km) from Disney Springs™ and 8.2 mi (13.2 km) from Walt Disney World® Resort.

Spacious Family Reunion 15br Home Pool Spa Game Rm Facility and Service
Make use of convenient amenities such as complimentary wireless internet access, an arcade/game room, and barbecue grills.

Spacious Family Reunion 15br Home Pool Spa Game Rm 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. Conveniences include a coffee/tea maker and a washer/dryer.

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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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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.

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Room

Home Away From Home Private Pool

Vacation Home

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Osceola
Home Away From Home Private Pool Location
When you stay at this vacation home in Four Corners, you'll be next to a golf course, within a 15-minute drive of ChampionsGate Golf Club and Mystic Dunes Golf Club. This golf vacation home is 12.1 mi (19.5 km) from Old Town and 12.9 mi (20.8 km) from ESPN Wide World of Sports Complex.

Home Away From Home Private Pool Facility and Service
Make use of convenient amenities such as complimentary wireless internet access, an arcade/game room, and barbecue grills.

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

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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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5 Bed With Private Splash Pool! 5 Bedroom Townhouse

Vacation Home

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Osceola
5 Bed With Private Splash Pool! 5 Bedroom 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 10.1 mi (16.2 km) from Disney's Animal Kingdom® Theme Park and 11.2 mi (18 km) from ESPN Wide World of Sports Complex.

5 Bed With Private Splash Pool! 5 Bedroom Townhouse Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Others

Champions Gate 6BR Private Theater Games Pool Spa

Vacation Home

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Osceola
Champions Gate 6BR Private Theater Games Pool Spa Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This vacation home is 12.5 mi (20.1 km) from Walt Disney World® Resort and 12.7 mi (20.4 km) from Old Town.

Champions Gate 6BR Private Theater Games Pool Spa 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.

Champions Gate 6BR Private Theater Games Pool Spa 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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1559sbd-the Retreat At Championsgate 4 Bedroom Townhouse

Vacation Home

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Osceola
1559sbd-the Retreat At Championsgate 4 Bedroom 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 vacation home is 11.4 mi (18.3 km) from Old Town and 12.1 mi (19.5 km) from ESPN Wide World of Sports Complex.

1559sbd-the Retreat At Championsgate 4 Bedroom 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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Exterior & Views

8812 Macapa Drive

Private Vacation Home

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Osceola
8812 Macapa Drive 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 Flamingo Crossings Town Center. This golf vacation home is 10.3 mi (16.6 km) from Disney's Animal Kingdom® Theme Park and 11.5 mi (18.6 km) from Old Town.

8812 Macapa Drive Facility and Service
Take advantage of recreational opportunities offered, including an indoor pool, an outdoor tennis court, and a fitness center. Additional amenities at this vacation home include complimentary wireless internet access and an arcade/game room.

8812 Macapa Drive Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a refrigerator and an oven. There's a private balcony. Conveniences include a microwave and a coffee/tea maker.

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Exterior

7 Bedrooms S / Solara Home

Vacation Home

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Osceola
7 Bedrooms S / Solara 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 8.6 mi (13.8 km) from Walt Disney World® Resort and 10.3 mi (16.5 km) from Disney's Animal Kingdom® Theme Park.

7 Bedrooms S / Solara Home Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Others

8919sid-the Retreat at Championsgate

Vacation Home

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Osceola
8919sid-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 11.5 mi (18.4 km) from Old Town and 12.2 mi (19.7 km) from ESPN Wide World of Sports Complex.

8919sid-the Retreat at Championsgate Rooms
Make yourself comfortable in this vacation home, which has a kitchen. There's a private balcony or patio.

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Beautiful Chic Radiance Home With Pool 5 Bedroom Townhouse

Vacation Home

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Osceola
Beautiful Chic Radiance Home With Pool 5 Bedroom Townhouse 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 8.4 mi (13.6 km) from Walt Disney World® Resort and 10.1 mi (16.2 km) from Disney's Animal Kingdom® Theme Park.

Beautiful Chic Radiance Home With Pool 5 Bedroom Townhouse Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Bedroom

Upstay - Theater Games Sleeps 16 Pool

Vacation Home

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Osceola
Upstay - Theater Games Sleeps 16 Pool 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 ESPN Wide World of Sports Complex and 10.4 mi (16.7 km) from Disney's Animal Kingdom® Theme Park.

Upstay - Theater Games Sleeps 16 Pool Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and an indoor pool.

Upstay - Theater Games Sleeps 16 Pool Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected. The bathroom has a bathtub or shower.

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4.0/5
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Spacious Townhouse With Private Pool,resort Amenities, and Tennis Courts

Vacation Home

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Osceola
Spacious Townhouse With Private Pool,resort Amenities, and Tennis Courts 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 Old Town. This vacation home is 8 mi (12.8 km) from Disney's Animal Kingdom® Theme Park and 9.2 mi (14.8 km) from ESPN Wide World of Sports Complex.

Spacious Townhouse With Private Pool,resort Amenities, and Tennis Courts Facility and Service
Enjoy a range of recreational amenities, including a hot tub, an outdoor tennis court, and a sauna. Additional features at this vacation home include complimentary wireless internet access and an arcade/game room.

Spacious Townhouse With Private Pool,resort Amenities, and Tennis Courts 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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Snowbird-friendly Home Near Disney W/private Heated Pool, Lanai, Shared Tennis

Vacation Home

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Osceola
Snowbird-friendly Home Near Disney W/private Heated Pool, Lanai, Shared Tennis Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, a 2-minute drive from Mystic Dunes Golf Club and 9 minutes from Walt Disney World® Resort. This vacation home is 7.1 mi (11.4 km) from ESPN Wide World of Sports Complex and 7.5 mi (12.1 km) from Old Town.

Snowbird-friendly Home Near Disney W/private Heated Pool, Lanai, Shared Tennis Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Snowbird-friendly Home Near Disney W/private Heated Pool, Lanai, Shared Tennis 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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Vacation Homes in Osceola

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