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Vacation Homes in Osceola

Osceola
Sat, 14 Nov 2026 - Sun, 15 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 1.000+ Vacation Homes in Osceola
Children's theme room

Ravishing Four Bd w/ Pool Close to Disney 4947

Vacation Home

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Osceola
Ravishing Four Bd w/ Pool Close to Disney 4947 Location
With a stay at this vacation home in Kissimmee, you'll be a 4-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This family-friendly vacation home is 5.2 mi (8.3 km) from Disney Springs™ and 6.2 mi (10 km) from Walt Disney World® Resort.

Ravishing Four Bd w/ Pool Close to Disney 4947 Facility and Service
Enjoy a range of recreational amenities, including a complimentary water park, an outdoor pool, and a lazy river. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Ravishing Four Bd w/ Pool Close to Disney 4947 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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Resort Home With Private Pool, hot Tub, Tennis, Game Room, Gym, Sports Courts

Vacation Home

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Osceola
Resort Home With Private Pool, hot Tub, Tennis, Game Room, Gym, Sports 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 7.1 mi (11.5 km) from ESPN Wide World of Sports Complex and 8.2 mi (13.2 km) from Disney's Hollywood Studios®.

Resort Home With Private Pool, hot Tub, Tennis, Game Room, Gym, Sports Courts Facility and Service
Enjoy a range of recreational amenities, including an outdoor pool, an outdoor tennis court, and a sauna. Additional features at this vacation home include complimentary wireless internet access and an arcade/game room.

Resort Home With Private Pool, hot Tub, Tennis, Game Room, Gym, Sports Courts Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Others

Luxurious Resort Home Near Disney & Shopping!

Vacation Home

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Osceola
Luxurious Resort Home Near Disney & Shopping! 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 (12.3 km) from Disney Springs™ and 8.7 mi (14 km) from Walt Disney World® Resort.

Luxurious Resort Home Near Disney & Shopping! Facility and Service
Make use of convenient amenities such as complimentary wireless internet access, an arcade/game room, and barbecue grills.

Luxurious Resort Home Near Disney & Shopping! 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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Family Pool Home Near Disney!! Modern Decor, Bbq ,resort W/ Tons Of Amenities! 6 Bedroom Home

Vacation Home

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Osceola
Family Pool Home Near Disney!! Modern Decor, Bbq ,resort W/ Tons Of Amenities! 6 Bedroom Home Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center. This vacation home is 8.1 mi (13.1 km) from ESPN Wide World of Sports Complex and 8.3 mi (13.3 km) from Disney's Animal Kingdom® Theme Park.

Family Pool Home Near Disney!! Modern Decor, Bbq ,resort W/ Tons Of Amenities! 6 Bedroom Home Facility and Service
Enjoy the recreation opportunities such as an outdoor tennis court or make use of other amenities including barbecue grills.

Family Pool Home Near Disney!! Modern Decor, Bbq ,resort W/ Tons Of Amenities! 6 Bedroom 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

1533mc -non-renting The Retreat at Championsgate

Vacation Home

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Osceola
1533mc -non-renting 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 Old Town and ChampionsGate Golf Club. This golf vacation home is 11.9 mi (19.1 km) from ESPN Wide World of Sports Complex and 12 mi (19.2 km) from Walt Disney World® Resort.

1533mc -non-renting The Retreat at Championsgate Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

1533mc -non-renting The Retreat at Championsgate Rooms
Make yourself comfortable in your vacation home.

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Bathroom

5 Bed 8002

Vacation Home

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Osceola
5 Bed 8002 Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This vacation home is 8.1 mi (13 km) from Disney's Hollywood Studios® and 9.1 mi (14.6 km) from Disney's Animal Kingdom® Theme Park.

5 Bed 8002 Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a terrace.

5 Bed 8002 Rooms
Make yourself comfortable in this vacation home, which features a private hot tub and a flat-screen TV. Complimentary wireless internet access is available to keep you connected.

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4.0/5
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.

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South Facing Pool & Spa - Emerald Island Gated Resort

Vacation Home

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Osceola
South Facing Pool & Spa - Emerald Island Gated Resort Location
When you stay at this vacation home in Kissimmee, you'll be near the airport, within a 15-minute drive of Walt Disney World® Resort and Old Town. This family-friendly vacation home is 7.5 mi (12.1 km) from ESPN Wide World of Sports Complex and 8 mi (12.9 km) from Disney's Hollywood Studios®.

South Facing Pool & Spa - Emerald Island Gated Resort Facility and Service
Enjoy a range of recreational amenities, including an outdoor pool, a hot tub, and a fitness center. This vacation home also features an arcade/game room and barbecue grills.

South Facing Pool & Spa - Emerald Island Gated Resort Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and an outdoor private hot tub. 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. Conveniences include a separate sitting area and a microwave, as well as a phone with free local calls.

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Exterior

1077 Champions Gate

Vacation Home

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Osceola
1077 Champions Gate Location
With a stay at this vacation home, you'll be centrally located in Four Corners, within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This golf vacation home is 12.1 mi (19.5 km) from Old Town and 12.9 mi (20.7 km) from ESPN Wide World of Sports Complex.

1077 Champions Gate Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

1077 Champions Gate Rooms
Make yourself comfortable in this vacation home, which features a private pool. Wireless internet access (surcharge) is available to keep you connected.

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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.

See details
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Exterior & Views

Gorgeous 5Bd Single Family w/ Pool @ Storey Lake 2767O

Vacation Home

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Osceola
Gorgeous 5Bd Single Family w/ Pool @ Storey Lake 2767O 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 family-friendly vacation home is 7 mi (11.2 km) from Disney Springs™ and 8 mi (12.9 km) from Walt Disney World® Resort.

Gorgeous 5Bd Single Family w/ Pool @ Storey Lake 2767O Facility and Service
Take advantage of recreational opportunities offered, 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 5Bd Single Family w/ Pool @ Storey Lake 2767O 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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4.5/5
Fully Booked
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Children's theme room

Fantastic Eight Bedrooms SF w/ Screened Pool at Storey Lake Resort 2887

Vacation Home

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Osceola
Fantastic Eight Bedrooms SF w/ Screened Pool at Storey Lake Resort 2887 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 family-friendly vacation home is 6 mi (9.6 km) from Disney Springs™ and 7 mi (11.3 km) from Walt Disney World® Resort.

Fantastic Eight Bedrooms SF w/ Screened Pool at Storey Lake Resort 2887 Facility and Service
Take advantage of recreational opportunities offered, including a complimentary water park, an outdoor pool, and a lazy river. Additional features at this vacation home include concierge services, a television in a common area, and charcoal grills.

Fantastic Eight Bedrooms SF w/ Screened Pool at Storey Lake Resort 2887 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. Cable programming and a DVD player are provided for your entertainment, while complimentary wired internet access keeps you connected. Conveniences include a safe and a desk, and housekeeping is provided daily.

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4.0/5
Fully Booked
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Others

2704 Grand Harbour ct

Private Vacation Home

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Osceola
2704 Grand Harbour ct 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 Old Town. This golf vacation home is 7.8 mi (12.5 km) from Disney's Hollywood Studios® and 8.9 mi (14.3 km) from Epcot®.

2704 Grand Harbour ct Facility and Service
Be sure to enjoy recreational amenities including an outdoor tennis court and a fitness center. Additional features at this vacation home include complimentary wireless internet access and an arcade/game room.

2704 Grand Harbour ct 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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Living area

Buc2999 6 Bedroom Home

Vacation Home

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Osceola
Buc2999 6 Bedroom Home 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 6.6 mi (10.6 km) from Walt Disney World® Resort and 8.2 mi (13.3 km) from Disney's Animal Kingdom® Theme Park.

Buc2999 6 Bedroom 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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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
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Others

Lakeview Disney Resort 5br Townhome w Pool

Vacation Home

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Osceola
Lakeview Disney Resort 5br Townhome w Pool 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 8.7 mi (14.1 km) from Walt Disney World® Resort and 10.5 mi (17 km) from Disney's Animal Kingdom® Theme Park.

Lakeview Disney Resort 5br Townhome w Pool Facility and Service
Don't miss out on recreational opportunities including an outdoor tennis court and a fitness center. Additional amenities at this vacation home include complimentary wireless internet access and an arcade/game room.

Lakeview Disney Resort 5br Townhome w Pool 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

5BR Townhouse Near Disney Pool & Oasis Club

Vacation Home

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Osceola
5BR Townhouse Near Disney Pool & Oasis Club 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 11.5 mi (18.6 km) from Old Town and 12.3 mi (19.8 km) from ESPN Wide World of Sports Complex.

5BR Townhouse Near Disney Pool & Oasis Club Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a hot tub. Additional features at this villa include complimentary wireless internet access, an arcade/game room, and barbecue grills.

5BR Townhouse Near Disney Pool & Oasis Club Rooms
Your villa features a Smart TV. There's a private furnished patio. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. The bathroom has a bathtub or shower and complimentary toiletries.

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Sport & Beauty

851pbeach Amazing Champions Gate 9 Bedroom 5 Bed

Vacation Home

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Osceola
851pbeach Amazing Champions Gate 9 Bedroom 5 Bed Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Old Town. This spa vacation home is 4.9 mi (7.9 km) from ESPN Wide World of Sports Complex and 5.6 mi (8.9 km) from Disney's Hollywood Studios®.

851pbeach Amazing Champions Gate 9 Bedroom 5 Bed Facility and Service
Take time to pamper yourself with a visit to the full-service spa. If you're looking for recreational opportunities, you'll find an outdoor pool and a fitness center.

851pbeach Amazing Champions Gate 9 Bedroom 5 Bed Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and a microwave. An LED television and a video-game console are provided for your entertainment, while complimentary wireless internet access keeps you connected.

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Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629

Vacation Home

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Osceola
Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629 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 7.3 mi (11.7 km) from Disney Springs™ and 8.3 mi (13.3 km) from Walt Disney World® Resort.

Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629 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 concierge services, a television in a common area, and charcoal grills.

Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629 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. Cable programming and a DVD player are provided for your entertainment, while complimentary wired internet access keeps you connected. Conveniences include a safe and a desk, and you can also request a crib/infant bed (surcharge).

See details
4.3/5
Fully Booked
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Others

7 Bedrooms in Large Private Vacation Home by Florida Dream Homes

Vacation Home

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Osceola
7 Bedrooms in Large Private Vacation Home by Florida Dream Homes 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 7.4 mi (11.9 km) from ESPN Wide World of Sports Complex and 8.1 mi (13 km) from Disney's Hollywood Studios®.

7 Bedrooms in Large Private Vacation Home by Florida Dream Homes Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a terrace.

7 Bedrooms in Large Private Vacation Home by Florida Dream Homes Rooms
Make yourself comfortable in this vacation home, which features a private hot tub and a flat-screen TV. A kitchen makes it easy to prepare your meals. Complimentary wireless internet access is available to keep you connected. Conveniences include a phone and a washer/dryer.

See details
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Vacation Homes in Osceola

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