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Vacation Homes in Osceola

Osceola
Thu, 19 Nov 2026 - Fri, 20 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 2.000+ Vacation Homes in Osceola
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Aqua Townhouse With Games Room at Reunion

Vacation Home

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Osceola
Aqua Townhouse With Games Room at Reunion Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be within a 10-minute drive of Mystic Dunes Golf Club and ChampionsGate Golf Club. This vacation home is 6.8 mi (10.9 km) from Walt Disney World® Resort and 8.8 mi (14.1 km) from Old Town.

Aqua Townhouse With Games Room at Reunion Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Aqua Townhouse With Games Room at Reunion Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Exterior & Views

Windsor at Westside-8852hbcgjil by Florida Star Vacations

Private Vacation Home

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Osceola
Windsor at Westside-8852hbcgjil by Florida Star Vacations Location
With a stay at this vacation home in Kissimmee (Four Corners), you'll be within a 10-minute drive of Lake Davenport and Northeast Regional Park. This vacation home is 6.2 mi (10 km) from Walt Disney World® area and 8.2 mi (13.2 km) from Walt Disney World® Resort.

Windsor at Westside-8852hbcgjil by Florida Star Vacations Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Complimentary wireless Internet access is available to keep you connected.

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Enchanting Dog-friendly Home With Pool, Lanai, Central AC, & Washer/dryer

Vacation Home

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Osceola
Enchanting Dog-friendly Home With Pool, Lanai, Central AC, & Washer/dryer Location
Located in Kissimmee (The Hamlets), this vacation home is within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 6.6 mi (10.6 km) from Disney Springs™ and 7.6 mi (12.3 km) from Walt Disney World® Resort.

Enchanting Dog-friendly Home With Pool, Lanai, Central AC, & Washer/dryer Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Enchanting Dog-friendly Home With Pool, Lanai, Central AC, & Washer/dryer Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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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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Exterior & Views

Gorgeous 4 Bedroom w/ Pool Close to Disney 4836

Vacation Home

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Osceola
Gorgeous 4 Bedroom w/ Pool Close to Disney 4836 Location
With a stay at this vacation home in Kissimmee, you'll be 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 6.3 mi (10.1 km) from Walt Disney World® Resort.

Gorgeous 4 Bedroom w/ Pool Close to Disney 4836 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 concierge services, a television in a common area, and charcoal grills.

Gorgeous 4 Bedroom w/ Pool Close to Disney 4836 Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool 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.

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4.6/5
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Florida Dreaming 6 Bedroom Home

Vacation Home

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Osceola
Florida Dreaming 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 Mystic Dunes Golf Club. This vacation home is 7.8 mi (12.5 km) from ESPN Wide World of Sports Complex and 8.1 mi (13 km) from Old Town.

Florida Dreaming 6 Bedroom Home Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Exterior & Views

3BR 2BA Home in Windsor Palms by CV-8168

Vacation Home

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Osceola
3BR 2BA Home in Windsor Palms by CV-8168 Location
With a stay at this vacation home in Kissimmee, you'll be a 3-minute drive from Mystic Dunes Golf Club and 9 minutes from Walt Disney World® Resort. This vacation home is 6.9 mi (11 km) from ESPN Wide World of Sports Complex and 7.1 mi (11.5 km) from Old Town.

3BR 2BA Home in Windsor Palms by CV-8168 Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a flat-screen TV. A kitchen is outfitted with a full-sized refrigerator/freezer, an oven, and a stovetop. Complimentary wireless internet access keeps you connected, and a video-game console is provided for your entertainment. Conveniences include a microwave and a coffee/tea maker.

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Room

Sonoma Resort7 Bedroom Vacation Home 2606YA

Vacation Home

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Osceola
Sonoma Resort7 Bedroom Vacation Home 2606YA Location
Located in Kissimmee, Sonoma Resort7 Bedroom Vacation Home 2606YA is within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This hotel is 9.7 mi (15.6 km) from Disney Springs™ and 10.7 mi (17.3 km) from Walt Disney World® Resort.

Sonoma Resort7 Bedroom Vacation Home 2606YA Rooms
Make yourself at home in one of the air-conditioned rooms featuring private pools. Rooms have private balconies. Kitchens are outfitted with refrigerators, ovens, and stovetops. Conveniences include microwaves and coffee/tea makers.

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Exterior & Views

Gorgeous 4Bd w/ Pool @ Champions Gate 1196

Vacation Home

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Osceola
Gorgeous 4Bd w/ Pool @ Champions Gate 1196 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 family-friendly vacation home is 11.9 mi (19.2 km) from Old Town and 12.7 mi (20.4 km) from ESPN Wide World of Sports Complex.

Gorgeous 4Bd w/ Pool @ Champions Gate 1196 Facility and Service
Don't miss out on the many recreational opportunities, 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.

Gorgeous 4Bd w/ Pool @ Champions Gate 1196 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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3.5/5
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Luxurious Home Private Pool + Spa

Vacation Home

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Osceola
Luxurious Home Private Pool + Spa Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be a 4-minute drive from Reunion Resort Golf Course and 9 minutes from Mystic Dunes Golf Club. This vacation home is 7.5 mi (12.1 km) from Walt Disney World® Resort and 9.5 mi (15.3 km) from Old Town.

Luxurious Home Private Pool + Spa Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

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

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Others

Tropical Vibes

Vacation Home

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Osceola
Tropical Vibes Location
With a stay at Tropical Vibes in Kissimmee, you'll be a 4-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort. This vacation home is 6 mi (9.6 km) from Old Town and 6 mi (9.6 km) from ESPN Wide World of Sports Complex.

Tropical Vibes Rooms
Make yourself at home in one of the individually decorated guestrooms, featuring kitchens with refrigerators and ovens. Rooms have private furnished patios. 42-inch flat-screen televisions are provided, with digital programming available. Conveniences include separate sitting areas and microwaves.

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Sport & Beauty

Windsor Grand Retreat 11ppl!

Vacation Home

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Osceola
Windsor Grand Retreat 11ppl! Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, within a 10-minute drive of Flamingo Crossings Town Center and ChampionsGate Golf Club. This golf vacation home is 7.9 mi (12.7 km) from Walt Disney World® Resort and 9.5 mi (15.3 km) from Disney's Animal Kingdom® Theme Park.

Windsor Grand Retreat 11ppl! Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center.

Windsor Grand Retreat 11ppl! 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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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.

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4.1/5
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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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Room

Fantastic Townhome 5min -disney BBQ 116

Vacation Home

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Osceola
Fantastic Townhome 5min -disney BBQ 116 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 Old Town. This vacation home is 4.9 mi (7.9 km) from ESPN Wide World of Sports Complex and 5.6 mi (9 km) from Disney's Hollywood Studios®.

Fantastic Townhome 5min -disney BBQ 116 Facility and Service
Don't miss out on recreational opportunities including a hot tub and a fitness center. Additional amenities at this vacation home include complimentary wireless internet access and barbecue grills.

Fantastic Townhome 5min -disney BBQ 116 Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Storey Lake Resort 8 Bedroom Home Game Room + Pool 8 Home

Vacation Home

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Osceola
Storey Lake Resort 8 Bedroom Home Game Room + Pool 8 Home 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 7.1 mi (11.4 km) from Disney Springs™ and 8.1 mi (13.1 km) from Walt Disney World® Resort.

Storey Lake Resort 8 Bedroom Home Game Room + Pool 8 Home Facility and Service
Take in the views from a terrace.

Storey Lake Resort 8 Bedroom Home Game Room + Pool 8 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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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.

See details
4.5/5
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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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Others

Renovated 4 BDR With pvt Pool

Vacation Home

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Osceola
Renovated 4 BDR With pvt Pool Location
With a stay at this vacation home in Kissimmee, you'll be a 5-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This vacation home is 5.3 mi (8.5 km) from Disney Springs™ and 6.3 mi (10.2 km) from Walt Disney World® Resort.

Renovated 4 BDR With pvt Pool Facility and Service
Enjoy recreation amenities such as a fitness center or take in the view from a garden.

Renovated 4 BDR With pvt Pool Rooms
Make yourself comfortable in this vacation home, which has a kitchen.

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Paradise Palms Resort 6 Bedroom Private Pool+Spa Home 6 Home

Vacation Home

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Osceola
Paradise Palms Resort 6 Bedroom Private Pool+Spa Home 6 Home Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Mystic Dunes Golf Club and Flamingo Crossings Town Center. This vacation home is 5.1 mi (8.3 km) from Walt Disney World® Resort and 7.9 mi (12.7 km) from Old Town.

Paradise Palms Resort 6 Bedroom Private Pool+Spa Home 6 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.

See details
Fully Booked
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Vacation Homes in Osceola

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