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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
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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8848 BC - 8bds Windsor At Westside

Vacation Home

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Osceola
8848 BC - 8bds Windsor At Westside Location
When you stay at this vacation home in Kissimmee, you'll be on the beach, within a 15-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This golf vacation home is 9.1 mi (14.6 km) from Walt Disney World® Resort and 10.7 mi (17.3 km) from Disney's Animal Kingdom® Theme Park.

8848 BC - 8bds Windsor At Westside Facility and Service
Enjoy recreation amenities such as a fitness center or take in the view from a garden. Additional features at this vacation home include an arcade/game room and barbecue grills.

8848 BC - 8bds Windsor At Westside Rooms
Make yourself comfortable in this vacation home, which has a kitchen. Satellite television is provided for your entertainment. Conveniences include a desk and an iron/ironing board, and housekeeping is provided daily.

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Exterior & Views

4BR 3BA Home in Windsor Palms by CV-8112

Vacation Home

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Osceola
4BR 3BA Home in Windsor Palms by CV-8112 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 mi (11.3 km) from ESPN Wide World of Sports Complex and 7.2 mi (11.6 km) from Old Town.

4BR 3BA Home in Windsor Palms by CV-8112 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 DVD player is provided for your entertainment. Conveniences include a microwave and a coffee/tea maker.

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West Lucaya Village 4 Bedroom Townhome 4 Townhouse

Vacation Home

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Osceola
West Lucaya Village 4 Bedroom Townhome 4 Townhouse 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 Disney's Animal Kingdom® Theme Park and 8.6 mi (13.8 km) from ESPN Wide World of Sports Complex.

West Lucaya Village 4 Bedroom Townhome 4 Townhouse 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

Windsor at Westside Resort 6 Bedroom Home with Game Room 6 Home

Vacation Home

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Osceola
Windsor at Westside Resort 6 Bedroom Home with Game Room 6 Home 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 Disney's Animal Kingdom® Theme Park and 10.7 mi (17.2 km) from ESPN Wide World of Sports Complex.

Windsor at Westside Resort 6 Bedroom Home with Game Room 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.

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Exterior & Views

Beautiful 5 Bedroom Town Home with Splash Pool 5 Home by RedAwning

Vacation Home

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Osceola
Beautiful 5 Bedroom Town Home with Splash Pool 5 Home by RedAwning 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 8.6 mi (13.8 km) from Walt Disney World® Resort and 10.4 mi (16.7 km) from Disney's Animal Kingdom® Theme Park.

Beautiful 5 Bedroom Town Home with Splash Pool 5 Home by RedAwning Rooms
Make yourself comfortable in your air-conditioned vacation home, which features a microwave. Complimentary wireless internet access is available to keep you connected.

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Spacious 9-bedroom Orlando vacation home

Vacation Home

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Osceola
Spacious 9-bedroom Orlando vacation home Location
When you stay at this apartment in Kissimmee, you'll be in the entertainment district, within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This apartment is 10 mi (16.1 km) from Disney's Animal Kingdom® Theme Park and 11.2 mi (18 km) from ESPN Wide World of Sports Complex.

Spacious 9-bedroom Orlando vacation home Facility and Service
Enjoy recreational amenities such as an indoor pool and a waterslide.

Spacious 9-bedroom Orlando vacation home Rooms
Make yourself comfortable in your apartment. Complimentary wireless internet access is available to keep you connected. Conveniences include an electric kettle and an all-in-one washing machine and dryer.

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Others

Grhsec8402 - Emerald Island Resort - 6 Bed 6 Baths House

Vacation Home

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Osceola
Grhsec8402 - Emerald Island Resort - 6 Bed 6 Baths House Location
When you stay at this vacation home in Kissimmee, you'll be on the waterfront, within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This golf vacation home is 6.8 mi (11 km) from Old Town and 6.9 mi (11.1 km) from ESPN Wide World of Sports Complex.

Grhsec8402 - Emerald Island Resort - 6 Bed 6 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. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhsec8402 - Emerald Island Resort - 6 Bed 6 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
Unwind at the end of the day with a drink at the bar/lounge or the poolside bar.

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Dog-friendly Home With Private Pool, High-speed Wifi, Central AC, & Washer/dryer

Vacation Home

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Osceola
Dog-friendly Home With Private Pool, High-speed Wifi, Central AC, & Washer/dryer Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, 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 8.4 mi (13.5 km) from Old Town.

Dog-friendly Home With Private Pool, High-speed Wifi, Central AC, & Washer/dryer 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.

Dog-friendly Home With Private Pool, High-speed Wifi, 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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Exterior & Views

Stunning 5 Bd Home w/ Pool Close to Disney 4822

Vacation Home

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Osceola
Stunning 5 Bd Home w/ Pool Close to Disney 4822 Location
When you stay at this vacation home in Kissimmee, you'll be on a lake, 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.

Stunning 5 Bd Home w/ Pool Close to Disney 4822 Facility and Service
Be sure to enjoy recreational amenities, 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.

Stunning 5 Bd Home w/ Pool Close to Disney 4822 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 60-inch flat-screen television with cable programming provides entertainment.

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4.4/5
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Room

The Golf Vista Townhome at Reunion

Vacation Home

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Osceola
The Golf Vista Townhome at Reunion Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be a 1-minute drive from Reunion Resort Golf Course and 10 minutes from ChampionsGate Golf Club. This golf vacation home is 7.1 mi (11.4 km) from Walt Disney World® Resort and 9.3 mi (15 km) from ESPN Wide World of Sports Complex.

The Golf Vista Townhome at Reunion Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and barbecue grills.

The Golf Vista Townhome at Reunion Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Bedroom

Champions Gate The Force Awakens 1429

Private Vacation Home

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Osceola
Champions Gate The Force Awakens 1429 Location
Located in Four Corners, this vacation home is within a 15-minute drive of Reunion Resort Golf Course and Mystic Dunes Golf Club. This vacation home is 11.7 mi (18.8 km) from Old Town and 12.7 mi (20.4 km) from Walt Disney World® Resort.

Champions Gate The Force Awakens 1429 Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Champions Gate The Force Awakens 1429 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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Room

8886-CabotCliffs

Vacation Home

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Osceola
8886-CabotCliffs 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 12.1 mi (19.5 km) from Old Town and 12.6 mi (20.3 km) from Walt Disney World® Resort.

8886-CabotCliffs Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Others

Mvv7485 - 3BR House Near Disney With Hot Tub

Vacation Home

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Osceola
Mvv7485 - 3BR House Near Disney With Hot Tub Location
With a stay at this cottage in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and Old Town. This cottage is 4.8 mi (7.7 km) from ESPN Wide World of Sports Complex and 5.3 mi (8.5 km) from Disney's Hollywood Studios®.

Mvv7485 - 3BR House Near Disney With Hot Tub Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and barbecue grills.

Mvv7485 - 3BR House Near Disney With Hot Tub Rooms
Make yourself comfortable in this air-conditioned cottage, which features a fireplace. A kitchen is outfitted with an oven, a stovetop, and a microwave. Conveniences include a washer/dryer and an iron/ironing board.

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Exterior & Views

4 Bedroom Town Home with Pool

Vacation Home

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Osceola
4 Bedroom Town Home with Pool 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 vacation home is 5.2 mi (8.3 km) from Disney Springs™ and 6.1 mi (9.8 km) from ESPN Wide World of Sports Complex.

4 Bedroom Town Home with Pool Facility and Service
Take advantage of recreation opportunities such as a fitness center, or other amenities including wireless internet access (surcharge) and barbecue grills.

4 Bedroom Town Home with Pool Rooms
Your vacation home features a flat-screen TV.

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House at Solara Resort by Carpediem

Vacation Home

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Osceola
House at Solara Resort by Carpediem Location
With a stay at this apartment in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This apartment is 10.2 mi (16.4 km) from Disney's Animal Kingdom® Theme Park and 11.1 mi (17.9 km) from ESPN Wide World of Sports Complex.

House at Solara Resort by Carpediem Facility and Service
Take advantage of recreation opportunities including an outdoor pool and an indoor pool.

House at Solara Resort by Carpediem Rooms
Make yourself comfortable in this apartment, featuring a kitchen with a refrigerator and a stovetop. A flat-screen television is provided for your entertainment. Conveniences include a washer/dryer and a ceiling fan.

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Others

Grhdog9037 - Champions Gate Resort - 4 Bed 3 Baths Townhouse

Vacation Home

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Osceola
Grhdog9037 - Champions Gate Resort - 4 Bed 3 Baths 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 family-friendly vacation home is 11.5 mi (18.5 km) from Old Town and 12.2 mi (19.7 km) from ESPN Wide World of Sports Complex.

Grhdog9037 - Champions Gate Resort - 4 Bed 3 Baths Townhouse Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Grhdog9037 - Champions Gate Resort - 4 Bed 3 Baths Townhouse Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private plunge pool and a flat-screen TV. There's a private balcony or patio. A kitchen is outfitted with a refrigerator, an oven, and a microwave. Cable 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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Others

Ov3708 - Paradise Palms - 4 Bed 3 Baths Townhome

Vacation Home

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Osceola
Ov3708 - Paradise Palms - 4 Bed 3 Baths Townhome Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Walt Disney World® Resort and Old Town. This family-friendly vacation home is 8.1 mi (13.1 km) from Disney's Animal Kingdom® Theme Park and 9 mi (14.5 km) from ESPN Wide World of Sports Complex.

Ov3708 - Paradise Palms - 4 Bed 3 Baths Townhome Facility and Service
Practice your swing on the golf course and enjoy other recreational amenities, such as a complimentary water park and a hot tub. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Ov3708 - Paradise Palms - 4 Bed 3 Baths Townhome Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private plunge pool and a flat-screen TV. There's a private balcony or patio. A kitchen is outfitted with a refrigerator, an oven, and a microwave. Cable television is provided for your entertainment.

Restaurant and Cafe
Satisfy your appetite at the vacation home's coffee shop/cafe, or stop in at the grocery/convenience store. Relax with your favorite drink at the bar/lounge or the poolside bar.

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Cozy Family Home Boasting Entertainment for Everyone With Wifi

Vacation Home

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Osceola
Cozy Family Home Boasting Entertainment for Everyone With Wifi 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 5 mi (8 km) from ESPN Wide World of Sports Complex and 5.5 mi (8.8 km) from Disney's Hollywood Studios®.

Cozy Family Home Boasting Entertainment for Everyone With Wifi 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.

Cozy Family Home Boasting Entertainment for Everyone With Wifi Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Others

Luxury Getaway: Pool, Spa, Games, Theater

Vacation Home

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Osceola
Luxury Getaway: Pool, Spa, Games, Theater Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This vacation home is 10.1 mi (16.3 km) from Disney's Animal Kingdom® Theme Park and 11.3 mi (18.2 km) from ESPN Wide World of Sports Complex.

Luxury Getaway: Pool, Spa, Games, Theater 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.

Luxury Getaway: Pool, Spa, Games, Theater Rooms
Make yourself comfortable in your individually decorated vacation home. There's a private balcony or 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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Vacation Homes in Osceola

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