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Vacation Homes in Osceola

Osceola
Tue, 17 Nov 2026 - Wed, 18 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 1.000+ Vacation Homes in Osceola
Bedroom

5 Bedroom in Champions Gate

Vacation Home

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Osceola
5 Bedroom in Champions Gate Location
With a stay at this vacation home in Four Corners (Champions Gate), you'll be within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This spa vacation home is 12.7 mi (20.4 km) from Old Town and 13.2 mi (21.3 km) from Walt Disney World® Resort.

5 Bedroom in Champions Gate Facility and Service
Take time to pamper yourself with a visit to the full-service spa. You can take advantage of recreational amenities such as an outdoor pool and a fitness center.

5 Bedroom in Champions Gate Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a flat-screen TV. There's a private patio. A kitchen is outfitted with a refrigerator, an oven, and a microwave. Complimentary wireless internet access is available to keep you connected.

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Others

Ev230259 - Champions Gate Resort - 4 Bed 3 Baths Townhome

Vacation Home

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Osceola
Ev230259 - Champions Gate Resort - 4 Bed 3 Baths Townhome 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 Mystic Dunes Golf Club. This family-friendly vacation home is 11.5 mi (18.5 km) from Old Town and 12.3 mi (19.7 km) from ESPN Wide World of Sports Complex.

Ev230259 - Champions Gate Resort - 4 Bed 3 Baths Townhome Facility and Service
Practice your swing on the golf course or dip into one of the 2 hot tubs. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Ev230259 - Champions Gate Resort - 4 Bed 3 Baths Townhome Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. A flat-screen television is provided for your entertainment. Conveniences include a microwave and a washer/dryer.

Restaurant and Cafe
Enjoy a meal at the restaurant or snacks in the vacation home's coffee shop/cafe. Relax with your favorite drink at the bar/lounge or the poolside bar.

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Fully Booked
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Bedroom

Orlando Newest Resort Community Town 5 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
Orlando Newest Resort Community Town 5 Bedroom Townhouse 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 8.7 mi (14 km) from Walt Disney World® Resort and 10.3 mi (16.6 km) from Disney's Animal Kingdom® Theme Park.

Orlando Newest Resort Community Town 5 Bedroom Townhouse by RedAwning Rooms
Make yourself comfortable in this vacation home, which features a private pool. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment.

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Others

1579mvd-the Retreat at Champions Gate

Vacation Home

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Osceola
1579mvd-the Retreat at Champions Gate Location
With a stay at this condo in Four Corners (Champions Gate), you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This golf condo is 11.5 mi (18.5 km) from Old Town and 12.3 mi (19.8 km) from ESPN Wide World of Sports Complex.

1579mvd-the Retreat at Champions Gate Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center.

1579mvd-the Retreat at Champions Gate Rooms
Make yourself comfortable in this air-conditioned condo, featuring a kitchen with a refrigerator and a stovetop. A flat-screen television is provided for your entertainment. Conveniences include a microwave and an iron/ironing board.

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Bedroom

8929bismark

Vacation Home

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Osceola
8929bismark 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 8.4 mi (13.5 km) from Disney's Animal Kingdom® Theme Park and 9.3 mi (14.9 km) from ESPN Wide World of Sports Complex.

8929bismark Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center.

8929bismark Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and a microwave. Complimentary wireless internet access keeps you connected, and a flat-screen television is provided for your entertainment.

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Fully Booked
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Sport & Beauty

Grhcup8936 - Paradise Palms Resort - 5 Bed 4 Baths Townhouse

Vacation Home

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Osceola
Grhcup8936 - Paradise Palms Resort - 5 Bed 4 Baths Townhouse Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and Old Town. This family-friendly vacation home is 8.1 mi (13 km) from Disney's Animal Kingdom® Theme Park and 8.9 mi (14.4 km) from ESPN Wide World of Sports Complex.

Grhcup8936 - Paradise Palms Resort - 5 Bed 4 Baths Townhouse Facility and Service
Practice your swing on the golf course or dip into one of the 2 hot tubs. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhcup8936 - Paradise Palms Resort - 5 Bed 4 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
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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Sport & Beauty

Fv52288 - Paradise Palms - 5 Bed 4 Baths Townhome

Vacation Home

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Osceola
Fv52288 - Paradise Palms - 5 Bed 4 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 mi (12.9 km) from Disney's Animal Kingdom® Theme Park and 9.2 mi (14.9 km) from ESPN Wide World of Sports Complex.

Fv52288 - Paradise Palms - 5 Bed 4 Baths Townhome Facility and Service
Practice your swing on the golf course or dip into one of the 2 hot tubs. This vacation home also features complimentary wireless internet access, concierge services, and gift shops/newsstands.

Fv52288 - Paradise Palms - 5 Bed 4 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 programming along with a video-game console are provided for your entertainment.

Restaurant and Cafe
Grab a bite from the grocery/convenience store serving guests of this vacation home. Wrap up your day with a drink at the poolside bar.

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Exterior & Views

Tvpm-1191mbbv

Vacation Home

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Osceola
Tvpm-1191mbbv Location
With a stay at this villa in Kissimmee (Bellavida), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This villa is 8.5 mi (13.6 km) from Disney Springs™ and 8.9 mi (14.3 km) from Walt Disney World® Resort.

Tvpm-1191mbbv Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and barbecue grills.

Tvpm-1191mbbv Rooms
Make yourself comfortable in this air-conditioned villa, featuring a kitchen with an oven and a stovetop. Cable television is provided for your entertainment. Conveniences include a microwave and a dryer.

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Energetic Escape With Games Room at Encore

Vacation Home

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Osceola
Energetic Escape With Games Room at Encore Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 10-minute drive of Mystic Dunes Golf Club and Reunion Resort Golf Course. This vacation home is 5.6 mi (9.1 km) from Walt Disney World® Resort and 7.9 mi (12.7 km) from ESPN Wide World of Sports Complex.

Energetic Escape With Games Room at Encore Facility and Service
Take advantage of recreation opportunities such as a hot tub, or other amenities including complimentary wireless internet access and an arcade/game room.

Energetic Escape With Games Room at Encore Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Others

Champions Gate Laughter Is Timeless 751

Private Vacation Home

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Osceola
Champions Gate Laughter Is Timeless 751 Location
When you 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 11.9 mi (19.2 km) from Old Town and 12.6 mi (20.3 km) from Walt Disney World® Resort.

Champions Gate Laughter Is Timeless 751 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.

Champions Gate Laughter Is Timeless 751 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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Bedroom

Luxury 2 Bd Close to Disney @ Champions Gate 1071

Private Vacation Home

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Osceola
Luxury 2 Bd Close to Disney @ Champions Gate 1071 Location
Located in Four Corners, this vacation home is within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This family-friendly 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.

Luxury 2 Bd Close to Disney @ Champions Gate 1071 Facility and Service
Enjoy a range of recreational amenities, including a complimentary water park, an outdoor pool, and a lazy river. Additional features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Luxury 2 Bd Close to Disney @ Champions Gate 1071 Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a full-sized refrigerator/freezer and an oven. Wired and wireless internet access is complimentary, while a 60-inch Smart television with cable programming provides entertainment. Conveniences include a safe and a desk, and you can also request a rollaway/extra bed (surcharge).

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3.4/5
Fully Booked
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Others

Grhmvd1595 - Champions Gate Resort - 4 Bed 3 Baths Townhouse

Vacation Home

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Osceola
Grhmvd1595 - 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 12.3 mi (19.8 km) from ESPN Wide World of Sports Complex.

Grhmvd1595 - 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.

Grhmvd1595 - 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.

See details
Fully Booked
Let's check on other dates!
Others

Windsor At Westside-2018emdil 4 Bedroom Home by RedAwning

Vacation Home

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Osceola
Windsor At Westside-2018emdil 4 Bedroom Home by RedAwning 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 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®.

Windsor At Westside-2018emdil 4 Bedroom Home by RedAwning 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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Others

1128 Challenge dr

Private Vacation Home

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Osceola
1128 Challenge dr Location
When you stay at this vacation home in Four Corners, you'll be near the beach, within a 15-minute drive of Reunion Resort Golf Course and Mystic Dunes Golf Club. This vacation home is 11.9 mi (19.1 km) from Old Town and 13.2 mi (21.3 km) from Walt Disney World® Resort.

1128 Challenge dr Facility and Service
Don't miss out on the many recreational opportunities, including an outdoor pool, an indoor pool, and a fitness center. This vacation home also features complimentary wireless internet access and an arcade/game room.

1128 Challenge dr 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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Bedroom

Greenway Villa

Private Vacation Home

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Osceola
Greenway Villa Location
With a stay at this vacation home in Four Corners, you'll be next to a golf course, within a 15-minute drive of Reunion Resort Golf Course and ChampionsGate Golf Club. This golf vacation home is 11.7 mi (18.9 km) from Old Town and 12.6 mi (20.3 km) from ESPN Wide World of Sports Complex.

Greenway Villa Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

Greenway Villa Rooms
Make yourself comfortable in this vacation home, which features a private pool. Complimentary wireless internet access is available to keep you connected.

See details
Fully Booked
Let's check on other dates!
Sport & Beauty

West Lucaya Resort

Private Vacation Home

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Osceola
West Lucaya Resort Location
When you stay at this vacation home in Kissimmee, you'll be in the entertainment district, within a 10-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center. This vacation home is 7.5 mi (12.1 km) from Disney's Animal Kingdom® Theme Park and 8.7 mi (14.1 km) from Old Town.

West Lucaya Resort Facility and Service
Don't miss out on recreational opportunities including a hot tub and a fitness center.

West Lucaya Resort Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a full-sized refrigerator/freezer and an oven. A flat-screen television with cable programming provides entertainment, while complimentary wireless internet access keeps you connected. Conveniences include a separate sitting area and a microwave.

See details
Fully Booked
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Sport & Beauty

Home With Lakeview Close to Disney w Pool

Vacation Home

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Osceola
Home With Lakeview Close to Disney w Pool 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 5.7 mi (9.1 km) from ESPN Wide World of Sports Complex and 6.1 mi (9.8 km) from Disney's Hollywood Studios®.

Home With Lakeview Close to Disney w Pool 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.

Home With Lakeview Close to Disney 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. Conveniences include a coffee/tea maker and a washing machine.

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Fully Booked
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Stunning 9 Bd Single Family w/ Pool @ Champions Gate 1508

Vacation Home

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Osceola
Stunning 9 Bd Single Family w/ Pool @ Champions Gate 1508 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 family-friendly vacation home is 11.8 mi (19 km) from ESPN Wide World of Sports Complex and 11.9 mi (19.1 km) from Walt Disney World® Resort.

Stunning 9 Bd Single Family w/ Pool @ Champions Gate 1508 Facility and Service
Take advantage of recreational opportunities offered, 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.

Stunning 9 Bd Single Family w/ Pool @ Champions Gate 1508 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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4.0/5
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Others

Oakwater by PRP

Vacation Home

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Osceola
Oakwater by PRP 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 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®.

Oakwater by PRP Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including an arcade/game room.

Oakwater by PRP Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private hot tub. There's a private balcony. A kitchen is outfitted with a refrigerator, a microwave, and a dishwasher. Satellite programming and a DVD player are provided for your entertainment, while complimentary wireless internet access keeps you connected.

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Amazing 4bdr House Near Disney

Vacation Home

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Osceola
Amazing 4bdr House Near Disney Location
With a stay at this villa in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center. This villa is 7.1 mi (11.5 km) from Disney's Animal Kingdom® Theme Park and 8.3 mi (13.4 km) from Old Town.

Amazing 4bdr House Near Disney 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 and an arcade/game room.

Amazing 4bdr House Near Disney Rooms
Make yourself comfortable in this villa, which features a private pool and a flat-screen TV. There's a private patio. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include a separate sitting area and a washer/dryer, and you can also request a crib/infant bed (complimentary).

See details
Fully Booked
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Vacation Homes in Osceola

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