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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
Others

1542mvd-the Retreat at Champions Gate

Vacation Home

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Osceola
1542mvd-the Retreat at Champions Gate 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 11.6 mi (18.7 km) from Old Town and 12.4 mi (19.9 km) from ESPN Wide World of Sports Complex.

1542mvd-the Retreat at Champions Gate Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

1542mvd-the Retreat at Champions Gate Rooms
Make yourself comfortable in this vacation home, which has a kitchen.

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Exterior & Views

Lucaya Vacation Homes

Vacation Home

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Osceola
Lucaya Vacation Homes Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Disney Springs™ and Orange County Convention Center. This vacation home is 8.1 mi (13 km) from Epcot® and 10.1 mi (16.3 km) from Magic Kingdom® Park.

Lucaya Vacation Homes Facility and Service
Enjoy recreational amenities such as a hot tub and a fitness center.

Lucaya Vacation Homes Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. A 40-inch Smart television with cable programming provides entertainment, while complimentary wireless internet access keeps you connected. Conveniences include a microwave and a coffee/tea maker.

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3.3/5
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Sport & Beauty

Ov4268 - Paradise Palms - 4 Bed 3 Baths Townhome

Vacation Home

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Osceola
Ov4268 - Paradise Palms - 4 Bed 3 Baths Townhome 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 family-friendly vacation home is 6.5 mi (10.4 km) from Walt Disney World® Resort and 8.2 mi (13.1 km) from Disney's Animal Kingdom® Theme Park.

Ov4268 - Paradise Palms - 4 Bed 3 Baths Townhome Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools. Additional features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Ov4268 - Paradise Palms - 4 Bed 3 Baths Townhome Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private plunge pool. There's a private balcony or patio. A kitchen is outfitted with a refrigerator, an oven, and a microwave. Conveniences include a washer/dryer and a ceiling fan.

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

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Bedroom

American Dream 6 Bedroom Home by RedAwning

Vacation Home

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Osceola
American Dream 6 Bedroom Home by RedAwning Location
With a stay at this vacation home in Kissimmee (Bellavida), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 9.1 mi (14.6 km) from Disney Springs™ and 9.5 mi (15.3 km) from Walt Disney World® Resort.

American Dream 6 Bedroom Home by RedAwning Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Escape Villa

Vacation Home

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Osceola
Escape Villa Location
Located in Kissimmee (Windsor Hills), this vacation home is within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This golf vacation home is 5.8 mi (9.4 km) from ESPN Wide World of Sports Complex and 6.1 mi (9.8 km) from Old Town.

Escape Villa Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center. Additional amenities at this vacation home include complimentary wireless internet access, an arcade/game room, and barbecue grills. Getting to nearby attractions is a breeze with the complimentary area shuttle.

Escape Villa Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a private hot tub. There's a private patio. A kitchen is outfitted with a dishwasher. An LCD television with cable programming is available for your entertainment, and a DVD player is also provided.

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

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Others

1664 Moon Valley dr

Private Vacation Home

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Osceola
1664 Moon Valley dr 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 Reunion Resort Golf Course and Mystic Dunes Golf Club. This golf vacation home is 11.3 mi (18.3 km) from Old Town and 12.3 mi (19.9 km) from Walt Disney World® Resort.

1664 Moon Valley dr Facility and Service
Take advantage of recreation opportunities including an indoor pool and a fitness center. Additional features at this vacation home include complimentary wireless internet access and an arcade/game room.

1664 Moon Valley dr Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower and designer toiletries.

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Lucaya 3 Bedroom 2 Bath Townhome!

Vacation Home

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Osceola
Lucaya 3 Bedroom 2 Bath Townhome! Location
With a stay at this vacation home in Kissimmee, you'll be a 3-minute drive from Old Town and 9 minutes from Orlando Vineland Premium Outlets. This vacation home is 5.5 mi (8.8 km) from Walt Disney World® Resort and 5.5 mi (8.9 km) from ESPN Wide World of Sports Complex.

Lucaya 3 Bedroom 2 Bath Townhome! Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including an arcade/game room.

Lucaya 3 Bedroom 2 Bath Townhome! Rooms
Make yourself comfortable in your vacation home.

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Others

Gatsby Storey by Orlando Short Term

Private Vacation Home

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Osceola
Gatsby Storey by Orlando Short Term Location
With a stay at this vacation home in Kissimmee, you'll be a 5-minute drive from Old Town and 10 minutes from Disney Springs™. This vacation home is 6.4 mi (10.3 km) from Walt Disney World�� Resort and 6.5 mi (10.5 km) from Disney's Hollywood Studios®.

Gatsby Storey by Orlando Short Term Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

Gatsby Storey by Orlando Short Term Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include a phone, as well as a coffee/tea maker and an iron/ironing board.

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Others

Celebrate at Club Cortile

Private Vacation Home

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Osceola
Celebrate at Club Cortile Location
When you stay at this vacation home in Kissimmee, you'll be in a shopping district, within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 6.4 mi (10.4 km) from Disney Springs™ and 7.5 mi (12 km) from Walt Disney World® Resort.

Celebrate at Club Cortile Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center.

Celebrate at Club Cortile Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. There's a private balcony or patio. Cable television is provided for your entertainment. Conveniences include a microwave and a coffee/tea maker.

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3.0/5
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Bedroom

2633 Trafalgar Village

Vacation Home

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Osceola
2633 Trafalgar Village Location
With a stay at this vacation home in Kissimmee (Trafalgar Village), you'll be within a 10-minute drive of Green Meadows Petting Farm and Shingle Creek Regional Park. This vacation home is 11 mi (17.7 km) from Old Town and 13.2 mi (21.2 km) from Orlando Vineland Premium Outlets.

2633 Trafalgar Village Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center.

2633 Trafalgar Village Rooms
Make yourself comfortable in this vacation home, which features a private hot tub and a Smart TV. There's a private patio. A kitchen is outfitted with a refrigerator. Complimentary wireless internet access is available to keep you connected.

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Bedroom

3236 TT Hub Townhome: 3br, 3ba, Sleeps 8

Vacation Home

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Osceola
3236 TT Hub Townhome: 3br, 3ba, Sleeps 8 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®.

3236 TT Hub Townhome: 3br, 3ba, Sleeps 8 Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including an arcade/game room.

3236 TT Hub Townhome: 3br, 3ba, Sleeps 8 Rooms
Make yourself comfortable in your vacation home.

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Sport & Beauty

Villa Leite

Vacation Home

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Osceola
Villa Leite Location
With a stay at this vacation home in Kissimmee, you'll be a 3-minute drive from Old Town and 9 minutes from Orlando Vineland Premium Outlets. This vacation home is 5.6 mi (9 km) from Walt Disney World® Resort and 5.6 mi (9 km) from ESPN Wide World of Sports Complex.

Villa Leite Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with an oven and a stovetop. Complimentary wireless internet access is available to keep you connected. Housekeeping is provided once per stay, and a rollaway/extra bed can be requested.

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Paradise Palms Resort 6 Bedroom Home with Game Room 6 Home

Vacation Home

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Osceola
Paradise Palms 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 Old Town. This vacation home is 8.6 mi (13.9 km) from Disney's Animal Kingdom® Theme Park and 9.3 mi (15 km) from ESPN Wide World of Sports Complex.

Paradise Palms 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 is available to keep you connected. Conveniences include a coffee/tea maker and a washing machine.

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Sport & Beauty

Oasis at Acadia Estates

Private Vacation Home

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Osceola
Oasis at Acadia Estates 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 Disney's Hollywood Studios®. This golf vacation home is 7.8 mi (12.5 km) from Disney's Animal Kingdom® Theme Park and 8.5 mi (13.6 km) from Disney Springs™.

Oasis at Acadia Estates Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with a refrigerator and an oven. There's a private balcony or patio. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include a microwave and a coffee/tea maker.

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Frozen Castle & Space Bunks/12br/resort Access!

Vacation Home

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Osceola
Frozen Castle & Space Bunks/12br/resort Access! Location
With a stay at this cottage in Kissimmee, you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This cottage is 7.2 mi (11.6 km) from Disney Springs™ and 8.2 mi (13.2 km) from Walt Disney World® Resort.

Frozen Castle & Space Bunks/12br/resort Access! Facility and Service
This smoke-free cottage offers complimentary parking nearby.

Frozen Castle & Space Bunks/12br/resort Access! Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with an oven and a stovetop. Cable television is provided for your entertainment. Conveniences include a microwave and a dryer, and you can also request a crib/infant bed (complimentary).

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Exterior & Views

Formosa Gardens

Vacation Home

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Osceola
Formosa Gardens Location
With a stay at this vacation home in Kissimmee, you'll be a 3-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort. This vacation home is 5.9 mi (9.5 km) from ESPN Wide World of Sports Complex and 6 mi (9.7 km) from Old Town.

Formosa Gardens 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 patio. A kitchen is outfitted with a full-sized refrigerator/freezer, an oven, and a stovetop. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. A private bathroom has a deep soaking tub and a hair dryer.

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1410 Wexford Way

Vacation Home

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Osceola
1410 Wexford Way Location
With a stay at this vacation home in Four Corners, you'll be within a 15-minute drive of Mystic Dunes Golf Club and ChampionsGate Golf Club. This family-friendly vacation home is 11.5 mi (18.6 km) from Old Town and 12.4 mi (20 km) from ESPN Wide World of Sports Complex.

1410 Wexford Way Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center.

1410 Wexford Way Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and a stovetop. There's a private balcony or patio. A flat-screen television and a video-game console are provided for your entertainment, while complimentary wireless internet access keeps you connected. Conveniences include a microwave and a coffee/tea maker.

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Room

Kis105-2601-4-pg - Shingle Creek Poolside Retreat

Vacation Home

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Osceola
Kis105-2601-4-pg - Shingle Creek Poolside Retreat Location
With a stay at this vacation home in Kissimmee, you'll be near the beach, just steps from Shingle Creek Regional Park and a 5-minute drive from Kissimmee Sports Arena and Rodeo. This vacation home is 10.2 mi (16.4 km) from Old Town and 11.6 mi (18.7 km) from Orlando Vineland Premium Outlets.

Kis105-2601-4-pg - Shingle Creek Poolside Retreat Facility and Service
Enjoy recreational amenities such as an outdoor pool and a sauna.

Kis105-2601-4-pg - Shingle Creek Poolside Retreat Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Sport & Beauty

Indian Ridge - 4 Bedroom Pool Home- 2408IR 4 Home by RedAwning

Vacation Home

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Osceola
Indian Ridge - 4 Bedroom Pool Home- 2408IR 4 Home by RedAwning Location
With a stay at this vacation home in Kissimmee, you'll be a 5-minute drive from Mystic Dunes Golf Club and 10 minutes from Walt Disney World® Resort. This vacation home is 7.4 mi (11.9 km) from ESPN Wide World of Sports Complex and 7.7 mi (12.3 km) from Old Town.

Indian Ridge - 4 Bedroom Pool Home- 2408IR 4 Home by RedAwning Facility and Service
Enjoy the recreation opportunities such as an outdoor tennis court or make use of other amenities including barbecue grills.

Indian Ridge - 4 Bedroom Pool Home- 2408IR 4 Home by RedAwning 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

8907 Champions Gate

Vacation Home

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Osceola
8907 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 11.5 mi (18.5 km) from Old Town and 12.3 mi (19.8 km) from ESPN Wide World of Sports Complex.

8907 Champions Gate Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

8907 Champions Gate Rooms
Make yourself comfortable in this vacation home, which features a private pool and a Smart TV. Wireless internet access (surcharge) is available to keep you connected.

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Vacation Homes in Osceola

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