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Vacation Homes in Osceola

Osceola
Mon, 16 Nov 2026 - Tue, 17 Nov 2026 (1 night)
1 Adult, 0 Children
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Showing 1.000+ Vacation Homes in Osceola
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

Grhcpr8950 - Paradise Palms Resort - 5 Bed 4 Baths Townhouse

Vacation Home

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Osceola
Grhcpr8950 - Paradise Palms Resort - 5 Bed 4 Baths Townhouse 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 (10.5 km) from Walt Disney World® Resort and 8.2 mi (13.1 km) from Disney's Animal Kingdom® Theme Park.

Grhcpr8950 - Paradise Palms Resort - 5 Bed 4 Baths Townhouse Facility and Service
Take advantage of recreational opportunities offered, including a complimentary water park, a hot tub, and an outdoor tennis court. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhcpr8950 - 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 programming and a video-game console are provided for your entertainment, while complimentary wireless internet access keeps you connected.

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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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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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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Others

5127 Crown Haven dr

Private Vacation Home

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Osceola
5127 Crown Haven dr Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, a 5-minute drive from Old Town and 10 minutes from Walt Disney World® Resort. This vacation home is 5.3 mi (8.5 km) from Disney Springs™ and 6 mi (9.7 km) from Disney's Hollywood Studios®.

5127 Crown Haven dr 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.

5127 Crown Haven dr Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a refrigerator and an oven. Conveniences include a microwave and a coffee/tea maker.

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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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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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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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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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Others

Lucaya Village Resort - 4 Bed 3 Bath Townhouse

Vacation Home

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Osceola
Lucaya Village Resort - 4 Bed 3 Bath Townhouse offers top-notch services and amenities, ensuring guests experience utmost comfort.Visitors can take advantage of the accessible parking options directly at the private villa. The private villa maintains a completely smoke-free zone, providing a breathable atmosphere. Each accommodation at Lucaya Village Resort - 4 Bed 3 Bath Townhouse is thoughtfully created and adorned to provide visitors with a comfortable, home-like atmosphere.In select rooms, guests can enjoy a touch of amusement with the availability of cable TV for their entertainment. Understanding the significance of bathroom amenities in enhancing guest contentment, the private villa offers a hair dryer within certain chosen rooms.
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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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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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Primary image

Sunlit Fun Lanai w/ Pool

Vacation Home

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Osceola
Sunlit Fun Lanai w/ Pool 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 7.4 mi (11.8 km) from ESPN Wide World of Sports Complex and 7.6 mi (12.2 km) from Old Town.

Sunlit Fun Lanai w/ Pool Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including gas grills.

Sunlit Fun Lanai w/ Pool Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool. Conveniences include a separate sitting area and a washer/dryer.

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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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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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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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Others

630 Pebble Beach dr

Private Vacation Home

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Osceola
630 Pebble Beach dr Location
When you stay at this vacation home in Four Corners, you'll be near the beach and 7 minutes by car from Highland Reserve Golf Club. This vacation home is 12 mi (19.3 km) from Old Town and 12.6 mi (20.2 km) from Walt Disney World® Resort.

630 Pebble Beach dr Facility and Service
Enjoy recreational amenities such as an indoor pool and a fitness center.

630 Pebble Beach 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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Sport & Beauty

Storey Lake 10br Lakeview Home Pool/spa Game Room

Vacation Home

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Osceola
Storey Lake 10br Lakeview Home Pool/spa Game Room 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 7.2 mi (11.7 km) from Disney Springs™ and 8.3 mi (13.4 km) from Walt Disney World® Resort.

Storey Lake 10br Lakeview Home Pool/spa Game Room Facility and Service
Make use of convenient amenities such as complimentary wireless internet access, an arcade/game room, and barbecue grills.

Storey Lake 10br Lakeview Home Pool/spa Game Room 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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Disney Getaway 3BR Lucaya Gated Resort Pool Gym

Private Vacation Home

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Osceola
Great care is taken to ensure guests experience comfort through top-notch services and amenities. When arriving by car, you'll be grateful for the on-site complimentary parking at country house. In order to ensure the utmost level of relaxation, the guestrooms feature an inviting design and are equipped with all basic necessities, creating a delightful stay experience.To ensure your satisfaction, certain rooms in the country house come fitted with linen service for a more pleasant stay.Several chosen accommodations at Disney Getaway 3BR Lucaya Gated Resort Pool Gym have a separate living room incorporated into the room design.In select rooms, visitors can enjoy a touch of amusement with the availability of television and cable TV for their entertainment needs.Rest assured, quenching your thirst is not a concern with a coffee or tea maker available in select accommodations. You'll be pleased to know that select guest bathrooms offer bathroom amenities such as a hair dryer, ensuring a comfortable stay. Throughout the day, engage in the entertaining activities available at Disney Getaway 3BR Lucaya Gated Resort Pool Gym. Guests who enjoy maintaining their fitness regimen while on holiday can visit the fitness center provided by country house.
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Vacation Homes in Osceola

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