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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
Exterior

Family Friendly 3Bd Close to Disney @Champions Gate 991

Vacation Home

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Osceola
Family Friendly 3Bd Close to Disney @Champions Gate 991 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 12.2 mi (19.6 km) from Old Town and 12.9 mi (20.8 km) from ESPN Wide World of Sports Complex.

Family Friendly 3Bd Close to Disney @Champions Gate 991 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.

Family Friendly 3Bd Close to Disney @Champions Gate 991 Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a full-sized refrigerator/freezer and an oven. A 60-inch Smart television with cable programming provides entertainment, while complimentary wired internet access keeps you connected. Conveniences include a safe and a desk, and you can also request a crib/infant bed (surcharge).

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Fantastic Townhouse in Lux community sleeps 8, 10' to Disney!!

Vacation Home

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Osceola
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Sport & Beauty

Sun Kissed Delight! Lovely Pool & Spa! 4 Bedroom Home by RedAwning

Vacation Home

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Osceola
Sun Kissed Delight! Lovely Pool & Spa! 4 Bedroom Home by RedAwning Location
With a stay at this vacation home in Kissimmee, you'll be a 2-minute drive from Mystic Dunes Golf Club and 8 minutes from Walt Disney World® Resort. This vacation home is 6.6 mi (10.6 km) from Old Town and 6.7 mi (10.8 km) from ESPN Wide World of Sports Complex.

Sun Kissed Delight! Lovely Pool & Spa! 4 Bedroom Home by RedAwning Facility and Service
Take advantage of recreation opportunities such as an outdoor pool, or other amenities including complimentary wireless internet access and barbecue grills.

Sun Kissed Delight! Lovely Pool & Spa! 4 Bedroom Home by RedAwning Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with an oven and a microwave. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include a coffee/tea maker and a washing machine.

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Others

Reunion 5 Bedroom Vacation Home 7824

Vacation Home

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Osceola
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Bellavida Resort Townhome - Private Plunge Pool, Minutes to Disney, Dog-friendly

Vacation Home

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Osceola
Bellavida Resort Townhome - Private Plunge Pool, Minutes to Disney, Dog-friendly 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 8.5 mi (13.6 km) from Disney Springs™ and 8.9 mi (14.4 km) from Walt Disney World® Resort.

Bellavida Resort Townhome - Private Plunge Pool, Minutes to Disney, Dog-friendly Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center. This vacation home also features complimentary wireless internet access and an arcade/game room.

Bellavida Resort Townhome - Private Plunge Pool, Minutes to Disney, Dog-friendly Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Exterior & Views

Great and practical townhouse in gated community, sleeps 6 10 min to Disney!

Vacation Home

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Osceola
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Exterior

1077 Champions Gate

Vacation Home

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Osceola
1077 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 12.1 mi (19.5 km) from Old Town and 12.9 mi (20.7 km) from ESPN Wide World of Sports Complex.

1077 Champions Gate Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

1077 Champions Gate Rooms
Make yourself comfortable in this vacation home, which features a private pool. Wireless internet access (surcharge) is available to keep you connected.

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Bright Luxe At Championsgate

Vacation Home

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Osceola
Bright Luxe At Championsgate 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 golf vacation home is 11.4 mi (18.3 km) from Old Town and 12.2 mi (19.6 km) from ESPN Wide World of Sports Complex.

Bright Luxe At Championsgate 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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Bedroom

Upstay24-PPLHomeThemeRoomsPoolSpaCinema

Vacation Home

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Osceola
Upstay24-PPLHomeThemeRoomsPoolSpaCinema 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 7.3 mi (11.8 km) from Disney Springs™ and 8 mi (12.9 km) from Walt Disney World® Resort.

Upstay24-PPLHomeThemeRoomsPoolSpaCinema Facility and Service
Enjoy recreational amenities such as an outdoor pool and an indoor pool.

Upstay24-PPLHomeThemeRoomsPoolSpaCinema Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected. Conveniences include a washer/dryer and an iron/ironing board.

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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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Cw7740 Windsor Hills Resort Vacation Home

Vacation Home

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Osceola
Cw7740 Windsor Hills Resort Vacation Home Location
With a stay at this cottage in Kissimmee (Windsor Hills), you'll be a 4-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort. This cottage is 5.6 mi (9 km) from ESPN Wide World of Sports Complex and 5.9 mi (9.4 km) from Old Town.

Cw7740 Windsor Hills Resort Vacation Home Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Cw7740 Windsor Hills Resort Vacation Home Rooms
Make yourself comfortable in this air-conditioned cottage, which has a kitchen. Cable television is provided for your entertainment. Conveniences include a coffee/tea maker and a dryer.

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Room

Le Reve 4 Bedroom Vacation Home 4404

Vacation Home

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Osceola
Le Reve 4 Bedroom Vacation Home 4404 Location
With a stay at Le Reve 4 Bedroom Vacation Home 4404 in Kissimmee, you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This hotel is 8.1 mi (13.1 km) from Disney Springs™ and 9 mi (14.5 km) from ESPN Wide World of Sports Complex.

Le Reve 4 Bedroom Vacation Home 4404 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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Family Home W/shared Pool,wifi,ac,lake Views - Close to Walt Disney World Resort

Vacation Home

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Osceola
Family Home W/shared Pool,wifi,ac,lake Views - Close to Walt Disney World Resort 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 4.8 mi (7.7 km) from ESPN Wide World of Sports Complex and 5.5 mi (8.8 km) from Disney's Hollywood Studios®.

Family Home W/shared Pool,wifi,ac,lake Views - Close to Walt Disney World Resort Facility and Service
Be sure to enjoy recreational amenities including an outdoor tennis court and a fitness center. This vacation home also features complimentary wireless internet access and an arcade/game room.

Family Home W/shared Pool,wifi,ac,lake Views - Close to Walt Disney World Resort Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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View from room

Private Pool! 8 Min to Disney!

Vacation Home

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Osceola
Private Pool! 8 Min to Disney! Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, a 5-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This golf vacation home is 5.3 mi (8.5 km) from Disney Springs™ and 6.3 mi (10.1 km) from Walt Disney World® Resort.

Private Pool! 8 Min to Disney! 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.

Private Pool! 8 Min to Disney! Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Lobby

Serene 3BR Encantada Retreat With Private Pool Near Disney

Vacation Home

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Osceola
Serene 3BR Encantada Retreat With Private Pool Near Disney Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 15-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 7 mi (11.2 km) from Disney's Animal Kingdom® Theme Park and 8.2 mi (13.2 km) from ESPN Wide World of Sports Complex.

Serene 3BR Encantada Retreat With Private Pool Near Disney Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Serene 3BR Encantada Retreat With Private Pool Near Disney Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Others

Enjoy Orlando With Us - Reunion Resort - Feature Packed Spacious 3 Beds 2 Baths Townhome - 6 Miles To Disney

Vacation Home

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Osceola
Enjoy Orlando With Us - Reunion Resort - Feature Packed Spacious 3 Beds 2 Baths Townhome - 6 Miles To Disney Location
Located in Kissimmee (Reunion), this vacation home is within a 10-minute drive of Reunion Resort Golf Course and Mystic Dunes Golf Club. This family-friendly vacation home is 6 mi (9.7 km) from Walt Disney World® Resort and 8.1 mi (13 km) from ESPN Wide World of Sports Complex.

Enjoy Orlando With Us - Reunion Resort - Feature Packed Spacious 3 Beds 2 Baths Townhome - 6 Miles To Disney Facility and Service
Dip into one of the 8 outdoor pools or enjoy other recreational amenities including a complimentary water park and outdoor tennis courts. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Enjoy Orlando With Us - Reunion Resort - Feature Packed Spacious 3 Beds 2 Baths Townhome - 6 Miles To Disney 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. A flat-screen television with cable programming is available for your entertainment, and a video-game console is also provided. 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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Others

Villa Victória - Encantada Resort

Vacation Home

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Osceola
Villa Victória - Encantada Resort 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 7.2 mi (11.6 km) from Disney's Animal Kingdom® Theme Park and 7.4 mi (11.8 km) from ESPN Wide World of Sports Complex.

Villa Victória - Encantada Resort Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including complimentary wireless internet access.

Villa Victória - Encantada Resort Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with an oven and a stovetop. Complimentary wireless internet access is available to keep you connected. Conveniences include a dryer and an iron/ironing board, and housekeeping is provided once per stay.

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Windsor Palms Resort 4 Bedroom Pool Home + Game Room 4 Home

Vacation Home

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Osceola
Windsor Palms Resort 4 Bedroom Pool Home + Game Room 4 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 mi (11.3 km) from ESPN Wide World of Sports Complex and 7.1 mi (11.5 km) from Old Town.

Windsor Palms Resort 4 Bedroom Pool Home + Game Room 4 Home Rooms
Make yourself comfortable in your vacation home, featuring a refrigerator and a Smart TV. Complimentary wireless internet access is available to keep you connected. The bathroom has a bathtub or shower.Conveniences include a coffee/tea maker and a washing machine.

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The Art House Home for 8

Vacation Home

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Osceola
The Art House Home for 8 Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, a 4-minute drive from Mystic Dunes Golf Club and 9 minutes from Walt Disney World® Resort. This golf vacation home is 6.4 mi (10.3 km) from ESPN Wide World of Sports Complex and 6.7 mi (10.7 km) from Old Town.

The Art House Home for 8 Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including gas grills.

The Art House Home for 8 Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool. Conveniences include a desk and a separate sitting area.

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Sport & Beauty

1575mvd-the Retreat at Championsgate

Vacation Home

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Osceola
1575mvd-the Retreat at Championsgate 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 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.

1575mvd-the Retreat at Championsgate Facility and Service
Be sure to enjoy recreational amenities, including an outdoor pool, an outdoor tennis court, and a fitness center.

1575mvd-the Retreat at Championsgate Rooms
Make yourself comfortable in your vacation home.

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Vacation Homes in Osceola

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