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Vacation Homes in Osceola

Osceola
Sat, 14 Nov 2026 - Sun, 15 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 1.000+ Vacation Homes in Osceola
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Windsor At Westside-2112amwjil 7 Bedroom Home by RedAwning

Vacation Home

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Osceola
Windsor At Westside-2112amwjil 7 Bedroom Home by RedAwning 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.

Windsor At Westside-2112amwjil 7 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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Charming Resort House w/ Private Pool & Fast Wifi

Vacation Home

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Osceola
Charming Resort House w/ Private Pool & Fast Wifi 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 vacation home is 6.7 mi (10.8 km) from Walt Disney World® Resort and 8.2 mi (13.2 km) from Old Town.

Charming Resort House w/ Private Pool & Fast Wifi Facility and Service
Enjoy a range of recreational amenities, including an outdoor pool, an outdoor tennis court, and a fitness center.

Charming Resort House w/ Private Pool & Fast Wifi Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Sport & Beauty

Grhcat8980 - Paradise Palms Resort - 5 Bed 4 Baths Townhouse

Vacation Home

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Osceola
Grhcat8980 - Paradise Palms Resort - 5 Bed 4 Baths Townhouse 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 8.2 mi (13.2 km) from Disney's Animal Kingdom® Theme Park and 9.1 mi (14.6 km) from ESPN Wide World of Sports Complex.

Grhcat8980 - Paradise Palms Resort - 5 Bed 4 Baths Townhouse Facility and Service
Dip into one of the 2 hot tubs or enjoy other recreational amenities including a complimentary water park and an outdoor tennis court. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Grhcat8980 - 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 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. Quench your thirst with your favorite drink at the poolside bar.

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Others

Ov2811 - Windsor Hills Resort - 3 Bed 3 Baths Townhome

Vacation Home

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Osceola
Ov2811 - Windsor Hills Resort - 3 Bed 3 Baths Townhome Location
Located in Kissimmee (Windsor Hills), this vacation home is within a 10-minute drive of Walt Disney World® Resort and Old Town. This family-friendly vacation home is 5.6 mi (9 km) from ESPN Wide World of Sports Complex and 6 mi (9.7 km) from Disney's Hollywood Studios®.

Ov2811 - Windsor Hills Resort - 3 Bed 3 Baths Townhome Facility and Service
While the golfer in the family is out on the course, try one of the other recreational amenities offered, such as a complimentary water park or a hot tub. Additional features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Ov2811 - Windsor Hills Resort - 3 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
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

1577sw - The Retreat At Championsgate 5 Bedroom Home by RedAwning

Vacation Home

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Osceola
1577sw - The Retreat At Championsgate 5 Bedroom Home by RedAwning 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 vacation home is 11.4 mi (18.4 km) from Old Town and 12.2 mi (19.6 km) from ESPN Wide World of Sports Complex.

1577sw - The Retreat At Championsgate 5 Bedroom Home by RedAwning Rooms
Make yourself comfortable in your vacation home, which features a refrigerator. 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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Beautiful Sun-inspired Home in Champions Gate Community With Resort Amenities

Vacation Home

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Osceola
Beautiful Sun-inspired Home in Champions Gate Community With Resort Amenities Location
When you stay at this vacation home in Four Corners, you'll be near the beach, within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This 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.

Beautiful Sun-inspired Home in Champions Gate Community With Resort Amenities Facility and Service
Don't miss out on recreational opportunities including an outdoor tennis court and a fitness center. Additional amenities at this vacation home include complimentary wireless internet access and an arcade/game room.

Beautiful Sun-inspired Home in Champions Gate Community With Resort Amenities Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Exterior & Views

Tropical Serenity at Margaritaville

Private Vacation Home

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Osceola
Tropical Serenity at Margaritaville Location
When you stay at this vacation home in Kissimmee, you'll be in a shopping district, within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This vacation home is 6.7 mi (10.8 km) from Old Town and 7.1 mi (11.4 km) from Disney's Hollywood Studios®.

Tropical Serenity at Margaritaville 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. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. Conveniences include a microwave and a coffee/tea maker.

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4.0/5
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Bedroom

Upstay 19 Resort Home Pool HotTub Disney

Vacation Home

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Osceola
Upstay 19 Resort Home Pool HotTub Disney 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 mi (11.3 km) from Disney Springs™ and 7.7 mi (12.4 km) from Walt Disney World® Resort.

Upstay 19 Resort Home Pool HotTub Disney Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and an indoor pool.

Upstay 19 Resort Home Pool HotTub Disney 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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Windsor Westside Resort 6 Bedroom Private Pool Home 6 Home

Vacation Home

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Osceola
Windsor Westside Resort 6 Bedroom Private Pool Home 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 10.1 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.

Windsor Westside Resort 6 Bedroom Private Pool Home 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

Cumbrian Retreat

Vacation Home

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Osceola
Cumbrian Retreat Location
With a stay at this vacation home in Kissimmee (Cumbrian Lakes), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 10.3 mi (16.5 km) from Disney Springs™ and 10.5 mi (16.8 km) from ESPN Wide World of Sports Complex.

Cumbrian Retreat 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.

Cumbrian Retreat 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 lanai. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Digital television is provided for your entertainment.

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Lovely Home With a Private Pool, Grill, Washer/dryer, & AC - Snowbird Friendly

Vacation Home

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Osceola
Lovely Home With a Private Pool, Grill, Washer/dryer, & AC - Snowbird Friendly Location
With a stay at this vacation home in Kissimmee (Lindfields), you'll be within a 10-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center. This vacation home is 7.3 mi (11.8 km) from Disney's Animal Kingdom® Theme Park and 8.4 mi (13.5 km) from Old Town.

Lovely Home With a Private Pool, Grill, Washer/dryer, & AC - Snowbird Friendly Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Lovely Home With a Private Pool, Grill, Washer/dryer, & AC - Snowbird Friendly Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Sport & Beauty

9039dld00

Vacation Home

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Osceola
9039dld00 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 (19.7 km) from ESPN Wide World of Sports Complex.

9039dld00 Facility and Service
Take advantage of recreational opportunities offered, including an outdoor pool, a hot tub, and a fitness center. Additional features at this vacation home include complimentary wireless internet access and an arcade/game room.

9039dld00 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 an LED television is provided for your entertainment.

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Simba's Lake House

Vacation Home

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Osceola
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Exterior & Views

4829lullaby 4 Bedroom Townhouse

Vacation Home

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Osceola
4829lullaby 4 Bedroom Townhouse 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 6.2 mi (10 km) from Walt Disney World® Resort.

4829lullaby 4 Bedroom Townhouse Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Bedroom

4200 Paragraph Drive

Vacation Home

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Osceola
4200 Paragraph Drive 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 family-friendly vacation home is 7.5 mi (12 km) from Disney Springs™ and 8.6 mi (13.8 km) from Walt Disney World® Resort.

4200 Paragraph Drive Facility and Service
Be sure to enjoy recreational amenities, including an outdoor pool, a lazy river, and a waterslide. Additional features at this vacation home include complimentary wireless internet access and barbecue grills.

4200 Paragraph Drive Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. Cable television is provided for your entertainment. Conveniences include a microwave and a dryer.

Restaurant and Cafe
At this vacation home, enjoy a satisfying meal at the restaurant.

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3.0/5
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Room

Bright Modern Home @storey Lake

Vacation Home

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Osceola
Bright Modern Home @storey Lake Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 7.4 mi (12 km) from Disney Springs™ and 8.4 mi (13.6 km) from Walt Disney World® Resort.

Bright Modern Home @storey Lake Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center. Additional amenities at this vacation home include an arcade/game room and barbecue grills.

Bright Modern Home @storey Lake Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Elegant Townhouse With Pool Views at Reunion

Vacation Home

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Osceola
Elegant Townhouse With Pool Views at Reunion Location
Located in Kissimmee (Reunion), this vacation home is within a 10-minute drive of Mystic Dunes Golf Club and ChampionsGate Golf Club. This vacation home is 6.7 mi (10.8 km) from Walt Disney World® Resort and 8.7 mi (14 km) from Old Town.

Elegant Townhouse With Pool Views at Reunion Facility and Service
Make use of convenient amenities, which include an arcade/game room and barbecue grills.

Elegant Townhouse With Pool Views at Reunion Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Room

Gated-entry Townhome, With Shared Pool, Central AC, Near Theme Parks

Vacation Home

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Osceola
Gated-entry Townhome, With Shared Pool, Central AC, Near Theme Parks Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 7.1 mi (11.4 km) from Disney Springs™ and 8.1 mi (13 km) from ESPN Wide World of Sports Complex.

Gated-entry Townhome, With Shared Pool, Central AC, Near Theme Parks Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Gated-entry Townhome, With Shared Pool, Central AC, Near Theme Parks Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Windsor Palms Resort 3 Bedroom Pool Townhome 3 Townhouse

Vacation Home

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Osceola
Windsor Palms Resort 3 Bedroom Pool Townhome 3 Townhouse 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 7.1 mi (11.4 km) from ESPN Wide World of Sports Complex and 7.3 mi (11.8 km) from Old Town.

Windsor Palms Resort 3 Bedroom Pool Townhome 3 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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Tropical Retreat With Screened in Private Pool and Spa at Reunion

Vacation Home

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Osceola
Tropical Retreat With Screened in Private Pool and Spa at Reunion Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be a 3-minute drive from Reunion Resort Golf Course and 6 minutes from ChampionsGate Golf Club. This golf vacation home is 8.2 mi (13.2 km) from Walt Disney World® Resort and 9.9 mi (15.9 km) from Old Town.

Tropical Retreat With Screened in Private Pool and Spa at Reunion Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Tropical Retreat With Screened in Private Pool and Spa at Reunion Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

See details
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Vacation Homes in Osceola

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