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Vacation Homes in Osceola

Osceola
Sun, 15 Nov 2026 - Mon, 16 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 1.000+ Vacation Homes in Osceola
Others

Fv53300 - Paradise Palms - 4 Bed 3 Baths Townhome

Vacation Home

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Osceola
Fv53300 - Paradise Palms - 4 Bed 3 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 8.2 mi (13.3 km) from Disney's Animal Kingdom® Theme Park and 9.1 mi (14.7 km) from ESPN Wide World of Sports Complex.

Fv53300 - Paradise Palms - 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 features at this vacation home include complimentary wireless internet access, concierge services, and an arcade/game room.

Fv53300 - Paradise Palms - 4 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 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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Bedroom

Grhcdw9161 - Champions Gate Resort - 6 Bed 6 Baths House

Vacation Home

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Osceola
Grhcdw9161 - Champions Gate Resort - 6 Bed 6 Baths House 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 family-friendly vacation home is 12.7 mi (20.5 km) from Old Town and 13.3 mi (21.4 km) from Walt Disney World® Resort.

Grhcdw9161 - Champions Gate Resort - 6 Bed 6 Baths House Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools or 2 hot tubs. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhcdw9161 - Champions Gate Resort - 6 Bed 6 Baths House Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private plunge pool and a private hot tub. There's a private balcony or patio. A kitchen is outfitted with a refrigerator, an oven, and a microwave. A flat-screen 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. Relax with your favorite drink at the bar/lounge or the poolside bar.

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Bright and Sunny Townhouse With Games Room at Reunion

Vacation Home

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Osceola
Bright and Sunny Townhouse With Games Room 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.

Bright and Sunny Townhouse With Games Room at Reunion Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a hot tub. This vacation home also features complimentary wireless internet access and an arcade/game room.

Bright and Sunny Townhouse With Games Room at Reunion Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Pool

Windsor Westside 5 Bedroom Vacation Home 1820

Vacation Home

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Osceola
Windsor Westside 5 Bedroom Vacation Home 1820 Location
With a stay at Windsor Westside 5 Bedroom Vacation Home 1820 in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This hotel is 10.3 mi (16.5 km) from Disney's Animal Kingdom® Theme Park and 11.3 mi (18.2 km) from ESPN Wide World of Sports Complex.

Windsor Westside 5 Bedroom Vacation Home 1820 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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Comfortable 4 BDR House near Disney in Orlando

Vacation Home

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Osceola
Comfortable 4 BDR House near Disney in Orlando 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 Old Town. This vacation home is 5.3 mi (8.5 km) from ESPN Wide World of Sports Complex and 5.8 mi (9.3 km) from Disney's Hollywood Studios®.

Comfortable 4 BDR House near Disney in Orlando Facility and Service
Take in the views from a terrace and a garden and make use of amenities such as barbecue grills.

Comfortable 4 BDR House near Disney in Orlando Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a refrigerator and a microwave. There's a private balcony or patio. A 32-inch flat-screen television with cable programming provides entertainment, while complimentary wireless internet access keeps you connected. Conveniences include a safe and a desk.

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Exterior & Views

Ov1311 - Emerald Island - 4 Bed 3 Baths Townhome

Vacation Home

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Osceola
Ov1311 - Emerald Island - 4 Bed 3 Baths Townhome 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 family-friendly vacation home is 6.9 mi (11 km) from Old Town and 6.9 mi (11.1 km) from ESPN Wide World of Sports Complex.

Ov1311 - Emerald Island - 4 Bed 3 Baths Townhome Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools or 2 hot tubs. This vacation home also features complimentary wireless internet access, concierge services, and an arcade/game room.

Ov1311 - Emerald Island - 4 Bed 3 Baths Townhome Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private plunge pool and a private hot tub. There's a private balcony or patio. A kitchen is outfitted with a refrigerator, an oven, and a microwave. A flat-screen television is provided for your entertainment.

Restaurant and Cafe
Relax with your favorite drink at the bar/lounge or the poolside bar.

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Championsgate Resort 5 Bedroom Private Pool Home 5 Home

Vacation Home

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Osceola
Championsgate Resort 5 Bedroom Private Pool Home 5 Home 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 vacation home is 11.9 mi (19.1 km) from Old Town and 12.2 mi (19.6 km) from ESPN Wide World of Sports Complex.

Championsgate Resort 5 Bedroom Private Pool Home 5 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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Exterior & Views

Laguna Villas

Vacation Home

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Osceola
3.7/5
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Others

Grand Cumbrian - Four Bedroom Home

Vacation Home

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Osceola
Grand Cumbrian - Four Bedroom Home 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 10.2 mi (16.4 km) from Disney Springs™ and 10.3 mi (16.5 km) from ESPN Wide World of Sports Complex.

Grand Cumbrian - Four Bedroom Home Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including an arcade/game room.

Grand Cumbrian - Four Bedroom Home 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. Digital television is provided for your entertainment. Conveniences include a separate sitting area and a coffee/tea maker.

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Venetian Beauty

Vacation Home

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Osceola
Venetian Beauty Location
With a stay at this vacation home in Kissimmee (Venetian Bay Villages), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 9.4 mi (15.1 km) from Disney Springs™ and 10.4 mi (16.8 km) from Walt Disney World® Resort.

Venetian Beauty Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

Venetian Beauty 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 and a hair dryer. Conveniences include a phone and a dryer.

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Exterior & Views

Bella Vida Resort Townhouse w/ Pool & Fast Wifi

Vacation Home

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Osceola
Bella Vida Resort Townhouse w/ Pool & Fast Wifi 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 (13.7 km) from Disney Springs™ and 8.6 mi (13.9 km) from ESPN Wide World of Sports Complex.

Bella Vida Resort Townhouse w/ Pool & Fast Wifi Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center. Additional amenities at this vacation home include complimentary wireless internet access and barbecue grills.

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

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Art Deco Townhouse With Games Room at Reunion

Vacation Home

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Osceola
Art Deco Townhouse With Games Room at Reunion Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be within a 10-minute drive of Mystic Dunes Golf Club and ChampionsGate Golf Club. This golf vacation home is 6.7 mi (10.8 km) from Walt Disney World® Resort and 8.7 mi (14.1 km) from Old Town.

Art Deco Townhouse With Games Room at Reunion Facility and Service
Take in the views from a terrace and make use of amenities such as complimentary wireless internet access and an arcade/game room.

Art Deco Townhouse With Games Room at Reunion Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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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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Exterior & Views

Lucaya Village Resort - 3 Beds and 2 Baths. ID: 57417

Vacation Home

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Osceola
Lucaya Village Resort - 3 Beds and 2 Baths. ID: 57417 Location
With a stay at this vacation home in Kissimmee, you'll be a 3-minute drive from Old Town and 8 minutes from Orlando Vineland Premium Outlets. This vacation home is 5.3 mi (8.6 km) from Disney Springs™ and 5.5 mi (8.9 km) from Walt Disney World® Resort.

Lucaya Village Resort - 3 Beds and 2 Baths. ID: 57417 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.

Lucaya Village Resort - 3 Beds and 2 Baths. ID: 57417 Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with a refrigerator and a microwave. Conveniences include a washing machine and an iron/ironing board.

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Hollywood Retreat! Sleeps 14!

Vacation Home

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Osceola
Hollywood Retreat! Sleeps 14! 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 12.1 mi (19.5 km) from ESPN Wide World of Sports Complex.

Hollywood Retreat! Sleeps 14! Facility and Service
Take advantage of recreation opportunities such as an outdoor pool, or other amenities including complimentary wireless internet access and a picnic area.

Hollywood Retreat! Sleeps 14! 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 lanai. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Digital television is provided for your entertainment.

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1513fd - The Retreat at Championsgate

Vacation Home

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Osceola
1513fd - 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 11.2 mi (18 km) from Old Town and 12 mi (19.3 km) from ESPN Wide World of Sports Complex.

1513fd - The Retreat at Championsgate Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

1513fd - The Retreat at Championsgate Rooms
Make yourself comfortable in this vacation home, which has a kitchen.

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Sport & Beauty

Bella Vida 4570 IHR 1020

Vacation Home

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Osceola
Bella Vida 4570 IHR 1020 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 (13.7 km) from Disney Springs™ and 8.6 mi (13.9 km) from ESPN Wide World of Sports Complex.

Bella Vida 4570 IHR 1020 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 a picnic area.

Bella Vida 4570 IHR 1020 Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and a microwave. A flat-screen television along with a DVD player are provided for your entertainment.

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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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Ov3007 - Windsor Hills Resort - 3 Bed 3 Baths Townhome

Vacation Home

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Osceola
Ov3007 - 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®.

Ov3007 - Windsor Hills Resort - 3 Bed 3 Baths Townhome Facility and Service
Practice your swing on the golf course and enjoy other recreational amenities, such as a complimentary water park and a hot tub. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Ov3007 - 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. 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. Relax with your favorite drink at the bar/lounge or the poolside bar.

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Others

Storey Lake Escape by Orlando Short Term

Private Vacation Home

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Osceola
Storey Lake Escape by Orlando Short Term Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Old Town and Disney Springs™. This vacation home is 6.4 mi (10.4 km) from Walt Disney World® Resort and 6.6 mi (10.6 km) from Disney's Hollywood Studios®.

Storey Lake Escape by Orlando Short Term Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

Storey Lake Escape 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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Vacation Homes in Osceola

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