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Vacation Homes in Osceola

Osceola
Wed, 18 Nov 2026 - Thu, 19 Nov 2026 (1 night)
1 Adult, 0 Children
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Showing 2.000+ Vacation Homes in Osceola
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Ultimate 8BR Family Fun in Resort Near Disney!

Vacation Home

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Osceola
Ultimate 8BR Family Fun in Resort Near Disney! 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 mi (16.1 km) from ESPN Wide World of Sports Complex and 10.2 mi (16.4 km) from Disney's Animal Kingdom® Theme Park.

Ultimate 8BR Family Fun in Resort Near Disney! Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Ultimate 8BR Family Fun in Resort Near Disney! Rooms
Make yourself comfortable in your individually decorated vacation home. There's a private balcony or patio. The bathroom has a bathtub or shower and designer toiletries.

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Bedroom

Florida Breeze

Vacation Home

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Osceola
Florida Breeze 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 family-friendly vacation home is 8.7 mi (14 km) from Disney Springs™ and 9.1 mi (14.7 km) from Walt Disney World® Resort.

Florida Breeze Facility and Service
Take advantage of recreation opportunities including 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.

Florida Breeze Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and an outdoor private hot tub. A kitchen is outfitted with a full-sized refrigerator/freezer, an oven, and a stovetop. A 55-inch Smart television with digital programming provides entertainment, while complimentary wireless internet access keeps you connected. Conveniences include a microwave and a coffee/tea maker, as well as a phone with free local calls.

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Family-friendly Home w/ Pool Near Flowrider Surf Club

Vacation Home

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Osceola
Family-friendly Home w/ Pool Near Flowrider Surf Club Location
Located in Kissimmee, this vacation home is within a 15-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This vacation home is 8.6 mi (13.9 km) from Walt Disney World® Resort and 10.3 mi (16.6 km) from Disney's Animal Kingdom® Theme Park.

Family-friendly Home w/ Pool Near Flowrider Surf Club Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center. Additional features at this vacation home include complimentary wireless internet access and an arcade/game room.

Family-friendly Home w/ Pool Near Flowrider Surf Club Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Sport & Beauty

Ev216592 - Windsor At Westside Resort - 5 Bed 4 Baths Townhome

Vacation Home

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Osceola
Ev216592 - Windsor At Westside Resort - 5 Bed 4 Baths Townhome Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This family-friendly vacation home is 10.3 mi (16.6 km) from Disney's Animal Kingdom® Theme Park and 11.2 mi (18 km) from ESPN Wide World of Sports Complex.

Ev216592 - Windsor At Westside Resort - 5 Bed 4 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. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Ev216592 - Windsor At Westside Resort - 5 Bed 4 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. A kitchen is outfitted with a refrigerator, an oven, and a microwave. A flat-screen television is provided for your entertainment.

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

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Others

Championsgate Luxury Townhome Private Pool Game

Vacation Home

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Osceola
Championsgate Luxury Townhome Private Pool Game Location
With a stay at this vacation home in Four Corners, you'll be 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.

Championsgate Luxury Townhome Private Pool Game Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center.

Championsgate Luxury Townhome Private Pool Game Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower and designer toiletries.

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Mvy7632 - 4BR House Near Disney

Vacation Home

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Osceola
Mvy7632 - 4BR House Near Disney Location
With a stay at this cottage in Kissimmee, you'll be a 4-minute drive from Walt Disney World® Resort and 9 minutes from Old Town. This cottage is 4.8 mi (7.7 km) from ESPN Wide World of Sports Complex and 5.3 mi (8.5 km) from Disney's Hollywood Studios®.

Mvy7632 - 4BR House Near Disney Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and barbecue grills.

Mvy7632 - 4BR House Near Disney Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with an oven and a stovetop. Conveniences include a microwave and a dryer.

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Welcome to Your Family Luxurious Calabria Villa

Vacation Home

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Osceola
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Bedroom

Magic and Fun at Windsor

Vacation Home

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Osceola
Magic and Fun at Windsor 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 5.4 mi (8.7 km) from ESPN Wide World of Sports Complex and 5.9 mi (9.5 km) from Disney's Hollywood Studios®.

Magic and Fun at Windsor Facility and Service
Make use of convenient amenities such as babysitting (surcharge), an arcade/game room, and a picnic area.

Magic and Fun at Windsor Rooms
Make yourself comfortable in your individually decorated vacation home, featuring an espresso maker and a Smart TV. Your pillowtop bed comes with Egyptian cotton sheets. Complimentary wireless internet access is available to keep you connected. Conveniences include a coffee/tea maker and a washer/dryer.

Important Information
The following facilities are closed seasonally each year. They will be closed from December 1 to January 15:
  • Laundry facilities
  • Parking area
  • Swimming pool


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Room

New Welcoming Resort Home w/ Private Pool, Sleeps 20

Vacation Home

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Osceola
New Welcoming Resort Home w/ Private Pool, Sleeps 20 Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 15-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This vacation home is 8.5 mi (13.7 km) from Walt Disney World® Resort and 10.2 mi (16.3 km) from Disney's Animal Kingdom® Theme Park.

New Welcoming Resort Home w/ Private Pool, Sleeps 20 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.

New Welcoming Resort Home w/ Private Pool, Sleeps 20 Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Charming Townhouse w/ Pool Near Disney Parks!

Vacation Home

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Osceola
Charming Townhouse w/ Pool Near Disney Parks! 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 8.7 mi (14 km) from Disney Springs™ and 9 mi (14.4 km) from Walt Disney World® Resort.

Charming Townhouse w/ Pool Near Disney Parks! Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Charming Townhouse w/ Pool Near Disney Parks! Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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5BR Townhouse Near Disney Pool & Oasis Club

Vacation Home

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Osceola
5BR Townhouse Near Disney Pool & Oasis Club Location
With a stay at this villa in Four Corners (Champions Gate), you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This villa is 11.5 mi (18.6 km) from Old Town and 12.3 mi (19.8 km) from ESPN Wide World of Sports Complex.

5BR Townhouse Near Disney Pool & Oasis Club Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a hot tub. Additional features at this villa include complimentary wireless internet access, an arcade/game room, and barbecue grills.

5BR Townhouse Near Disney Pool & Oasis Club Rooms
Your villa features a Smart TV. There's a private furnished patio. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. The bathroom has a bathtub or shower and complimentary toiletries.

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Luxury Champions Gate Town Home townhouse

Vacation Home

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Osceola
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Bathroom

9BR Reunion Mansion Pool, Spa & Home Theater

Vacation Home

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Osceola
9BR Reunion Mansion Pool, Spa & Home Theater 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 vacation home is 7 mi (11.2 km) from Walt Disney World® Resort and 9 mi (14.4 km) from Old Town.

9BR Reunion Mansion Pool, Spa & Home Theater Facility and Service
Enjoy recreational amenities such as an outdoor pool and a hot tub. This vacation home also features complimentary wireless internet access and an arcade/game room.

9BR Reunion Mansion Pool, Spa & Home Theater Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Super Luxury Modern Home Prime Location

Vacation Home

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Osceola
Super Luxury Modern Home Prime Location 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 7.5 mi (12.1 km) from Disney Springs™ and 8.5 mi (13.7 km) from Walt Disney World® Resort.

Super Luxury Modern Home Prime Location Facility and Service
Take in the views from a garden and make use of amenities such as complimentary wireless internet access and barbecue grills.

Super Luxury Modern Home Prime Location Rooms
Make yourself comfortable in your vacation home.

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5BR Resort Home w/ Private Pool Near Disney

Vacation Home

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Osceola
5BR Resort Home w/ Private Pool Near Disney Location
With a stay at 5BR Resort Home w/ Private Pool Near Disney in Kissimmee, you'll be within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This ranch is 12.3 mi (19.9 km) from Old Town and 12.5 mi (20.1 km) from Walt Disney World® Resort.

5BR Resort Home w/ Private Pool Near Disney Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a hot tub. Additional amenities at this ranch include complimentary wireless internet access, an arcade/game room, and barbecue grills.

5BR Resort Home w/ Private Pool Near Disney Rooms
Stay in one of the guestrooms featuring Smart televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms have bathtubs or showers and complimentary toiletries. Conveniences include separate sitting areas and sofa beds, and you can also request cribs/infant beds (complimentary).

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Storey Lake Resort 5 Bedroom Townhome Pet Friendly 5 Townhouse

Vacation Home

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Osceola
Storey Lake Resort 5 Bedroom Townhome Pet Friendly 5 Townhouse 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 6.9 mi (11.1 km) from Disney Springs™ and 8 mi (12.8 km) from Walt Disney World® Resort.

Storey Lake Resort 5 Bedroom Townhome Pet Friendly 5 Townhouse 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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Championsgate Resort 4 Bedroom Private Pool Townhome 4 Townhouse

Vacation Home

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Osceola
Championsgate Resort 4 Bedroom Private Pool Townhome 4 Townhouse Location
With a stay at this vacation home in Four Corners, you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This vacation home is 11.9 mi (19.2 km) from Old Town and 12.7 mi (20.5 km) from ESPN Wide World of Sports Complex.

Championsgate Resort 4 Bedroom Private Pool Townhome 4 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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Exterior & Views

Family-friendly Paradise Palms Townhouse With Pool Access

Vacation Home

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Osceola
Family-friendly Paradise Palms Townhouse With Pool Access Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Mystic Dunes Golf Club and Flamingo Crossings Town Center. This vacation home is 5.2 mi (8.4 km) from Walt Disney World® Resort and 8 mi (12.8 km) from Old Town.

Family-friendly Paradise Palms Townhouse With Pool Access Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Exterior & Views

820dsd - The Retreat At Championsgate 7 Bedroom Home by RedAwning

Vacation Home

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Osceola
820dsd - The Retreat At Championsgate 7 Bedroom Home by RedAwning 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®.

820dsd - The Retreat At Championsgate 7 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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651dsd-the Retreat At Championsgate 5 Bedroom Home by RedAwning

Vacation Home

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Osceola
651dsd-the Retreat At Championsgate 5 Bedroom Home by RedAwning Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of ChampionsGate Golf Club and Posner Village. This vacation home is 12.3 mi (19.9 km) from Old Town and 13.1 mi (21.1 km) from ESPN Wide World of Sports Complex.

651dsd-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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Vacation Homes in Osceola

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