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Vacation Homes in Osceola

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

1571sand

Vacation Home

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Osceola
1571sand 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 11.4 mi (18.3 km) from Old Town and 12.2 mi (19.6 km) from ESPN Wide World of Sports Complex.

1571sand Facility and Service
Enjoy a range of recreational amenities, including an outdoor pool, a hot tub, and a fitness center. This vacation home also features complimentary wireless internet access and an arcade/game room.

1571sand Rooms
Make yourself comfortable in this air-conditioned vacation home, which has a kitchen. Wired and wireless internet access is complimentary, while a flat-screen television and a DVD player provide entertainment. Conveniences include a refrigerator and a washer/dryer.

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Airy House With Private Pool in Encore

Vacation Home

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Osceola
Airy House With Private Pool in Encore 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 Mystic Dunes Golf Club. This vacation home is 7.6 mi (12.3 km) from ESPN Wide World of Sports Complex and 8.1 mi (13.1 km) from Disney's Hollywood Studios®.

Airy House With Private Pool in Encore Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a hot tub.

Airy House With Private Pool in Encore Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Elegant Home With Pool & Spa, Close to Disney

Vacation Home

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Osceola
Elegant Home With Pool & Spa, Close to 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 9.1 mi (14.7 km) from Disney Springs™ and 10.1 mi (16.2 km) from Walt Disney World® Resort.

Elegant Home With Pool & Spa, Close to Disney Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Elegant Home With Pool & Spa, Close to Disney 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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Exterior & Views

Casa Del Sol At Indian Creek Four Corners 4 Bedroom Villa

Vacation Home

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Osceola
Casa Del Sol At Indian Creek Four Corners 4 Bedroom Villa Location
With a stay at this villa in Kissimmee, you'll be a 4-minute drive from Mystic Dunes Golf Club and 10 minutes from Walt Disney World® Resort. This villa is 6.8 mi (10.9 km) from ESPN Wide World of Sports Complex and 7.1 mi (11.4 km) from Old Town.

Casa Del Sol At Indian Creek Four Corners 4 Bedroom Villa Rooms
Make yourself comfortable in your villa. Complimentary wireless internet access is available to keep you connected.

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DISNEY area Luxurious House-Private Pool

Vacation Home

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Osceola
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Sport & Beauty

Orlando Select Vacation Homes

Vacation Home

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Osceola
Orlando Select Vacation Homes Location
With a stay at Orlando Select Vacation Homes in Kissimmee, you'll be a 4-minute drive from Mystic Dunes Golf Club and 5 minutes from Walt Disney World® Resort. This luxury vacation home is 5.3 mi (8.5 km) from ESPN Wide World of Sports Complex and 5.4 mi (8.8 km) from Old Town.

Orlando Select Vacation Homes Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center. This vacation home also features complimentary wireless internet access and barbecue grills.

Orlando Select Vacation Homes Rooms
Make yourself at home in one of the 9 air-conditioned rooms featuring microwaves and flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms have deep soaking bathtubs and hair dryers. Conveniences include phones, as well as coffee/tea makers and washers/dryers.

Restaurant and Cafe
Quench your thirst with your favorite drink at the bar/lounge.

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4.0/5
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Exterior & Views

Lucaya Resort by FunQuest Vacation

Vacation Home

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Osceola
Lucaya Resort by FunQuest Vacation Location
With a stay at Lucaya Resort by FunQuest Vacation in Kissimmee, you'll be a 3-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This vacation home is 5.1 mi (8.2 km) from Disney Springs™ and 5.5 mi (8.9 km) from ESPN Wide World of Sports Complex.

Lucaya Resort by FunQuest Vacation Facility and Service
Take advantage of recreational opportunities offered, including an outdoor pool, a hot tub, and a fitness center. This vacation home also features complimentary wireless internet access, a picnic area, and barbecue grills.

Lucaya Resort by FunQuest Vacation Rooms
Make yourself at home in one of the 20 air-conditioned rooms featuring kitchens with refrigerators and microwaves. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include phones, as well as coffee/tea makers and washing machines.

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4.0/5
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Room

Championsgate Resort 6 Bedroom Private Pool Home with Theater 6 Home

Vacation Home

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Osceola
Championsgate Resort 6 Bedroom Private Pool Home with Theater 6 Home 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 vacation home is 12.7 mi (20.5 km) from Old Town and 13.3 mi (21.4 km) from ESPN Wide World of Sports Complex.

Championsgate Resort 6 Bedroom Private Pool Home with Theater 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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Bedroom

Aco249241 - Lucaya Village - 3 Bed 2 Baths Townhome

Vacation Home

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Osceola
Aco249241 - Lucaya Village - 3 Bed 2 Baths Townhome 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 golf vacation home is 5.3 mi (8.5 km) from Disney Springs™ and 5.5 mi (8.8 km) from Walt Disney World® Resort.

Aco249241 - Lucaya Village - 3 Bed 2 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 an outdoor pool or a hot tub. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Aco249241 - Lucaya Village - 3 Bed 2 Baths Townhome 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 is provided for your entertainment. Conveniences include a microwave and a sofa bed.

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Non-renting - 1586pd - The Retreat at Championsgate

Vacation Home

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Osceola
Non-renting - 1586pd - The Retreat at Championsgate 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 golf villa is 11.4 mi (18.3 km) from Old Town and 12.2 mi (19.6 km) from ESPN Wide World of Sports Complex.

Non-renting - 1586pd - The Retreat at Championsgate Facility and Service
Don't miss out on the many recreational opportunities, including an outdoor pool, an outdoor tennis court, and a fitness center.

Non-renting - 1586pd - The Retreat at Championsgate Rooms
Make yourself comfortable in this air-conditioned villa, featuring a kitchen with a refrigerator and a stovetop. A flat-screen television is provided for your entertainment. Conveniences include a microwave and an iron/ironing board.

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Kissimmee Retreat 6BR House Sleeps 14

Vacation Home

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Osceola
Kissimmee Retreat 6BR House Sleeps 14 Location
With a stay at this villa in Kissimmee, you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This villa is 5.9 mi (9.6 km) from Disney Springs™ and 6.8 mi (11 km) from Walt Disney World® Resort.

Kissimmee Retreat 6BR House Sleeps 14 Rooms
Make yourself comfortable in your villa. Complimentary wireless internet access is available to keep you connected. Conveniences include a washing machine and an iron/ironing board.

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1559fd - The Retreat at Championsgate

Vacation Home

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Osceola
1559fd - 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 11.3 mi (18.2 km) from Old Town and 12.1 mi (19.4 km) from ESPN Wide World of Sports Complex.

1559fd - The Retreat at Championsgate Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

1559fd - The Retreat at Championsgate Rooms
Make yourself comfortable in your air-conditioned vacation home, which features a flat-screen TV. The bathroom features complimentary toiletries and a hair dryer.

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Fully Booked
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Sport & Beauty

Grhmap8952 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse

Vacation Home

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Osceola
Grhmap8952 - Paradise Palms Resort - 4 Bed 3 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.

Grhmap8952 - Paradise Palms Resort - 4 Bed 3 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. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhmap8952 - Paradise Palms Resort - 4 Bed 3 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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Advantage Vacation Homes

Vacation Home

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Osceola
Advantage Vacation Homes Location
Located in Kissimmee, this vacation home is in the suburbs, a 3-minute drive from Orange Lake Golf and 8 minutes from Northeast Regional Park. This vacation home is 5.9 mi (9.4 km) from Highland Reserve Golf Club and 7 mi (11.2 km) from Disney's Animal Kingdom® Theme Park.

Advantage Vacation Homes Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. This vacation home also features complimentary wireless internet access and tour/ticket assistance.

Advantage Vacation Homes Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with a full-sized refrigerator/freezer and a stovetop. Complimentary wired and wireless internet access keeps you connected, and cable programming provides entertainment. Conveniences include a separate sitting area and a microwave.

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3.8/5(100 Reviews)
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Bedroom

18Guest LakeView Home w HotTub Cinema

Vacation Home

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Osceola
18Guest LakeView Home w HotTub Cinema Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 6.9 mi (11.1 km) from Disney Springs™ and 7.9 mi (12.8 km) from Walt Disney World® Resort.

18Guest LakeView Home w HotTub Cinema Rooms
Make yourself comfortable in your air-conditioned vacation home. Complimentary wireless internet access is available to keep you connected.

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1.0/5
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Sport & Beauty

Lovely New Pool Home At Windsor At Westside-2167tc 8 Bedroom Home by RedAwning

Vacation Home

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Osceola
Lovely New Pool Home At Windsor At Westside-2167tc 8 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 10.3 mi (16.5 km) from Disney's Animal Kingdom® Theme Park and 11.2 mi (18 km) from ESPN Wide World of Sports Complex.

Lovely New Pool Home At Windsor At Westside-2167tc 8 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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2243 Wyndham Palms way

Private Vacation Home

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Osceola
2243 Wyndham Palms way 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 8.2 mi (13.3 km) from Disney's Hollywood Studios® and 9.2 mi (14.9 km) from Disney's Animal Kingdom® Theme Park.

2243 Wyndham Palms way Facility and Service
Be sure to enjoy recreational amenities, including an outdoor pool, an indoor pool, and an outdoor tennis court. Additional features at this vacation home include complimentary wireless internet access and an arcade/game room.

2243 Wyndham Palms way 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.

See details
4.0/5
Fully Booked
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Sport & Beauty

Townhome With Private Pool, BBQ & Free Waterpark!

Vacation Home

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Osceola
Townhome With Private Pool, BBQ & Free Waterpark! 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 family-friendly vacation home is 10.2 mi (16.5 km) from Disney's Animal Kingdom® Theme Park and 10.9 mi (17.5 km) from ESPN Wide World of Sports Complex.

Townhome With Private Pool, BBQ & Free Waterpark! Facility and Service
Enjoy recreational amenities such as an outdoor pool and a lazy river. Additional amenities at this vacation home include complimentary wireless internet access, an arcade/game room, and barbecue grills.

Townhome With Private Pool, BBQ & Free Waterpark! 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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5.0/5
Fully Booked
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Sport & Beauty

1804 Tropical Palms Circle

Vacation Home

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Osceola
1804 Tropical Palms Circle 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 11.4 mi (18.4 km) from ESPN Wide World of Sports Complex.

1804 Tropical Palms Circle Facility and Service
Enjoy recreational amenities such as an outdoor pool and a waterslide. Additional features at this vacation home include complimentary wireless internet access, an arcade/game room, and barbecue grills.

1804 Tropical Palms Circle Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. There's a private patio. 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.

See details
5.0/5
Fully Booked
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Sport & Beauty

Casa Palmero 5 Bedroom Home by RedAwning

Vacation Home

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Osceola
Casa Palmero 5 Bedroom Home by RedAwning 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 8.6 mi (13.9 km) from Disney's Animal Kingdom® Theme Park and 9.3 mi (15 km) from ESPN Wide World of Sports Complex.

Casa Palmero 5 Bedroom 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.

Casa Palmero 5 Bedroom Home by RedAwning Rooms
Make yourself comfortable in your individually decorated vacation home. Complimentary wireless internet access is available to keep you connected.

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Fully Booked
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Vacation Homes in Osceola

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