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Vacation Homes in Osceola

Osceola
Wed, 18 Nov 2026 - Thu, 19 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 2.000+ Vacation Homes in Osceola
Others

1300bw- Non Renting 5/1/2022 The Retreat at Championsgate

Vacation Home

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Osceola
1300bw- Non Renting 5/1/2022 The Retreat at Championsgate 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 golf vacation home is 12.7 mi (20.5 km) from Old Town and 13.3 mi (21.4 km) from Walt Disney World® Resort.

1300bw- Non Renting 5/1/2022 The Retreat at Championsgate Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

1300bw- Non Renting 5/1/2022 The Retreat at Championsgate Rooms
Make yourself comfortable in this vacation home, which has a kitchen.

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Windsor Greenview Home Pool SPA No Rear Neighbor!

Vacation Home

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Osceola
Windsor Greenview Home Pool SPA No Rear Neighbor! 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 10.2 mi (16.4 km) from Disney's Animal Kingdom® Theme Park and 11.1 mi (17.8 km) from ESPN Wide World of Sports Complex.

Windsor Greenview Home Pool SPA No Rear Neighbor! 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.

Windsor Greenview Home Pool SPA No Rear Neighbor! Rooms
Make yourself comfortable in your individually decorated vacation home. There's a private patio. The bathroom has a bathtub or shower and designer toiletries. Conveniences include a coffee/tea maker and a washer/dryer.

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4 Bed Town Home With Pool Champions Gate 4 Bedroom Townhouse

Vacation Home

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Osceola
4 Bed Town Home With Pool Champions Gate 4 Bedroom Townhouse Location
Located in Four Corners, this vacation home is within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This vacation home is 12.2 mi (19.7 km) from Old Town and 13 mi (21 km) from ESPN Wide World of Sports Complex.

4 Bed Town Home With Pool Champions Gate 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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Beautiful 5 Bed Pool Home In Reunion-1223ms 5 Bedroom Home by RedAwning

Vacation Home

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Osceola
Beautiful 5 Bed Pool Home In Reunion-1223ms 5 Bedroom Home by RedAwning Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be within a 15-minute drive of Walt Disney World® Resort and Reunion Resort Golf Course. This vacation home is 9.6 mi (15.5 km) from ESPN Wide World of Sports Complex and 10.1 mi (16.3 km) from Disney's Hollywood Studios®.

Beautiful 5 Bed Pool Home In Reunion-1223ms 5 Bedroom Home by RedAwning Rooms
Make yourself comfortable in your vacation home. There's a private patio. Complimentary wireless internet access is available to keep you connected. Conveniences include a washing machine and an iron/ironing board.

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Casablanca Villaview by Orlando Short Term

Vacation Home

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Osceola
Casablanca Villaview by Orlando Short Term Location
With a stay at this vacation home in Kissimmee (Eagle Pointe South), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 9.5 mi (15.3 km) from Disney Springs™ and 9.7 mi (15.5 km) from ESPN Wide World of Sports Complex.

Casablanca Villaview 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 refrigerator and a coffee/tea maker.

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4.5/5
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3BR Reunion Resort Retreat With Private Pool, spa & Golf Nearby

Vacation Home

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Osceola
3BR Reunion Resort Retreat With Private Pool, spa & Golf Nearby Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be within a 15-minute drive of Reunion Resort Golf Course and ChampionsGate Golf Club. This vacation home is 7.7 mi (12.4 km) from Walt Disney World® Resort and 10 mi (16 km) from ESPN Wide World of Sports Complex.

3BR Reunion Resort Retreat With Private Pool, spa & Golf Nearby Facility and Service
Enjoy recreational amenities such as an outdoor pool and a hot tub.

3BR Reunion Resort Retreat With Private Pool, spa & Golf Nearby Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Sport & Beauty

16 Guest Lakefront Home w Pool BBQ

Vacation Home

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Osceola
16 Guest Lakefront Home w Pool BBQ 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 8.8 mi (14.1 km) from Disney Springs™ and 9.6 mi (15.4 km) from ESPN Wide World of Sports Complex.

16 Guest Lakefront Home w Pool BBQ Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center.

16 Guest Lakefront Home w Pool BBQ Rooms
Make yourself comfortable in this vacation home, which features a private pool and a Smart TV. A kitchen makes it easy to prepare your meals. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment.

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2.0/5
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Sport & Beauty

Tropical Escape by Orlando Short Term

Vacation Home

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Osceola
Tropical Escape by Orlando Short Term 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 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.

Tropical Escape by Orlando Short Term Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

Tropical Escape by Orlando Short Term Rooms
Make yourself comfortable in this 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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Noble Estate With Private Pool at Reunion

Vacation Home

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Osceola
Noble Estate With Private Pool at Reunion Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be within a 10-minute drive of Reunion Resort Golf Course and Mystic Dunes Golf Club. This vacation home is 7.1 mi (11.4 km) from Walt Disney World® Resort and 9.1 mi (14.7 km) from Old Town.

Noble Estate With Private Pool at Reunion Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a hot tub. Additional features at this vacation home include complimentary wireless internet access, an arcade/game room, and barbecue grills.

Noble Estate With Private Pool at Reunion Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Bedroom

4562 Seven Dwarfs

Vacation Home

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Osceola
4562 Seven Dwarfs 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 6.3 mi (10.1 km) from Disney Springs™ and 7.2 mi (11.6 km) from ESPN Wide World of Sports Complex.

4562 Seven Dwarfs Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

4562 Seven Dwarfs Rooms
Make yourself comfortable in this vacation home, which features a private hot tub. There's a private patio. A kitchen is outfitted with a refrigerator. Conveniences include a dryer and an iron/ironing board.

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Bedroom

7669 Windsor Hills

Vacation Home

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Osceola
7669 Windsor Hills Location
Located in Kissimmee (Windsor Hills), 7669 Windsor Hills is within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This vacation home is 5.9 mi (9.6 km) from Old Town and 6.1 mi (9.9 km) from ESPN Wide World of Sports Complex.

7669 Windsor Hills Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including concierge services.

7669 Windsor Hills Rooms
Make yourself at home in one of the 6 air-conditioned rooms featuring private pools and private hot tubs. Kitchens are outfitted with refrigerators, stovetops, and microwaves. Satellite programming and DVD players are provided for your entertainment, while complimentary wireless internet access keeps you connected. Conveniences include coffee/tea makers and washers/dryers.

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Stunning 4 Bd W/ Pool @ Storey Lake Resort 2613

Vacation Home

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Osceola
Stunning 4 Bd W/ Pool @ Storey Lake Resort 2613 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 7.5 mi (12.1 km) from Disney Springs™ and 8.5 mi (13.8 km) from Walt Disney World® Resort.

Stunning 4 Bd W/ Pool @ Storey Lake Resort 2613 Rooms
Make yourself comfortable in your vacation home.

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5.0/5
Fully Booked
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Exterior & Views

3193tocoa

Vacation Home

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Osceola
3193tocoa 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 luxury vacation home is 5.5 mi (8.8 km) from Disney Springs™ and 6.1 mi (9.9 km) from Walt Disney World® Resort.

3193tocoa Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

3193tocoa Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and a microwave. There's a private balcony or patio. Complimentary wireless internet access keeps you connected, and a flat-screen television is provided for your entertainment.

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8830ilc - The Retreat at Championsgate

Vacation Home

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Osceola
8830ilc - The Retreat at Championsgate Location
Located in Four Corners (Champions Gate), this vacation home is within a 10-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This golf vacation home is 11.1 mi (17.9 km) from Old Town and 11.9 mi (19.2 km) from ESPN Wide World of Sports Complex.

8830ilc - The Retreat at Championsgate Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

8830ilc - The Retreat at Championsgate Rooms
Make yourself comfortable in this vacation home, which has a kitchen.

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Sport & Beauty

Villa W/private Pool & Game Room Near Disney!

Vacation Home

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Osceola
Villa W/private Pool & Game Room Near Disney! 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 family-friendly vacation home is 6.3 mi (10.2 km) from Disney Springs™ and 7.3 mi (11.7 km) from ESPN Wide World of Sports Complex.

Villa W/private Pool & Game Room Near Disney! Facility and Service
Enjoy a range of recreational amenities, including an outdoor pool, a lazy river, and a waterslide. This vacation home also features complimentary wireless internet access, an arcade/game room, and barbecue grills.

Villa W/private Pool & Game Room Near Disney! Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a flat-screen TV. There's a private balcony or patio. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Cable television is provided for your entertainment.

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

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Exterior & Views

Grand Superior 3BD Townhouse near Disney

Vacation Home

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Osceola
Experience an abundance of unparalleled facilities and features at Grand Superior 3BD Townhouse near Disney.Maintain seamless communication using the complimentary Wi-Fi at country house.Kindly note that smoking is prohibited in the country house to ensure fresher air for all visitors.For visitors wishing to smoke, designated smoking zones can be found. At Grand Superior 3BD Townhouse near Disney, every guestroom is provided with convenient amenities and fittings to ensure a comfortable stay. Certain rooms offer in-room amusement features such as the cable TV for your enjoyment.
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1570 Carey Palm Circle

Vacation Home

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Osceola
1570 Carey Palm Circle Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This family-friendly vacation home is 8.6 mi (13.8 km) from Walt Disney World® Resort and 10.3 mi (16.5 km) from Disney's Animal Kingdom® Theme Park.

1570 Carey Palm Circle Facility and Service
Enjoy recreational amenities such as 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.

1570 Carey Palm Circle Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a flat-screen TV. There's a private patio. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment.

Restaurant and Cafe
Take advantage of the vacation home's late night room service.

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4.0/5
Fully Booked
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Bedroom

Relaxing 4bed 3Ba Champions Gate Pool

Vacation Home

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Osceola
Relaxing 4bed 3Ba Champions Gate Pool Location
With a stay at this condo in Four Corners, you'll be within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This condo is 12.1 mi (19.4 km) from Old Town and 12.6 mi (20.3 km) from Walt Disney World® Resort.

Relaxing 4bed 3Ba Champions Gate Pool Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center.

Relaxing 4bed 3Ba Champions Gate Pool Rooms
Make yourself comfortable in this air-conditioned condo, featuring a kitchen with a refrigerator and a microwave. Complimentary wireless internet access keeps you connected, and a flat-screen television is provided for your entertainment. Conveniences include a dryer and an iron/ironing board.

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Free Waterpark 5Bd Close To Disney W/ Pool @ Storey Lake Resort 2497

Vacation Home

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Osceola
Free Waterpark 5Bd Close To Disney W/ Pool @ Storey Lake Resort 2497 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 7.5 mi (12.1 km) from Disney Springs™ and 8.5 mi (13.7 km) from Walt Disney World® Resort.

Free Waterpark 5Bd Close To Disney W/ Pool @ Storey Lake Resort 2497 Facility and Service
Enjoy recreation amenities such as a fitness center or take in the view from a garden.

Free Waterpark 5Bd Close To Disney W/ Pool @ Storey Lake Resort 2497 Rooms
Make yourself comfortable in your vacation home, featuring a refrigerator and a DVD player. There's a private patio. Conveniences include a desk and an electric kettle.

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4.5/5
Fully Booked
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Sport & Beauty

Villa Telles - Storey Lake

Vacation Home

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Osceola
Villa Telles - Storey Lake 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 5.8 mi (9.3 km) from Disney Springs™ and 6.7 mi (10.7 km) from ESPN Wide World of Sports Complex.

Villa Telles - Storey Lake Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with an oven and a stovetop. Complimentary wireless internet access is available to keep you connected. Housekeeping is provided once per stay, and a rollaway/extra bed can be requested.

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Vacation Homes in Osceola

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