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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

5 Bed With Fantastic Game Room In Fun Resort! 5 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
5 Bed With Fantastic Game Room In Fun Resort! 5 Bedroom Townhouse 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 10.4 mi (16.8 km) from Disney's Animal Kingdom® Theme Park and 11.3 mi (18.2 km) from ESPN Wide World of Sports Complex.

5 Bed With Fantastic Game Room In Fun Resort! 5 Bedroom Townhouse by RedAwning Rooms
Make yourself comfortable in your air-conditioned vacation home. Complimentary wireless internet access is available to keep you connected.

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Spacious Disney Area Townhouse w/ Pool & Free Parking

Vacation Home

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Osceola
Spacious Disney Area Townhouse w/ Pool & Free Parking Location
With a stay at this vacation home in Kissimmee, you'll be a 3-minute drive from Old Town and 9 minutes from Orlando Vineland Premium Outlets. This vacation home is 5.6 mi (9 km) from Walt Disney World® Resort and 5.6 mi (9.1 km) from ESPN Wide World of Sports Complex.

Spacious Disney Area Townhouse w/ Pool & Free Parking Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including complimentary wireless internet access.

Spacious Disney Area Townhouse w/ Pool & Free Parking Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Room

Parkside Paradise

Vacation Home

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Osceola
Parkside Paradise Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be a 5-minute drive from Reunion Resort Golf Course and 6 minutes from ChampionsGate Golf Club. This vacation home is 9.6 mi (15.4 km) from Old Town and 10.3 mi (16.6 km) from ESPN Wide World of Sports Complex.

Parkside Paradise Facility and Service
Take in the views from a garden and make use of amenities such as an arcade/game room and a picnic area. This vacation home also features gas grills and complimentary use of a nearby fitness facility.

Parkside Paradise Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected. Conveniences include a coffee/tea maker and a washer/dryer.

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4-bedroom House at Storey Lake With Private Pool

Vacation Home

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Osceola
4-bedroom House at Storey Lake With Private Pool 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 5.8 mi (9.4 km) from Disney Springs™ and 6.8 mi (11 km) from Walt Disney World® Resort.

4-bedroom House at Storey Lake With Private Pool Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and an indoor pool.

4-bedroom House at Storey Lake With Private Pool Rooms
Your villa features a Smart TV. There's a private furnished patio. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. The bathroom has a bathtub or shower and complimentary toiletries.

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Room

Charming Home Ideal Location Spacious Game Room

Vacation Home

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Osceola
Charming Home Ideal Location Spacious Game Room 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 6.2 mi (10 km) from Disney Springs™ and 7.2 mi (11.6 km) from Walt Disney World® Resort.

Charming Home Ideal Location Spacious Game Room Facility and Service
Take in the views from a garden.

Charming Home Ideal Location Spacious Game Room Rooms
Make yourself comfortable in your vacation home.

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4 BDR South-Facing Disney Retreat

Private Vacation Home

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Osceola
4 BDR South-Facing Disney Retreat Location
With a stay at this vacation home in Kissimmee (Seasons), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 8.5 mi (13.6 km) from Disney Springs™ and 8.7 mi (14.1 km) from Walt Disney World® Resort.

4 BDR South-Facing Disney Retreat Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a terrace.

4 BDR South-Facing Disney Retreat Rooms
Make yourself comfortable in your air-conditioned vacation home, which features a Smart TV. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. Conveniences include a coffee/tea maker and a washer/dryer.

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Stunning Getaway With Games & Clubhouse Amenities - Near Parks

Vacation Home

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Osceola
Stunning Getaway With Games & Clubhouse Amenities - Near Parks 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 (21.3 km) from Orlando Vineland Premium Outlets.

Stunning Getaway With Games & Clubhouse Amenities - Near Parks Facility and Service
Don't miss out on recreational opportunities including a hot tub and a fitness center. Additional features at this vacation home include complimentary wireless internet access and an arcade/game room.

Stunning Getaway With Games & Clubhouse Amenities - Near Parks Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Brand New Champions Gate Resort, Game Room, Near Attractions!!

Vacation Home

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Osceola
Brand New Champions Gate Resort, Game Room, Near Attractions!! Location
When you stay at this vacation home in Four Corners, you'll be next to a golf course, within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This golf vacation home is 11.9 mi (19.1 km) from Old Town and 12.7 mi (20.4 km) from ESPN Wide World of Sports Complex.

Brand New Champions Gate Resort, Game Room, Near Attractions!! Facility and Service
Don't miss out on the many recreational opportunities, including an outdoor pool, a hot tub, and a fitness center.

Brand New Champions Gate Resort, Game Room, Near Attractions!! Rooms
Make yourself comfortable in this vacation home, which features a private pool and a Smart TV. 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 a ceiling fan.

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Cw7740 Windsor Hills Resort Vacation Home

Vacation Home

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Osceola
Cw7740 Windsor Hills Resort Vacation Home Location
With a stay at this cottage in Kissimmee (Windsor Hills), you'll be a 4-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort. This cottage is 5.6 mi (9 km) from ESPN Wide World of Sports Complex and 5.9 mi (9.4 km) from Old Town.

Cw7740 Windsor Hills Resort Vacation Home Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Cw7740 Windsor Hills Resort Vacation Home Rooms
Make yourself comfortable in this air-conditioned cottage, which has a kitchen. Cable television is provided for your entertainment. Conveniences include a coffee/tea maker and a dryer.

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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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5BR Bear's Den Estate Arcade, Pool & Game Room

Vacation Home

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Osceola
5BR Bear's Den Estate Arcade, Pool & Game Room 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.

5BR Bear's Den Estate Arcade, Pool & Game Room Facility and Service
Enjoy recreational amenities such as 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.

5BR Bear's Den Estate Arcade, Pool & Game Room Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Family Pool Home Near Disney!! Modern Decor, Bbq ,resort W/ Tons Of Amenities! 6 Bedroom Home

Vacation Home

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Osceola
Family Pool Home Near Disney!! Modern Decor, Bbq ,resort W/ Tons Of Amenities! 6 Bedroom Home Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center. This vacation home is 8.1 mi (13.1 km) from ESPN Wide World of Sports Complex and 8.3 mi (13.3 km) from Disney's Animal Kingdom® Theme Park.

Family Pool Home Near Disney!! Modern Decor, Bbq ,resort W/ Tons Of Amenities! 6 Bedroom Home Facility and Service
Enjoy the recreation opportunities such as an outdoor tennis court or make use of other amenities including barbecue grills.

Family Pool Home Near Disney!! Modern Decor, Bbq ,resort W/ Tons Of Amenities! 6 Bedroom 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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Lovely Family Townhome In Great Location-2200scd 4 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
Lovely Family Townhome In Great Location-2200scd 4 Bedroom Townhouse by RedAwning 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 9.3 mi (15 km) from Disney Springs™ and 10.4 mi (16.7 km) from Walt Disney World® Resort.

Lovely Family Townhome In Great Location-2200scd 4 Bedroom Townhouse by RedAwning Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Family Fun Play House Near Disney

Vacation Home

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Osceola
Family Fun Play House Near Disney Location
Located in Kissimmee, this villa is within a 15-minute drive of Walt Disney World® Resort and Old Town. This villa is 7.1 mi (11.4 km) from ESPN Wide World of Sports Complex and 7.6 mi (12.2 km) from Disney's Hollywood Studios®.

Family Fun Play House Near Disney 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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Ohana Haven 5 Bedroom Home

Vacation Home

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Osceola
Ohana Haven 5 Bedroom Home Location
With a stay at this vacation home in Kissimmee (Windsor Hills), you'll be a 5-minute drive from Mystic Dunes Golf Club and 8 minutes from Walt Disney World® Resort. This vacation home is 6.1 mi (9.9 km) from ESPN Wide World of Sports Complex and 6.4 mi (10.3 km) from Old Town.

Ohana Haven 5 Bedroom Home Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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1497 Rolling Fairway Drive

Private Vacation Home

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Osceola
1497 Rolling Fairway Drive Location
When you stay at this vacation home in Four Corners, you'll be near the beach and 6 minutes by car from Highland Reserve Golf Club. This vacation home is 12.6 mi (20.2 km) from Old Town and 13.3 mi (21.3 km) from Walt Disney World® Resort.

1497 Rolling Fairway Drive Facility and Service
Take advantage of recreational opportunities offered, including an outdoor pool, an indoor pool, and a fitness center. Additional features at this vacation home include complimentary wireless internet access and an arcade/game room.

1497 Rolling Fairway Drive 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.

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Championsgate Resort 4 Bedroom Townhome Pet Friendly 4 Townhouse

Vacation Home

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Osceola
Championsgate Resort 4 Bedroom Townhome Pet Friendly 4 Townhouse 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 11.5 mi (18.5 km) from Old Town and 12.2 mi (19.7 km) from ESPN Wide World of Sports Complex.

Championsgate Resort 4 Bedroom Townhome Pet Friendly 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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Themed Disney Home w/ Pool & Game Room

Vacation Home

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Osceola
Themed Disney Home w/ Pool & Game Room Location
Located in Kissimmee (Veranda Palms), Themed Disney Home w/ Pool & Game Room is within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This golf vacation home is 6.8 mi (10.9 km) from Disney Springs™ and 7.8 mi (12.6 km) from Walt Disney World® Resort.

Themed Disney Home w/ Pool & Game Room Facility and Service
Head straight for the casino, or wait for that lucky feeling while you enjoy one of the other recreational opportunities, such as an outdoor pool and a fitness center.

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4BR Themed Townhouse Pool Near Disney

Vacation Home

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Osceola
4BR Themed Townhouse Pool Near Disney Location
Located in Kissimmee, this villa is within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This villa is 8.2 mi (13.1 km) from Disney Springs™ and 9.1 mi (14.7 km) from Walt Disney World® Resort.

4BR Themed Townhouse Pool Near Disney Facility and Service
Take advantage of recreation opportunities such as an outdoor pool, or other amenities including complimentary wireless internet access and barbecue grills.

4BR Themed Townhouse Pool Near Disney Rooms
Your villa features a Smart TV. There's a private 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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Windsor Palms Resort 5 Bedroom with Game Room 5 Home

Vacation Home

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Osceola
Windsor Palms Resort 5 Bedroom with Game Room 5 Home Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 8.3 mi (13.4 km) from Disney's Hollywood Studios® and 9.3 mi (15 km) from Disney's Animal Kingdom® Theme Park.

Windsor Palms Resort 5 Bedroom with Game Room 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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Vacation Homes in Osceola

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