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Vacation Homes in Osceola

Osceola
Fri, 13 Nov 2026 - Sat, 14 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 1.000+ Vacation Homes in Osceola
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South Facing W/ Private Pool & Spa

Vacation Home

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Osceola
South Facing W/ Private Pool & Spa Location
With a stay at this vacation home in Kissimmee (Crescent Lakes), you'll be within a 10-minute drive of Green Meadows Petting Farm and Shingle Creek Regional Park. This family-friendly vacation home is 11.8 mi (18.9 km) from Old Town and 14 mi (22.5 km) from Orlando Vineland Premium Outlets.

South Facing W/ Private Pool & Spa Facility and Service
Take advantage of recreational opportunities offered, including an outdoor pool, a hot tub, and an outdoor tennis court.

South Facing W/ Private Pool & Spa Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a Smart TV. A kitchen is outfitted with a full-sized refrigerator/freezer, an oven, and a stovetop. Digital programming and a video-game console are provided for your entertainment, while complimentary wireless internet access keeps you connected. Conveniences include a separate sitting area and a microwave, as well as a phone with free local calls.

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Interior

Special Offer Great House w Pvt Pool at Champions Gate

Vacation Home

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Osceola
Special Offer Great House w Pvt Pool at Champions Gate 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 11.4 mi (18.3 km) from Old Town and 12.1 mi (19.5 km) from ESPN Wide World of Sports Complex.

Special Offer Great House w Pvt Pool at Champions Gate Rooms
Make yourself comfortable in this air-conditioned villa, which has a kitchen. Cable television is provided for your entertainment. Conveniences include a dryer and an iron/ironing board.

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Bedroom

Blue Lagoon by Orlando Short Term

Vacation Home

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Osceola
Blue Lagoon 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.

Blue Lagoon by Orlando Short Term Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center.

Blue Lagoon 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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Room

Super fun Spacious Family Home With top Amenities Pool/spa Sleeps 24

Vacation Home

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Osceola
Super fun Spacious Family Home With top Amenities Pool/spa Sleeps 24 Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, 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 7.3 mi (11.8 km) from Walt Disney World® Resort.

Super fun Spacious Family Home With top Amenities Pool/spa Sleeps 24 Facility and Service
Don't miss out on the many recreational opportunities, including an outdoor pool, a hot tub, and a fitness center. Additional amenities at this vacation home include complimentary wireless internet access, an arcade/game room, and barbecue grills.

Super fun Spacious Family Home With top Amenities Pool/spa Sleeps 24 Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Living area

Storey Lake Resort 5 Bedroom Private Pool Home 5 Home

Vacation Home

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Osceola
Storey Lake Resort 5 Bedroom Private Pool Home 5 Home Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This golf vacation home is 6.1 mi (9.8 km) from Disney Springs™ and 6.9 mi (11 km) from ESPN Wide World of Sports Complex.

Storey Lake Resort 5 Bedroom Private Pool Home 5 Home 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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Windsor Palms Resort 3 Bedroom Private Pool Townhome 3 Townhouse

Vacation Home

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Osceola
Windsor Palms Resort 3 Bedroom Private Pool Townhome 3 Townhouse 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 7.1 mi (11.5 km) from ESPN Wide World of Sports Complex and 7.6 mi (12.3 km) from Disney's Hollywood Studios®.

Windsor Palms Resort 3 Bedroom Private Pool Townhome 3 Townhouse Rooms
Make yourself comfortable in your vacation home, featuring a refrigerator and a Smart TV. 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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Sport & Beauty

Storey Lake Resort, Private Pool, Near Famous Attractions!!

Vacation Home

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Osceola
Storey Lake Resort, Private Pool, Near Famous Attractions!! 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 6.5 mi (10.5 km) from Walt Disney World® Resort and 6.7 mi (10.7 km) from Disney's Hollywood Studios®.

Storey Lake Resort, Private Pool, Near Famous Attractions!! Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center.

Storey Lake Resort, Private Pool, Near Famous Attractions!! Rooms
Make yourself comfortable in this vacation home, which features a private pool. Complimentary wireless internet access is available to keep you connected.

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Boutique Luxury Home, Private Pool Close to Disney

Vacation Home

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Osceola
Boutique Luxury Home, Private Pool Close to Disney 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 Mystic Dunes Golf Club. This vacation home is 7.5 mi (12.1 km) from Walt Disney World® Resort and 9.5 mi (15.4 km) from Old Town.

Boutique Luxury Home, Private Pool Close to Disney Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Boutique Luxury Home, Private Pool Close to Disney Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Stylish Home With Themed Bedroom at Reunion

Vacation Home

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Osceola
Stylish Home With Themed Bedroom at Reunion 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 Mystic Dunes Golf Club. This golf vacation home is 7.4 mi (11.9 km) from Walt Disney World® Resort and 9.4 mi (15.2 km) from Old Town.

Stylish Home With Themed Bedroom at Reunion Facility and Service
Enjoy recreational amenities such as an outdoor pool and a hot tub. Additional amenities at this vacation home include complimentary wireless internet access and an arcade/game room.

Stylish Home With Themed Bedroom at Reunion Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Interior

Discounted 12br w Barbie Castle/dino Slide/games

Vacation Home

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Osceola
Discounted 12br w Barbie Castle/dino Slide/games Location
Located in Kissimmee, this cottage is within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This cottage is 7.2 mi (11.5 km) from Disney Springs™ and 8.2 mi (13.2 km) from Walt Disney World® Resort.

Discounted 12br w Barbie Castle/dino Slide/games Facility and Service
This smoke-free cottage offers complimentary parking nearby.

Discounted 12br w Barbie Castle/dino Slide/games Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with an oven and a stovetop. Cable television is provided for your entertainment. Conveniences include a microwave and a dryer, and you can also request a crib/infant bed (complimentary).

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Others

Windsor Hills Cozy Home Pool/spa 2 Mile to Disney

Private Vacation Home

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Osceola
Windsor Hills Cozy Home Pool/spa 2 Mile to Disney Location
With a stay at this vacation home in Kissimmee (Windsor Hills), you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This vacation home is 6.2 mi (9.9 km) from Old Town and 6.5 mi (10.5 km) from Disney's Hollywood Studios®.

Windsor Hills Cozy Home Pool/spa 2 Mile to Disney Facility and Service
Take advantage of recreation opportunities including an outdoor tennis court and a fitness center. This vacation home also features complimentary wireless internet access, an arcade/game room, and barbecue grills.

Windsor Hills Cozy Home Pool/spa 2 Mile to Disney Rooms
Make yourself comfortable in your air-conditioned vacation home, which features an MP3 docking station. There's a private patio. The bathroom has a bathtub or shower and designer toiletries. Conveniences include a coffee/tea maker and a washing machine.

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Beautiful Tranquil Relaxing Home With Private Pool 4 Bedroom Townhouse

Vacation Home

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Osceola
Beautiful Tranquil Relaxing Home With Private Pool 4 Bedroom Townhouse 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 10.3 mi (16.6 km) from Disney's Animal Kingdom® Theme Park and 11.4 mi (18.3 km) from ESPN Wide World of Sports Complex.

Beautiful Tranquil Relaxing Home With Private Pool 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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Sport & Beauty

Willow Bend

Vacation Home

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Osceola
Willow Bend Location
With a stay at this vacation home in Kissimmee (Crescent Lakes), you'll be within a 10-minute drive of Green Meadows Petting Farm and Shingle Creek Regional Park. This family-friendly vacation home is 11.9 mi (19.2 km) from Old Town and 14.1 mi (22.7 km) from Orlando Vineland Premium Outlets.

Willow Bend Facility and Service
Be sure to enjoy recreational amenities, including an outdoor pool, a hot tub, and an outdoor tennis court.

Willow Bend Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a full-sized refrigerator/freezer and an oven. Complimentary wireless internet access is available to keep you connected. Conveniences include a microwave and a coffee/tea maker, and housekeeping is provided on request.

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5.0/5
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Bathroom

Ov4086 - Encantada Resort - 2 Bed 2.5 Baths Townhome

Vacation Home

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Osceola
Ov4086 - Encantada Resort - 2 Bed 2.5 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 Flamingo Crossings Town Center. This vacation home is 6.8 mi (11 km) from Disney's Animal Kingdom® Theme Park and 7.7 mi (12.5 km) from ESPN Wide World of Sports Complex.

Ov4086 - Encantada Resort - 2 Bed 2.5 Baths Townhome Facility and Service
Take advantage of recreation opportunities including a fitness center and a seasonal outdoor pool. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Ov4086 - Encantada Resort - 2 Bed 2.5 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 washer/dryer.

Restaurant and Cafe
At this vacation home, enjoy a satisfying meal at the restaurant. Unwind at the end of the day with a drink at the bar/lounge or the poolside bar.

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Exterior & Views

Shd4720

Vacation Home

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Osceola
Shd4720 Location
With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This cottage is 6 mi (9.6 km) from Disney Springs™ and 6.6 mi (10.7 km) from Walt Disney World® Resort.

Shd4720 Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with an oven and a stovetop. Conveniences include a desk and a microwave.

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Others

Storey Lake Resort, Private Pool, Near Famous Attractions!!

Private Vacation Home

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Osceola
Storey Lake Resort, Private Pool, Near Famous Attractions!! 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 7.3 mi (11.7 km) from Disney Springs™ and 8.3 mi (13.3 km) from Walt Disney World® Resort.

Storey Lake Resort, Private Pool, Near Famous Attractions!! Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center.

Storey Lake Resort, Private Pool, Near Famous Attractions!! Rooms
Make yourself comfortable in this vacation home, which features a private pool. Complimentary wireless internet access is available to keep you connected.

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Exterior & Views

Nottingham Home with Pool in Terra Verde

Vacation Home

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Osceola
Nottingham Home with Pool in Terra Verde 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 8.9 mi (14.3 km) from Disney Springs™ and 9.2 mi (14.7 km) from Walt Disney World® Resort.

Nottingham Home with Pool in Terra Verde Facility and Service
Take in the views from a garden and make use of amenities such as complimentary wireless internet access.

Nottingham Home with Pool in Terra Verde 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 patio. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Cable programming and a DVD player are provided for your entertainment, while complimentary wireless internet access keeps you connected.

Restaurant and Cafe
Wrap up your day with a drink at the poolside bar.

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Others

Gated Community, Amazing 4/3 Vacation Home With Private Pool Near Disney!!!

Vacation Home

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Osceola
Gated Community, Amazing 4/3 Vacation Home With Private Pool Near Disney!!! Location
With a stay at Gated Community, Amazing 4/3 Vacation Home With Private Pool Near Disney!!! in Kissimmee (Crystal Cove), you'll be within a 15-minute drive of Old Town and Disney Springs™. This vacation home is 8.3 mi (13.3 km) from ESPN Wide World of Sports Complex and 8.5 mi (13.7 km) from Walt Disney World® Resort.

Gated Community, Amazing 4/3 Vacation Home With Private Pool Near Disney!!! Rooms
Make yourself at home in of the guestrooms featuring private pools. Complimentary wireless internet access is available to keep you connected.

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Room

8904-TropicalHaven

Vacation Home

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Osceola
8904-TropicalHaven 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 10.1 mi (16.3 km) from Disney's Animal Kingdom® Theme Park and 11.3 mi (18.2 km) from ESPN Wide World of Sports Complex.

8904-TropicalHaven Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a garden.

8904-TropicalHaven Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected. Conveniences include a washing machine and an iron/ironing board.

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Exterior & Views

1439rf - The Retreat At Championsgate 6 Bedroom Home by RedAwning

Vacation Home

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Osceola
1439rf - The Retreat At Championsgate 6 Bedroom Home by RedAwning 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 12.8 mi (20.6 km) from Old Town and 13.4 mi (21.5 km) from Walt Disney World® Resort.

1439rf - The Retreat At Championsgate 6 Bedroom Home by RedAwning Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including barbecue grills.

1439rf - The Retreat At Championsgate 6 Bedroom Home by RedAwning Rooms
Make yourself comfortable in your vacation home, which features a refrigerator. There's a private patio. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. The bathroom has a bathtub or shower and complimentary toiletries.

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Vacation Homes in Osceola

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