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Vacation Homes in Osceola

Osceola
Mon, 16 Nov 2026 - Tue, 17 Nov 2026 (1 night)
1 Adult, 0 Children
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Showing 1.000+ Vacation Homes in Osceola
Bedroom

8881 QL Serenity Haven Luxurious Disney World

Vacation Home

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Osceola
8881 QL Serenity Haven Luxurious Disney World Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This golf vacation home is 10.2 mi (16.4 km) from Disney's Animal Kingdom® Theme Park and 11.4 mi (18.4 km) from ESPN Wide World of Sports Complex.

8881 QL Serenity Haven Luxurious Disney World Facility and Service
Take advantage of recreation opportunities including an outdoor tennis court and a fitness center.

8881 QL Serenity Haven Luxurious Disney World Rooms
Make yourself comfortable in your vacation home.

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Bedroom

Emerald_island_8640

Vacation Home

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Osceola
Emerald_island_8640 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 7.3 mi (11.8 km) from ESPN Wide World of Sports Complex and 7.8 mi (12.5 km) from Disney's Hollywood Studios®.

Emerald_island_8640 Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

Emerald_island_8640 Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a private hot tub. There's a private patio. A kitchen is outfitted with a refrigerator, a stovetop, and a microwave. Wired and wireless internet access is complimentary, and a flat-screen television with satellite programming provides entertainment. A private bathroom has a jetted bathtub and a hair dryer.

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2.0/5
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Bedroom

Casa del Sol

Vacation Home

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Osceola
Casa del Sol 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 8.4 mi (13.5 km) from Disney's Animal Kingdom® Theme Park and 9.3 mi (15 km) from ESPN Wide World of Sports Complex.

Casa del Sol Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

Casa del Sol 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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5.0/5
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Dog-friendly Home With Shared Pool, Wifi, Central AC, and Private Washer/dryer

Vacation Home

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Osceola
Dog-friendly Home With Shared Pool, Wifi, Central AC, and Private Washer/dryer Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, a 3-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This vacation home is 5.3 mi (8.5 km) from Disney Springs™ and 5.7 mi (9.1 km) from ESPN Wide World of Sports Complex.

Dog-friendly Home With Shared Pool, Wifi, Central AC, and Private Washer/dryer Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and barbecue grills.

Dog-friendly Home With Shared Pool, Wifi, Central AC, and Private Washer/dryer Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Interior

Rc164p Fairway Fun Castle

Vacation Home

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Osceola
Rc164p Fairway Fun Castle Location
With a stay at this cottage in Kissimmee (Reunion), you'll be within a 15-minute drive of Reunion Resort Golf Course and Mystic Dunes Golf Club. This cottage is 7.6 mi (12.2 km) from Walt Disney World® Resort and 9.6 mi (15.4 km) from Old Town.

Rc164p Fairway Fun Castle Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and barbecue grills.

Rc164p Fairway Fun Castle 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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Crystal Cove by Fairytale VR

Vacation Home

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Osceola
Crystal Cove by Fairytale VR Location
With a stay at Crystal Cove by Fairytale VR in Kissimmee (Crystal Cove), you'll be within a 15-minute drive of Old Town and 192 Flea Market. This vacation home is 7 mi (11.3 km) from Walt Disney World® area and 9.3 mi (14.9 km) from Walt Disney World® Resort.

Crystal Cove by Fairytale VR Rooms
Treat yourself to a stay in one of the 2 guestrooms, featuring private pools. Kitchens are outfitted with full-sized refrigerators/freezers, ovens, and stovetops. Complimentary wireless Internet access is available to keep you connected. Conveniences include phones, as well as desks and microwaves.

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Solara Resort 4 Bedroom Home with Private Pool 4 Home

Vacation Home

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Osceola
Solara Resort 4 Bedroom Home with Private Pool 4 Home Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, within a 15-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This golf vacation home is 8.7 mi (14 km) from Walt Disney World® Resort and 10.3 mi (16.6 km) from Disney's Animal Kingdom® Theme Park.

Solara Resort 4 Bedroom Home with Private Pool 4 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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Extraordinary Solara 7BR Private Pool/spa Near Disney

Vacation Home

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Osceola
Extraordinary Solara 7BR Private Pool/spa Near Disney 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 vacation home is 8.7 mi (14.1 km) from Walt Disney World® Resort and 10.5 mi (17 km) from Disney's Animal Kingdom® Theme Park.

Extraordinary Solara 7BR Private Pool/spa Near Disney Facility and Service
Make use of convenient amenities such as complimentary wireless internet access, an arcade/game room, and barbecue grills.

Extraordinary Solara 7BR Private Pool/spa Near 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

Sweet Magnolia 4 Bedroom Home by RedAwning

Vacation Home

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Osceola
Sweet Magnolia 4 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 Mystic Dunes Golf Club. This vacation home is 6.3 mi (10.1 km) from ESPN Wide World of Sports Complex and 6.7 mi (10.8 km) from Old Town.

Sweet Magnolia 4 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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Interior

ChampionsGate 9 Bedroom Pool Home with Game Room 9 Home

Vacation Home

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Osceola
ChampionsGate 9 Bedroom Pool Home with Game Room 9 Home 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 11.8 mi (19 km) from Old Town and 12.6 mi (20.2 km) from ESPN Wide World of Sports Complex.

ChampionsGate 9 Bedroom Pool Home with Game Room 9 Home 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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Spacious Home With Private Pool, Fast Wifi, Work Space & Games - Snowbirds OK

Vacation Home

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Osceola
Spacious Home With Private Pool, Fast Wifi, Work Space & Games - Snowbirds OK 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 11.3 mi (18.2 km) from Old Town and 12.2 mi (19.6 km) from ESPN Wide World of Sports Complex.

Spacious Home With Private Pool, Fast Wifi, Work Space & Games - Snowbirds OK Facility and Service
Take advantage of recreation opportunities such as a fitness center, or other amenities including complimentary wireless internet access and an arcade/game room.

Spacious Home With Private Pool, Fast Wifi, Work Space & Games - Snowbirds OK Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Others

Wonderful Home With Private Pool at Reunion

Vacation Home

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Osceola
Wonderful Home 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 6.9 mi (11.1 km) from Walt Disney World® Resort and 8.9 mi (14.4 km) from Old Town.

Wonderful Home With Private Pool at Reunion Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a hot tub. Additional amenities at this vacation home include complimentary wireless internet access and an arcade/game room.

Wonderful Home 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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Windsor Hills Resort 6 Bedroom Private Pool+Spa Home 6 Home

Vacation Home

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Osceola
Windsor Hills Resort 6 Bedroom Private Pool+Spa Home 6 Home Location
Located in Kissimmee (Windsor Hills), this vacation home is within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This vacation home is 6.3 mi (10.2 km) from ESPN Wide World of Sports Complex and 6.3 mi (10.2 km) from Old Town.

Windsor Hills Resort 6 Bedroom Private Pool+Spa Home 6 Home 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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Windsor Hills Resort 4 Bedroom Private Pool Home 4 Home

Vacation Home

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Osceola
Windsor Hills Resort 4 Bedroom Private Pool Home 4 Home 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 Old Town. This vacation home is 5.2 mi (8.4 km) from ESPN Wide World of Sports Complex and 6.1 mi (9.8 km) from Disney's Hollywood Studios®.

Windsor Hills Resort 4 Bedroom Private Pool Home 4 Home 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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Others

Mvv7485 - 3BR House Near Disney With Hot Tub

Vacation Home

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Osceola
Mvv7485 - 3BR House Near Disney With Hot Tub Location
With a stay at this cottage in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and 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®.

Mvv7485 - 3BR House Near Disney With Hot Tub Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and barbecue grills.

Mvv7485 - 3BR House Near Disney With Hot Tub Rooms
Make yourself comfortable in this air-conditioned cottage, which features a fireplace. A kitchen is outfitted with an oven, a stovetop, and a microwave. Conveniences include a washer/dryer and an iron/ironing board.

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Others

Sun & Fun Storey Lake

Vacation Home

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Osceola
Sun & Fun Storey Lake 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 6.2 mi (9.9 km) from Disney Springs™ and 7.1 mi (11.4 km) from Walt Disney World® Resort.

Sun & Fun Storey Lake Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center. Additional amenities at this vacation home include complimentary wireless internet access and an arcade/game room.

Sun & Fun Storey Lake 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 lanai. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Digital television is provided for your entertainment.

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Private pool

Gorgeous 4 Bd w/ Pool at Champions Gate Resort 1020

Vacation Home

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Osceola
Gorgeous 4 Bd w/ Pool at Champions Gate Resort 1020 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 family-friendly vacation home is 12.2 mi (19.6 km) from Old Town and 13 mi (20.8 km) from ESPN Wide World of Sports Complex.

Gorgeous 4 Bd w/ Pool at Champions Gate Resort 1020 Facility and Service
Enjoy a range of recreational amenities, including a complimentary water park, an outdoor pool, and a lazy river. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Gorgeous 4 Bd w/ Pool at Champions Gate Resort 1020 Rooms
Treat yourself to a stay in this individually decorated 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. Wired and wireless internet access is complimentary, while a DVD player and cable programming provide entertainment. Conveniences include a safe and a desk, and you can also request a crib/infant bed (surcharge).

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Grhlk2740 - Emerald Island Resort - 7 Bed 4 Baths House

Vacation Home

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Osceola
Grhlk2740 - Emerald Island Resort - 7 Bed 4 Baths House Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This golf vacation home is 7.1 mi (11.4 km) from ESPN Wide World of Sports Complex and 7.2 mi (11.6 km) from Old Town.

Grhlk2740 - Emerald Island Resort - 7 Bed 4 Baths House Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools or 2 hot tubs. Additional features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhlk2740 - Emerald Island Resort - 7 Bed 4 Baths House 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 or patio. A kitchen is outfitted with a refrigerator, an oven, and a microwave. A flat-screen television is provided for your entertainment.

Restaurant and Cafe
Unwind at the end of the day with a drink at the bar/lounge or the poolside bar.

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Stunning 4 Bd Close to Disney @ Storey Lake 2569

Vacation Home

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Osceola
Stunning 4 Bd Close to Disney @ Storey Lake 2569 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 family-friendly vacation home is 7.6 mi (12.2 km) from Disney Springs™ and 8.6 mi (13.8 km) from Walt Disney World® Resort.

Stunning 4 Bd Close to Disney @ Storey Lake 2569 Facility and Service
Don't miss out on the many recreational opportunities, including a complimentary water park, an outdoor pool, and a lazy river. Additional features at this vacation home include concierge services, a television in a common area, and charcoal grills.

Stunning 4 Bd Close to Disney @ Storey Lake 2569 Rooms
Treat yourself to a stay in this individually decorated 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. Cable programming and a DVD player are provided for your entertainment, while complimentary wired internet access keeps you connected. Conveniences include a safe and a desk, and you can also request a crib/infant bed (surcharge).

See details
5.0/5
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1576tl-the Retreat at Champions Gate

Vacation Home

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Osceola
1576tl-the Retreat at Champions Gate 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 11.4 mi (18.3 km) from Old Town and 12.2 mi (19.6 km) from ESPN Wide World of Sports Complex.

1576tl-the Retreat at Champions Gate Facility and Service
Be sure to enjoy recreational amenities, including an outdoor pool, an outdoor tennis court, and a fitness center. This vacation home also features an arcade/game room and barbecue grills.

1576tl-the Retreat at Champions Gate Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. A flat-screen television is provided for your entertainment. Conveniences include a microwave and an iron/ironing board.

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

See details
Fully Booked
Let's check on other dates!
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Vacation Homes in Osceola

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