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Vacation Homes in Osceola

Osceola
Sat, 14 Nov 2026 - Sun, 15 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 1.000+ Vacation Homes in Osceola
Bedroom

8802 Macapa Drive

Private Vacation Home

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Osceola
8802 Macapa Drive Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center. This family-friendly vacation home is 10.4 mi (16.7 km) from Disney's Animal Kingdom® Theme Park and 11.6 mi (18.7 km) from Old Town.

8802 Macapa Drive Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including an arcade/game room.

8802 Macapa Drive 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 dishwasher. Complimentary wireless internet access is available to keep you connected.

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Pp8953 - 4BR House With Pool Near Disney Area

Vacation Home

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Osceola
Pp8953 - 4BR House With Pool Near Disney Area 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 8 mi (12.8 km) from Disney's Animal Kingdom® Theme Park and 9.2 mi (14.8 km) from ESPN Wide World of Sports Complex.

Pp8953 - 4BR House With Pool Near Disney Area Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Pp8953 - 4BR House With Pool Near Disney Area Rooms
Make yourself comfortable in this individually decorated cottage, featuring a kitchen with an oven and a stovetop. There's a private patio. Conveniences include a microwave and a washer/dryer.

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Sport & Beauty

Ip60288 - Paradise Palms - 5 Bed 4 Baths Townhome

Vacation Home

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Osceola
Ip60288 - Paradise Palms - 5 Bed 4 Baths Townhome 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 family-friendly vacation home is 8.3 mi (13.4 km) from Disney's Animal Kingdom® Theme Park and 9.2 mi (14.8 km) from ESPN Wide World of Sports Complex.

Ip60288 - Paradise Palms - 5 Bed 4 Baths Townhome Facility and Service
Practice your swing on the golf course or dip into one of the 2 hot tubs. Additional features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Ip60288 - Paradise Palms - 5 Bed 4 Baths Townhome 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 balcony or patio. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. 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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Bedroom

8912prw- NON Renting July 7, 2022 Windsor at Westside

Vacation Home

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Osceola
8912prw- NON Renting July 7, 2022 Windsor at Westside Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, within a 10-minute drive of Walt Disney World® Resort and Old Town. This golf vacation home is 4.9 mi (7.9 km) from ESPN Wide World of Sports Complex and 5.6 mi (8.9 km) from Disney's Hollywood Studios®.

8912prw- NON Renting July 7, 2022 Windsor at Westside Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

8912prw- NON Renting July 7, 2022 Windsor at Westside Rooms
Make yourself comfortable in your vacation home.

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Others

Elegant Home With Resort Amenities, Gameroom

Private Vacation Home

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Osceola
Elegant Home With Resort Amenities, Gameroom Location
With a stay at this vacation home in Four Corners, you'll be within a 15-minute drive of Old Town and Reunion Resort Golf Course. This vacation home is 12.1 mi (19.4 km) from Walt Disney World® Resort and 12 mi (19.3 km) from ESPN Wide World of Sports Complex.

Elegant Home With Resort Amenities, Gameroom Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Elegant Home With Resort Amenities, Gameroom 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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Sport & Beauty

Ov4255 - Paradise Palms - 4 Bed 3 Baths Townhome

Vacation Home

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Osceola
Ov4255 - Paradise Palms - 4 Bed 3 Baths Townhome Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Walt Disney World® Resort and Old Town. This golf vacation home is 8.1 mi (13.1 km) from Disney's Animal Kingdom® Theme Park and 9 mi (14.5 km) from ESPN Wide World of Sports Complex.

Ov4255 - Paradise Palms - 4 Bed 3 Baths Townhome Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Ov4255 - Paradise Palms - 4 Bed 3 Baths Townhome Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private plunge pool. There's a private balcony or patio. A kitchen is outfitted with a refrigerator, an oven, and a microwave. Conveniences include a washer/dryer and a ceiling fan.

Restaurant and Cafe
Grab a bite from the grocery/convenience store serving guests of this vacation home. Wrap up your day with a drink at the poolside bar.

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Exterior & Views

2614 Veranda Palms

Vacation Home

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Osceola
2614 Veranda Palms 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 (11.2 km) from Disney Springs™ and 7.6 mi (12.2 km) from Walt Disney World® Resort.

2614 Veranda Palms Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

2614 Veranda Palms 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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Fully Booked
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Exterior & Views

7BR 4.5BA Home in Emerald Island Resort by CV-2708

Vacation Home

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Osceola
7BR 4.5BA Home in Emerald Island Resort by CV-2708 Location
When you stay at this vacation home in Kissimmee, you'll be on the waterfront, within a 15-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 7.5 mi (12 km) from ESPN Wide World of Sports Complex and 8.1 mi (13.1 km) from Disney's Hollywood Studios®.

7BR 4.5BA Home in Emerald Island Resort by CV-2708 Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a flat-screen TV. A kitchen is outfitted with a full-sized refrigerator/freezer, an oven, and a stovetop. Complimentary wireless internet access keeps you connected, and a video-game console is provided for your entertainment. Conveniences include a microwave and a coffee/tea maker.

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Bedroom

Turquoise Breeze Close to Disney

Vacation Home

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Osceola
Turquoise Breeze Close to Disney Location
With a stay at this vacation home in Kissimmee (Historic Downtown Kissimmee), you'll be within a 5-minute walk of Kissimmee Lakefront Park and Lake Tohopekaliga. This golf vacation home is 9.7 mi (15.6 km) from Old Town and 11.6 mi (18.7 km) from Orlando Vineland Premium Outlets.

Turquoise Breeze Close to Disney Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a refrigerator and an oven. There's a private furnished patio. A 42-inch flat-screen television is provided, with digital programming available.

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3.8/5
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Room

Fun, Dog-friendly Home With Private Pool, High-speed Wifi, W/d, & Game Rooms

Vacation Home

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Osceola
Fun, Dog-friendly Home With Private Pool, High-speed Wifi, W/d, & Game Rooms Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 15-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This vacation home is 9.1 mi (14.6 km) from Walt Disney World® Resort and 10.9 mi (17.5 km) from Disney's Animal Kingdom® Theme Park.

Fun, Dog-friendly Home With Private Pool, High-speed Wifi, W/d, & Game Rooms 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.

Fun, Dog-friendly Home With Private Pool, High-speed Wifi, W/d, & Game Rooms Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

See details
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Bedroom

Rolling_hills_7965

Vacation Home

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Osceola
Rolling_hills_7965 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 6.2 mi (10 km) from ESPN Wide World of Sports Complex and 6.6 mi (10.7 km) from Old Town.

Rolling_hills_7965 Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a garden.

Rolling_hills_7965 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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Room

Spacious Home W/private Pool, Hot Tub & Game Room Near Disney

Vacation Home

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Osceola
Spacious Home W/private Pool, Hot Tub & Game Room Near Disney Location
Located in Kissimmee (Indian Ridge), this vacation home is within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This vacation home is 6.9 mi (11.1 km) from ESPN Wide World of Sports Complex and 7.2 mi (11.5 km) from Old Town.

Spacious Home W/private Pool, Hot Tub & Game Room Near Disney Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a hot tub. This vacation home also features complimentary wireless internet access, an arcade/game room, and barbecue grills.

Spacious Home W/private Pool, Hot Tub & Game Room Near Disney Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Fully Booked
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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.

See details
Fully Booked
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Magical Family Vacation Home near Disney World at Storey Lake, Star Wars Gameroom, Pool, Theater, Mi

Vacation Home

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Osceola
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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
Fully Booked
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Luxury 7BR 7BA House w Private Pool Disney

Vacation Home

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Osceola
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Solara Resort 5 Bedroom Home with Pool + Game Room 5 Home

Vacation Home

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Osceola
Solara Resort 5 Bedroom Home with Pool + 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 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.

Solara Resort 5 Bedroom Home with Pool + 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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Exterior & Views

5 Bedroom House for 10 at Storey Lake

Vacation Home

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Osceola
5 Bedroom House for 10 at 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 6 mi (9.6 km) from Disney Springs™ and 6.7 mi (10.8 km) from ESPN Wide World of Sports Complex.

5 Bedroom House for 10 at Storey Lake Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center.

5 Bedroom House for 10 at Storey Lake Rooms
Make yourself comfortable in this air-conditioned vacation home, 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.

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Stunning 5Bd W/ Pool Close To Disney At Champions Gate 8956

Vacation Home

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Osceola
Stunning 5Bd W/ Pool Close To Disney At Champions Gate 8956 Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This vacation home is 12.5 mi (20.1 km) from Walt Disney World® Resort and 12.7 mi (20.4 km) from Old Town.

Stunning 5Bd W/ Pool Close To Disney At Champions Gate 8956 Rooms
Make yourself comfortable in your vacation home.

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5.0/5
Fully Booked
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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
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 7.5 mi (12.1 km) from Disney Springs™ and 8.6 mi (13.9 km) from Walt Disney World® Resort.

Storey Lake Resort 5 Bedroom Private Pool Home 5 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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Vacation Homes in Osceola

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