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Vacation Homes in Osceola

Osceola
Tue, 17 Nov 2026 - Wed, 18 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 1.000+ Vacation Homes in Osceola
Room

Spacious 9br, 9BA Resort Home w/ Private Pool

Vacation Home

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Osceola
Spacious 9br, 9BA Resort Home w/ Private Pool Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This golf vacation home is 9.6 mi (15.4 km) from Disney Springs™ and 10.6 mi (17.1 km) from Walt Disney World® Resort.

Spacious 9br, 9BA Resort Home w/ Private Pool Facility and Service
Enjoy a range of recreational amenities, including an outdoor pool, a hot tub, and a fitness center. Additional amenities at this vacation home include complimentary wireless internet access and barbecue grills.

Spacious 9br, 9BA Resort Home w/ Private Pool Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Disney Area 3BR Condo Pool and Free Parking

Vacation Home

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Osceola
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Sport & Beauty

Bella Vidatown With Full Size Pool! 4 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
Bella Vidatown With Full Size Pool! 4 Bedroom Townhouse by RedAwning Location
With a stay at this vacation home in Kissimmee (Bellavida), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 8.5 mi (13.7 km) from Disney Springs™ and 8.7 mi (14 km) from ESPN Wide World of Sports Complex.

Bella Vidatown With Full Size Pool! 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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Others

5 Bed 4720

Vacation Home

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Osceola
5 Bed 4720 Location
With a stay at this vacation home in Kissimmee (Crystal Cove), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 8.1 mi (13.1 km) from Disney Springs™ and 8.2 mi (13.1 km) from ESPN Wide World of Sports Complex.

5 Bed 4720 Facility and Service
This smoke-free vacation home features a playground.

5 Bed 4720 Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a flat-screen TV. There's a private lanai. A kitchen is outfitted with a stovetop and a dishwasher. Complimentary wired and wireless internet access keeps you connected, and a DVD player is provided for your entertainment.

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Sport & Beauty

Villa Mascarenhas Villa 4 Plenitude Villas

Vacation Home

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Osceola
Villa Mascarenhas Villa 4 Plenitude Villas 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 5.5 mi (8.9 km) from Walt Disney World® Resort and 5.6 mi (9 km) from Disney's Hollywood Studios®.

Villa Mascarenhas Villa 4 Plenitude Villas 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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Bedroom

Olaf's Endless Summer

Vacation Home

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Osceola
Olaf's Endless Summer Location
Located in Kissimmee (Windsor Hills), this vacation home is within a 10-minute drive of Walt Disney World® Resort and Old Town. This family-friendly vacation home is 5.3 mi (8.6 km) from ESPN Wide World of Sports Complex and 6 mi (9.7 km) from Disney's Hollywood Studios®.

Olaf's Endless Summer Facility and Service
Take advantage of recreational opportunities offered, including a complimentary water park, an outdoor pool, and a hot tub. Additional features at this vacation home include complimentary wireless internet access, an arcade/game room, and a picnic area.

Olaf's Endless Summer Rooms
Treat yourself to a stay in this individually decorated 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 an iron/ironing board, and housekeeping is provided on a limited basis.

Restaurant and Cafe
You can enjoy a meal at Windsor Hills Market Gril serving the guests of this vacation home, or stop in at the snack bar/deli. Wrap up your day with a drink at the bar/lounge.

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Sport & Beauty

Jasmine 4 Bedrooms

Vacation Home

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Osceola
Jasmine 4 Bedrooms 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 family-friendly vacation home is 8.3 mi (13.4 km) from Disney Springs™ and 8.6 mi (13.8 km) from Walt Disney World® Resort.

Jasmine 4 Bedrooms Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a hot tub. This vacation home also features complimentary wireless internet access and barbecue grills.

Jasmine 4 Bedrooms Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool and an outdoor private hot tub. There's a private furnished patio. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. A 55-inch Smart television with digital programming provides entertainment, while complimentary wireless internet access keeps you connected.

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5.0/5
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Lively Home With Galactic Themed Bedroom at Encore

Vacation Home

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Osceola
Lively Home With Galactic Themed Bedroom at Encore Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This vacation home is 7.5 mi (12 km) from ESPN Wide World of Sports Complex and 8 mi (12.8 km) from Disney's Hollywood Studios®.

Lively Home With Galactic Themed Bedroom at Encore Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a hot tub.

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

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Others

Windsor Hills Resort 4 Bedroom House Dog Friendly 4 Home

Vacation Home

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Osceola
Windsor Hills Resort 4 Bedroom House Dog Friendly 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 Mystic Dunes Golf Club. This vacation home is 6.3 mi (10.2 km) from ESPN Wide World of Sports Complex and 6.4 mi (10.3 km) from Old Town.

Windsor Hills Resort 4 Bedroom House Dog Friendly 4 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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Others

C'est Banana! 2341

Vacation Home

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Osceola
C'est Banana! 2341 Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This vacation home is 7.9 mi (12.8 km) from Walt Disney World® Resort and 9.7 mi (15.6 km) from Disney's Animal Kingdom® Theme Park.

C'est Banana! 2341 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.

C'est Banana! 2341 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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House with pool in resort

Vacation Home

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Osceola
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Others

Exclusive Windsor Home Near Theme Parks

Private Vacation Home

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Osceola
Exclusive Windsor Home Near Theme Parks Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Flamingo Crossings Town Center and Mystic Dunes Golf Club. 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.

Exclusive Windsor Home Near Theme Parks Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Exclusive Windsor Home Near Theme Parks 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

Berkeley Executive - Five Bedroom Home

Private Vacation Home

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Osceola
Berkeley Executive - Five Bedroom Home Location
With a stay at this vacation home in Kissimmee, you'll be steps from Remington Golf Club and a 3-minute drive from Osceola Center for the Arts. This vacation home is 13.4 mi (21.5 km) from Old Town and 14.2 mi (22.9 km) from Florida Mall.

Berkeley Executive - Five Bedroom Home Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including an arcade/game room.

Berkeley Executive - Five Bedroom Home Rooms
Make yourself comfortable in this vacation home, which features a private pool. There's a private patio. A kitchen is outfitted with a refrigerator, a stovetop, and a microwave. Complimentary wireless internet access is available to keep you connected.

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Exterior & Views

Lucaya 4 Bedrooms 3 Baths Townhome in Gated Community

Vacation Home

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Osceola
Lucaya 4 Bedrooms 3 Baths Townhome in Gated Community Location
With a stay at this vacation home in Kissimmee, you'll be a 3-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This vacation home is 5.2 mi (8.4 km) from Disney Springs™ and 5.5 mi (8.9 km) from ESPN Wide World of Sports Complex.

Lucaya 4 Bedrooms 3 Baths Townhome in Gated Community 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.

Lucaya 4 Bedrooms 3 Baths Townhome in Gated Community Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with a refrigerator and a microwave. Conveniences include a washing machine and an iron/ironing board.

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Exterior & Views

Villa Ariel- Storey Lake

Vacation Home

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Osceola
Great care is taken to ensure guests experience comfort through top-notch services and amenities. Remain linked during your visit by utilizing the complimentary internet access available. Parking is accessible, supplied by the home for guests who arrive by car. Repeatedly enjoy your best-loved attire with the aid of the laundromat available at Villa Ariel- Storey Lake.Crafted for coziness, every guestroom provides an array of features, guaranteeing a tranquil night's sleep while maintaining the level of comfort.Maintain your cleanliness and feel revitalized using a hair dryer available in select guest restrooms.
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1.8/5
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8974 California Palm Road

Vacation Home

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Osceola
8974 California Palm Road 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 8.1 mi (13.1 km) from Disney's Animal Kingdom® Theme Park and 9.7 mi (15.6 km) from Disney's Hollywood Studios®.

8974 California Palm Road Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center.

8974 California Palm Road Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and a stovetop. There's a private balcony or patio. Complimentary wireless internet access is available to keep you connected. Conveniences include a microwave and a coffee/tea maker.

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Room

Stylish Sleek Home With Full Kitchen at Encore

Vacation Home

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Osceola
Stylish Sleek Home With Full Kitchen at Encore Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 10-minute drive of Mystic Dunes Golf Club and Reunion Resort Golf Course. This vacation home is 5.5 mi (8.8 km) from Walt Disney World® Resort and 7.7 mi (12.4 km) from ESPN Wide World of Sports Complex.

Stylish Sleek Home With Full Kitchen at Encore Facility and Service
Take advantage of recreation opportunities such as a hot tub, or other amenities including complimentary wireless internet access and an arcade/game room.

Stylish Sleek Home With Full Kitchen at Encore Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Bathroom

Ip60302 - Fiesta Key - 3 Bed 2.5 Baths Townhome

Vacation Home

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Osceola
Ip60302 - Fiesta Key - 3 Bed 2.5 Baths Townhome Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This golf vacation home is 10 mi (16.1 km) from Disney Springs™ and 10 mi (16.2 km) from ESPN Wide World of Sports Complex.

Ip60302 - Fiesta Key - 3 Bed 2.5 Baths Townhome Facility and Service
Practice your swing on the golf course and enjoy other recreational amenities, such as an outdoor pool and an outdoor tennis court. Additional features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Ip60302 - Fiesta Key - 3 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. A flat-screen television with cable programming is available for your entertainment, and a video-game console is also provided. Conveniences include a microwave and a washer/dryer.

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Ormond Retreat 3 Bedroom Townhouse

Vacation Home

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Osceola
Ormond Retreat 3 Bedroom Townhouse 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 8.4 mi (13.6 km) from Disney Springs™ and 8.7 mi (14 km) from Walt Disney World® Resort.

Ormond Retreat 3 Bedroom Townhouse Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Bedroom

Laguna Reef by Orlando Short Term

Vacation Home

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Osceola
Laguna Reef by Orlando Short Term 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 vacation home is 11.2 mi (18.1 km) from Old Town and 12 mi (19.3 km) from ESPN Wide World of Sports Complex.

Laguna Reef by Orlando Short Term Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center.

Laguna Reef 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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Vacation Homes in Osceola

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