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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
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Encore 8BR Home, Pool & Spa, 10 Min to Disney

Vacation Home

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Osceola
Encore 8BR Home, Pool & Spa, 10 Min to Disney 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 ChampionsGate Golf Club. 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.

Encore 8BR Home, Pool & Spa, 10 Min to Disney Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a hot tub.

Encore 8BR Home, Pool & Spa, 10 Min to Disney Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Sport & Beauty

7605reclife

Vacation Home

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Osceola
7605reclife Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 4.9 mi (8 km) from ESPN Wide World of Sports Complex and 5.8 mi (9.4 km) from Disney's Hollywood Studios®.

7605reclife Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center.

7605reclife Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with a refrigerator and a microwave.

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Room

Ultimate Themed Luxury - Game Room Theater Pool

Vacation Home

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Osceola
Ultimate Themed Luxury - Game Room Theater Pool 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 6.1 mi (9.8 km) from Disney Springs™ and 7.1 mi (11.5 km) from Walt Disney World® Resort.

Ultimate Themed Luxury - Game Room Theater Pool Facility and Service
Take in the views from a garden.

Ultimate Themed Luxury - Game Room Theater Pool Rooms
Make yourself comfortable in your vacation home.

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Room

Beautiful Home With Private Pool, Screened Lanai, Wifi, Private W/d, and AC

Vacation Home

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Osceola
Beautiful Home With Private Pool, Screened Lanai, Wifi, Private W/d, and AC Location
With a stay at this vacation home in Kissimmee (Lake Berkley), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 9 mi (14.5 km) from Disney Springs™ and 9.2 mi (14.8 km) from Walt Disney World® Resort.

Beautiful Home With Private Pool, Screened Lanai, Wifi, Private W/d, and AC Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Beautiful Home With Private Pool, Screened Lanai, Wifi, Private W/d, and AC Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Bedroom

8917stin New Luxury Furnished 5 Bedroom 4 Bathroom

Vacation Home

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Osceola
8917stin New Luxury Furnished 5 Bedroom 4 Bathroom 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 11.5 mi (18.4 km) from Old Town and 12.2 mi (19.7 km) from ESPN Wide World of Sports Complex.

8917stin New Luxury Furnished 5 Bedroom 4 Bathroom Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center.

8917stin New Luxury Furnished 5 Bedroom 4 Bathroom 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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Grhmvd1508 - Champions Gate Resort - 6 Bed 6 Baths House

Vacation Home

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Osceola
Grhmvd1508 - Champions Gate Resort - 6 Bed 6 Baths House 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 11.8 mi (18.9 km) from Old Town and 12.5 mi (20.2 km) from ESPN Wide World of Sports Complex.

Grhmvd1508 - Champions Gate Resort - 6 Bed 6 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. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Grhmvd1508 - Champions Gate Resort - 6 Bed 6 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
Enjoy a meal at the restaurant or snacks in the vacation home's coffee shop/cafe. Unwind at the end of the day with a drink at the bar/lounge or the poolside bar.

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Others

9004srl-solara

Vacation Home

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Osceola
9004srl-solara Location
When you stay at this villa 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 villa is 8.6 mi (13.8 km) from Walt Disney World® Resort and 10.4 mi (16.7 km) from Disney's Animal Kingdom® Theme Park.

9004srl-solara Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including an arcade/game room.

9004srl-solara Rooms
Make yourself comfortable in this villa, which has a kitchen.

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Others

801dsd-the Retreat at Championsgate

Vacation Home

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Osceola
801dsd-the Retreat at Championsgate 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®.

801dsd-the Retreat at Championsgate Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center.

801dsd-the Retreat at Championsgate Rooms
Make yourself comfortable in your vacation home.

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Windsor-5 Bed Townhouse W Splashpool-3801Ww

Vacation Home

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Osceola
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Spacious 4Bd W/ Pool & Close To Disney @ Storey Lake 2560

Vacation Home

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Osceola
Spacious 4Bd W/ Pool & Close To Disney @ Storey Lake 2560 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 7.6 mi (12.2 km) from Disney Springs™ and 8.6 mi (13.8 km) from Walt Disney World® Resort.

Spacious 4Bd W/ Pool & Close To Disney @ Storey Lake 2560 Facility and Service
Take in the views from a garden and make use of amenities such as barbecue grills.

Spacious 4Bd W/ Pool & Close To Disney @ Storey Lake 2560 Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a full-sized refrigerator/freezer and a stovetop. Conveniences include a desk and a microwave.

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5.0/5
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Grhrfd1469 - Champions Gate Resort - 9 Bed 5 Baths House

Vacation Home

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Osceola
Grhrfd1469 - Champions Gate Resort - 9 Bed 5 Baths House 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 family-friendly vacation home is 12.8 mi (20.7 km) from Old Town and 13.4 mi (21.6 km) from Walt Disney World® Resort.

Grhrfd1469 - Champions Gate Resort - 9 Bed 5 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 amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhrfd1469 - Champions Gate Resort - 9 Bed 5 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
Enjoy a meal at the restaurant or snacks in the vacation home's coffee shop/cafe. Relax with your favorite drink at the bar/lounge or the poolside bar.

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Fully Booked
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Spacious 4Bd Disney W Resort Access At Lucaya 3210

Vacation Home

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Osceola
Spacious 4Bd Disney W Resort Access At Lucaya 3210 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 7.1 mi (11.4 km) from Disney's Animal Kingdom® Theme Park and 8.3 mi (13.3 km) from Old Town.

Spacious 4Bd Disney W Resort Access At Lucaya 3210 Rooms
Make yourself comfortable in this vacation home, which has a kitchen.

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Mvv7460 - 3BR House Near Disney w/ Hot tub

Vacation Home

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Osceola
Mvv7460 - 3BR House Near Disney w/ Hot tub Location
With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Old Town. This cottage is 4.7 mi (7.5 km) from ESPN Wide World of Sports Complex and 5.2 mi (8.3 km) from Disney's Hollywood Studios®.

Mvv7460 - 3BR House Near Disney w/ Hot tub Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and barbecue grills.

Mvv7460 - 3BR House Near Disney w/ 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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Exterior & Views

Stars Align Storey Lake by Shine Villas villa

Vacation Home

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Osceola
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601dsd-the Retreat At Championsgate 5 Bedroom Home by RedAwning

Vacation Home

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Osceola
601dsd-the Retreat At Championsgate 5 Bedroom Home by RedAwning Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of ChampionsGate Golf Club and Four Corners FC. This vacation home is 12.5 mi (20.2 km) from Old Town and 13 mi (20.9 km) from ESPN Wide World of Sports Complex.

601dsd-the Retreat At Championsgate 5 Bedroom Home by RedAwning Rooms
Make yourself comfortable in your vacation home, which features a refrigerator. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. The bathroom has a bathtub or shower.Conveniences include a coffee/tea maker and a washing machine.

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Exterior & Views

5 Bedroom 5 Bathroom Villa

Vacation Home

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Osceola
5 Bedroom 5 Bathroom Villa 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 family-friendly 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.

5 Bedroom 5 Bathroom Villa Facility and Service
Take time to pamper yourself with a visit to the full-service spa. This villa also features complimentary wireless internet access and an arcade/game room.

5 Bedroom 5 Bathroom Villa Rooms
Make yourself comfortable in this villa, which has a kitchen. There's a private lanai. Complimentary wireless internet access keeps you connected, and a flat-screen television is provided for your entertainment.

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Others

Candy Palm 4 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
Candy Palm 4 Bedroom Townhouse by RedAwning Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Flamingo Crossings Town Center and Mystic Dunes Golf Club. This vacation home is 6.5 mi (10.5 km) from Walt Disney World® Resort and 8.3 mi (13.4 km) from Disney's Animal Kingdom® Theme Park.

Candy Palm 4 Bedroom Townhouse 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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Sport & Beauty

Grhval8172 - Reunion Resort - 8 Bed 8 Baths House

Vacation Home

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Osceola
Grhval8172 - Reunion Resort - 8 Bed 8 Baths House Location
With a stay at this vacation home in Kissimmee (Champions Gate), you'll be within a 15-minute drive of Reunion Resort Golf Course and Mystic Dunes Golf Club. This family-friendly vacation home is 8.4 mi (13.5 km) from Walt Disney World® Resort and 10.2 mi (16.4 km) from ESPN Wide World of Sports Complex.

Grhval8172 - Reunion Resort - 8 Bed 8 Baths House Facility and Service
Dip into one of the 8 outdoor pools or 2 hot tubs and enjoy other recreational amenities, which include a complimentary water park. Additional features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhval8172 - Reunion Resort - 8 Bed 8 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 with cable programming is available for your entertainment, and a video-game console is also provided.

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

Gorgeous Decor 4 Bd w/ Pool Close to Disney 4820

Vacation Home

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Osceola
Gorgeous Decor 4 Bd w/ Pool Close to Disney 4820 Location
With a stay at this vacation home in Kissimmee, you'll be a 4-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This family-friendly vacation home is 5.2 mi (8.4 km) from Disney Springs™ and 6.2 mi (10 km) from Walt Disney World® Resort.

Gorgeous Decor 4 Bd w/ Pool Close to Disney 4820 Facility and Service
Don't miss out on the many recreational opportunities, 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 Decor 4 Bd w/ Pool Close to Disney 4820 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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Veranda Palm Resort 12br 2486

Vacation Home

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Osceola
Veranda Palm Resort 12br 2486 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 7.6 mi (12.2 km) from Disney Springs™ and 8.3 mi (13.3 km) from Walt Disney World® Resort.

Veranda Palm Resort 12br 2486 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.

Veranda Palm Resort 12br 2486 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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Vacation Homes in Osceola

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