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Vacation Homes in Osceola

Osceola
Mon, 16 Nov 2026 - Tue, 17 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 1.000+ Vacation Homes in Osceola
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Grhmvd1596 - Champions Gate Resort - 5 Bed 4 Baths Townhouse

Vacation Home

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Osceola
Grhmvd1596 - Champions Gate Resort - 5 Bed 4 Baths Townhouse 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 family-friendly vacation home is 11.5 mi (18.6 km) from Old Town and 12.3 mi (19.8 km) from ESPN Wide World of Sports Complex.

Grhmvd1596 - Champions Gate Resort - 5 Bed 4 Baths Townhouse Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools. Additional features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhmvd1596 - Champions Gate Resort - 5 Bed 4 Baths Townhouse Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private plunge pool and a flat-screen TV. There's a private balcony or patio. A kitchen is outfitted with a refrigerator, an oven, and a microwave. Cable 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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Interior entrance

Wonderful 5Bd Close to Disney @ Storey Lake 2980

Vacation Home

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Osceola
Wonderful 5Bd Close to Disney @ Storey Lake 2980 Location
Located in Kissimmee, this vacation home is 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 (13.9 km) from Walt Disney World® Resort.

Wonderful 5Bd Close to Disney @ Storey Lake 2980 Facility and Service
Enjoy a range of recreational amenities, including a complimentary water park, an outdoor pool, and a lazy river. Additional features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Wonderful 5Bd Close to Disney @ Storey Lake 2980 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 rollaway/extra bed (surcharge).

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5.0/5
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Grhcdw9151 - Champions Gate Resort - 9 Bed 5 Baths House

Vacation Home

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Osceola
Grhcdw9151 - 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 12.7 mi (20.5 km) from Old Town and 13.3 mi (21.4 km) from Walt Disney World® Resort.

Grhcdw9151 - 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 features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhcdw9151 - 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.

See details
Fully Booked
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Championsgate Resort 5 Bedroom Pool Home 5 Home

Vacation Home

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Osceola
Championsgate Resort 5 Bedroom Pool Home 5 Home 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 golf vacation home is 12.8 mi (20.6 km) from Old Town and 13.3 mi (21.4 km) from ESPN Wide World of Sports Complex.

Championsgate Resort 5 Bedroom 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 is available to keep you connected. Conveniences include a coffee/tea maker and a washing machine.

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Magical Dreams 5 Bedroom Home

Vacation Home

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Osceola
Magical Dreams 5 Bedroom Home Location
With a stay at this vacation home in Kissimmee (Indian Point), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 9.4 mi (15.1 km) from Disney Springs™ and 9.5 mi (15.3 km) from ESPN Wide World of Sports Complex.

Magical Dreams 5 Bedroom Home Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Others

Ov1457 - Emerald Island - 3 Bed 3 Baths Townhome

Vacation Home

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Osceola
Ov1457 - Emerald Island - 3 Bed 3 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 Mystic Dunes Golf Club. This family-friendly vacation home is 6.7 mi (10.8 km) from ESPN Wide World of Sports Complex and 6.8 mi (10.9 km) from Old Town.

Ov1457 - Emerald Island - 3 Bed 3 Baths Townhome Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Ov1457 - Emerald Island - 3 Bed 3 Baths Townhome Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a refrigerator and an oven. There's a private balcony or patio. 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.

Restaurant and Cafe
Relax with your favorite drink at the bar/lounge or the poolside bar.

See details
Fully Booked
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Sport & Beauty

Grhbch3069 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse

Vacation Home

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Osceola
Grhbch3069 - Paradise Palms Resort - 4 Bed 3 Baths 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 family-friendly vacation home is 7.9 mi (12.7 km) from Disney's Animal Kingdom® Theme Park and 9.1 mi (14.7 km) from ESPN Wide World of Sports Complex.

Grhbch3069 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse 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.

Grhbch3069 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private plunge pool and a flat-screen TV. There's a private balcony or patio. A kitchen is outfitted with a refrigerator, an oven, and a microwave. Cable television is provided for your entertainment.

Restaurant and Cafe
Satisfy your appetite at the vacation home's coffee shop/cafe, or stop in at the grocery/convenience store. Relax with your favorite drink at the bar/lounge or the poolside bar.

See details
Fully Booked
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Exterior & Views

6BR 4BA Home in Windsor Hills by CV-2564

Vacation Home

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Osceola
6BR 4BA Home in Windsor Hills by CV-2564 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 5.9 mi (9.5 km) from ESPN Wide World of Sports Complex and 6.4 mi (10.3 km) from Old Town.

6BR 4BA Home in Windsor Hills by CV-2564 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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Infinity Pool Oasis With Golf Views at Reunion

Vacation Home

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Osceola
Infinity Pool Oasis With Golf Views at Reunion Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be within a 15-minute drive of Walt Disney World® Resort and Reunion Resort Golf Course. This vacation home is 9.4 mi (15.1 km) from ESPN Wide World of Sports Complex and 9.9 mi (15.9 km) from Disney's Hollywood Studios®.

Infinity Pool Oasis With Golf Views at Reunion Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a hot tub. This vacation home also features complimentary wireless internet access, an arcade/game room, and barbecue grills.

Infinity Pool Oasis With Golf Views at Reunion Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Vacation home Orlando Florida United States

Vacation Home

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Osceola
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Living area

Modern Oasis Near Shopping n Golf Course w Pool

Vacation Home

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Osceola
Modern Oasis Near Shopping n Golf Course w Pool Location
With a stay at this vacation home in Four Corners, you'll be near the beach, within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This vacation home is 12 mi (19.4 km) from Old Town and 12.7 mi (20.4 km) from Walt Disney World® Resort.

Modern Oasis Near Shopping n Golf Course w Pool Facility and Service
Take advantage of recreation opportunities including an outdoor pool and an outdoor tennis court. Additional amenities at this vacation home include complimentary wireless internet access and an arcade/game room.

Modern Oasis Near Shopping n Golf Course w Pool 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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Others

Grhbuc2995 - Paradise Palms Resort - 5 Bed 5 Baths House

Vacation Home

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Osceola
Grhbuc2995 - Paradise Palms Resort - 5 Bed 5 Baths House Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Walt Disney World® Resort and Old Town. This family-friendly vacation home is 8.4 mi (13.5 km) from Disney's Animal Kingdom® Theme Park and 9.3 mi (14.9 km) from ESPN Wide World of Sports Complex.

Grhbuc2995 - Paradise Palms Resort - 5 Bed 5 Baths House Facility and Service
Practice your swing on the golf course or dip into one of the 3 hot tubs. Additional features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhbuc2995 - Paradise Palms Resort - 5 Bed 5 Baths House Rooms
Treat yourself to a stay in this individually furnished 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
Satisfy your appetite at the vacation home's coffee shop/cafe, or stop in at the grocery/convenience store. Relax with your favorite drink at the bar/lounge or the poolside bar.

See details
Fully Booked
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Others

Allamanda Holiday Home 4 Bedroom

Vacation Home

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Osceola
Allamanda Holiday Home 4 Bedroom 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 8.5 mi (13.7 km) from Disney Springs™ and 8.7 mi (13.9 km) from ESPN Wide World of Sports Complex.

Allamanda Holiday Home 4 Bedroom Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a hot tub.

Allamanda Holiday Home 4 Bedroom Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool and a private hot tub. A kitchen is outfitted with a refrigerator. Complimentary wireless internet access is available to keep you connected. Conveniences include a separate sitting area and a coffee/tea maker, as well as a phone with free local calls.

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4.0/5
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Spacious Home With Private Pool, Clubhouse - Near Theme Parks

Vacation Home

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Osceola
Spacious Home With Private Pool, Clubhouse - Near Theme Parks 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 family-friendly vacation home is 11.5 mi (18.5 km) from Old Town and 12.3 mi (19.7 km) from ESPN Wide World of Sports Complex.

Spacious Home With Private Pool, Clubhouse - Near Theme Parks 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 complimentary wireless internet access, an arcade/game room, and barbecue grills.

Spacious Home With Private Pool, Clubhouse - Near Theme Parks Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Others

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

1472rf-the Retreat at Championsgate

Vacation Home

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Osceola
1472rf-the Retreat at Championsgate 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 golf vacation home is 12.8 mi (20.6 km) from Old Town and 13.4 mi (21.6 km) from Walt Disney World® Resort.

1472rf-the Retreat at Championsgate Facility and Service
Be sure to enjoy recreational amenities, including an outdoor pool, an outdoor tennis court, and a fitness center.

1472rf-the Retreat at Championsgate Rooms
Make yourself comfortable in your vacation home.

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5 Bed 5 Bath In 5 Star Resort Near Disney! 5 Bedroom Home by RedAwning

Vacation Home

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Osceola
5 Bed 5 Bath In 5 Star Resort Near Disney! 5 Bedroom Home by RedAwning Location
With a stay at this vacation home in Kissimmee, you'll be a 5-minute drive from Old Town and 8 minutes from Orlando Vineland Premium Outlets. This vacation home is 5.9 mi (9.5 km) from Disney Springs™ and 6.7 mi (10.8 km) from ESPN Wide World of Sports Complex.

5 Bed 5 Bath In 5 Star Resort Near Disney! 5 Bedroom Home by RedAwning Rooms
Make yourself comfortable in this air-conditioned vacation home, which has a kitchen. Complimentary wireless internet access is available to keep you connected.

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ACO KISSIMMEE VACATION HOMES

Vacation Home

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Osceola
This unpretentious hotel can be found in Kissimmee Area.
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Sport & Beauty

8832cruden

Vacation Home

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Osceola
8832cruden Location
With a stay at this vacation home in Four Corners, you'll be within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This spa vacation home is 12.3 mi (19.8 km) from Old Town and 12.5 mi (20.2 km) from Walt Disney World® Resort.

8832cruden Facility and Service
Take time to pamper yourself with a visit to the full-service spa. If you're looking for recreational opportunities, you'll find an outdoor pool and a fitness center.

8832cruden Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and a microwave. An LED television and a video-game console are provided for your entertainment, while complimentary wireless internet access keeps you connected.

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Radiant Retreat With Golf Course Views at Reunion

Vacation Home

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Osceola
Radiant Retreat With Golf Course Views 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 vacation home is 7.5 mi (12.1 km) from Walt Disney World® Resort and 9.5 mi (15.3 km) from Old Town.

Radiant Retreat With Golf Course Views at Reunion 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.

Radiant Retreat With Golf Course Views at Reunion 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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Vacation Homes in Osceola

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