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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
Exterior & Views

Shd4720

Vacation Home

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Osceola
Shd4720 Location
With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This cottage is 6 mi (9.6 km) from Disney Springs™ and 6.6 mi (10.7 km) from Walt Disney World® Resort.

Shd4720 Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with an oven and a stovetop. Conveniences include a desk and a microwave.

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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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The Delightful Home 1132

Private Vacation Home

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Osceola
The Delightful Home 1132 Location
With a stay at this vacation home in Four Corners, you'll be within a 15-minute drive of Reunion Resort Golf Course and Mystic Dunes Golf Club. This vacation home is 11.8 mi (19 km) from Old Town and 13.2 mi (21.2 km) from Walt Disney World® Resort.

The Delightful Home 1132 Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including complimentary wireless internet access.

The Delightful Home 1132 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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Ov2564 - Windsor Palms Resort - 4 Bed 2 Baths Townhome

Vacation Home

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Osceola
Ov2564 - Windsor Palms Resort - 4 Bed 2 Baths Townhome 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 7 mi (11.3 km) from ESPN Wide World of Sports Complex and 8.1 mi (13.1 km) from Disney's Hollywood Studios®.

Ov2564 - Windsor Palms Resort - 4 Bed 2 Baths Townhome Facility and Service
While the golfer in the family is out on the course, try one of the other recreational amenities offered, such as a complimentary water park or a hot tub. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Ov2564 - Windsor Palms Resort - 4 Bed 2 Baths Townhome 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 programming along with a DVD player are 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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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.

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Outdoor pool

Six BR Home at ChampionsGate Resort

Vacation Home

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Osceola
Six BR Home at ChampionsGate Resort 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 11.6 mi (18.7 km) from Old Town and 12.4 mi (19.9 km) from ESPN Wide World of Sports Complex.

Six BR Home at ChampionsGate Resort Facility and Service
While the golfer in the family is out on the course, try one of the other recreational amenities offered, such as outdoor tennis courts or an outdoor pool.

Six BR Home at ChampionsGate Resort Rooms
Treat yourself to a stay in this individually furnished vacation home, which features a private pool and an outdoor private hot tub. There's a private furnished lanai. A kitchen is outfitted with a full-sized refrigerator/freezer, 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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Exterior & Views

3081 Beach Palm Avenue

Private Vacation Home

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Osceola
3081 Beach Palm Avenue Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 15-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 8 mi (12.9 km) from Disney's Animal Kingdom® Theme Park and 9.6 mi (15.4 km) from Disney's Hollywood Studios®.

3081 Beach Palm Avenue Facility and Service
Don't miss out on the many recreational opportunities, including an outdoor pool, an indoor pool, and an outdoor tennis court. Additional amenities at this vacation home include complimentary wireless internet access and an arcade/game room.

3081 Beach Palm Avenue Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a refrigerator and an oven. There's a private balcony. Conveniences include a microwave and a coffee/tea maker.

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Stunning 4Bd W/ Pool @ Storey Lake 4239

Vacation Home

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Osceola
Stunning 4Bd W/ Pool @ Storey Lake 4239 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 (13.9 km) from Walt Disney World® Resort.

Stunning 4Bd W/ Pool @ Storey Lake 4239 Rooms
Make yourself comfortable in this vacation home, which has a kitchen.

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Grhshm9028 - Champions Gate Resort - 6 Bed 6 Baths House

Vacation Home

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Osceola
Grhshm9028 - Champions Gate Resort - 6 Bed 6 Baths House 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 11.7 mi (18.9 km) from Old Town and 12.5 mi (20.1 km) from ESPN Wide World of Sports Complex.

Grhshm9028 - 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. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhshm9028 - 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. Relax with your favorite drink at the bar/lounge or the poolside bar.

See details
Fully Booked
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Exterior & Views

4 Bed 8065

Vacation Home

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Osceola
4 Bed 8065 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 6.3 mi (10.1 km) from ESPN Wide World of Sports Complex and 7 mi (11.2 km) from Disney's Hollywood Studios®.

4 Bed 8065 Facility and Service
This smoke-free vacation home features a playground.

4 Bed 8065 Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a stovetop and a dishwasher. There's a private patio. Wired and wireless internet access is complimentary, while a flat-screen television and a DVD player provide entertainment. Conveniences include a desk and a washer/dryer.

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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.

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Exterior & Views

Windsor Hills Resort 3 Bedroom 1st Floor Condo with Resort Access 3 Condo

Private Vacation Home

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Osceola
Windsor Hills Resort 3 Bedroom 1st Floor Condo with Resort Access 3 Condo Location
With a stay at this condo in Kissimmee (Windsor Hills), you'll be within a 10-minute drive of Walt Disney World® Resort and Old Town. This condo is 5.7 mi (9.2 km) from ESPN Wide World of Sports Complex and 6.1 mi (9.8 km) from Disney's Hollywood Studios®.

Windsor Hills Resort 3 Bedroom 1st Floor Condo with Resort Access 3 Condo Rooms
Make yourself comfortable in this condo, 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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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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Fireworks Night -Storey Lake by Shine Villas 709 apts

Vacation Home

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Osceola
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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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5BR Nemo Room Townhouse Pool, 10min Disney

Vacation Home

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Osceola
5BR Nemo Room Townhouse Pool, 10min Disney Location
With a stay at this villa in Kissimmee, you'll be within a 10-minute drive of Flamingo Crossings Town Center and Mystic Dunes Golf Club. This villa is 6.5 mi (10.5 km) from Walt Disney World® Resort and 8.2 mi (13.2 km) from Disney's Animal Kingdom® Theme Park.

5BR Nemo Room Townhouse Pool, 10min Disney Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a hot tub. Additional amenities at this villa include complimentary wireless internet access, an arcade/game room, and barbecue grills.

5BR Nemo Room Townhouse Pool, 10min Disney Rooms
Your villa features a Smart TV. There's a private furnished patio. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. The bathroom has a bathtub or shower and complimentary toiletries.

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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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2 Bed Champions Gate Golf Resort 2 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
2 Bed Champions Gate Golf Resort 2 Bedroom Townhouse by RedAwning 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 vacation home is 12.1 mi (19.5 km) from Old Town and 12.9 mi (20.7 km) from ESPN Wide World of Sports Complex.

2 Bed Champions Gate Golf Resort 2 Bedroom Townhouse by RedAwning Rooms
Make yourself comfortable in your air-conditioned vacation home, which features a microwave. Complimentary wireless internet access is available to keep you connected.

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Grhokc8484 - Emerald Island Resort - 5 Bed 4 Baths House

Vacation Home

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Osceola
Grhokc8484 - Emerald Island Resort - 5 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 (11.5 km) from Old Town and 7.2 mi (11.5 km) from ESPN Wide World of Sports Complex.

Grhokc8484 - Emerald Island Resort - 5 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 amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhokc8484 - Emerald Island Resort - 5 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
Relax with your favorite drink at the bar/lounge or the poolside bar.

See details
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Vacation Homes in Osceola

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