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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
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1513fd - The Retreat at Championsgate

Vacation Home

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Osceola
1513fd - The Retreat at Championsgate 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 golf vacation home is 11.2 mi (18 km) from Old Town and 12 mi (19.3 km) from ESPN Wide World of Sports Complex.

1513fd - The Retreat at Championsgate Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

1513fd - The Retreat at Championsgate Rooms
Make yourself comfortable in this vacation home, which has a kitchen.

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8949 Amelia Downs Trail

Private Vacation Home

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Osceola
8949 Amelia Downs Trail 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 Flamingo Crossings Town Center. This vacation home is 10.2 mi (16.3 km) from Disney's Animal Kingdom® Theme Park and 11.2 mi (18.1 km) from ESPN Wide World of Sports Complex.

8949 Amelia Downs Trail Facility and Service
Enjoy recreational amenities such as an outdoor pool and an indoor pool. Additional amenities at this vacation home include complimentary wireless internet access and an arcade/game room.

8949 Amelia Downs Trail 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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Marvelous Retreat With Themed Bedrooms at Encore

Vacation Home

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Osceola
Marvelous Retreat With Themed Bedrooms 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 ChampionsGate Golf Club. This vacation home is 5.6 mi (8.9 km) from Walt Disney World® Resort and 7.8 mi (12.5 km) from ESPN Wide World of Sports Complex.

Marvelous Retreat With Themed Bedrooms at Encore Facility and Service
Enjoy recreational amenities such as an outdoor pool and a hot tub. This vacation home also features complimentary wireless internet access and an arcade/game room.

Marvelous Retreat With Themed Bedrooms at Encore Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Storey Lake Resort 6 Bedroom Private Pool Home with Game Room 6 Home

Vacation Home

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Osceola
Storey Lake Resort 6 Bedroom Private Pool Home with Game Room 6 Home 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 6.2 mi (10 km) from Disney Springs™ and 7.2 mi (11.6 km) from ESPN Wide World of Sports Complex.

Storey Lake Resort 6 Bedroom Private Pool Home with Game Room 6 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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Exterior & Views

7766 5-bedoom Orlando Vacation Home-windsor Hills

Vacation Home

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Osceola
7766 5-bedoom Orlando Vacation Home-windsor Hills 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 family-friendly vacation home is 6.1 mi (9.8 km) from Old Town and 6.2 mi (10 km) from ESPN Wide World of Sports Complex.

7766 5-bedoom Orlando Vacation Home-windsor Hills Facility and Service
Take time to pamper yourself with a visit to the full-service spa. You're sure to appreciate the recreational amenities, including an outdoor pool and a fitness center. Additional features at this vacation home include an arcade/game room, gift shops/newsstands, and barbecue grills.

7766 5-bedoom Orlando Vacation Home-windsor Hills 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, an oven, and a stovetop. Wired and wireless internet access is complimentary, while a flat-screen television and a DVD player provide entertainment.

Restaurant and Cafe
Quench your thirst with your favorite drink at the bar/lounge.

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5 Bedrooms Townhome w- Splashpool - 8205SA 5 Townhouse by RedAwning

Vacation Home

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Osceola
5 Bedrooms Townhome w- Splashpool - 8205SA 5 Townhouse by RedAwning Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Old Town and HCA Florida Osceola Hospital. This vacation home is 10.6 mi (17.1 km) from Orlando Vineland Premium Outlets and 10.8 mi (17.3 km) from Disney Springs™.

5 Bedrooms Townhome w- Splashpool - 8205SA 5 Townhouse by RedAwning Facility and Service
Enjoy the recreation opportunities such as an outdoor tennis court or make use of other amenities including barbecue grills.

5 Bedrooms Townhome w- Splashpool - 8205SA 5 Townhouse by RedAwning 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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Ov3007 - Windsor Hills Resort - 3 Bed 3 Baths Townhome

Vacation Home

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Osceola
Ov3007 - Windsor Hills Resort - 3 Bed 3 Baths Townhome 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 5.6 mi (9 km) from ESPN Wide World of Sports Complex and 6 mi (9.7 km) from Disney's Hollywood Studios®.

Ov3007 - Windsor Hills Resort - 3 Bed 3 Baths Townhome Facility and Service
Practice your swing on the golf course and enjoy other recreational amenities, such as a complimentary water park and a hot tub. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Ov3007 - Windsor Hills Resort - 3 Bed 3 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. 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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Bathroom

Ip60335 - Coral Cay Resort - 4 Bed 3 Baths Townhome

Vacation Home

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Osceola
Ip60335 - Coral Cay Resort - 4 Bed 3 Baths Townhome 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 family-friendly vacation home is 7.2 mi (11.5 km) from Disney Springs™ and 8.1 mi (13.1 km) from ESPN Wide World of Sports Complex.

Ip60335 - Coral Cay Resort - 4 Bed 3 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.

Ip60335 - Coral Cay Resort - 4 Bed 3 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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Magical Townhouse with balcony at Summerville resort SU7528

Vacation Home

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Osceola
Magical Townhouse with balcony at Summerville resort SU7528 Location
With a stay at this condo in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Old Town. This condo is 5 mi (8 km) from ESPN Wide World of Sports Complex and 5.6 mi (9.1 km) from Disney's Hollywood Studios®.

Magical Townhouse with balcony at Summerville resort SU7528 Facility and Service
Take in the views from a terrace and make use of amenities such as complimentary wireless internet access and an arcade/game room.

Magical Townhouse with balcony at Summerville resort SU7528 Rooms
Make yourself comfortable in this air-conditioned condo, featuring a kitchen with a refrigerator and an oven. Complimentary wireless internet access keeps you connected, and a flat-screen television is provided for your entertainment. Conveniences include a phone, as well as a microwave and a coffee/tea maker.

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4.3/5
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Hollywood Retreat! Sleeps 14!

Vacation Home

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Osceola
Hollywood Retreat! Sleeps 14! 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 golf vacation home is 11.4 mi (18.3 km) from Old Town and 12.1 mi (19.5 km) from ESPN Wide World of Sports Complex.

Hollywood Retreat! Sleeps 14! Facility and Service
Take advantage of recreation opportunities such as an outdoor pool, or other amenities including complimentary wireless internet access and a picnic area.

Hollywood Retreat! Sleeps 14! 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 furnished lanai. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Digital television is provided for your entertainment.

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Themed Rooms & Pool in Storey Lake Resort

Vacation Home

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Osceola
Themed Rooms & Pool in Storey Lake Resort 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 8.7 mi (14 km) from Walt Disney World® Resort.

Themed Rooms & Pool in Storey Lake Resort Facility and Service
Make use of convenient amenities such as complimentary wireless internet access, an arcade/game room, and barbecue grills.

Themed Rooms & Pool in Storey Lake Resort 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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Bedroom

Ov2634 - Emerald Island - 4 Bed 3 Baths Townhome

Vacation Home

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Osceola
Ov2634 - Emerald Island - 4 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 6.9 mi (11 km) from Old Town and 6.9 mi (11.1 km) from ESPN Wide World of Sports Complex.

Ov2634 - Emerald Island - 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.

Ov2634 - Emerald Island - 4 Bed 3 Baths Townhome 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. 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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Room

Four Bedrooms TownHome Close to Disney 5162A

Vacation Home

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Osceola
Four Bedrooms TownHome Close to Disney 5162A Location
When you stay at this vacation home in Kissimmee, you'll be on a lake, a 5-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This family-friendly vacation home is 5.3 mi (8.5 km) from Disney Springs™ and 6 mi (9.6 km) from Walt Disney World® Resort.

Four Bedrooms TownHome Close to Disney 5162A Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Four Bedrooms TownHome Close to Disney 5162A Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool and a Smart TV. There's a private balcony or patio. A kitchen is outfitted with a full-sized refrigerator/freezer, an oven, and a stovetop. Wired and wireless internet access is complimentary, while a 60-inch flat-screen television with cable programming provides entertainment.

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3.6/5
Fully Booked
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4569tb NON Renting 09/13/2021 -storey Lake

Vacation Home

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Osceola
4569tb NON Renting 09/13/2021 -storey Lake Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This golf vacation home is 5.8 mi (9.4 km) from Disney Springs™ and 6.8 mi (11 km) from ESPN Wide World of Sports Complex.

4569tb NON Renting 09/13/2021 -storey Lake Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

4569tb NON Renting 09/13/2021 -storey Lake Rooms
Make yourself comfortable in your vacation home.

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Exterior & Views

Gorgeous 4bd/3ba Reunion Resort Near Disneyland

Vacation Home

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Osceola
Gorgeous 4bd/3ba Reunion Resort Near Disneyland Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be within a 10-minute drive of Reunion Resort Golf Course and Mystic Dunes Golf Club. This vacation home is 6 mi (9.6 km) from Walt Disney World® Resort and 8 mi (13 km) from ESPN Wide World of Sports Complex.

Gorgeous 4bd/3ba Reunion Resort Near Disneyland Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a hot tub.

Gorgeous 4bd/3ba Reunion Resort Near Disneyland Rooms
Make yourself comfortable in this air-conditioned vacation home, which has a kitchen. There's a private balcony or patio.

See details
1.0/5
Fully Booked
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Aco238226 - Emerald Island Resort - 3 Bed 2.5 Baths Townhome

Vacation Home

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Osceola
Aco238226 - Emerald Island Resort - 3 Bed 2.5 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 golf vacation home is 6.8 mi (11 km) from Old Town and 6.9 mi (11.1 km) from ESPN Wide World of Sports Complex.

Aco238226 - Emerald Island Resort - 3 Bed 2.5 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.

Aco238226 - Emerald Island Resort - 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 is provided for your entertainment. Conveniences include a microwave and a sofa bed.

Restaurant and Cafe
Unwind at the end of the day with a drink at the bar/lounge or the poolside bar.

See details
Fully Booked
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Sport & Beauty

6BR Windsor Palms Home by FS FL VH-8036

Vacation Home

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Osceola
6BR Windsor Palms Home by FS FL VH-8036 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 8.2 mi (13.2 km) from Disney's Hollywood Studios® and 9.2 mi (14.8 km) from Disney's Animal Kingdom® Theme Park.

6BR Windsor Palms Home by FS FL VH-8036 Facility and Service
Take advantage of recreation opportunities such as an outdoor pool, or other amenities including an arcade/game room and a picnic area.

6BR Windsor Palms Home by FS FL VH-8036 Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool and an LCD TV. Your pillowtop bed comes with a down comforter. A kitchen is outfitted with a full-sized refrigerator/freezer, an oven, and a microwave. Cable programming and a DVD player are provided for your entertainment, while complimentary wireless internet access keeps you connected.

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Storey Lake Escape by Orlando Short Term

Private Vacation Home

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Osceola
Storey Lake Escape by Orlando Short Term Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Old Town and Disney Springs™. This vacation home is 6.4 mi (10.4 km) from Walt Disney World® Resort and 6.6 mi (10.6 km) from Disney's Hollywood Studios®.

Storey Lake Escape by Orlando Short Term Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

Storey Lake Escape by Orlando Short Term Rooms
Make yourself comfortable in this air-conditioned 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.

See details
1.0/5
Fully Booked
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Family-friendly Oasis With Game Room & Pool

Vacation Home

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Osceola
Family-friendly Oasis With Game Room & Pool Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of ChampionsGate Golf Club 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.

Family-friendly Oasis With Game Room & Pool 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.

Family-friendly Oasis With Game Room & Pool Rooms
Make yourself comfortable in your individually decorated vacation home. There's a private patio. The bathroom has a bathtub or shower and designer toiletries. Conveniences include a coffee/tea maker and a washer/dryer.

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

Vacation Home

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Osceola
Championsgate Resort 5 Bedroom Private Pool Home 5 Home 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 Mystic Dunes Golf Club. This vacation home is 11.9 mi (19.1 km) from Old Town and 12.2 mi (19.6 km) from ESPN Wide World of Sports Complex.

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

See details
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Vacation Homes in Osceola

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