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Vacation Homes in Osceola

Osceola
Sat, 14 Nov 2026 - Sun, 15 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 1.000+ Vacation Homes in Osceola
Others

6/5 Home at Sonoma Resort, Private Pool, and Much More!!

Vacation Home

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Osceola
6/5 Home at Sonoma Resort, Private Pool, and Much More!! Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Old Town and Shingle Creek Regional Park. This vacation home is 9.6 mi (15.4 km) from Orlando Vineland Premium Outlets and 9.7 mi (15.7 km) from Disney Springs™.

6/5 Home at Sonoma Resort, Private Pool, and Much More!! Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center.

6/5 Home at Sonoma Resort, Private Pool, and Much More!! Rooms
Make yourself comfortable in this vacation home, which features a private pool. Complimentary wireless internet access is available to keep you connected.

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Food & Drinks

Elegant Brand New 9 Bedrooms House With Private Pool at Solara Resort (8929)

Vacation Home

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Osceola
Elegant Brand New 9 Bedrooms House With Private Pool at Solara Resort (8929) Location
Located in Kissimmee, this vacation home is within a 15-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This family-friendly vacation home is 8.8 mi (14.2 km) from Walt Disney World® Resort and 10.6 mi (17.1 km) from Disney's Animal Kingdom® Theme Park.

Elegant Brand New 9 Bedrooms House With Private Pool at Solara Resort (8929) 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, a waterslide, and a hot tub. This vacation home also features complimentary wireless internet access, concierge services, and an arcade/game room.

Elegant Brand New 9 Bedrooms House With Private Pool at Solara Resort (8929) 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 full-sized refrigerator/freezer, an oven, and a stovetop. A 82-inch Smart television with cable programming provides entertainment, while complimentary wireless internet access keeps you connected.

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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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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Exterior & Views

361-8-pc-perfect Villa With Private Pool

Vacation Home

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Osceola
361-8-pc-perfect Villa With Private Pool Location
With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This cottage is 7.2 mi (11.6 km) from ESPN Wide World of Sports Complex and 7.7 mi (12.4 km) from Disney's Hollywood Studios®.

361-8-pc-perfect Villa With Private Pool Rooms
Make yourself comfortable in this air-conditioned cottage, which has a kitchen. Cable television is provided for your entertainment. Conveniences include a dryer and an iron/ironing board.

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Others

Ov1953 - Windsor Palms Resort - 4 Bed 3 Baths Townhome

Vacation Home

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Osceola
Ov1953 - Windsor Palms 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 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®.

Ov1953 - Windsor Palms Resort - 4 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 outdoor tennis courts. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and an arcade/game room.

Ov1953 - Windsor Palms Resort - 4 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 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. Wrap up your day with a drink at the bar/lounge.

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Haven Station at Storey Lake by Shine Villas townhouse

Vacation Home

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Osceola
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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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Exterior & Views

Lucaya 3 Bedroom 2 Bath Townhome With Sophisticated Kitchen

Vacation Home

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Osceola
Lucaya 3 Bedroom 2 Bath Townhome With Sophisticated Kitchen 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 3 Bedroom 2 Bath Townhome With Sophisticated Kitchen Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including an arcade/game room.

Lucaya 3 Bedroom 2 Bath Townhome With Sophisticated Kitchen Rooms
Make yourself comfortable in this vacation home, which has a kitchen.

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Exterior & Views

Fd51442 - Bella Vida Resort - 4 Bed 3 Baths Townhouse

Vacation Home

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Osceola
Fd51442 - Bella Vida Resort - 4 Bed 3 Baths Townhouse 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 8.7 mi (14 km) from Disney Springs™ and 8.8 mi (14.2 km) from ESPN Wide World of Sports Complex.

Fd51442 - Bella Vida Resort - 4 Bed 3 Baths Townhouse Facility and Service
Don't miss out on the many recreational opportunities, including a hot tub, a fitness center, and a seasonal outdoor pool. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Fd51442 - Bella Vida Resort - 4 Bed 3 Baths Townhouse 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
Grab a bite from the grocery/convenience store serving guests of this vacation home.

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Bathroom

1439rf - The Retreat at Championsgate

Vacation Home

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Osceola
1439rf - 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 (21.5 km) from Walt Disney World® Resort.

1439rf - The Retreat at Championsgate Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center.

1439rf - The Retreat at Championsgate Rooms
Make yourself comfortable in your vacation home.

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Sport & Beauty

Grhmap8975 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse

Vacation Home

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Osceola
Grhmap8975 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse 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 (13.4 km) from Disney's Animal Kingdom® Theme Park and 9.2 mi (14.9 km) from ESPN Wide World of Sports Complex.

Grhmap8975 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse Facility and Service
Dip into one of the 2 hot tubs or enjoy other recreational amenities including a complimentary water park 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.

Grhmap8975 - 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 programming along with a video-game console are provided for your entertainment.

Restaurant and Cafe
Grab a bite from the grocery/convenience store serving guests of this vacation home. Quench your thirst with your favorite drink at the poolside bar.

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Others

Grand Palm Community, Picnic Benches, Tennis Court and Much More!!

Vacation Home

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Osceola
Grand Palm Community, Picnic Benches, Tennis Court and Much More!! Location
With a stay at this vacation home in Kissimmee (Grand Palms), you'll be within a 10-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center. This vacation home is 7.3 mi (11.7 km) from Disney's Animal Kingdom® Theme Park and 8.4 mi (13.4 km) from Old Town.

Grand Palm Community, Picnic Benches, Tennis Court and Much More!! Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center.

Grand Palm Community, Picnic Benches, Tennis Court and Much More!! Rooms
Make yourself comfortable in this vacation home, which features a fireplace. A kitchen is outfitted with a refrigerator. Complimentary wireless internet access is available to keep you connected.

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Exterior & Views

Veranda Palms 8 Bedroom Home with Pool(2208)

Vacation Home

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Osceola
Veranda Palms 8 Bedroom Home with Pool(2208) offers top-notch services and amenities, ensuring guests experience utmost comfort. Visitors can take advantage of complimentary parking directly at the country house. Each accommodation at Veranda Palms 8 Bedroom Home with Pool(2208) is thoughtfully created and adorned to provide visitors with a comfortable, home-like atmosphere.In select rooms of the country house, guests can enjoy the advantage of having linen service available for their convenience.At Veranda Palms 8 Bedroom Home with Pool(2208), uniquely crafted rooms provide various layout choices, featuring spaces equipped with separate living room and balcony or terrace. In select rooms, guests can enjoy a touch of amusement with the availability of television for their entertainment. Rest assured, in a few chosen rooms, the presence of a coffee or tea maker can be found. Understanding the significance of bathroom amenities in enhancing guest contentment, the country house offers a hair dryer within certain chosen rooms. Should you be particularly discerning in your dining choices, you will surely appreciate having access to the on-site BBQ facilities provided at this location.Throughout the day, engage in the entertaining activities available at Veranda Palms 8 Bedroom Home with Pool(2208). For individuals who don't want to skip their exercise routine, visiting the country house fitness center ensures you maintain your vitality and wellness.
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Bathroom

Villa Linda - Bella Vida

Vacation Home

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Osceola
Villa Linda - Bella Vida 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 9 mi (14.5 km) from Disney Springs™ and 9.5 mi (15.2 km) from Walt Disney World® Resort.

Villa Linda - Bella Vida 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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Exterior & Views

8702 Papaya DR, 2bed

Vacation Home

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Osceola
8702 Papaya DR, 2bed Location
With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center. This cottage is 6.9 mi (11.1 km) from Disney's Animal Kingdom® Theme Park and 8.1 mi (13 km) from Old Town.

8702 Papaya DR, 2bed Rooms
Make yourself comfortable in this air-conditioned cottage, which features a fireplace. A kitchen makes it easy to prepare your meals. Cable television is provided for your entertainment. Conveniences include a dryer and an iron/ironing board.

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Others

Aco234120 - Windsor At Westside Resort - 4 Bed 3 Baths Townhome

Vacation Home

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Osceola
Aco234120 - Windsor At Westside 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 Walt Disney World® Resort and ChampionsGate Golf Club. This family-friendly vacation home is 10.2 mi (16.5 km) from Disney's Animal Kingdom® Theme Park and 11.1 mi (17.9 km) from ESPN Wide World of Sports Complex.

Aco234120 - Windsor At Westside Resort - 4 Bed 3 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 features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Aco234120 - Windsor At Westside Resort - 4 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 or patio. A kitchen is outfitted with a refrigerator, an oven, and a microwave. Cable television is provided for your entertainment.

Restaurant and Cafe
Grab a bite from the grocery/convenience store serving guests of this vacation home. Relax with your favorite drink at the bar/lounge or the poolside bar.

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Exterior & Views

7662reclife

Vacation Home

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Osceola
7662reclife 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®.

7662reclife Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with a refrigerator and a microwave.

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Bedroom

8914sid- the Retreat at Championsgate

Vacation Home

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Osceola
8914sid- the Retreat at Championsgate 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 golf villa is 11.5 mi (18.5 km) from Old Town and 12.2 mi (19.7 km) from ESPN Wide World of Sports Complex.

8914sid- the Retreat at Championsgate Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center.

8914sid- the Retreat at Championsgate Rooms
Make yourself comfortable in this air-conditioned villa, featuring a kitchen with a refrigerator and a stovetop. A flat-screen television is provided for your entertainment. Conveniences include a microwave and an iron/ironing board.

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Exterior & Views

2914 Salted Rim Road

Vacation Home

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Osceola
2914 Salted Rim Road Location
With a stay at this vacation home in Kissimmee, you'll be a 4-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort. This vacation home is 5.8 mi (9.3 km) from Old Town and 6 mi (9.7 km) from ESPN Wide World of Sports Complex.

2914 Salted Rim Road Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. There's a private balcony. Cable television is provided for your entertainment. Conveniences include a microwave and a dryer.

Restaurant and Cafe
At this vacation home, enjoy a satisfying meal at the restaurant.

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7BR Luxe Mansion Private Pool & Golf Views

Vacation Home

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Osceola
7BR Luxe Mansion Private Pool & Golf Views Location
Located in Kissimmee (Reunion), this vacation home is within a 10-minute drive of Reunion Resort Golf Course and Mystic Dunes Golf Club. This vacation home is 6.7 mi (10.9 km) from Walt Disney World® Resort and 8.8 mi (14.1 km) from Old Town.

7BR Luxe Mansion Private Pool & Golf Views 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.

7BR Luxe Mansion Private Pool & Golf Views Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Vacation Homes in Osceola

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