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Vacation Homes in Osceola

Osceola
Tue, 17 Nov 2026 - Wed, 18 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 1.000+ Vacation Homes in Osceola
Others

Spacious Getaway With Pool, Near Orlando Parks

Vacation Home

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Osceola
Spacious Getaway With Pool, Near Orlando 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 vacation home is 11.7 mi (18.8 km) from Old Town and 12.5 mi (20.1 km) from ESPN Wide World of Sports Complex.

Spacious Getaway With Pool, Near Orlando Parks Facility and Service
Make use of convenient amenities such as complimentary wireless internet access, an arcade/game room, and barbecue grills.

Spacious Getaway With Pool, Near Orlando Parks 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 washing machine.

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Windsor Palms Resort 3 Bedroom Private Pool Townhome 3 Townhouse

Vacation Home

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Osceola
Windsor Palms Resort 3 Bedroom Private Pool Townhome 3 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 vacation home is 7.1 mi (11.5 km) from ESPN Wide World of Sports Complex and 7.6 mi (12.3 km) from Disney's Hollywood Studios®.

Windsor Palms Resort 3 Bedroom Private Pool Townhome 3 Townhouse Rooms
Make yourself comfortable in your vacation home, featuring a refrigerator and a Smart TV. Complimentary wireless internet access is available to keep you connected. The bathroom has a bathtub or shower.Conveniences include a coffee/tea maker and a washing machine.

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Boutique Luxury Home, Private Pool Close to Disney

Vacation Home

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Osceola
Boutique Luxury Home, Private Pool Close to Disney 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 (15.4 km) from Old Town.

Boutique Luxury Home, Private Pool Close to Disney Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Boutique Luxury Home, Private Pool Close 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

Cumbrian Retreat

Vacation Home

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Osceola
Cumbrian Retreat Location
With a stay at this vacation home in Kissimmee (Cumbrian Lakes), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 10.3 mi (16.5 km) from Disney Springs™ and 10.5 mi (16.8 km) from ESPN Wide World of Sports Complex.

Cumbrian Retreat 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.

Cumbrian Retreat 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 lanai. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Digital television is provided for your entertainment.

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6Br Retreat W/ South Pool, Spa & Game Room Fun

Vacation Home

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Osceola
6Br Retreat W/ South Pool, Spa & Game Room Fun Location
With a stay at this vacation home in Kissimmee (Crescent Lakes), you'll be within a 10-minute drive of Green Meadows Petting Farm and Shingle Creek Regional Park. This family-friendly vacation home is 12 mi (19.3 km) from Old Town and 14.2 mi (22.9 km) from Orlando Vineland Premium Outlets.

6Br Retreat W/ South Pool, Spa & Game Room Fun Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including an arcade/game room.

6Br Retreat W/ South Pool, Spa & Game Room Fun Rooms
Make yourself comfortable in this vacation home, which features a private pool and an outdoor private hot tub. There's a private patio. A kitchen is outfitted with a full-sized refrigerator/freezer, an oven, and a stovetop. A 75-inch Smart television with digital programming provides entertainment, while complimentary wireless internet access keeps you connected.

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3.0/5
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Others

Green View Home Near Clubhouse 7799

Private Vacation Home

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Osceola
Green View Home Near Clubhouse 7799 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 Old Town. This vacation home is 6.2 mi (10 km) from Disney's Hollywood Studios® and 7.9 mi (12.7 km) from Disney Springs™.

Green View Home Near Clubhouse 7799 Facility and Service
Take advantage of recreation opportunities such as a fitness center, or other amenities including complimentary wireless internet access and an arcade/game room.

Green View Home Near Clubhouse 7799 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.

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Exterior & Views

Lucaya 4 Bedrooms 3 Baths Townhome With Central Kitchen

Vacation Home

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Osceola
Lucaya 4 Bedrooms 3 Baths Townhome With Central 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 4 Bedrooms 3 Baths Townhome With Central Kitchen Facility and Service
Take advantage of recreation opportunities such as a fitness center, or other amenities including complimentary wireless internet access and an arcade/game room.

Lucaya 4 Bedrooms 3 Baths Townhome With Central Kitchen Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with a refrigerator and a microwave. Conveniences include a washing machine and an iron/ironing board.

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Bedroom

1533cpc Solara Resort

Vacation Home

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Osceola
1533cpc Solara Resort Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This vacation home is 10.2 mi (16.5 km) from Disney's Animal Kingdom® Theme Park and 10.9 mi (17.5 km) from ESPN Wide World of Sports Complex.

1533cpc Solara Resort Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

1533cpc Solara Resort Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a flat-screen TV. There's a private furnished balcony/patio. A kitchen is outfitted with a refrigerator 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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Exterior & Views

7BR Pool Home Emerald Island by SHV-8409

Private Vacation Home

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Osceola
7BR Pool Home Emerald Island by SHV-8409 Location
With a stay at 7BR Pool Home Emerald Island by SHV-8409 in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This vacation home is 6.9 mi (11.1 km) from ESPN Wide World of Sports Complex and 7.2 mi (11.6 km) from Old Town.

7BR Pool Home Emerald Island by SHV-8409 Rooms
Make yourself at home in one of the 11 air-conditioned rooms featuring private pools and private hot tubs. Kitchens are outfitted with full-sized refrigerators/freezers, ovens, and microwaves. Flat-screen televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Bathrooms have deep soaking bathtubs and complimentary toiletries.

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Tropical Retreat With Screened in Private Pool and Spa at Reunion

Vacation Home

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Osceola
Tropical Retreat With Screened in Private Pool and Spa at Reunion Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be a 3-minute drive from Reunion Resort Golf Course and 6 minutes from ChampionsGate Golf Club. This golf vacation home is 8.2 mi (13.2 km) from Walt Disney World® Resort and 9.9 mi (15.9 km) from Old Town.

Tropical Retreat With Screened in Private Pool and Spa at Reunion Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Tropical Retreat With Screened in Private Pool and Spa 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

4bed 3Ba Storey Lake Home w. Pool

Vacation Home

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Osceola
4bed 3Ba Storey Lake Home w. 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 5.5 mi (8.8 km) from Disney Springs™ and 6.5 mi (10.5 km) from Walt Disney World® Resort.

4bed 3Ba Storey Lake Home w. Pool Facility and Service
Take advantage of recreation opportunities such as a fitness center, or other amenities including wireless internet access (surcharge) and barbecue grills.

4bed 3Ba Storey Lake Home w. Pool Rooms
Your vacation home features a flat-screen TV.

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Exterior & Views

Marg Retreat by Orlando Short Term

Vacation Home

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Osceola
Marg Retreat by Orlando Short Term Location
With a stay at this vacation home in Kissimmee (Trafalgar Village), you'll be within a 10-minute drive of Green Meadows Petting Farm and Shingle Creek Regional Park. This vacation home is 11 mi (17.7 km) from Old Town and 13.2 mi (21.3 km) from Orlando Vineland Premium Outlets.

Marg Retreat by Orlando Short Term Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center.

Marg Retreat by Orlando Short Term Rooms
Make yourself comfortable in this 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.

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Exterior & Views

4BR 3BA Home in Windsor Palms by CV-8115

Vacation Home

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Osceola
4BR 3BA Home in Windsor Palms by CV-8115 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 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.

4BR 3BA Home in Windsor Palms by CV-8115 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 DVD player is provided for your entertainment. Conveniences include a microwave and a coffee/tea maker.

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Sport & Beauty

Storey Lake Resort 8br Cozy Home With Theater 2916

Vacation Home

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Osceola
Storey Lake Resort 8br Cozy Home With Theater 2916 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 mi (11.2 km) from Disney Springs™ and 8.1 mi (13 km) from Walt Disney World® Resort.

Storey Lake Resort 8br Cozy Home With Theater 2916 Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Storey Lake Resort 8br Cozy Home With Theater 2916 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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Solara Resort 5 Bedroom Private Pool Townhome 5 Townhouse

Vacation Home

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Osceola
Solara Resort 5 Bedroom Private Pool Townhome 5 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 ChampionsGate Golf Club. This vacation home is 10.1 mi (16.2 km) from Disney's Animal Kingdom® Theme Park and 11.3 mi (18.1 km) from ESPN Wide World of Sports Complex.

Solara Resort 5 Bedroom Private Pool Townhome 5 Townhouse 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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Others

Grhcdw9157 - Champions Gate Resort - 6 Bed 6 Baths House

Vacation Home

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Osceola
Grhcdw9157 - 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 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.

Grhcdw9157 - 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.

Grhcdw9157 - 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 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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Sport & Beauty

Kissimmee Vacation Homes by Shine FM

Vacation Home

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Osceola
Kissimmee Vacation Homes by Shine FM Location
With a stay at Kissimmee Vacation Homes by Shine FM in Kissimmee, you'll be a 5-minute drive from Mystic Dunes Golf Club and 8 minutes from Walt Disney World® Resort. This condo is 6.6 mi (10.7 km) from Old Town and 6.8 mi (10.9 km) from ESPN Wide World of Sports Complex.

Kissimmee Vacation Homes by Shine FM Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a garden.

Kissimmee Vacation Homes by Shine FM Rooms
Treat yourself to a stay in one of the 4 individually decorated guestrooms, featuring private pools and flat-screen televisions. Kitchens are outfitted with refrigerators, ovens, and stovetops. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include desks and microwaves, and housekeeping is provided once per stay.

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4.1/5
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Others

1576tl-the Retreat at Champions Gate

Vacation Home

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Osceola
1576tl-the Retreat at Champions Gate 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 12.2 mi (19.6 km) from ESPN Wide World of Sports Complex.

1576tl-the Retreat at Champions Gate 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 an arcade/game room and barbecue grills.

1576tl-the Retreat at Champions Gate Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. A flat-screen television is provided for your entertainment. Conveniences include a microwave and an iron/ironing board.

Restaurant and Cafe
Wrap up your day with a drink at the bar/lounge.

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Living area

Buc2999 6 Bedroom Home

Vacation Home

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Osceola
Buc2999 6 Bedroom Home 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 6.6 mi (10.6 km) from Walt Disney World® Resort and 8.2 mi (13.3 km) from Disney's Animal Kingdom® Theme Park.

Buc2999 6 Bedroom 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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Others

Luxury Town With Splash Pool In Solara Resort 4 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
Luxury Town With Splash Pool In Solara Resort 4 Bedroom Townhouse by RedAwning Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This vacation home is 8.6 mi (13.9 km) from Walt Disney World® Resort and 10.4 mi (16.8 km) from Disney's Animal Kingdom® Theme Park.

Luxury Town With Splash Pool In Solara Resort 4 Bedroom Townhouse by RedAwning Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a microwave and a dishwasher. Complimentary wireless internet access is available to keep you connected.

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Vacation Homes in Osceola

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