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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
Bedroom

Windsor_palms_102

Vacation Home

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Osceola
Windsor_palms_102 Location
When you stay at this condo in Kissimmee, you'll be next to a golf course, within a 15-minute drive of Walt Disney World® Resort and Old Town. This golf condo is 7.2 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_102 Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center. This condo also features concierge services, an arcade/game room, and gift shops/newsstands.

Windsor_palms_102 Rooms
Make yourself comfortable in this air-conditioned condo, which features a private hot tub and a flat-screen TV. There's a private patio. A kitchen is outfitted with a refrigerator, a stovetop, and a microwave. Complimentary wired and wireless internet access keeps you connected, and satellite programming provides entertainment. A private bathroom has a jetted bathtub and a hair dryer.

Restaurant and Cafe
Grab a bite from the snack bar/deli serving guests of this condo. Quench your thirst with your favorite drink at the bar/lounge.

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Bright Luxe At Championsgate

Vacation Home

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Osceola
Bright Luxe 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 11.4 mi (18.3 km) from Old Town and 12.2 mi (19.6 km) from ESPN Wide World of Sports Complex.

Bright Luxe At Championsgate Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool. Conveniences include a separate sitting area and a washer/dryer.

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Room

8886-CabotCliffs

Vacation Home

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Osceola
8886-CabotCliffs 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 vacation home is 12.1 mi (19.5 km) from Old Town and 12.6 mi (20.3 km) from Walt Disney World® Resort.

8886-CabotCliffs Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Gorgeous Home With Private Pool With Spa, Pool Table & gas Grill

Vacation Home

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Osceola
Gorgeous Home With Private Pool With Spa, Pool Table & gas Grill 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 ChampionsGate Golf Club. This vacation home is 10.2 mi (16.4 km) from Disney's Animal Kingdom® Theme Park and 11.4 mi (18.3 km) from ESPN Wide World of Sports Complex.

Gorgeous Home With Private Pool With Spa, Pool Table & gas Grill Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center. Additional features at this vacation home include complimentary wireless internet access and an arcade/game room.

Gorgeous Home With Private Pool With Spa, Pool Table & gas Grill Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Others

3br, 2.5ba Townhome W/ Lake View, Sunny Rear Yard 3 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
3br, 2.5ba Townhome W/ Lake View, Sunny Rear Yard 3 Bedroom 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 Orlando Vineland Premium Outlets. This vacation home is 8.9 mi (14.3 km) from Disney Springs™ and 9.2 mi (14.8 km) from Walt Disney World® Resort.

3br, 2.5ba Townhome W/ Lake View, Sunny Rear Yard 3 Bedroom Townhouse by RedAwning Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Exterior & Views

510 BS - 5BD Elegant Escape: Private Haven

Vacation Home

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Osceola
510 BS - 5BD Elegant Escape: Private Haven Location
When you stay at this vacation home in Kissimmee, you'll be on the beach, within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This vacation home is 7.6 mi (12.2 km) from ESPN Wide World of Sports Complex and 8.1 mi (13 km) from Disney's Hollywood Studios®.

510 BS - 5BD Elegant Escape: Private Haven Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including an arcade/game room.

510 BS - 5BD Elegant Escape: Private Haven Rooms
Make yourself comfortable in your vacation home. Conveniences include an electric kettle and an iron/ironing board.

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Others

Way Too Many Bottles

Private Vacation Home

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Osceola
Way Too Many Bottles 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 6.2 mi (9.9 km) from Old Town and 6.5 mi (10.5 km) from Disney's Hollywood Studios®.

Way Too Many Bottles Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a refrigerator and an oven. There's a private balcony. Digital television is provided for your entertainment. Conveniences include a separate sitting area and a microwave.

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Modern Stay w Full Resort-access Near Disney

Vacation Home

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Osceola
Modern Stay w Full Resort-access Near Disney Location
When you stay at this vacation home in Four Corners, you'll be next to a golf course, within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This golf vacation home is 12.1 mi (19.4 km) from Old Town and 12.8 mi (20.7 km) from ESPN Wide World of Sports Complex.

Modern Stay w Full Resort-access Near Disney Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including complimentary wireless internet access.

Modern Stay w Full Resort-access Near Disney Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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7814 Beechfield Street

Private Vacation Home

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Osceola
7814 Beechfield Street 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 (9.9 km) from Disney's Hollywood Studios® and 7.9 mi (12.7 km) from Disney Springs™.

7814 Beechfield Street Facility and Service
Be sure to enjoy recreational amenities, 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.

7814 Beechfield Street 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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Beautiful Golf Course View Townhome!

Vacation Home

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Osceola
Beautiful Golf Course View Townhome! 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 12.2 mi (19.6 km) from Old Town and 12.6 mi (20.3 km) from Walt Disney World® Resort.

Beautiful Golf Course View Townhome! Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

Beautiful Golf Course View Townhome! Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Others

House W/pool And Jacuzzi In Paradise Palms-3151pp 6 Bedroom Home by RedAwning

Vacation Home

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Osceola
House W/pool And Jacuzzi In Paradise Palms-3151pp 6 Bedroom Home by RedAwning 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 8.5 mi (13.6 km) from Disney's Animal Kingdom® Theme Park and 9.3 mi (15 km) from ESPN Wide World of Sports Complex.

House W/pool And Jacuzzi In Paradise Palms-3151pp 6 Bedroom Home by RedAwning Rooms
Make yourself comfortable in your vacation home, which features a refrigerator. 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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Lavish Estate With Home Theater in Reunion

Vacation Home

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Osceola
Lavish Estate With Home Theater in 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 km) from Walt Disney World® Resort and 9.5 mi (15.2 km) from Old Town.

Lavish Estate With Home Theater in Reunion Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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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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Exterior & Views

Luxury 4 Bedroom Storey Lake Townhome 2444Reading 4 Townhouse

Vacation Home

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Osceola
Luxury 4 Bedroom Storey Lake Townhome 2444Reading 4 Townhouse 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.

Luxury 4 Bedroom Storey Lake Townhome 2444Reading 4 Townhouse Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected.

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Exterior & Views

Gorgeous 4 Bd w/ Pool at Storey Lake Resort 4277

Vacation Home

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Osceola
Gorgeous 4 Bd w/ Pool at Storey Lake Resort 4277 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 7.1 mi (11.4 km) from Disney Springs™ and 8.2 mi (13.2 km) from Walt Disney World® Resort.

Gorgeous 4 Bd w/ Pool at Storey Lake Resort 4277 Facility and Service
Don't miss out on the many recreational opportunities, including a complimentary water park, an outdoor pool, and a lazy river. Additional amenities at this vacation home include concierge services, a television in a common area, and charcoal grills.

Gorgeous 4 Bd w/ Pool at Storey Lake Resort 4277 Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a full-sized refrigerator/freezer and an oven. A 60-inch Smart television with cable programming provides entertainment, while complimentary wired internet access keeps you connected. Conveniences include a safe and a desk, and you can also request a crib/infant bed (surcharge).

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Exterior & Views

Stunning 4 Bd w/ Pool Close to Disney @ Champions Gate 990

Vacation Home

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Osceola
Stunning 4 Bd w/ Pool Close to Disney @ Champions Gate 990 Location
Located in Four Corners, this vacation home is within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This family-friendly vacation home is 12.2 mi (19.6 km) from Old Town and 12.9 mi (20.8 km) from ESPN Wide World of Sports Complex.

Stunning 4 Bd w/ Pool Close to Disney @ Champions Gate 990 Facility and Service
Be sure to enjoy recreational amenities, including a complimentary water park, an outdoor pool, and a lazy river. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Stunning 4 Bd w/ Pool Close to Disney @ Champions Gate 990 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 crib/infant bed (surcharge).

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Exclusive Champions Gate Retreat w/ Private Pool

Vacation Home

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Osceola
Exclusive Champions Gate Retreat w/ Private Pool Location
When you stay at this vacation home in Four Corners, you'll be next to a golf course, within a 15-minute drive of Reunion Resort Golf Course and ChampionsGate Golf Club. This golf vacation home is 11.7 mi (18.9 km) from Old Town and 12.6 mi (20.3 km) from ESPN Wide World of Sports Complex.

Exclusive Champions Gate Retreat w/ Private Pool Facility and Service
Make use of convenient amenities such as complimentary wireless internet access, an arcade/game room, and barbecue grills.

Exclusive Champions Gate Retreat w/ Private Pool 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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Spacious Home With Private Pool, Fast Wifi, Work Space & Games - Snowbirds OK

Vacation Home

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Osceola
Spacious Home With Private Pool, Fast Wifi, Work Space & Games - Snowbirds OK 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 11.3 mi (18.2 km) from Old Town and 12.2 mi (19.6 km) from ESPN Wide World of Sports Complex.

Spacious Home With Private Pool, Fast Wifi, Work Space & Games - Snowbirds OK 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.

Spacious Home With Private Pool, Fast Wifi, Work Space & Games - Snowbirds OK Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Chic Property With Private Pool in Encore

Vacation Home

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Osceola
Chic Property With Private Pool in 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 Reunion Resort Golf Course. This vacation home is 5.6 mi (9 km) from Walt Disney World® Resort and 7.6 mi (12.3 km) from ESPN Wide World of Sports Complex.

Chic Property With Private Pool in Encore Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a hot tub. Additional features at this vacation home include complimentary wireless internet access and an arcade/game room.

Chic Property With Private Pool in Encore Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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9203 Sommerset Hills Drive

Vacation Home

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Osceola
9203 Sommerset Hills Drive provides flawless service and all the necessary facilities for visitors. For visitors traveling by automobile, complimentary parking is available. Kindly note that smoking is prohibited in the country house to ensure fresher air for all visitors.At 9203 Sommerset Hills Drive, every guestroom is provided with convenient amenities and fittings to ensure a comfortable stay. Elevate your experience at country house with the knowledge that certain rooms are equipped with linen service, ensuring a more pleasant stay for you. A few accommodations within 9203 Sommerset Hills Drive offer unique design elements such as a separate living room.Certain rooms offer in-room amusement features such as the cable TV for your enjoyment. In select rooms within the country house, a refrigerator and a coffee or tea maker is available to cater to your requirements when desired. Essential restroom facilities are equally significant, and at the country house, some visitor bathrooms offer a hair dryer to enhance your experience. At the country house, an assortment of easily accessible and delicious meal choices are available to satisfy your appetite whenever it strikes. At the country house, discerning guests can also enjoy on-site culinary facilities like BBQ facilities tailored to their preferences.
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Vacation Homes in Osceola

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