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Hotels in Osceola

Osceola
Sat, 14 Nov 2026 - Sun, 15 Nov 2026 (1 night)
1 Room, 1 Adult, 0 Children
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Showing 5.000+ hotels in Osceola

Ov2920 - Windsor Hills Resort - 6 Bed 4 Baths Villa

Osceola
Ov2920 - Windsor Hills Resort - 6 Bed 4 Baths Villa Location
Located in Kissimmee (Windsor Hills), this villa is within a 10-minute drive of Walt Disney World® Resort and Old Town. This family-friendly villa is 5.6 mi (9 km) from ESPN Wide World of Sports Complex and 6 mi (9.7 km) from Disney's Hollywood Studios®.

Ov2920 - Windsor Hills Resort - 6 Bed 4 Baths Villa Facility and Service
Practice your swing on the golf course or dip into one of the 2 hot tubs. Additional features at this villa include complimentary wireless internet access, concierge services, and a television in a common area.

Ov2920 - Windsor Hills Resort - 6 Bed 4 Baths Villa Rooms
Make yourself comfortable in this air-conditioned villa, 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 villa'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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6BR Championsgate Villa Pool, Spa & Game Room

Osceola
6BR Championsgate Villa Pool, Spa & Game Room 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 11.7 mi (18.8 km) from Old Town and 12.4 mi (20 km) from ESPN Wide World of Sports Complex.

6BR Championsgate Villa Pool, Spa & Game Room Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

6BR Championsgate Villa Pool, Spa & Game Room Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Others

Luxury 4BR Home w/ Pool Near Disney!

Osceola
Luxury 4BR Home w/ Pool Near Disney! Location
When you stay at this villa in Four Corners, you'll be in the suburbs, within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This villa is 12 mi (19.4 km) from Old Town and 12.8 mi (20.6 km) from ESPN Wide World of Sports Complex.

Luxury 4BR Home w/ Pool Near Disney! Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a hot tub. Additional features at this villa include complimentary wireless internet access and barbecue grills.

Luxury 4BR Home w/ Pool Near Disney! Rooms
Your villa features a flat-screen TV. There's a private furnished patio. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. The bathroom has a shower and complimentary toiletries.

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Bedroom

Beautiful Townhome With Hot Tub 13

Osceola
Beautiful Townhome With Hot Tub 13 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 5.4 mi (8.7 km) from Disney Springs™ and 6.1 mi (9.8 km) from Walt Disney World® Resort.

Beautiful Townhome With Hot Tub 13 Facility and Service
Take advantage of recreation opportunities such as an outdoor pool, or other amenities including complimentary wireless internet access and barbecue grills.

Beautiful Townhome With Hot Tub 13 Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with an oven and a stovetop. There's a private balcony. Conveniences include a microwave and a washer/dryer.

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Sport & Beauty

Fs55568 - Oakwater Resort - 2 Bed 2 Baths Townhome

Osceola
Fs55568 - Oakwater Resort - 2 Bed 2 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 Old Town. This golf vacation home is 5.1 mi (8.2 km) from ESPN Wide World of Sports Complex and 5.6 mi (9 km) from Disney's Hollywood Studios®.

Fs55568 - Oakwater Resort - 2 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 an outdoor pool or a hot tub. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Fs55568 - Oakwater Resort - 2 Bed 2 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 or patio. A flat-screen television with cable programming is available for your entertainment, and a DVD player is also provided. Conveniences include a microwave and a sofa bed.

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Shv118 - Windsor At Westside #19- 9 Bed 6 Baths Villa

Osceola
Shv118 - Windsor At Westside #19- 9 Bed 6 Baths Villa Location
With a stay at this villa in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This family-friendly villa is 10.2 mi (16.4 km) from Disney's Animal Kingdom® Theme Park and 11.1 mi (17.8 km) from ESPN Wide World of Sports Complex.

Shv118 - Windsor At Westside #19- 9 Bed 6 Baths Villa Facility and Service
Practice your swing on the golf course or dip into one of the 2 hot tubs. Additional features at this villa include complimentary wireless internet access, concierge services, and an arcade/game room.

Shv118 - Windsor At Westside #19- 9 Bed 6 Baths Villa Rooms
Make yourself comfortable in this individually decorated villa, 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 villa. Relax with your favorite drink at the bar/lounge or the poolside bar.

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Others

Ov2575 - Windsor Palms Resort - 4 Bed 3 Baths Townhome

Osceola
Ov2575 - Windsor Palms Resort - 4 Bed 3 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®.

Ov2575 - Windsor Palms 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 amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Ov2575 - 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 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 with cable programming is available for your entertainment, and a DVD player is also provided.

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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Fully Booked
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Others

Ip60497 - Island Club West - 3 Bed 2 Baths Condo

Osceola
Ip60497 - Island Club West - 3 Bed 2 Baths Condo Location
With a stay at this condo in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center. This golf condo is 7.2 mi (11.5 km) from Disney's Animal Kingdom® Theme Park and 8 mi (12.9 km) from ESPN Wide World of Sports Complex.

Ip60497 - Island Club West - 3 Bed 2 Baths Condo 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 hot tub or an outdoor tennis court. Additional features at this condo include complimentary wireless internet access, concierge services, and a television in a common area.

Ip60497 - Island Club West - 3 Bed 2 Baths Condo Rooms
Make yourself comfortable in this air-conditioned condo, 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.

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Others

Beautiful, Modern Home W/private Pool! Near WDW

Osceola
Beautiful, Modern Home W/private Pool! Near WDW Location
With a stay at this cottage in Kissimmee, you'll be a 5-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This family-friendly cottage is 5.3 mi (8.5 km) from Disney Springs™ and 6.3 mi (10.1 km) from Walt Disney World® Resort.

Beautiful, Modern Home W/private Pool! Near WDW Facility and Service
Enjoy a range of recreational amenities, including an outdoor pool, a lazy river, and a waterslide. Additional features at this cottage include complimentary wireless internet access and barbecue grills.

Beautiful, Modern Home W/private Pool! Near WDW Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with a refrigerator and an oven. Cable television is provided for your entertainment. Conveniences include a microwave and a dryer.

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

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2.7/5
Fully Booked
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Exterior & Views

GRH438831 - Windsor Palms Resort - 3 Bed 3 Baths Townhome

Osceola
Great care is taken to ensure guests experience comfort through top-notch services and amenities.Stay connected with your associates, as complimentary Wi-Fi is available during your entire visit. In order to ensure the utmost level of relaxation, the guestrooms feature an inviting design and are equipped with all basic necessities, creating a delightful stay experience.To ensure your satisfaction, certain rooms in the private villa come fitted with linen service for a more pleasant stay. Several chosen accommodations at GRH438831 - Windsor Palms Resort - 3 Bed 3 Baths Townhome have a separate living room incorporated into the room design. In select rooms, visitors can enjoy a touch of amusement with the availability of television and cable TV for their entertainment needs. Within specific rooms, a refrigerator and a coffee or tea maker is conveniently available for your use. You'll be pleased to know that select guest bathrooms offer bathroom amenities such as a hair dryer, ensuring a comfortable stay.
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Bathroom

Trafalgar Retreat by Orlando Short Term

Osceola
Trafalgar 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 11.3 mi (18.3 km) from Old Town and 13.6 mi (21.8 km) from Orlando Vineland Premium Outlets.

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

Trafalgar 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 refrigerator and a coffee/tea maker.

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3.0/5
Fully Booked
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Charming Estate With Themed Bedrooms at Encore

Osceola
Charming Estate With Themed Bedrooms at Encore Location
When you stay at this villa in Kissimmee, you'll be near the beach, within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This villa 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®.

Charming Estate With Themed Bedrooms at Encore Facility and Service
Take advantage of recreation opportunities such as a hot tub, or other amenities including complimentary wireless internet access and an arcade/game room.

Charming Estate With Themed Bedrooms at Encore Rooms
Make yourself comfortable in your individually decorated villa. The bathroom has a bathtub or shower.

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Sw40 - 3BR Apartment Near Disney With Resort Pool

Osceola
Sw40 - 3BR Apartment Near Disney With Resort Pool Location
With a stay at this apartment in Kissimmee, you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This apartment is 7 mi (11.3 km) from Disney Springs™ and 8 mi (12.9 km) from Walt Disney World® Resort.

Sw40 - 3BR Apartment Near Disney With Resort Pool Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Sw40 - 3BR Apartment Near Disney With Resort Pool Rooms
Make yourself comfortable in this individually decorated apartment, featuring a kitchen with an oven and a stovetop. Conveniences include a microwave and a washer/dryer.

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Magical 15BR Villa w Pool Cinema & Themed Fun

Osceola
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Exterior & Views

1426 Wexford WAY Davenport, 8bed

Osceola
1426 Wexford WAY Davenport, 8bed 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 villa is 11.7 mi (18.9 km) from Old Town and 12.5 mi (20.1 km) from ESPN Wide World of Sports Complex.

1426 Wexford WAY Davenport, 8bed Facility and Service
Enjoy recreation amenities such as a fitness center or take in the view from a garden. This villa also features complimentary wireless internet access and barbecue grills.

1426 Wexford WAY Davenport, 8bed Rooms
Make yourself comfortable in this air-conditioned villa, which has a kitchen. There's a private patio. Conveniences include a dryer and an iron/ironing board, and you can also request a crib/infant bed (complimentary).

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Sport & Beauty

7783tb Windsor Hills Resort 5 Bed 5 Bath

Osceola
7783tb Windsor Hills Resort 5 Bed 5 Bath Location
Located in Kissimmee (Windsor Hills), this vacation home is within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This spa vacation home is 5.6 mi (9 km) from ESPN Wide World of Sports Complex and 6.1 mi (9.8 km) from Old Town.

7783tb Windsor Hills Resort 5 Bed 5 Bath 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.

7783tb Windsor Hills Resort 5 Bed 5 Bath Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and a microwave. Complimentary wireless internet access keeps you connected, and a flat-screen television is provided for your entertainment.

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Fully Booked
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Others

Exclusive Windsor Home Near Theme Parks

Osceola
Exclusive Windsor Home Near Theme Parks Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Flamingo Crossings Town Center 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.

Exclusive Windsor Home Near Theme Parks Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Exclusive Windsor Home Near Theme 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 washer/dryer.

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Solara Resort 8 Bedroom Private Pool Home 8 Home

Osceola
Solara Resort 8 Bedroom Private Pool Home 8 Home 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 10.1 mi (16.3 km) from Disney's Animal Kingdom® Theme Park and 11 mi (17.7 km) from ESPN Wide World of Sports Complex.

Solara Resort 8 Bedroom Private Pool Home 8 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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Escape Villa

Osceola
Escape Villa Location
Located in Kissimmee (Windsor Hills), this vacation home is within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This golf vacation home is 5.8 mi (9.4 km) from ESPN Wide World of Sports Complex and 6.1 mi (9.8 km) from Old Town.

Escape Villa Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center. Additional amenities at this vacation home include complimentary wireless internet access, an arcade/game room, and barbecue grills. Getting to nearby attractions is a breeze with the complimentary area shuttle.

Escape Villa 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 dishwasher. An LCD television with cable programming is available for your entertainment, and a DVD player is also provided.

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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Bedroom

2619ca 10 Bedroom Villa by Redawning

Osceola
2619ca 10 Bedroom Villa by Redawning Location
Located in Kissimmee, this villa is within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This villa is 9.6 mi (15.5 km) from Disney Springs™ and 10.1 mi (16.3 km) from ESPN Wide World of Sports Complex.

2619ca 10 Bedroom Villa by Redawning Rooms
Make yourself comfortable in your villa. Complimentary wireless internet access is available to keep you connected. The bathroom has a bathtub or shower.

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Hotels in Osceola

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