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Villas in Osceola

Osceola
Tue, 10 Nov 2026 - Wed, 11 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 1.000+ Villas in Osceola

Ov2551 - Windsor Hills Resort - 5 Bed 5 Baths Villa

Villa

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Osceola
Ov2551 - Windsor Hills Resort - 5 Bed 5 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®.

Ov2551 - Windsor Hills Resort - 5 Bed 5 Baths Villa Facility and Service
Practice your swing on the golf course or dip into one of the 2 hot tubs. This villa also features complimentary wireless internet access, concierge services, and a television in a common area.

Ov2551 - Windsor Hills Resort - 5 Bed 5 Baths Villa Rooms
Make yourself comfortable in this air-conditioned villa, 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 villa's coffee shop/cafe. Relax with your favorite drink at the bar/lounge or the poolside bar.

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Condominium villas near Disney Orlando Florida

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Osceola
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4 Bedroom/3 Bath South Facing Pool/Spa Villa 4 Villa by RedAwning

Villa

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Osceola
4 Bedroom/3 Bath South Facing Pool/Spa Villa 4 Villa by RedAwning Location
With a stay at this villa in Kissimmee, you'll be a 3-minute drive from Mystic Dunes Golf Club and 10 minutes from Walt Disney World® Resort. This family-friendly villa is 7 mi (11.2 km) from ESPN Wide World of Sports Complex and 7.2 mi (11.5 km) from Old Town.

4 Bedroom/3 Bath South Facing Pool/Spa Villa 4 Villa by RedAwning Facility and Service
Be sure to enjoy recreational amenities including an outdoor tennis court and a fitness center.

4 Bedroom/3 Bath South Facing Pool/Spa Villa 4 Villa by RedAwning Rooms
Make yourself comfortable in this air-conditioned villa, which has a kitchen. Complimentary wireless internet access is available to keep you connected. Conveniences include a microwave and a coffee/tea maker.

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6BR Townhome w/ Pool 10 Min to Disney

Villa

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Osceola
6BR Townhome w/ Pool 10 Min to Disney Location
With a stay at this villa in Kissimmee, you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This villa is 6 mi (9.7 km) from Disney Springs™ and 6.9 mi (11.1 km) from Walt Disney World® Resort.

6BR Townhome w/ Pool 10 Min to Disney Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a hot tub. Additional amenities at this villa include complimentary wireless internet access, barbecue grills, and a vending machine.

6BR Townhome w/ Pool 10 Min to 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 bathtub or shower and complimentary toiletries.

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Others

9 Bed Storey Lake Villa Pictures Coming Soon 9 Bedroom Home by RedAwning

Villa

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Osceola
9 Bed Storey Lake Villa Pictures Coming Soon 9 Bedroom Home by RedAwning Location
With a stay at this villa in Kissimmee, you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This villa is 6.2 mi (9.9 km) from Disney Springs™ and 7.1 mi (11.5 km) from ESPN Wide World of Sports Complex.

9 Bed Storey Lake Villa Pictures Coming Soon 9 Bedroom Home by RedAwning Facility and Service
Enjoy recreation amenities such as an outdoor tennis court or take in the view from a terrace. Additional features at this villa include complimentary wireless internet access and an arcade/game room.

9 Bed Storey Lake Villa Pictures Coming Soon 9 Bedroom Home by RedAwning Rooms
Make yourself comfortable in this air-conditioned villa, which has a kitchen. A flat-screen television with cable programming provides entertainment, while complimentary wireless internet access keeps you connected.

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Pool

1573fd · Beautiful 6Br Villa/ Near Clubhouse

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Osceola
1573fd · Beautiful 6Br Villa/ Near Clubhouse 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 11.3 mi (18.2 km) from Old Town and 12.1 mi (19.5 km) from ESPN Wide World of Sports Complex.

1573fd · Beautiful 6Br Villa/ Near Clubhouse Facility and Service
Take in the views from a garden and make use of amenities such as complimentary wireless internet access.

1573fd · Beautiful 6Br Villa/ Near Clubhouse Rooms
Make yourself comfortable in this air-conditioned villa, featuring a kitchen with an oven and a stovetop. Cable television is provided for your entertainment. Conveniences include a microwave and a dryer.

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Room

Amazing 4BR Villa - Perfect Getaway

Villa

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Osceola
Amazing 4BR Villa - Perfect Getaway 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 12.2 mi (19.7 km) from Old Town and 13 mi (20.9 km) from ESPN Wide World of Sports Complex.

Amazing 4BR Villa - Perfect Getaway Facility and Service
Be sure to enjoy recreational amenities, including an outdoor pool, an indoor pool, and a 24-hour fitness center. This villa also features complimentary wireless internet access and gas grills.

Amazing 4BR Villa - Perfect Getaway Rooms
Treat yourself to a stay in this individually decorated villa, which features a private pool. A kitchen is outfitted with an oven and a microwave. Cable television is provided for your entertainment. Conveniences include a dryer and an iron/ironing board.

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Sport & Beauty

1669MVD Amazing Champions Gate 8 Bedroom 5 Bed Villa by RedAwning

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Osceola
1669MVD Amazing Champions Gate 8 Bedroom 5 Bed Villa by RedAwning 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 11.5 mi (18.4 km) from Old Town and 12.2 mi (19.7 km) from ESPN Wide World of Sports Complex.

1669MVD Amazing Champions Gate 8 Bedroom 5 Bed Villa by RedAwning Rooms
Make yourself comfortable in your villa. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. The bathroom has a bathtub or shower.

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Others

Luxury 6BR Encore Home w/ Pool Near Disney

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Osceola
Luxury 6BR Encore Home w/ Pool Near Disney Location
With a stay at this villa in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This villa is 7.3 mi (11.8 km) from ESPN Wide World of Sports Complex and 7.8 mi (12.6 km) from Disney's Hollywood Studios®.

Luxury 6BR Encore Home w/ Pool Near Disney Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a hot tub. This villa also features complimentary wireless internet access, an arcade/game room, and a vending machine.

Luxury 6BR Encore Home w/ Pool Near Disney Rooms
Make yourself comfortable in your air-conditioned villa, which features a Smart 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 bathtub or shower and complimentary toiletries.

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Exterior & Views

8 Bdrm Champions Gate Villa

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8 Bdrm Champions Gate Villa 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 family-friendly vacation home is 4.9 mi (7.9 km) from ESPN Wide World of Sports Complex and 5.6 mi (8.9 km) from Disney's Hollywood Studios®.

8 Bdrm Champions Gate Villa 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. This vacation home also features an arcade/game room and barbecue grills.

8 Bdrm Champions Gate Villa Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and a microwave. An LED television and a video-game console are provided for your entertainment, while complimentary wireless internet access keeps you connected.

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Living area

Stylish 4 Ensuite Home Near Disney, Free BBQ Grill

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Osceola
Stylish 4 Ensuite Home Near Disney, Free BBQ Grill Location
With a stay at this villa in Kissimmee, you'll be a 4-minute drive from Walt Disney World® Resort and 9 minutes from Old Town. This villa is 4.8 mi (7.7 km) from ESPN Wide World of Sports Complex and 5.3 mi (8.5 km) from Disney's Hollywood Studios®.

Stylish 4 Ensuite Home Near Disney, Free BBQ Grill Facility and Service
Take advantage of recreation opportunities such as an outdoor pool or take in the view from a terrace and a garden. Additional amenities at this villa include complimentary wireless internet access, a picnic area, and gas grills.

Stylish 4 Ensuite Home Near Disney, Free BBQ Grill Rooms
Make yourself comfortable in this air-conditioned villa, featuring a kitchen with an oven and a stovetop. There's a private patio. Cable television is provided for your entertainment. Conveniences include a microwave and a dryer.

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Dining

1671mv Big Ticket Luxury 9beds Villa

Villa

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Osceola
1671mv Big Ticket Luxury 9beds Villa Location
With a stay at this cottage in Four Corners (Champions Gate), you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This cottage is 11.5 mi (18.5 km) from Old Town and 12.3 mi (19.7 km) from ESPN Wide World of Sports Complex.

1671mv Big Ticket Luxury 9beds Villa 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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4BR West Lucaya Home Near Disney

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Osceola
4BR West Lucaya Home Near Disney Location
With a stay at this villa in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center. This villa is 7.5 mi (12 km) from Disney's Animal Kingdom® Theme Park and 8.2 mi (13.2 km) from ESPN Wide World of Sports Complex.

4BR West Lucaya Home Near Disney Facility and Service
Take advantage of recreation opportunities such as an outdoor pool or take in the view from a terrace and a garden. Additional amenities at this villa include complimentary wireless internet access and an arcade/game room.

4BR West Lucaya Home Near Disney Rooms
Make yourself comfortable in this air-conditioned villa, which features a private pool and a Smart TV. There's a private furnished patio. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include a separate sitting area and a washer/dryer, and you can also request a crib/infant bed (complimentary).

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Family Retreat at Terra Verde Resort Near Disney

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Osceola
Family Retreat at Terra Verde Resort Near Disney Location
Located in Kissimmee, this villa is within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This villa is 9 mi (14.5 km) from Disney Springs™ and 9.3 mi (14.9 km) from Walt Disney World® Resort.

Family Retreat at Terra Verde Resort Near Disney Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and barbecue grills.

Family Retreat at Terra Verde Resort Near Disney Rooms
Make yourself comfortable in this air-conditioned villa, featuring a kitchen with an oven and a stovetop. Conveniences include a microwave and a dryer.

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Ov1969 - Emerald Island - 6 Bed 5 Baths Villa

Villa

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Osceola
Ov1969 - Emerald Island - 6 Bed 5 Baths Villa Location
With a stay at this villa in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This family-friendly villa is 6.9 mi (11 km) from Old Town and 6.9 mi (11.1 km) from ESPN Wide World of Sports Complex.

Ov1969 - Emerald Island - 6 Bed 5 Baths Villa Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools. This villa also features complimentary wireless internet access, concierge services, and a television in a common area.

Ov1969 - Emerald Island - 6 Bed 5 Baths Villa Rooms
Make yourself comfortable in this air-conditioned villa, 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
Wrap up your day with a drink at the poolside bar.

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Championsgate 5br, Private Pool & Themed Rooms

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Osceola
Championsgate 5br, Private Pool & Themed Rooms Location
When you stay at Championsgate 5br, Private Pool & Themed Rooms 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 11.9 mi (19.1 km) from Old Town and 12.6 mi (20.3 km) from ESPN Wide World of Sports Complex.

Championsgate 5br, Private Pool & Themed Rooms Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a hot tub. Additional amenities at this villa include complimentary wireless internet access, an arcade/game room, and barbecue grills.

Championsgate 5br, Private Pool & Themed Rooms Rooms
Stay in one of the guestrooms featuring Smart televisions. Rooms have private furnished patios. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. Bathrooms have bathtubs or showers and complimentary toiletries.

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Solara Resort Grand 7-bedroom Villa With Private Pool, Spa & Themed Rooms

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Osceola
Solara Resort Grand 7-bedroom Villa With Private Pool, Spa & Themed Rooms Location
Located in Kissimmee, this cottage is within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This cottage is 10.1 mi (16.3 km) from Disney's Animal Kingdom® Theme Park and 11.3 mi (18.2 km) from ESPN Wide World of Sports Complex.

Solara Resort Grand 7-bedroom Villa With Private Pool, Spa & Themed Rooms Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with an oven and a stovetop. Conveniences include a microwave and a dryer.

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Sport & Beauty

1528fd- The Retreat at Championsgate

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Osceola
1528fd- 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 11.2 mi (18.1 km) from Old Town and 12 mi (19.3 km) from ESPN Wide World of Sports Complex.

1528fd- The Retreat at Championsgate Facility and Service
Don't miss out on the many recreational opportunities, including an outdoor pool, an outdoor tennis court, and a fitness center.

1528fd- 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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Sport & Beauty

Ip60283 - Rolling Hills Estates - 4 Bed 3 Baths Villa

Villa

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Osceola
Ip60283 - Rolling Hills Estates - 4 Bed 3 Baths Villa Location
With a stay at this villa in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This golf villa is 6.3 mi (10.1 km) from ESPN Wide World of Sports Complex and 6.7 mi (10.8 km) from Old Town.

Ip60283 - Rolling Hills Estates - 4 Bed 3 Baths Villa Facility and Service
Practice your swing on the golf course and enjoy other recreational amenities, such as a seasonal outdoor pool. Additional amenities at this villa include complimentary wireless internet access, concierge services, and a television in a common area.

Ip60283 - Rolling Hills Estates - 4 Bed 3 Baths Villa Rooms
Make yourself comfortable in this air-conditioned villa, 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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Interior

Special Offer Townhome at Compass Bay

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Osceola
Special Offer Townhome at Compass Bay Location
With a stay at this villa in Kissimmee, you'll be a 5-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This villa is 5.2 mi (8.4 km) from Disney Springs™ and 5.9 mi (9.5 km) from Walt Disney World® Resort.

Special Offer Townhome at Compass Bay Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including complimentary wireless internet access.

Special Offer Townhome at Compass Bay Rooms
Make yourself comfortable in this air-conditioned villa, which has a kitchen. Cable television is provided for your entertainment. Conveniences include a dryer and an iron/ironing board.

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Villas in Osceola

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