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Villas in Osceola

Osceola
Sat, 07 Nov 2026 - Sun, 08 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 1.000+ Villas in Osceola
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3BR Championsgate Resort

Villa

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Osceola
3BR Championsgate Resort Location
With a stay at this villa in Four Corners, you'll be in the suburbs, within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This villa is 12 mi (19.3 km) from Old Town and 12.7 mi (20.5 km) from Walt Disney World® Resort.

3BR Championsgate Resort 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 and an arcade/game room.

3BR Championsgate Resort Rooms
Your villa 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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4BR Le Reve Townhome Pool & Themed Rooms

Villa

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Osceola
4BR Le Reve Townhome Pool & Themed Rooms Location
With a stay at this villa in Kissimmee, you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This villa is 8.2 mi (13.2 km) from Disney Springs™ and 9.2 mi (14.7 km) from Walt Disney World® Resort.

4BR Le Reve Townhome Pool & Themed Rooms Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. Additional amenities at this villa include complimentary wireless internet access and barbecue grills.

4BR Le Reve Townhome Pool & Themed Rooms Rooms
Your villa features a Smart TV. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. The bathroom has a bathtub or shower and complimentary toiletries. Conveniences include a washer/dryer, and a crib/infant bed (complimentary) can be requested.

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Ov2270 - Windsor Hills Resort - 5 Bed 5 Baths Villa

Villa

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Osceola
Ov2270 - Windsor Hills Resort - 5 Bed 5 Baths Villa Location
With a stay at this villa in Kissimmee (Windsor Hills), you'll be 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®.

Ov2270 - 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. Additional features at this villa include complimentary wireless internet access, concierge services, and an arcade/game room.

Ov2270 - 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 private hot tub. There's a private balcony. 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. Relax with your favorite drink at the bar/lounge or the poolside bar.

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Sophisticated Villa With Movie Room at Encore

Villa

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Osceola
Sophisticated Villa With Movie Room at 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 5.4 mi (8.8 km) from Walt Disney World® Resort and 7.7 mi (12.4 km) from ESPN Wide World of Sports Complex.

Sophisticated Villa With Movie Room at Encore 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.

Sophisticated Villa With Movie Room at Encore Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Lakeside Villa With Pool, Cinema & Games Room

Villa

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Osceola
Lakeside Villa With Pool, Cinema & Games Room Location
With a stay at this cottage in Kissimmee, you'll be within a 15-minute drive of Old Town and 192 Flea Market. This cottage is 9.6 mi (15.5 km) from Orlando Vineland Premium Outlets and 9.8 mi (15.7 km) from Disney Springs™.

Lakeside Villa With Pool, Cinema & Games Room Facility and Service
Take in the views from a garden and make use of amenities such as complimentary wireless internet access.

Lakeside Villa With Pool, Cinema & Games Room 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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6BR Home Private Pool 10 Min to Disney!

Villa

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Osceola
6BR Home Private 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 6.7 mi (10.7 km) from Walt Disney World® Resort.

6BR Home Private 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, an arcade/game room, and barbecue grills.

6BR Home Private 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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Ov3229 - Windsor Hills Resort - 6 Bed 4 Baths Villa

Villa

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Osceola
Ov3229 - Windsor Hills Resort - 6 Bed 4 Baths Villa Location
With a stay at this villa in Kissimmee (Windsor Hills), you'll be 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®.

Ov3229 - 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. This villa also features complimentary wireless internet access, concierge services, and a television in a common area.

Ov3229 - 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. 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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Fully Booked
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Others

6 min to Disney - Modern 4suite Home

Villa

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Osceola
6 min to Disney - Modern 4suite Home Location
With a stay at this villa in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Old Town. This villa is 4.8 mi (7.6 km) from ESPN Wide World of Sports Complex and 5.2 mi (8.4 km) from Disney's Hollywood Studios®.

6 min to Disney - Modern 4suite Home 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, barbecue grills, and a vending machine.

6 min to Disney - Modern 4suite Home 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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Ovm2258 - Indian Ridge - 4 Bed 2 Baths Villa

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Osceola
Ovm2258 - Indian Ridge - 4 Bed 2 Baths Villa Location
Located in Kissimmee (Indian Ridge), this villa is within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This golf villa is 6.7 mi (10.7 km) from ESPN Wide World of Sports Complex and 7.1 mi (11.5 km) from Old Town.

Ovm2258 - Indian Ridge - 4 Bed 2 Baths Villa Facility and Service
Practice your swing on the golf course and enjoy other recreational amenities, such as a hot tub and an outdoor tennis court. Additional amenities at this villa include complimentary wireless internet access, concierge services, and a television in a common area.

Ovm2258 - Indian Ridge - 4 Bed 2 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
Grab a bite from the grocery/convenience store serving guests of this villa.

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6BR Championsgate Home · Pool · Near Disney

Villa

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Osceola
6BR Championsgate Home · Pool · Near Disney 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 12.3 mi (19.9 km) from Old Town and 12.9 mi (20.8 km) from Walt Disney World® Resort.

6BR Championsgate Home · Pool · Near Disney Facility and Service
Take in the views from a garden and make use of amenities such as complimentary wireless internet access and an arcade/game room.

6BR Championsgate Home · Pool · Near Disney Rooms
Make yourself comfortable in your villa.

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Bedroom

1579pd-the Retreat at Championsgate

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Osceola
1579pd-the Retreat 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 12.1 mi (19.5 km) from ESPN Wide World of Sports Complex.

1579pd-the Retreat at Championsgate Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

1579pd-the Retreat at Championsgate Rooms
Make yourself comfortable in your vacation home. Cable television is provided for your entertainment.

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Splash & Stay! Free Waterpark/9br Villa/7 Mi Dsney 9 Bedroom Villa

Villa

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Osceola
Splash & Stay! Free Waterpark/9br Villa/7 Mi Dsney 9 Bedroom 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 villa 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.

Splash & Stay! Free Waterpark/9br Villa/7 Mi Dsney 9 Bedroom Villa Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center.

Splash & Stay! Free Waterpark/9br Villa/7 Mi Dsney 9 Bedroom Villa Rooms
Make yourself comfortable in this villa, featuring a kitchen with a refrigerator and an oven. Complimentary wireless internet access keeps you connected, and a Smart television is provided for your entertainment. Conveniences include a coffee/tea maker and a washing machine, and you can also request a crib/infant bed (surcharge).

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Magical 15BR Villa w Pool Cinema & Themed Fun

Villa

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Osceola
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Exterior & Views

Magnificent Star Wars & Designed Rooms Pool & Spa! 7 Bedroom Villa

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Osceola
Magnificent Star Wars & Designed Rooms Pool & Spa! 7 Bedroom Villa Location
With a stay at this villa in Four Corners, you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This villa is 11.9 mi (19.2 km) from Old Town and 12.7 mi (20.5 km) from ESPN Wide World of Sports Complex.

Magnificent Star Wars & Designed Rooms Pool & Spa! 7 Bedroom Villa Rooms
Make yourself comfortable in your villa. Complimentary wireless internet access is available to keep you connected.

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3bd/3ba Windsor Hills, 10 min to Disney

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Osceola
3bd/3ba Windsor Hills, 10 min to Disney Location
Located in Kissimmee (Windsor Hills), this villa is within a 10-minute drive of Walt Disney World® Resort and Old Town. This villa is 5.6 mi (9.1 km) from ESPN Wide World of Sports Complex and 6.1 mi (9.9 km) from Disney's Hollywood Studios®.

3bd/3ba Windsor Hills, 10 min to Disney Facility and Service
Enjoy recreational amenities such as an outdoor pool and a hot tub. Additional amenities at this villa include complimentary wireless internet access, a picnic area, and barbecue grills.

3bd/3ba Windsor Hills, 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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Disney Area 3BR Townhome + Resort Amenities

Villa

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Osceola
Disney Area 3BR Townhome + Resort Amenities 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 7.3 mi (11.8 km) from Disney's Animal Kingdom® Theme Park and 8.5 mi (13.7 km) from Old Town.

Disney Area 3BR Townhome + Resort Amenities 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 and a vending machine.

Disney Area 3BR Townhome + Resort Amenities Rooms
Make yourself comfortable in your villa. 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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Villas at Island Club Community, Pools, Jacuzzi and More!

Villa

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Osceola
Villas at Island Club Community, Pools, Jacuzzi and More! 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 condo is 7.2 mi (11.6 km) from Disney's Animal Kingdom® Theme Park and 8 mi (12.9 km) from ESPN Wide World of Sports Complex.

Villas at Island Club Community, Pools, Jacuzzi and More! Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center.

Villas at Island Club Community, Pools, Jacuzzi and More! Rooms
Make yourself comfortable in your condo. Complimentary wireless internet access is available to keep you connected.

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Exterior & Views

Sunshine Park at Windsor Hills villa

Villa

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Osceola
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Family & Kids

Family-friendly Luxury Home Near Disney & More

Villa

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Osceola
Family-friendly Luxury Home Near Disney & More Location
When you stay at this villa in Kissimmee, you'll be near the beach, within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This villa is 8.8 mi (14.1 km) from Disney Springs™ and 9.8 mi (15.7 km) from Walt Disney World® Resort.

Family-friendly Luxury Home Near Disney & More Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Family-friendly Luxury Home Near Disney & More Rooms
Make yourself comfortable in your individually decorated villa. The bathroom has a bathtub or shower and designer toiletries. Conveniences include a coffee/tea maker and a washer/dryer.

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Bedroom

Storey Lake 9 BR Villa with Game Room

Villa

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Osceola
Storey Lake 9 BR Villa with Game Room 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 spa vacation home is 6 mi (9.6 km) from Disney Springs™ and 6.7 mi (10.8 km) from ESPN Wide World of Sports Complex.

Storey Lake 9 BR Villa with Game Room Facility and Service
Take time to pamper yourself with a visit to the full-service spa. You can take advantage of recreational amenities such as an outdoor pool and a fitness center.

Storey Lake 9 BR Villa with Game Room 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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Villas in Osceola

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