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Villas in Osceola

Osceola
Sat, 14 Nov 2026 - Sun, 15 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 1.000+ Villas in Osceola
Interior

Encantada Resort - Spacious 3-bedroom Villa With Private Pool Near Disney

Villa

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Osceola
Encantada Resort - Spacious 3-bedroom Villa With Private Pool Near Disney Location
With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center. This cottage is 6.7 mi (10.8 km) from ESPN Wide World of Sports Complex and 6.9 mi (11.2 km) from Disney's Animal Kingdom® Theme Park.

Encantada Resort - Spacious 3-bedroom Villa With Private Pool Near Disney Rooms
Make yourself comfortable in this air-conditioned cottage, which features a fireplace. A kitchen makes it easy to prepare your meals.

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Exterior & Views

Encore Club #1 - 10 Bedroom Private Pool Villa in Reunion Golf Resort

Villa

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Osceola
Encore Club #1 - 10 Bedroom Private Pool Villa in Reunion Golf Resort 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 7.4 mi (11.9 km) from ESPN Wide World of Sports Complex and 8.1 mi (13.1 km) from Disney's Hollywood Studios®.

Encore Club #1 - 10 Bedroom Private Pool Villa in Reunion Golf Resort Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools or 2 hot tubs. This villa also features complimentary wireless internet access, an arcade/game room, and a television in a common area.

Encore Club #1 - 10 Bedroom Private Pool Villa in Reunion Golf Resort Rooms
Make yourself comfortable in this air-conditioned 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 DVD player is also provided. Conveniences include a microwave and a sofa bed.

Restaurant and Cafe
Enjoy a meal at the restaurant or snacks in the villa's coffee shop/cafe. Wrap up your day with a drink at the bar/lounge.

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Others

Pool, Spa, Playground and More at Villas at Laguna Bay!!

Villa

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Osceola
Pool, Spa, Playground and More at Villas at Laguna Bay!! Location
With a stay at this condo in Kissimmee, you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This condo is 7.4 mi (12 km) from Disney Springs™ and 7.6 mi (12.3 km) from ESPN Wide World of Sports Complex.

Pool, Spa, Playground and More at Villas at Laguna Bay!! Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

Pool, Spa, Playground and More at Villas at Laguna Bay!! Rooms
Make yourself comfortable in your condo. Complimentary wireless internet access is available to keep you connected.

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Others

Jurassic Water View @storey Lake by Shine Villas! Sleeps up to 24! #021

Private Villa

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Osceola
Jurassic Water View @storey Lake by Shine Villas! Sleeps up to 24! #021 Location
When you stay at this cottage in Kissimmee, you'll be next to a golf course, within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This golf cottage is 7.5 mi (12 km) from Disney Springs™ and 8.6 mi (13.8 km) from Walt Disney World® Resort.

Jurassic Water View @storey Lake by Shine Villas! Sleeps up to 24! #021 Facility and Service
Pamper yourself with a visit to the spa, which offers massages.

Jurassic Water View @storey Lake by Shine Villas! Sleeps up to 24! #021 Rooms
Make yourself comfortable in this cottage, which features a private pool and a flat-screen TV. Complimentary wireless internet access keeps you connected, and a video-game console is provided for your entertainment.

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Ov2417 - Windsor Palms Resort - 6 Bed 3.5 Baths Villa

Villa

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Osceola
Ov2417 - Windsor Palms Resort - 6 Bed 3.5 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 Old Town. This family-friendly villa 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®.

Ov2417 - Windsor Palms Resort - 6 Bed 3.5 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 an arcade/game room.

Ov2417 - Windsor Palms Resort - 6 Bed 3.5 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. Unwind at the end of the day with a drink at the bar/lounge or the poolside bar.

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Your Dream Vacation 9BR Villa

Villa

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Osceola
Your Dream Vacation 9BR Villa Location
With a stay at this villa in Four Corners, you'll be within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This villa is 12.1 mi (19.5 km) from Old Town and 12.6 mi (20.2 km) from Walt Disney World® Resort.

Your Dream Vacation 9BR Villa Facility and Service
Take advantage of recreation opportunities such as an outdoor pool or take in the view from a terrace and a garden.

Your Dream Vacation 9BR Villa Rooms
Make yourself comfortable in your villa. Complimentary wireless internet access is available to keep you connected. Conveniences include an electric kettle and a washer/dryer.

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Windsor Hills Resort Vacation 3BR

Villa

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Osceola
Windsor Hills Resort Vacation 3BR 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 villa is 5.9 mi (9.5 km) from ESPN Wide World of Sports Complex and 6.1 mi (9.7 km) from Disney's Hollywood Studios®.

Windsor Hills Resort Vacation 3BR Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Windsor Hills Resort Vacation 3BR 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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Aco244924 - Paradise Palms Resort - 6 Bed 5 Baths Villa

Villa

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Osceola
Aco244924 - Paradise Palms Resort - 6 Bed 5 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 Old Town. This family-friendly villa is 8.2 mi (13.2 km) from Disney's Animal Kingdom® Theme Park and 9.1 mi (14.6 km) from ESPN Wide World of Sports Complex.

Aco244924 - Paradise Palms Resort - 6 Bed 5 Baths Villa 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 complimentary water park or a hot tub. This villa also features complimentary wireless internet access, concierge services, and a television in a common area.

Aco244924 - Paradise Palms Resort - 6 Bed 5 Baths Villa Rooms
Make yourself comfortable in this air-conditioned villa, featuring a kitchen with a refrigerator and an oven. There's a private balcony. A flat-screen television is provided for your entertainment. Conveniences include a microwave and a washer/dryer.

Restaurant and Cafe
Satisfy your appetite at the villa's coffee shop/cafe, or stop in at the grocery/convenience store. Unwind at the end of the day with a drink at the bar/lounge or the poolside bar.

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Storey Lake 4BR w/ Private Pool Near Disney

Villa

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Osceola
Storey Lake 4BR w/ Private Pool Near Disney Location
With a stay at this villa in Kissimmee, you'll be a 4-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This villa is 5.1 mi (8.2 km) from Disney Springs™ and 6.1 mi (9.9 km) from Walt Disney World® Resort.

Storey Lake 4BR w/ Private Pool Near Disney Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center. Additional features at this villa include complimentary wireless internet access, an arcade/game room, and barbecue grills.

Storey Lake 4BR w/ Private Pool Near Disney Rooms
Your villa features a flat-screen TV. There's a private patio. Complimentary wireless internet access is available to keep you connected. The bathroom has a bathtub or shower and complimentary toiletries.

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5BR Veranda Palms Home Near Disney for 14

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Osceola
5BR Veranda Palms Home Near Disney for 14 Location
Located in Kissimmee (Veranda Palms), this villa is within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This villa is 6.8 mi (10.9 km) from Disney Springs™ and 7.8 mi (12.6 km) from Walt Disney World® Resort.

5BR Veranda Palms Home Near Disney for 14 Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a hot tub. Additional features at this villa include complimentary wireless internet access and barbecue grills.

5BR Veranda Palms Home Near Disney for 14 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.

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Room

Chic 3BR Retreat Patio With BBQ all Suites

Villa

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Osceola
Chic 3BR Retreat Patio With BBQ all Suites 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®.

Chic 3BR Retreat Patio With BBQ all Suites Rooms
Make yourself comfortable in your villa.

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5BR Home Near Disney With Pool & Game Room

Villa

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Osceola
5BR Home Near Disney With Pool & Game Room Location
With a stay at this villa in Kissimmee (Trafalgar Village), you'll be within a 10-minute drive of Green Meadows Petting Farm and Shingle Creek Regional Park. This villa is 11.1 mi (17.8 km) from Old Town and 13.3 mi (21.4 km) from Orlando Vineland Premium Outlets.

5BR Home Near Disney With Pool & Game Room Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a hot tub. Additional features at this villa include complimentary wireless internet access and barbecue grills.

5BR Home Near Disney With Pool & Game Room Rooms
Make yourself comfortable in this villa, featuring a kitchen with a full-sized refrigerator/freezer and a stovetop. There's a private patio. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. Conveniences include a washer/dryer, and a crib/infant bed (complimentary) can be requested.

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Others

Star Hideaway at Storey Lake by Shine Villas #716

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Osceola
Star Hideaway at Storey Lake by Shine Villas #716 Location
When you stay at this apartment in Kissimmee, you'll be next to a golf course, within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This golf apartment is 5.9 mi (9.4 km) from Disney Springs™ and 6.8 mi (11 km) from Walt Disney World® Resort.

Star Hideaway at Storey Lake by Shine Villas #716 Facility and Service
Relax at the full-service spa, where you can enjoy massages.

Star Hideaway at Storey Lake by Shine Villas #716 Rooms
Your apartment features a flat-screen TV. Complimentary wireless internet access is available to keep you connected.

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Others

Condominium villas near Disney Orlando Florida

Villa

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Osceola
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Upstay Spacious 3BR Home w/ Resort Clubhouse Pool

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Osceola
Upstay Spacious 3BR Home w/ Resort Clubhouse Pool Location
When you stay at this villa in Kissimmee, you'll be near the airport, within a 15-minute drive of Walt Disney World® Resort and Old Town. This family-friendly villa 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.

Upstay Spacious 3BR Home w/ Resort Clubhouse Pool Facility and Service
Don't miss out on the many recreational opportunities, including an outdoor pool, a hot tub, and a fitness center. Additional amenities at this villa include complimentary wireless internet access and an arcade/game room.

Upstay Spacious 3BR Home w/ Resort Clubhouse Pool Rooms
Make yourself comfortable in your air-conditioned villa, which features a Smart TV. Cable television is provided for your entertainment.

Restaurant and Cafe
Unwind at the end of the day with a drink at the bar/lounge or the poolside bar.

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Interior

1564fd · Dazzling 6Br Villa W Pool&spa

Villa

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Osceola
1564fd · Dazzling 6Br Villa W Pool&spa 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 (19.4 km) from ESPN Wide World of Sports Complex.

1564fd · Dazzling 6Br Villa W Pool&spa Rooms
Make yourself comfortable in this air-conditioned villa, which has a kitchen. Cable television is provided for your entertainment.

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Sport & Beauty

Spacious Home W/private Pool/spa & Free Waterpark!

Villa

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Osceola
Spacious Home W/private Pool/spa & Free Waterpark! Location
With a stay at this cottage in Kissimmee (Windsor Hills), you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This family-friendly cottage is 5.6 mi (9 km) from ESPN Wide World of Sports Complex and 6.1 mi (9.7 km) from Old Town.

Spacious Home W/private Pool/spa & Free Waterpark! Facility and Service
Enjoy a range of recreational amenities, including an outdoor pool, a waterslide, and a fitness center. Additional features at this cottage include complimentary wireless internet access, an arcade/game room, and barbecue grills.

Spacious Home W/private Pool/spa & Free Waterpark! Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with a refrigerator and an oven. There's a private patio. Cable television is provided for your entertainment. Conveniences include a microwave and a coffee/tea maker.

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3.0/5
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6BR Villa w/ Pool, Spa & Resort Close to Disney

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Osceola
6BR Villa w/ Pool, Spa & Resort Close to Disney Location
With a stay at this villa in Kissimmee, you'll be within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This villa is 12.3 mi (19.8 km) from Walt Disney World® Resort and 12.4 mi (20 km) from Old Town.

6BR Villa w/ Pool, Spa & Resort Close to 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, concierge services, and an arcade/game room.

6BR Villa w/ Pool, Spa & Resort Close to Disney 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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Others

5BR Pool Home + Game Room @ Champions Gate

Villa

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Osceola
5BR Pool Home + Game Room @ Champions Gate Location
With a stay at this villa in Kissimmee, you'll be within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This villa is 12.5 mi (20.1 km) from Walt Disney World® Resort and 12.7 mi (20.4 km) from Old Town.

5BR Pool Home + Game Room @ Champions Gate Facility and Service
Don't miss out on the many recreational opportunities, including an outdoor pool, an indoor pool, and a hot tub. Additional amenities at this villa include complimentary wireless internet access, an arcade/game room, and barbecue grills.

5BR Pool Home + Game Room @ Champions Gate 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

Lucaya Resort 3BR Near Disney w/ Gym & Pool

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Osceola
Lucaya Resort 3BR Near Disney w/ Gym & Pool Location
With a stay at this villa in Kissimmee, you'll be a 3-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 5.6 mi (9 km) from Walt Disney World® Resort.

Lucaya Resort 3BR Near Disney w/ Gym & Pool Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a hot tub. Additional features at this villa include complimentary wireless internet access, an arcade/game room, and barbecue grills.

Lucaya Resort 3BR Near Disney w/ Gym & Pool Rooms
Your villa features a flat-screen TV. There's a private furnished patio. 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.

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Villas in Osceola

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