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Villas in Osceola

Osceola
Sun, 15 Nov 2026 - Mon, 16 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 1.000+ Villas in Osceola

Emerald Island #4 - 7 Bed 6 Baths Villa

Villa

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Osceola
Emerald Island #4 - 7 Bed 6 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.

Emerald Island #4 - 7 Bed 6 Baths Villa Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools. Additional amenities at this villa include complimentary wireless internet access, concierge services, and an arcade/game room.

Emerald Island #4 - 7 Bed 6 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 or patio. A flat-screen television is provided for your entertainment. Conveniences include a microwave and a sofa bed.

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

See details
Fully Booked
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Ov3060 - Champions Gate Resort - 8 Bed 5 Baths Villa

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Osceola
Ov3060 - Champions Gate Resort - 8 Bed 5 Baths Villa 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 family-friendly villa is 11.8 mi (19 km) from Old Town and 12.6 mi (20.3 km) from ESPN Wide World of Sports Complex.

Ov3060 - Champions Gate Resort - 8 Bed 5 Baths Villa Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools or 2 hot tubs. Additional features at this villa include complimentary wireless internet access, concierge services, and a television in a common area.

Ov3060 - Champions Gate Resort - 8 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 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. Relax with your favorite drink at the bar/lounge or the poolside bar.

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Modern 6BR Villa Heated Pool Solara Resort

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Osceola
Modern 6BR Villa Heated Pool Solara Resort Location
With a stay at this villa in Kissimmee, you'll be within a 15-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This villa is 8.5 mi (13.7 km) from Walt Disney World® Resort and 10.2 mi (16.4 km) from Disney's Animal Kingdom® Theme Park.

Modern 6BR Villa Heated Pool Solara Resort Facility and Service
Don't miss out on the many recreational opportunities, including a health club, an outdoor pool, and a hot tub. This villa also features complimentary wireless internet access and barbecue grills.

Modern 6BR Villa Heated Pool Solara Resort 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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5.0/5
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Grand Villa With Games Room at Encore

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Osceola
Grand Villa With Games Room at Encore Location
When you stay at this villa in Kissimmee, you'll be near the beach, within a 10-minute drive of Mystic Dunes Golf Club and Reunion Resort Golf Course. This villa is 5.6 mi (9 km) from Walt Disney World® Resort and 7.8 mi (12.6 km) from ESPN Wide World of Sports Complex.

Grand Villa With Games Room at Encore Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Grand Villa With Games Room at Encore Rooms
Make yourself comfortable in your individually decorated villa. The bathroom has a bathtub or shower.

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Je59004 - Champions Gate Resort - 8 Bed 5 Baths Villa

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Osceola
Je59004 - Champions Gate Resort - 8 Bed 5 Baths Villa Location
With a stay at this villa in Four Corners (Champions Gate), you'll be within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This family-friendly villa is 12.9 mi (20.7 km) from Old Town and 13.4 mi (21.6 km) from Walt Disney World® Resort.

Je59004 - Champions Gate Resort - 8 Bed 5 Baths Villa Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools or 2 hot tubs. Additional amenities at this villa include complimentary wireless internet access, concierge services, and a television in a common area.

Je59004 - Champions Gate Resort - 8 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 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.

See details
Fully Booked
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558- Stunning 5BR 4 BA Veranda Palms Villa with South-Facing Pool

Villa

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Osceola
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Others

Townhome Splash Pool BBQ Free Water Park!

Villa

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Osceola
Townhome Splash Pool BBQ Free Water Park! Location
With a stay at this cottage in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This family-friendly cottage is 10.2 mi (16.4 km) from Disney's Animal Kingdom® Theme Park and 11 mi (17.7 km) from ESPN Wide World of Sports Complex.

Townhome Splash Pool BBQ Free Water Park! Facility and Service
Take advantage of recreational opportunities offered, including an outdoor pool, a lazy river, and a fitness center. This cottage also features complimentary wireless internet access, an arcade/game room, and gas grills.

Townhome Splash Pool BBQ Free Water Park! Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with a refrigerator and an oven. A flat-screen 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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5.0/5
Fully Booked
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Room

Modern 5BR Near Disney Private Pool

Villa

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Osceola
Modern 5BR Near Disney Private Pool Location
With a stay at this villa in Four Corners, you'll be within a 15-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center. This villa is 9.3 mi (14.9 km) from Disney's Animal Kingdom® Theme Park and 10.5 mi (16.8 km) from ESPN Wide World of Sports Complex.

Modern 5BR Near Disney Private Pool Facility and Service
Take in the views from a garden.

Modern 5BR Near Disney Private Pool Rooms
Make yourself comfortable in your villa.

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Fully Booked
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Exterior & Views

Champions Gate Resort Homes

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Osceola
Champions Gate Homes offer a refined Florida villa experience combining generous space, modern comfort and resort leisure close to Orlando’s headline attractions. These spacious 5 to 9-bedroom homes (sleeping up to 18 guests) include Wi‑Fi, a complimentary welcome pack on arrival, and a private screened swimming pool for laid-back days in the sunshine. Some villas may also feature an in-villa games room or spa, making them ideal for larger families and groups wanting extra entertainment and relaxation between park visits. Set within the 1, 500-acre Champions Gate Resort in Osceola County, the community is just 12 miles from Walt Disney World Resort, with Orlando International Airport around 27 miles away for easy arrivals and departures. Resort amenities are centred around the stylish clubhouse and the Oasis Water Park, with a resort-style pool, spacious spa, water slides, shaded cabanas, a children’s splash park and a winding lazy river. Guests can also enjoy shared facilities including a fitness centre, private cinema, playground, games room and volleyball courts, plus excellent sports options such as a championship 18-hole golf course with driving range and putting green, a pro shop and locker rooms, five clay tennis courts, four pickleball courts and a separate tennis clubhouse. Each villa includes a contemporary fully equipped kitchen with countertops, appliances, a breakfast bar and formal dining space, while on-site dining is available at the poolside tiki bar and the golf clubhouse grill. Please note some resort facilities may still be under construction, so disruption is possible. Florida State Law also requires all guests to complete online registration and pay a Property Protection Fee of $8 per day (capped at $120) by credit/debit card; registration must be completed to download the accommodation voucher approximately 14 days before arrival.
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Others

6bd/5.5ba Lux Pool Near Disney

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Osceola
6bd/5.5ba Lux Pool Near Disney 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 villa is 7.2 mi (11.5 km) from ESPN Wide World of Sports Complex and 7.7 mi (12.3 km) from Disney's Hollywood Studios®.

6bd/5.5ba Lux Pool Near Disney Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a hot tub. Additional amenities at this villa include complimentary wireless internet access, an arcade/game room, and a picnic area.

6bd/5.5ba Lux 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 bathtub or shower and complimentary toiletries.

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Fully Booked
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Sport & Beauty

Ip60119 - Rolling Hills Estates - 4 Bed 3 Baths Villa

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Osceola
Ip60119 - Rolling Hills Estates - 4 Bed 3 Baths Villa Location
With a stay at this villa in Kissimmee, you'll be a 5-minute drive from Mystic Dunes Golf Club and 9 minutes from Walt Disney World® Resort. This villa is 6 mi (9.7 km) from ESPN Wide World of Sports Complex and 6.5 mi (10.4 km) from Old Town.

Ip60119 - Rolling Hills Estates - 4 Bed 3 Baths Villa Facility and Service
Take advantage of recreation opportunities such as a seasonal outdoor pool, or other amenities including complimentary wireless internet access and concierge services.

Ip60119 - 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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Living area

Cup8946

Villa

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Osceola
Cup8946 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 villa is 7.9 mi (12.7 km) from Disney's Animal Kingdom® Theme Park and 9.1 mi (14.7 km) from ESPN Wide World of Sports Complex.

Cup8946 Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Cup8946 Rooms
Make yourself comfortable in this air-conditioned villa, which has a kitchen. Cable television is provided for your entertainment. Conveniences include a coffee/tea maker and a dryer.

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Others

Comfort and Space Townhome With Mickey Room

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Osceola
Comfort and Space Townhome With Mickey Room Location
With a stay at Comfort and Space Townhome With Mickey Room in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Old Town. This villa is 4.8 mi (7.7 km) from ESPN Wide World of Sports Complex and 5.5 mi (8.8 km) from Disney's Animal Kingdom® Theme Park.

Comfort and Space Townhome With Mickey Room Rooms
Make yourself at home in one of the 19 guestrooms.

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Exterior & Views

8942tw 8 Bedroom Villa by RedAwning

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Osceola
8942tw 8 Bedroom 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 11.4 mi (18.4 km) from Old Town and 12.2 mi (19.7 km) from ESPN Wide World of Sports Complex.

8942tw 8 Bedroom Villa by RedAwning Rooms
Make yourself comfortable in your air-conditioned villa. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. The bathroom has a bathtub or shower.Conveniences include a phone and a washer/dryer.

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Ov4201 - Windsor Hills Resort - 6 Bed 4 Baths Villa

Villa

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Osceola
Ov4201 - 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®.

Ov4201 - 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 outdoor pools. Additional amenities at this villa include complimentary wireless internet access, concierge services, and a television in a common area.

Ov4201 - 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 with cable programming is available for your entertainment, and a video-game console is also provided.

Restaurant and Cafe
Grab a bite from the grocery/convenience store serving guests of this villa. Wrap up your day with a drink at the poolside bar.

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Sport & Beauty

Stylish Home w/ Private Pool, 10 Min. From Disney!

Villa

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Osceola
Stylish Home w/ Private Pool, 10 Min. From Disney! Location
With a stay at this vacation home in Kissimmee, you'll be a 4-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This family-friendly vacation home is 5.2 mi (8.4 km) from Disney Springs™ and 6.2 mi (10 km) from Walt Disney World® Resort.

Stylish Home w/ Private Pool, 10 Min. From Disney! Facility and Service
Enjoy a range of recreational amenities, including an outdoor pool, a lazy river, and a waterslide. Additional features at this vacation home include complimentary wireless internet access and barbecue grills.

Stylish Home w/ Private Pool, 10 Min. From Disney! Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. Cable television is provided for your entertainment. Conveniences include a desk and a microwave.

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

See details
4.8/5
Fully Booked
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Dazzling 7BR Villa with Pool & Game Room

Villa

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Osceola
Dazzling 7BR Villa with Pool & Game Room 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 6.8 mi (10.9 km) from ESPN Wide World of Sports Complex and 6.8 mi (11 km) from Old Town.

Dazzling 7BR Villa with Pool & Game Room Facility and Service
Take advantage of recreation opportunities such as an outdoor pool or take in the view from a terrace and a garden.

Dazzling 7BR Villa with Pool & Game Room Rooms
Make yourself comfortable in your villa. Complimentary wireless internet access is available to keep you connected.

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Fully Booked
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Sport & Beauty

Villa Minnie - Lucaya Village

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Osceola
Villa Minnie - Lucaya Village Location
With a stay at this condo in Kissimmee, you'll be a 3-minute drive from Old Town and 8 minutes from Orlando Vineland Premium Outlets. This condo is 5.3 mi (8.6 km) from Disney Springs™ and 5.5 mi (8.9 km) from Walt Disney World® Resort.

Villa Minnie - Lucaya Village Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including complimentary wireless internet access.

Villa Minnie - Lucaya Village Rooms
Make yourself comfortable in this air-conditioned condo, featuring a kitchen with an oven and a stovetop. Complimentary wireless internet access is available to keep you connected. Conveniences include a microwave and a sofa bed, and housekeeping is provided once per stay.

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6BR Championsgate Home · Pool · Near Disney

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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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Fully Booked
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Shv1189ha - 7 Bedroom Villa In Crystal Cove, Sleeps Up To 16, Just 6 Miles To Disney

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Osceola
Shv1189ha - 7 Bedroom Villa In Crystal Cove, Sleeps Up To 16, Just 6 Miles To Disney Location
With a stay at this villa in Kissimmee (Crystal Cove), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This family-friendly villa is 8 mi (12.8 km) from Disney Springs™ and 8.2 mi (13.1 km) from ESPN Wide World of Sports Complex.

Shv1189ha - 7 Bedroom Villa In Crystal Cove, Sleeps Up To 16, Just 6 Miles To Disney 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 villa include complimentary wireless internet access, concierge services, and a television in a common area.

Shv1189ha - 7 Bedroom Villa In Crystal Cove, Sleeps Up To 16, Just 6 Miles To Disney Rooms
Treat yourself to a stay in this individually decorated villa, which features a private pool and a flat-screen TV. There's a private balcony or patio. A kitchen is outfitted with a stovetop and a dishwasher. Cable programming along with a video-game console are provided for your entertainment.

Restaurant and Cafe
At this villa, enjoy a satisfying meal at the restaurant. Quench your thirst with your favorite drink at the poolside bar.

See details
3.7/5
Fully Booked
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Villas in Osceola

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