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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
Others

Luxury 2BR / Mickey Room & Resort Amenities!

Villa

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Osceola
Luxury 2BR / Mickey Room & Resort Amenities! 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 11.9 mi (19.1 km) from Old Town and 12.7 mi (20.4 km) from ESPN Wide World of Sports Complex.

Luxury 2BR / Mickey Room & Resort Amenities! Facility and Service
Take advantage of recreation opportunities such as an outdoor pool or take in the view from a terrace and a garden. This villa also features complimentary wireless internet access, an arcade/game room, and a vending machine.

Luxury 2BR / Mickey Room & Resort Amenities! Rooms
Make yourself comfortable in this villa, which features a private pool and a flat-screen TV. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include a separate sitting area, and a crib/infant bed (complimentary) can be requested.

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Modern Villa With Private Pool in Encore

Villa

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Osceola
Modern Villa With Private Pool in 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 5.6 mi (9 km) from Walt Disney World® Resort and 7.8 mi (12.6 km) from ESPN Wide World of Sports Complex.

Modern Villa With Private Pool in Encore Facility and Service
Enjoy the recreation opportunities such as a hot tub or make use of other amenities including complimentary wireless internet access.

Modern Villa With Private Pool in Encore Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Exterior & Views

Daisy's Den - Five Bedroom Home

Villa

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Osceola
Daisy's Den - Five Bedroom Home Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This vacation home is 7 mi (11.3 km) from Old Town and 7.1 mi (11.5 km) from ESPN Wide World of Sports Complex.

Daisy's Den - Five Bedroom Home 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.

Daisy's Den - Five Bedroom Home Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool and a flat-screen TV. There's a private furnished lanai. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Digital television is provided for your entertainment.

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Ov2134 - Reunion Resort - 3 Bed 3 Baths Villa

Villa

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Osceola
Ov2134 - Reunion Resort - 3 Bed 3 Baths Villa Location
Located in Kissimmee (Reunion), this villa is within a 10-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This family-friendly villa is 7.3 mi (11.7 km) from Walt Disney World® Resort and 9 mi (14.4 km) from Disney's Animal Kingdom® Theme Park.

Ov2134 - Reunion Resort - 3 Bed 3 Baths Villa Facility and Service
Practice your swing on the golf course or dip into one of the 8 outdoor pools. This villa also features complimentary wireless internet access, concierge services, and a television in a common area.

Ov2134 - Reunion Resort - 3 Bed 3 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 washer/dryer.

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

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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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Encantada Resort Home w/ Priv Pool Near Disney

Villa

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Osceola
Encantada Resort Home w/ Priv Pool Near Disney Location
Located in Kissimmee, this villa is within a 15-minute drive of Walt Disney World® Resort and Old Town. This villa is 6.9 mi (11.1 km) from Disney's Animal Kingdom® Theme Park and 8.1 mi (13.1 km) from ESPN Wide World of Sports Complex.

Encantada Resort Home w/ Priv Pool Near Disney Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. Additional features at this villa include complimentary wireless internet access and an arcade/game room.

Encantada Resort Home w/ Priv Pool Near Disney 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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Spacious Family Villa With Private Pool, spa and Movie Loft

Villa

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Osceola
Spacious Family Villa With Private Pool, spa and Movie Loft Location
With a stay at this vacation home in Kissimmee, you'll be near the beach, within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This vacation home is 12.3 mi (19.8 km) from Old Town and 13.1 mi (21 km) from ESPN Wide World of Sports Complex.

Spacious Family Villa With Private Pool, spa and Movie Loft 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.

Spacious Family Villa With Private Pool, spa and Movie Loft Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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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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Others

Luxury 8BR Villa w/ Pool, Game & Theater Room

Villa

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Osceola
Luxury 8BR Villa w/ Pool, Game & Theater 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 7.4 mi (11.9 km) from ESPN Wide World of Sports Complex and 7.9 mi (12.7 km) from Disney's Hollywood Studios®.

Luxury 8BR Villa w/ Pool, Game & Theater Room Facility and Service
Be sure to enjoy recreational amenities, including an outdoor pool, an indoor pool, and a hot tub. Additional amenities at this villa include complimentary wireless internet access, concierge services, and barbecue grills.

Luxury 8BR Villa w/ Pool, Game & Theater Room 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

Windsor At Westside #12 - 8 Bed 6 Baths Villa

Villa

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Osceola
Windsor At Westside #12 - 8 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.

Windsor At Westside #12 - 8 Bed 6 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 an arcade/game room.

Windsor At Westside #12 - 8 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. Quench your thirst with your favorite drink at the poolside bar.

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4BR Townhome w/ Pool + Themed Bedrooms

Villa

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Osceola
4BR Townhome w/ Pool + Themed Bedrooms Location
Located in Kissimmee, this villa is within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This villa is 7.5 mi (12 km) from Disney Springs™ and 8.5 mi (13.6 km) from Walt Disney World® Resort.

4BR Townhome w/ Pool + Themed Bedrooms 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, an arcade/game room, and barbecue grills.

4BR Townhome w/ Pool + Themed Bedrooms 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 separate bathtub and shower and complimentary toiletries.

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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.

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Food & Drinks

2089elcir 8 Bedroom Villa by RedAwning

Villa

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Osceola
2089elcir 8 Bedroom Villa 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 5.5 mi (8.9 km) from Disney Springs™ and 6.5 mi (10.5 km) from Walt Disney World® Resort.

2089elcir 8 Bedroom Villa by RedAwning Rooms
Make yourself comfortable in your air-conditioned villa. Complimentary wireless internet access is available to keep you connected.

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Others

8 Bed Windsor At Westside Resort! 8 Bedroom Villa by RedAwning

Villa

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Osceola
8 Bed Windsor At Westside Resort! 8 Bedroom Villa by RedAwning 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 10.3 mi (16.6 km) from Disney's Animal Kingdom® Theme Park and 11.2 mi (18 km) from ESPN Wide World of Sports Complex.

8 Bed Windsor At Westside Resort! 8 Bedroom Villa by RedAwning Facility and Service
Enjoy recreation amenities such as an outdoor tennis court or take in the view from a terrace.

8 Bed Windsor At Westside Resort! 8 Bedroom Villa by RedAwning Rooms
Make yourself comfortable in this air-conditioned villa, which features a private pool. There's a private lanai. A kitchen makes it easy to prepare your meals. Complimentary wireless internet access is available to keep you connected.

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Others

3BR Lucaya Village Home, Sleeps 8

Villa

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Osceola
3BR Lucaya Village Home, Sleeps 8 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.

3BR Lucaya Village Home, Sleeps 8 Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a hot tub. This villa also features complimentary wireless internet access and a vending machine.

3BR Lucaya Village Home, Sleeps 8 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

Compass Bay 4bdr Renovated BBQ Near Disney

Villa

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Osceola
Compass Bay 4bdr Renovated BBQ Near Disney 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 5.3 mi (8.6 km) from Disney Springs™ and 6 mi (9.7 km) from Walt Disney World® Resort.

Compass Bay 4bdr Renovated BBQ Near Disney 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. Additional amenities at this villa include a picnic area and barbecue grills.

Compass Bay 4bdr Renovated BBQ 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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Ov3426 - Paradise Palms - 5 Bed 4 Baths Villa

Villa

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Osceola
Ov3426 - Paradise Palms - 5 Bed 4 Baths Villa Location
Located in Kissimmee, this villa is within a 15-minute drive of Walt Disney World® Resort and Old Town. This golf villa is 7.9 mi (12.8 km) from Disney's Animal Kingdom® Theme Park and 9.1 mi (14.7 km) from ESPN Wide World of Sports Complex.

Ov3426 - Paradise Palms - 5 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 shopping on site.

Ov3426 - Paradise Palms - 5 Bed 4 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. A kitchen is outfitted with a refrigerator, an oven, and a microwave. Cable television is provided for your entertainment.

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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Others

5BR w/ South Pool, Game Room Storey Lake

Villa

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Osceola
5BR w/ South Pool, Game Room Storey Lake Location
With a stay at 5BR w/ South Pool, Game Room Storey Lake in Kissimmee, you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets.

5BR w/ South Pool, Game Room Storey Lake Facility and Service
Enjoy recreational amenities such as an outdoor pool and a hot tub.

5BR w/ South Pool, Game Room Storey Lake Rooms
There's a private furnished patio. A flat-screen television with cable programming provides entertainment, while complimentary wireless internet access keeps you connected. The bathroom has a bathtub or shower and complimentary toiletries. Conveniences include a separate sitting area and a sofa bed, and you can also request a crib/infant bed (complimentary).

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Others

Family Home at Storey Lake w/ Pool

Villa

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Osceola
Family Home at Storey Lake w/ Pool 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 5.3 mi (8.5 km) from Disney Springs™ and 6.3 mi (10.2 km) from Walt Disney World® Resort.

Family Home at Storey Lake w/ Pool 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 barbecue grills.

Family Home at Storey Lake w/ Pool 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

Large Villa W/private Pool & Game Room! Waterpark

Villa

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Osceola
Large Villa W/private Pool & Game Room! Waterpark 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 10.3 mi (16.6 km) from Disney's Animal Kingdom® Theme Park and 11.2 mi (18 km) from ESPN Wide World of Sports Complex.

Large Villa W/private Pool & Game Room! Waterpark Facility and Service
Be sure to enjoy recreational amenities, including an outdoor pool, a lazy river, and a fitness center. Additional amenities at this cottage include complimentary wireless internet access and an arcade/game room.

Large Villa W/private Pool & Game Room! Waterpark 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 coffee/tea maker.

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

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4.3/5
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Villas in Osceola

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