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Villas in Osceola

Osceola
Fri, 13 Nov 2026 - Sat, 14 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 1.000+ Villas in Osceola

Ov650 - Emerald Island - 6 Bed 5.5 Baths Villa

Villa

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Osceola
Ov650 - Emerald Island - 6 Bed 5.5 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.

Ov650 - Emerald Island - 6 Bed 5.5 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. This villa also features complimentary wireless internet access, concierge services, and a television in a common area.

Ov650 - Emerald Island - 6 Bed 5.5 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
Relax with your favorite drink at the bar/lounge or the poolside bar.

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7458 Magic Village 8 Guests - 8 min Disney

Villa

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Osceola
7458 Magic Village 8 Guests - 8 min 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 4.8 mi (7.6 km) from Old Town and 4.8 mi (7.7 km) from ESPN Wide World of Sports Complex.

7458 Magic Village 8 Guests - 8 min 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 and barbecue grills.

7458 Magic Village 8 Guests - 8 min Disney Rooms
Make yourself comfortable in this villa, which has a kitchen. A flat-screen television with cable programming provides entertainment, while complimentary wireless internet access keeps you connected. Conveniences include a separate sitting area and a sofa bed, and you can also request a crib/infant bed (complimentary).

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Exterior & Views

Beautiful Home Near Disney With Private Pool! 5 Bedroom Villa by RedAwning

Villa

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Osceola
Beautiful Home Near Disney With Private Pool! 5 Bedroom Villa by RedAwning 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 4.9 mi (7.9 km) from ESPN Wide World of Sports Complex and 5.6 mi (8.9 km) from Disney's Hollywood Studios®.

Beautiful Home Near Disney With Private Pool! 5 Bedroom Villa by RedAwning Facility and Service
This smoke-free villa offers games.

Beautiful Home Near Disney With Private Pool! 5 Bedroom Villa by RedAwning Rooms
Make yourself comfortable in this air-conditioned villa, which has a kitchen. Complimentary wireless internet access keeps you connected, and a Smart television is provided for your entertainment. Conveniences include a dryer and an iron/ironing board.

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Others

5BR Villa w/ Pool & Disney Themes

Villa

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Osceola
5BR Villa w/ Pool & Disney Themes 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 (12.1 km) from Disney Springs™ and 8.5 mi (13.7 km) from Walt Disney World® Resort.

5BR Villa w/ Pool & Disney Themes Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a terrace. This villa also features complimentary wireless internet access, an arcade/game room, and barbecue grills.

5BR Villa w/ Pool & Disney Themes 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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Sport & Beauty

Pool Villa W/free Resort Access! Great Reviews!

Villa

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Osceola
Pool Villa W/free Resort Access! Great Reviews! 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 10.3 mi (16.5 km) from Disney's Animal Kingdom® Theme Park and 11.1 mi (17.9 km) from ESPN Wide World of Sports Complex.

Pool Villa W/free Resort Access! Great Reviews! Facility and Service
Be sure to enjoy recreational amenities, including an outdoor pool, a waterslide, and a fitness center. Additional features at this villa include complimentary wireless internet access, an arcade/game room, and barbecue grills.

Pool Villa W/free Resort Access! Great Reviews! Rooms
Make yourself comfortable in this air-conditioned villa, 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.

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

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Vacation Bliss-prime Resort, Unbeatable Location

Villa

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Osceola
Vacation Bliss-prime Resort, Unbeatable Location 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 6.4 mi (10.2 km) from Walt Disney World® Resort.

Vacation Bliss-prime Resort, Unbeatable Location Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a 24-hour fitness center. Additional features at this villa include complimentary wireless internet access and gas grills.

Vacation Bliss-prime Resort, Unbeatable Location Rooms
Treat yourself to a stay in this individually decorated villa, which features a private pool and a Smart TV. A kitchen is outfitted with an oven and a microwave. Cable television is provided for your entertainment. Conveniences include a desk and a separate sitting area.

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Exterior & Views

Comfy Themed Home, Private Pool, Prime Location

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Osceola
Comfy Themed Home, Private Pool, Prime Location Location
Located in Four Corners, this villa is within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This villa is 12 mi (19.4 km) from Old Town and 12.8 mi (20.6 km) from ESPN Wide World of Sports Complex.

Comfy Themed Home, Private Pool, Prime Location Facility and Service
Dip into one of the 2 outdoor pools or enjoy other recreational amenities, which include a 24-hour fitness center. Additional amenities at this villa include complimentary wireless internet access and gas grills.

Comfy Themed Home, Private Pool, Prime Location Rooms
Treat yourself to a stay in this individually decorated villa, which features a private pool and a Smart TV. There's a private balcony or patio. A kitchen is outfitted with an oven and a microwave. Cable television is provided for your entertainment.

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Exterior & Views

Compass Bay Family Comfort & Resort Amenities

Private Villa

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Osceola
Compass Bay Family Comfort & Resort Amenities 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 5.4 mi (8.7 km) from Disney Springs™ and 5.6 mi (9 km) from ESPN Wide World of Sports Complex.

Compass Bay Family Comfort & Resort Amenities Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. This villa also features complimentary wireless internet access, an arcade/game room, and barbecue grills.

Compass Bay Family Comfort & Resort Amenities Rooms
Make yourself comfortable in this villa, featuring a kitchen with a stovetop and a microwave. A flat-screen television with cable programming provides entertainment, while complimentary wireless internet access keeps you connected. Conveniences include a separate sitting area and a washer/dryer, and you can also request a crib/infant bed (complimentary).

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Living area

Windsor Hills Resort 3 Bedroom Private Pool Townhome 0874

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Osceola
Windsor Hills Resort 3 Bedroom Private Pool Townhome 0874 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 6.1 mi (9.9 km) from Disney's Hollywood Studios® and 6.2 mi (9.9 km) from ESPN Wide World of Sports Complex.

Windsor Hills Resort 3 Bedroom Private Pool Townhome 0874 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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Exterior & Views

Sunny Villa near Disney with Margaritaville Resort Island H20 Access - 8170CP

Villa

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Osceola
Experience an abundance of unparalleled facilities and features at Sunny Villa near Disney with Margaritaville Resort Island H20 Access - 8170CP. Maintain seamless communication using the complimentary Wi-Fi at private villa.Car hire offerings at the private villa enhance the ease of discovering Orlando (FL). Guests can avail parking facilities at the private villa. During your stay at this fantastic private villa, the attentive front desk personnel can provide you with a range of amenities such as concierge service, luggage storage and safety deposit boxes.Kindly note that smoking is prohibited in the private villa to ensure fresher air for all visitors. For visitors wishing to smoke, designated smoking zones can be found.At Sunny Villa near Disney with Margaritaville Resort Island H20 Access - 8170CP, every guestroom is provided with convenient amenities and fittings to ensure a comfortable stay. Elevate your experience at private villa with the knowledge that certain rooms are equipped with linen service, ensuring a more pleasant stay for you. A few accommodations within Sunny Villa near Disney with Margaritaville Resort Island H20 Access - 8170CP offer unique design elements such as a balcony or terrace. Certain rooms offer in-room amusement features such as the television for your enjoyment.In select rooms within the private villa, a refrigerator and a coffee or tea maker is available to cater to your requirements when desired. It is worth noting that certain guest bathrooms feature a hair dryer and toiletries for your convenience. Enjoy an entertaining evening with your fellow travelers at the private villa's bar. At Sunny Villa near Disney with Margaritaville Resort Island H20 Access - 8170CP, visitors have the option to receive groceries directly in their accommodation, ensuring outstanding comfort and simplicity when it comes to meals.During your stay at private villa, an array of engaging activities and amenities guarantees a delightful experience.Discover the fitness amenities at private villa to maintain your health and strength during your getaway.
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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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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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Wonderful Villa 5min From Theme Park Hot Tub & BBQ 112

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Osceola
Wonderful Villa 5min From Theme Park Hot Tub & BBQ 112 Location
When you stay at this villa in Kissimmee, you'll be near the beach, within a 10-minute drive of Walt Disney World® Resort and Old Town. This villa is 5.1 mi (8.3 km) from ESPN Wide World of Sports Complex and 5.6 mi (9.1 km) from Disney's Hollywood Studios®.

Wonderful Villa 5min From Theme Park Hot Tub & BBQ 112 Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center. This villa also features complimentary wireless internet access and barbecue grills.

Wonderful Villa 5min From Theme Park Hot Tub & BBQ 112 Rooms
Make yourself comfortable in your individually decorated villa. The bathroom has a bathtub or shower.

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5Bd Villa Private Pool & Spa at Solara Resort 1820

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Osceola
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Exterior & Views

Perfect Storey Lake Home for Great Vacation

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Osceola
Perfect Storey Lake Home for Great Vacation 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.

Perfect Storey Lake Home for Great Vacation Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a 24-hour fitness center. Additional amenities at this villa include complimentary wireless internet access and gas grills.

Perfect Storey Lake Home for Great Vacation Rooms
Make yourself comfortable in this air-conditioned 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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Whispering Palms - Luxury 4-Bedroom Pool Home Near 4 Villa

Villa

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Osceola
Whispering Palms - Luxury 4-Bedroom Pool Home Near 4 Villa Location
Located in Kissimmee, this villa is 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 7.6 mi (12.3 km) from Disney's Hollywood Studios®.

Whispering Palms - Luxury 4-Bedroom Pool Home Near 4 Villa Rooms
Make yourself comfortable in your villa. Complimentary wireless internet access is available to keep you connected.

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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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Reunion Resort 6BR Pool Home & Game Room

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Osceola
Reunion Resort 6BR Pool Home & Game Room Location
With a stay at this villa in Kissimmee, you'll be within a 10-minute drive of Mystic Dunes Golf Club and Reunion Resort Golf Course. This villa is 5.5 mi (8.8 km) from Walt Disney World® Resort and 7.7 mi (12.4 km) from ESPN Wide World of Sports Complex.

Reunion Resort 6BR Pool Home & Game Room Facility and Service
Enjoy recreational amenities such as an outdoor pool and a hot tub. This villa also features complimentary wireless internet access, an arcade/game room, and barbecue grills.

Reunion Resort 6BR Pool Home & Game Room Rooms
Your villa features a Smart 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 separate bathtub and shower and complimentary toiletries.

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Ov2182 - Emerald Island - 7 Bed 5.5 Baths Villa

Villa

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Osceola
Ov2182 - Emerald Island - 7 Bed 5.5 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.

Ov2182 - Emerald Island - 7 Bed 5.5 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.

Ov2182 - Emerald Island - 7 Bed 5.5 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
Relax with your favorite drink at the bar/lounge or the poolside bar.

See details
Fully Booked
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Ovm3553 - Emerald Island - 5 Bed 3 Baths Villa

Villa

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Osceola
Ovm3553 - Emerald Island - 5 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 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.

Ovm3553 - Emerald Island - 5 Bed 3 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. This villa also features complimentary wireless internet access, concierge services, and an arcade/game room.

Ovm3553 - Emerald Island - 5 Bed 3 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
Unwind at the end of the day with a drink at the bar/lounge or the poolside bar.

See details
Fully Booked
Let's check on other dates!
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Villas in Osceola

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