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Villas in Osceola

Osceola
Sun, 08 Nov 2026 - Mon, 09 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 1.000+ Villas in Osceola
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Beautiful Villa at Championsgate

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Osceola
Beautiful Villa at Championsgate 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 golf villa is 11.3 mi (18.1 km) from Old Town and 12 mi (19.4 km) from ESPN Wide World of Sports Complex.

Beautiful Villa at Championsgate Rooms
Treat yourself to a stay in this individually decorated villa, which features a private pool. Conveniences include a separate sitting area and a washer/dryer.

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Wonderful Villa 5min Disney BBQ 102

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Osceola
Wonderful Villa 5min Disney BBQ 102 Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, a 5-minute drive from Mystic Dunes Golf Club and 6 minutes from Walt Disney World® Resort. This vacation home is 5.1 mi (8.2 km) from ESPN Wide World of Sports Complex and 5.4 mi (8.6 km) from Old Town.

Wonderful Villa 5min Disney BBQ 102 Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center. This vacation home also features complimentary wireless internet access and barbecue grills.

Wonderful Villa 5min Disney BBQ 102 Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Sport & Beauty

Disney Dreams Luxury Private Water Park 6 Bedroom Villa by RedAwning

Villa

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Osceola
Disney Dreams Luxury Private Water Park 6 Bedroom Villa by RedAwning Location
When you stay at this villa in Kissimmee, you'll be next to a golf course, within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This golf villa is 7.5 mi (12 km) from ESPN Wide World of Sports Complex and 7.8 mi (12.6 km) from Disney's Hollywood Studios®.

Disney Dreams Luxury Private Water Park 6 Bedroom Villa by RedAwning Facility and Service
Don't miss out on the many recreational opportunities, including an outdoor pool, an outdoor tennis court, and a fitness center.

Disney Dreams Luxury Private Water Park 6 Bedroom Villa by RedAwning Rooms
Make yourself comfortable in this villa, which features a private hot tub. Complimentary wireless internet access is available to keep you connected. Conveniences include a refrigerator and a coffee/tea maker.

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Ov4202 - Windsor At Westside - 7 Bed 5.5 Baths Villa

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Osceola
Ov4202 - Windsor At Westside - 7 Bed 5.5 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 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.

Ov4202 - Windsor At Westside - 7 Bed 5.5 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 an outdoor pool. Additional features at this villa include complimentary wireless internet access, concierge services, and a television in a common area.

Ov4202 - Windsor At Westside - 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 with cable programming is available for your entertainment, and a video-game console is also provided.

Restaurant and Cafe
Quench your thirst with your favorite drink at the poolside bar.

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Ov2625 - Emerald Island - 5 Bed 4 Baths Villa

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Osceola
Ov2625 - Emerald Island - 5 Bed 4 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.

Ov2625 - Emerald Island - 5 Bed 4 Baths Villa Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools. Additional features at this villa include complimentary wireless internet access, concierge services, and an arcade/game room.

Ov2625 - Emerald Island - 5 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
Wrap up your day with a drink at the poolside bar.

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Je53742 - Reunion Resort - 7 Bed 7 Baths Villa

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Osceola
Je53742 - Reunion Resort - 7 Bed 7 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.

Je53742 - Reunion Resort - 7 Bed 7 Baths Villa Facility and Service
Practice your swing on the golf course or dip into one of the 8 outdoor pools or 2 hot tubs. Additional amenities at this villa include complimentary wireless internet access, concierge services, and an arcade/game room.

Je53742 - Reunion Resort - 7 Bed 7 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. Quench your thirst with your favorite drink at the bar/lounge.

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Interior

9031srl Luxury 9beds Villas With Pool Spa In Solara

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Osceola
9031srl Luxury 9beds Villas With Pool Spa In Solara 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 cottage 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.

9031srl Luxury 9beds Villas With Pool Spa In Solara Rooms
Make yourself comfortable in this air-conditioned cottage, which has a kitchen. Cable television is provided for your entertainment. Conveniences include a dryer and an iron/ironing board.

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Bedroom

Luxury Villa: Pool, Home Cinema, BBQ & Near Disney Parks

Private Villa

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Osceola
Luxury Villa: Pool, Home Cinema, BBQ & Near Disney Parks Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 9.7 mi (15.5 km) from Disney Springs™ and 10.6 mi (17 km) from Disney's Hollywood Studios®.

Luxury Villa: Pool, Home Cinema, BBQ & Near Disney Parks Facility and Service
Take advantage of recreation opportunities such as a hot tub, or other amenities including complimentary wireless internet access and an arcade/game room.

Luxury Villa: Pool, Home Cinema, BBQ & Near Disney Parks Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Sport & Beauty

Lf811or 3 Bedroom Villa by RedAwning

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Osceola
Lf811or 3 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 Flamingo Crossings Town Center. This villa is 7.1 mi (11.4 km) from Disney's Animal Kingdom® Theme Park and 8 mi (12.8 km) from ESPN Wide World of Sports Complex.

Lf811or 3 Bedroom Villa by RedAwning Rooms
Make yourself comfortable in your villa. Complimentary wireless internet access is available to keep you connected. Conveniences include an electric kettle and a washing machine.

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Exterior & Views

Luxury Villa At Windsor Island Resort 2010 Lelani 8 Bedroom Villa

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Osceola
Luxury Villa At Windsor Island Resort 2010 Lelani 8 Bedroom Villa 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.

Luxury Villa At Windsor Island Resort 2010 Lelani 8 Bedroom Villa Rooms
Make yourself comfortable in your villa. Complimentary wireless internet access is available to keep you connected.

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Others

Surfstyle at Margaritaville by Shine Villas 022

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Osceola
Surfstyle at Margaritaville by Shine Villas 022 Location
With a stay at this cottage in Kissimmee, you'll be a 4-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort. This spa cottage is 5.9 mi (9.6 km) from Old Town and 6.3 mi (10.2 km) from ESPN Wide World of Sports Complex.

Surfstyle at Margaritaville by Shine Villas 022 Facility and Service
Take time to pamper yourself with a visit to the full-service spa.

Surfstyle at Margaritaville by Shine Villas 022 Rooms
Your cottage features a flat-screen TV. Complimentary wireless internet access is available to keep you connected.

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Ov4224 - Reunion Resort - 6 Bed 5 Baths Villa

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Osceola
Ov4224 - Reunion Resort - 6 Bed 5 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.

Ov4224 - Reunion Resort - 6 Bed 5 Baths Villa Facility and Service
Practice your swing on the golf course or dip into one of the 8 outdoor pools. Additional features at this villa include complimentary wireless internet access, concierge services, and a television in a common area.

Ov4224 - Reunion Resort - 6 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 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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Others

3BR Townhome in Fiesta Key Near Disney Parks

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Osceola
3BR Townhome in Fiesta Key Near Disney Parks Location
Located in Kissimmee, this villa is within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This villa is 10 mi (16.1 km) from Disney Springs™ and 10.1 mi (16.3 km) from Walt Disney World® Resort.

3BR Townhome in Fiesta Key Near Disney Parks Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a hot tub. This villa also features complimentary wireless internet access and an arcade/game room.

3BR Townhome in Fiesta Key Near Disney Parks Rooms
Your villa features a Smart TV. 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. Conveniences include a desk and a separate sitting area, and you can also request a crib/infant bed (complimentary).

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Others

Storey Lake 5BR Townhome w/ Pool 8mi to Disney

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Osceola
Storey Lake 5BR Townhome w/ Pool 8mi to 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 (8.5 km) from Disney Springs™ and 6.3 mi (10.1 km) from Walt Disney World® Resort.

Storey Lake 5BR Townhome w/ Pool 8mi to Disney Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a hot tub. This villa also features complimentary wireless internet access and barbecue grills.

Storey Lake 5BR Townhome w/ Pool 8mi 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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Room

Precious Villa - 5 min to Disney

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Osceola
Precious Villa - 5 min to Disney Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 10-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 4.9 mi (8 km) from ESPN Wide World of Sports Complex and 5.6 mi (9.1 km) from Disney's Hollywood Studios®.

Precious Villa - 5 min to Disney Facility and Service
Take advantage of recreation opportunities such as an outdoor pool, or other amenities including complimentary wireless internet access and barbecue grills.

Precious Villa - 5 min to Disney Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Others

Resort Villa With Heated Pool and Ping Pong Table

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Osceola
Resort Villa With Heated Pool and Ping Pong Table 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 6.9 mi (11.1 km) from Walt Disney World® Resort.

Resort Villa With Heated Pool and Ping Pong Table 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 a picnic area.

Resort Villa With Heated Pool and Ping Pong Table 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

4BR Home w/ Pool Near Disney

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Osceola
4BR Home w/ Pool Near Disney 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 8.6 mi (13.8 km) from Walt Disney World® Resort.

4BR Home w/ Pool Near Disney Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a hot tub. This villa also features complimentary wireless internet access and barbecue grills.

4BR Home w/ 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 separate bathtub and shower and complimentary toiletries.

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Exterior & Views

4 Bed 3 Bath In A Gated Community With Pool 4 Bedroom Villa by RedAwning

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Osceola
4 Bed 3 Bath In A Gated Community With Pool 4 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 Old Town. This villa is 7.7 mi (12.3 km) from ESPN Wide World of Sports Complex and 8.2 mi (13.1 km) from Disney's Hollywood Studios®.

4 Bed 3 Bath In A Gated Community With Pool 4 Bedroom Villa by RedAwning Rooms
Make yourself comfortable in your villa. Complimentary wireless internet access is available to keep you connected.

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Exterior & Views

Lovely Lakeside 4-Bed Pool Home at Villa Sol-3125

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Osceola
Lovely Lakeside 4-Bed Pool Home at Villa Sol-3125 offers top-notch services and amenities, ensuring guests experience utmost comfort.Share your photos and respond to emails at your convenience, thanks to the free Wi-Fi internet access offered by home.Traveling with minimal luggage is achievable at Lovely Lakeside 4-Bed Pool Home at Villa Sol-3125 due to the home's laundromat ensuring your garments stay fresh.Each accommodation at Lovely Lakeside 4-Bed Pool Home at Villa Sol-3125 is thoughtfully created and adorned to provide visitors with a comfortable, home-like atmosphere. In select rooms, guests can enjoy a touch of amusement with the availability of television for their entertainment. Lovely Lakeside 4-Bed Pool Home at Villa Sol-3125 provides a superb assortment of leisure amenities for guests to enjoy.For individuals who don't want to skip their exercise routine, visiting the home fitness center ensures you maintain your vitality and wellness.
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Others

Pool Side @ Storey Lake Resort by Shine Villas #410

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Osceola
Pool Side @ Storey Lake Resort by Shine Villas #410 Location
When you stay at this condo 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 condo is 5.7 mi (9.2 km) from Disney Springs™ and 6.7 mi (10.8 km) from Walt Disney World® Resort.

Pool Side @ Storey Lake Resort by Shine Villas #410 Facility and Service
Relax at the full-service spa, where you can enjoy massages.

Pool Side @ Storey Lake Resort by Shine Villas #410 Rooms
Your condo features a flat-screen TV. Complimentary wireless internet access is available to keep you connected.

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Villas in Osceola

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