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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
Room

Amazing Family Villa - 5min From Disney

Villa

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Osceola
Amazing Family Villa - 5min From Disney 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 mi (8.1 km) from ESPN Wide World of Sports Complex and 5.3 mi (8.5 km) from Old Town.

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

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6BR Villa w/ Pool & Game Room Near Disney

Villa

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Osceola
6BR Villa w/ Pool & Game Room 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 11.6 mi (18.6 km) from Old Town and 12.3 mi (19.9 km) from ESPN Wide World of Sports Complex.

6BR Villa w/ Pool & Game Room Near Disney Facility and Service
Take advantage of recreational opportunities offered, including an outdoor pool, an indoor pool, and a hot tub. Additional features at this villa include complimentary wireless internet access, an arcade/game room, and barbecue grills.

6BR Villa w/ Pool & Game Room 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.

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Bedroom

9042sid- The Retreat at Championsgate

Villa

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Osceola
9042sid- The Retreat 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 villa is 11.2 mi (18.1 km) from Old Town and 12 mi (19.3 km) from ESPN Wide World of Sports Complex.

9042sid- The Retreat at Championsgate Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center.

9042sid- The Retreat at Championsgate Rooms
Make yourself comfortable in this air-conditioned villa, featuring a kitchen with a refrigerator and a stovetop. There's a private balcony or patio. A flat-screen television is provided for your entertainment. Conveniences include a microwave and an iron/ironing board.

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Beautifully Decorated Villa With Private Pool

Private Villa

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Osceola
Beautifully Decorated Villa With Private Pool Location
Located in Four Corners, Beautifully Decorated Villa With Private Pool is within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This vacation home is 12 mi (19.4 km) from Old Town and 12.8 mi (20.6 km) from ESPN Wide World of Sports Complex.

Beautifully Decorated Villa With Private Pool Rooms
Make yourself at home in one of the 23 guestrooms.

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Themed Family Getaway, Private Pool, Top Location

Villa

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Osceola
Themed Family Getaway, Private Pool, Top Location 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 Old Town and 12.4 mi (19.9 km) from Walt Disney World® Resort.

Themed Family Getaway, Private Pool, Top Location 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 gas grills.

Themed Family Getaway, Private Pool, Top Location Rooms
Treat yourself to a stay in this individually decorated villa, which features a private pool. There's a private patio. A kitchen is outfitted with an oven, a stovetop, and a microwave. Cable television is provided for your entertainment.

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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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Ov2658 - Windsor Hills Resort - 5 Bed 5 Baths Villa

Villa

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Osceola
Ov2658 - Windsor Hills Resort - 5 Bed 5 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®.

Ov2658 - Windsor Hills Resort - 5 Bed 5 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 a television in a common area.

Ov2658 - Windsor Hills Resort - 5 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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Others

Charming 4BR w/ Pool Near Disney - Storey Lake

Villa

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Osceola
Charming 4BR w/ Pool Near Disney - Storey Lake 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.

Charming 4BR w/ Pool Near Disney - Storey Lake 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, barbecue grills, and a vending machine.

Charming 4BR w/ Pool Near Disney - Storey Lake 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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6br Paradise Palms Villa, Private Pool, Game Room & More Privacy Near Disney 6 Bedroom Home

Villa

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Osceola
6br Paradise Palms Villa, Private Pool, Game Room & More Privacy Near Disney 6 Bedroom Home Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 7.9 mi (12.7 km) from Disney's Animal Kingdom® Theme Park and 9.1 mi (14.6 km) from ESPN Wide World of Sports Complex.

6br Paradise Palms Villa, Private Pool, Game Room & More Privacy Near Disney 6 Bedroom Home Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with a refrigerator and an oven. Complimentary wireless internet access is available to keep you connected. Conveniences include a coffee/tea maker and a washing machine.

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Others

Cozy 3BR in Champions Gate With Amazing Views!

Villa

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Osceola
Cozy 3BR in Champions Gate With Amazing Views! 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 12 mi (19.4 km) from Old Town and 12.8 mi (20.6 km) from ESPN Wide World of Sports Complex.

Cozy 3BR in Champions Gate With Amazing Views! Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Cozy 3BR in Champions Gate With Amazing Views! Rooms
Your villa features a flat-screen 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 separate sitting area and a washer/dryer, and you can also request a crib/infant bed (complimentary).

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Others

Spacious 12-bed Villa With Pool & Resort Amenities

Villa

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Osceola
Spacious 12-bed Villa With Pool & Resort Amenities Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 9.1 mi (14.6 km) from Disney Springs™ and 10 mi (16 km) from Walt Disney World® Resort.

Spacious 12-bed Villa With Pool & Resort Amenities Facility and Service
Take advantage of recreation opportunities such as a fitness center, or other amenities including complimentary wireless internet access and an arcade/game room.

Spacious 12-bed Villa With Pool & Resort Amenities Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower and designer toiletries. Conveniences include a coffee/tea maker and a washer/dryer.

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Family-friendly Villa w/ Private Pool Near Disney

Villa

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Osceola
Family-friendly Villa w/ Private Pool Near Disney Location
With a stay at this vacation home in Four Corners (Champions Gate), you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This vacation home is 11.5 mi (18.5 km) from Old Town and 12.3 mi (19.7 km) from ESPN Wide World of Sports Complex.

Family-friendly Villa w/ Private Pool 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.

Family-friendly Villa w/ Private Pool Near Disney Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

See details
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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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Others

Renovated 4BR Townhome w/ Disney Game Room

Villa

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Osceola
Renovated 4BR Townhome w/ Disney Game Room Location
Located in Kissimmee, this villa is within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This villa is 8.3 mi (13.3 km) from Disney Springs™ and 9.2 mi (14.9 km) from Walt Disney World® Resort.

Renovated 4BR Townhome w/ Disney Game Room Facility and Service
Take in the views from a garden and make use of amenities such as complimentary wireless internet access.

Renovated 4BR Townhome w/ Disney Game Room Rooms
Make yourself comfortable in your air-conditioned villa, which 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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Villa w/ Star Wars Rm & Resort Access Near Disney

Villa

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Osceola
Villa w/ Star Wars Rm & Resort Access Near Disney Location
With a stay at this cottage in Kissimmee, you'll be within a 15-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This cottage is 9 mi (14.5 km) from Walt Disney World® Resort and 10.7 mi (17.2 km) from Disney's Animal Kingdom® Theme Park.

Villa w/ Star Wars Rm & Resort Access Near Disney Facility and Service
This smoke-free cottage offers complimentary parking nearby.

Villa w/ Star Wars Rm & Resort Access Near Disney Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with an oven and a stovetop. Cable television is provided for your entertainment. Conveniences include a microwave and a dryer, and you can also request a crib/infant bed (complimentary).

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Ov2920 - Windsor Hills Resort - 6 Bed 4 Baths Villa

Villa

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Osceola
Ov2920 - Windsor Hills Resort - 6 Bed 4 Baths Villa Location
Located in Kissimmee (Windsor Hills), this villa is 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®.

Ov2920 - 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. Additional features at this villa include complimentary wireless internet access, concierge services, and a television in a common area.

Ov2920 - 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 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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Disney-area 4BR Townhome w/ Heated Pool

Villa

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Osceola
Disney-area 4BR Townhome w/ Heated Pool Location
When you stay at this villa in Four Corners, you'll be on a lake, within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This villa is 11.8 mi (19 km) from Old Town and 12.6 mi (20.3 km) from ESPN Wide World of Sports Complex.

Disney-area 4BR Townhome w/ Heated 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 features at this villa include complimentary wireless internet access, barbecue grills, and a vending machine.

Disney-area 4BR Townhome w/ Heated 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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4BR Reunion Resort Villa, Pool, Near Disney

Villa

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Osceola
4BR Reunion Resort Villa, Pool, Near Disney Location
With a stay at this villa in Kissimmee (Reunion), you'll be a 3-minute drive from Reunion Resort Golf Course and 6 minutes from ChampionsGate Golf Club. This villa is 8.1 mi (13.1 km) from Walt Disney World® Resort and 9.8 mi (15.8 km) from Old Town.

4BR Reunion Resort Villa, Pool, Near Disney 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, barbecue grills, and a vending machine.

4BR Reunion Resort Villa, Pool, Near Disney Rooms
Your villa features a flat-screen TV. There's a private 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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Decadent Penguin - Storey Lake by Shine Villas #704

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Osceola
Decadent Penguin - Storey Lake by Shine Villas #704 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.

Decadent Penguin - Storey Lake by Shine Villas #704 Facility and Service
Pamper yourself with a visit to the spa, which offers massages.

Decadent Penguin - Storey Lake by Shine Villas #704 Rooms
Your condo features a flat-screen TV. Complimentary wireless internet access is available to keep you connected.

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Ov2595 - Windsor Palms Resort - 6 Bed 4 Baths Villa

Villa

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Osceola
Ov2595 - Windsor Palms Resort - 6 Bed 4 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®.

Ov2595 - Windsor Palms Resort - 6 Bed 4 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. Additional features at this villa include complimentary wireless internet access, concierge services, and an arcade/game room.

Ov2595 - Windsor Palms Resort - 6 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 or patio. A kitchen is outfitted with a refrigerator, an oven, and a microwave. Cable programming along with a DVD player are 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
Let's check on other dates!
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Villas in Osceola

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