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Cottages in Osceola

Osceola
Thu, 12 Nov 2026 - Fri, 13 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 670 Cottages in Osceola
Sport & Beauty

Margaritaville Cottage, Private Pool, Near Disney!

Cottage

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Osceola
Margaritaville Cottage, Private Pool, Near Disney! Location
With a stay at this vacation home in Kissimmee, you'll be a 4-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort. This vacation home is 5.8 mi (9.3 km) from Old Town and 6.1 mi (9.9 km) from ESPN Wide World of Sports Complex.

Margaritaville Cottage, Private Pool, Near Disney! Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a garden.

Margaritaville Cottage, Private Pool, Near Disney! Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool. There's a private balcony. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Cable television is provided for your entertainment.

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

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4.1/5
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Others

5 Bedroom Resort Villa with Game Room & Pool

Cottage

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Osceola
5 Bedroom Resort Villa with Game Room & Pool Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This family-friendly vacation home is 6.1 mi (9.8 km) from Disney Springs™ and 6.8 mi (11 km) from ESPN Wide World of Sports Complex.

5 Bedroom Resort Villa with Game Room & Pool Facility and Service
Take time to pamper yourself with a visit to the full-service spa. You're sure to appreciate the recreational amenities, including an outdoor pool and a fitness center. Additional features at this vacation home include complimentary wireless internet access, an arcade/game room, and barbecue grills.

5 Bedroom Resort Villa with Game Room & Pool Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and a microwave. There's a private furnished balcony/patio. A flat-screen television with cable programming provides entertainment, while complimentary wireless internet access keeps you connected. Conveniences include a washer/dryer and an iron/ironing board.

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Bedroom

8 Bed 6 Ba Villa with Games, Pool & Spa

Cottage

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Osceola
8 Bed 6 Ba Villa with Games, Pool & Spa Location
Located in Kissimmee, this cottage is within a 15-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This spa cottage is 8.9 mi (14.4 km) from Walt Disney World® Resort and 10.6 mi (17.1 km) from Disney's Animal Kingdom® Theme Park.

8 Bed 6 Ba Villa with Games, Pool & Spa Facility and Service
Take time to pamper yourself with a visit to the full-service spa. If you're looking for recreational opportunities, you'll find an outdoor pool and a fitness center.

8 Bed 6 Ba Villa with Games, Pool & Spa Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with a refrigerator and a microwave. Complimentary wireless internet access keeps you connected, and a flat-screen television is provided for your entertainment. Conveniences include a dryer and an iron/ironing board.

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Fully Booked
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6 Bed 5 Bath Villa with Games, Pool & Spa

Cottage

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Osceola
6 Bed 5 Bath Villa with Games, Pool & Spa 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 spa villa is 6.1 mi (9.7 km) from Disney Springs™ and 6.8 mi (11 km) from ESPN Wide World of Sports Complex.

6 Bed 5 Bath Villa with Games, Pool & Spa Facility and Service
Take time to pamper yourself with a visit to the full-service spa. You're sure to appreciate the recreational amenities, including an outdoor pool and a fitness center. Additional amenities at this villa include complimentary wireless internet access and barbecue grills.

6 Bed 5 Bath Villa with Games, Pool & Spa Rooms
Make yourself comfortable in this air-conditioned villa, featuring a kitchen with a refrigerator and a microwave. Complimentary wireless internet access keeps you connected, and a flat-screen television is provided for your entertainment.

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Interior

Fun Family Home Mario Game Room & Star Wars

Cottage

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Osceola
Fun Family Home Mario Game Room & Star Wars 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.

Fun Family Home Mario Game Room & Star Wars Facility and Service
This smoke-free cottage offers complimentary parking nearby.

Fun Family Home Mario Game Room & Star Wars 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.

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Sport & Beauty

8462 Secret Key Cove

Cottage

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Osceola
8462 Secret Key Cove Location
With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This family-friendly cottage is 7 mi (11.3 km) from ESPN Wide World of Sports Complex and 7.1 mi (11.4 km) from Old Town.

8462 Secret Key Cove Facility and Service
Make use of convenient amenities such as complimentary wireless internet access, an arcade/game room, and barbecue grills.

8462 Secret Key Cove Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with a refrigerator and an oven. There's a private patio. Cable programming along with a video-game console are provided for your entertainment. Conveniences include a microwave and a dryer.

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Exterior & Views

Spacious Cottage with Private Pool near Disney with Margaritaville Resort Access - 8009SU

Cottage

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Osceola
Great care is taken to ensure guests experience comfort through top-notch services and amenities. Remain linked during your visit by utilizing the complimentary internet access available. Discovering Orlando (FL) becomes even more accessible, thanks to the car hire amenities provided at the home.Parking is accessible, supplied by the home for guests who arrive by car.Effortlessly plan your daily activities and travel requirements with concierge service, luggage storage and safety deposit boxes provided by the front desk services.During leisurely days and evenings, in-room amenities such as 24-hour room service and room service enable you to maximize your stay in the room. The home is completely smoke-free.In limited designated zones, smoking is exclusively permitted.Crafted for coziness, every guestroom provides an array of features, guaranteeing a tranquil night's sleep while maintaining the level of comfort.For an elevated experience at home, select rooms are equipped with linen service to improve your stay.At Spacious Cottage with Private Pool near Disney with Margaritaville Resort Access - 8009SU, a selection of rooms can be found that showcase unique design elements such as a balcony or terrace.Expand your in-room entertainment choices with various amenities, such as television offered in certain accommodations.Rest assured that your hydration needs will be met, as some guestrooms are equipped with a refrigerator and a coffee or tea maker.Maintain your cleanliness and comfort using a hair dryer and toiletries available in select guest restrooms. Experience a fantastic evening effortlessly! Relish an entertaining night without venturing beyond the confines of the bar.Experience unparalleled comfort as groceries can be brought right to your room at Spacious Cottage with Private Pool near Disney with Margaritaville Resort Access - 8009SU through their distinctive delivery assistance.Indulge in the numerous pursuits available at Spacious Cottage with Private Pool near Disney with Margaritaville Resort Access - 8009SU.Eliminate those holiday calories by stopping by home and making use of their well-equipped exercise amenities.
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Sport & Beauty

1631la Luxury 6 Bed Villa With Pool & Spa

Cottage

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Osceola
1631la Luxury 6 Bed Villa With Pool & Spa Location
With a stay at this cottage in Kissimmee, you'll be within a 15-minute drive of ChampionsGate Golf Club and Mystic Dunes Golf Club. This spa cottage is 9 mi (14.4 km) from Walt Disney World® Resort and 10.8 mi (17.3 km) from Disney's Animal Kingdom® Theme Park.

1631la Luxury 6 Bed Villa With Pool & Spa Facility and Service
Take time to pamper yourself with a visit to the full-service spa. If you're looking for recreational opportunities, you'll find an outdoor pool and a fitness center.

1631la Luxury 6 Bed Villa With Pool & Spa Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with a refrigerator and a microwave. A flat-screen television and a DVD player are provided for your entertainment, while complimentary wireless internet access keeps you connected.

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Fully Booked
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Interior

8814 Geneve CT, Kissimmee, 4 BED

Cottage

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Osceola
8814 Geneve CT, Kissimmee, 4 BED Location
Located in Kissimmee, this cottage is within a 15-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This cottage is 8.8 mi (14.1 km) from Walt Disney World® Resort and 10.4 mi (16.8 km) from Disney's Animal Kingdom® Theme Park.

8814 Geneve CT, Kissimmee, 4 BED Rooms
Make yourself comfortable in this air-conditioned cottage, which has a kitchen.

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Interior

Luxe Stay! Spider-man Arcade & Theater Near Disney

Cottage

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Osceola
Luxe Stay! Spider-man Arcade & Theater Near Disney Location
With a stay at this cottage in Kissimmee, you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This cottage is 9.1 mi (14.6 km) from Disney Springs™ and 9.9 mi (15.9 km) from Walt Disney World® Resort.

Luxe Stay! Spider-man Arcade & Theater Near Disney Facility and Service
This smoke-free cottage offers complimentary parking nearby.

Luxe Stay! Spider-man Arcade & Theater 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.

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Fully Booked
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Bathroom

5 Bed 5 Ba Villa with Game Room, Pool & Spa

Cottage

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Osceola
5 Bed 5 Ba Villa with Game Room, Pool & Spa Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be within a 15-minute drive of Reunion Resort Golf Course and Mystic Dunes Golf Club. This family-friendly vacation home is 7.6 mi (12.3 km) from Walt Disney World® Resort and 9.6 mi (15.5 km) from Old Town.

5 Bed 5 Ba Villa with Game Room, Pool & Spa Facility and Service
Take time to pamper yourself with a visit to the full-service spa.

5 Bed 5 Ba Villa with Game Room, Pool & Spa Rooms
Make yourself comfortable in this air-conditioned vacation home, which has a kitchen. There's a private balcony or patio. A flat-screen television is provided for your entertainment.

See details
Fully Booked
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Exterior & Views

8 Bdrm Villa W Game Room and Cinema

Cottage

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Osceola
8 Bdrm Villa W Game Room and Cinema 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 spa vacation home is 11.6 mi (18.7 km) from Old Town and 12.4 mi (19.9 km) from ESPN Wide World of Sports Complex.

8 Bdrm Villa W Game Room and Cinema Facility and Service
Take time to pamper yourself with a visit to the full-service spa. You're sure to appreciate the recreational amenities, including an outdoor pool and a fitness center.

8 Bdrm Villa W Game Room and Cinema Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and a microwave. Complimentary wireless internet access keeps you connected, and a flat-screen television is provided for your entertainment.

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Exterior & Views

1585fd Amazing Champions Gate 5 Bedroom 5 Bed

Cottage

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Osceola
1585fd Amazing Champions Gate 5 Bedroom 5 Bed Location
With a stay at this cottage in Four Corners (Champions Gate), you'll be within a 15-minute drive of ChampionsGate Golf Club and Mystic Dunes Golf Club. This spa cottage is 11.3 mi (18.2 km) from Old Town and 12.1 mi (19.5 km) from ESPN Wide World of Sports Complex.

1585fd Amazing Champions Gate 5 Bedroom 5 Bed Facility and Service
Take time to pamper yourself with a visit to the full-service spa. You're sure to appreciate the recreational amenities, including an outdoor pool and a fitness center.

1585fd Amazing Champions Gate 5 Bedroom 5 Bed Rooms
Make yourself comfortable in this air-conditioned cottage, which has a kitchen. There's a private lanai. Wired and wireless internet access is complimentary, while a flat-screen television and a DVD player provide entertainment. Conveniences include a refrigerator and a washer/dryer.

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Interior

7601-7-bl-designer Decorated With Whimsical Themed Rooms

Cottage

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Osceola
7601-7-bl-designer Decorated With Whimsical Themed Rooms Location
With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This cottage is 7.3 mi (11.8 km) from ESPN Wide World of Sports Complex and 7.9 mi (12.7 km) from Disney's Hollywood Studios®.

7601-7-bl-designer Decorated With Whimsical Themed Rooms 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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Sport & Beauty

Lakeside Spa, AC in Games Room - Tropics! 822

Cottage

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Osceola
Lakeside Spa, AC in Games Room - Tropics! 822 Location
With a stay at this cottage in Kissimmee (Cumbrian Lakes), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This spa cottage is 10.4 mi (16.7 km) from Disney Springs™ and 10.7 mi (17.2 km) from Walt Disney World® Resort.

Lakeside Spa, AC in Games Room - Tropics! 822 Facility and Service
Take time to pamper yourself with a visit to the full-service spa.

Lakeside Spa, AC in Games Room - Tropics! 822 Rooms
Make yourself comfortable in this cottage, which features a private pool and a flat-screen TV. Complimentary wireless internet access is available to keep you connected.

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Fully Booked
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Windsor Hills Resort 5 Bedroom Updated Pool Home 0853

Cottage

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Osceola
Windsor Hills Resort 5 Bedroom Updated Pool Home 0853 Location
With a stay at this cottage in Kissimmee (Windsor Hills), you'll be a 4-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort. This cottage is 5.5 mi (8.9 km) from ESPN Wide World of Sports Complex and 5.8 mi (9.3 km) from Old Town.

Windsor Hills Resort 5 Bedroom Updated Pool Home 0853 Facility and Service
Take advantage of recreation opportunities such as an outdoor pool, or other amenities including complimentary wireless internet access and barbecue grills.

Windsor Hills Resort 5 Bedroom Updated Pool Home 0853 Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with an oven and a stovetop. There's a private patio. Cable television is provided for your entertainment. Conveniences include a microwave and a dryer.

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Meadow Manor - 10 Mins to Disney! Pool/spa

Cottage

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Osceola
Meadow Manor - 10 Mins to Disney! Pool/spa Location
With a stay at this cottage in Kissimmee (Calabria), you'll be within a 15-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center. This cottage is 8.7 mi (14 km) from Disney's Animal Kingdom® Theme Park and 9.9 mi (16 km) from Old Town.

Meadow Manor - 10 Mins to Disney! Pool/spa Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. Additional features at this cottage include complimentary wireless internet access, an arcade/game room, and gas grills.

Meadow Manor - 10 Mins to Disney! Pool/spa Rooms
Make yourself comfortable in this air-conditioned cottage, which has a kitchen. Cable television is provided for your entertainment. Conveniences include a coffee/tea maker and complimentary bottled water.

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Exterior & Views

5 Bed 5 Ba Villa with Game Room, Pool & Spa

Cottage

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Osceola
5 Bed 5 Ba Villa with Game Room, Pool & Spa 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 spa cottage is 10.2 mi (16.3 km) from Disney's Animal Kingdom® Theme Park and 11.2 mi (18.1 km) from ESPN Wide World of Sports Complex.

5 Bed 5 Ba Villa with Game Room, Pool & Spa Facility and Service
Take time to pamper yourself with a visit to the full-service spa. This cottage also features wireless internet access (surcharge) and barbecue grills.

5 Bed 5 Ba Villa with Game Room, Pool & Spa Rooms
Your cottage features a flat-screen TV.

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Exterior & Views

Furnished 8 Bed 5 Bath Villa

Cottage

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Osceola
Furnished 8 Bed 5 Bath 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 spa 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.

Furnished 8 Bed 5 Bath Villa Facility and Service
Take time to pamper yourself with a visit to the full-service spa. Additional features at this villa include wireless internet access (surcharge), an arcade/game room, and barbecue grills.

Furnished 8 Bed 5 Bath Villa Rooms
Make yourself comfortable in this villa, which has a kitchen. An LED television is provided for your entertainment.

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Interior

Discounted! Spidey/avengers/sw Bunks, Pool, Arcade

Cottage

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Osceola
Discounted! Spidey/avengers/sw Bunks, Pool, Arcade Location
With a stay at this cottage in Kissimmee, you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This cottage is 7.2 mi (11.6 km) from Disney Springs™ and 8.2 mi (13.3 km) from Walt Disney World® Resort.

Discounted! Spidey/avengers/sw Bunks, Pool, Arcade Facility and Service
This smoke-free cottage offers complimentary parking nearby.

Discounted! Spidey/avengers/sw Bunks, Pool, Arcade 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.

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Fully Booked
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Cottages in Osceola

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