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Cottages in Osceola

Osceola
Mon, 16 Nov 2026 - Tue, 17 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 655 Cottages in Osceola
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Lakeview 10br Pool, Spa & Star Wars Game Room

Cottage

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Osceola
Lakeview 10br Pool, Spa & Star Wars Game Room Location
Located in Kissimmee, this cottage is within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This cottage is 7.3 mi (11.8 km) from Disney Springs™ and 8.4 mi (13.6 km) from Walt Disney World® Resort.

Lakeview 10br Pool, Spa & Star Wars Game Room Facility and Service
This smoke-free cottage offers complimentary parking nearby.

Lakeview 10br Pool, Spa & Star Wars Game Room 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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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

9044st00 Premium-lot Location

Cottage

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Osceola
9044st00 Premium-lot Location 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 Reunion Resort Golf Course. This spa cottage is 11.4 mi (18.3 km) from Old Town and 12.2 mi (19.6 km) from ESPN Wide World of Sports Complex.

9044st00 Premium-lot Location 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.

9044st00 Premium-lot Location 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 an LCD television is provided for your entertainment.

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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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2011 Fleming Mist Place

Cottage

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Osceola
2011 Fleming Mist Place Location
Located in Kissimmee, this cottage is within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This family-friendly 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.

2011 Fleming Mist Place Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a waterslide. Additional features at this cottage include complimentary wireless internet access, an arcade/game room, and barbecue grills.

2011 Fleming Mist Place 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.

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

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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.

See details
4.1/5
Fully Booked
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Others

Near Disney w Pool, Hot Tub, BBQ & Game Room

Cottage

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Osceola
Near Disney w Pool, Hot Tub, BBQ & Game Room 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 mi (16.2 km) from Disney's Animal Kingdom® Theme Park and 11.2 mi (18.1 km) from ESPN Wide World of Sports Complex.

Near Disney w Pool, Hot Tub, BBQ & Game Room Facility and Service
Take advantage of recreational opportunities offered, including a complimentary water park, an outdoor pool, and a hot tub. This cottage also features complimentary wireless internet access, an arcade/game room, and gas grills.

Near Disney w Pool, Hot Tub, BBQ & Game Room Rooms
Make yourself comfortable in this individually decorated cottage, which features a kitchen. A 55-inch Smart television is provided, with digital programming available.

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

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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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Fully Booked
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Exterior & Views

6 Bedroom 5 Bathroom Vacation Home

Cottage

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Osceola
6 Bedroom 5 Bathroom Vacation Home Location
With a stay at this condo in Four Corners (Champions Gate), you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This spa condo is 11.3 mi (18.2 km) from Old Town and 12.1 mi (19.4 km) from ESPN Wide World of Sports Complex.

6 Bedroom 5 Bathroom Vacation Home 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.

6 Bedroom 5 Bathroom Vacation Home Rooms
Make yourself comfortable in this air-conditioned condo, 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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Fully Booked
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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.

See details
Fully Booked
Let's check on other dates!
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Mvp9018sdcg

Cottage

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Osceola
Mvp9018sdcg 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 Reunion Resort Golf Course. This cottage is 10.9 mi (17.6 km) from Walt Disney World® Resort and 11.3 mi (18.1 km) from Old Town.

Mvp9018sdcg Rooms
Make yourself comfortable in this air-conditioned cottage, which has a kitchen. Cable television is provided for your entertainment.

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Interior

Epic Game Loft & Space-themed Theater Experience

Cottage

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Osceola
Epic Game Loft & Space-themed Theater Experience Location
Located in Kissimmee, this cottage is within a 15-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This cottage is 8.7 mi (14.1 km) from Walt Disney World® Resort and 10.4 mi (16.7 km) from Disney's Animal Kingdom® Theme Park.

Epic Game Loft & Space-themed Theater Experience Facility and Service
This smoke-free cottage offers complimentary parking nearby.

Epic Game Loft & Space-themed Theater Experience 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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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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Interior

Star Wars & Encanto Bunk Rooms + Pool @ Storeylake

Cottage

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Osceola
Star Wars & Encanto Bunk Rooms + Pool @ Storeylake 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 mi (11.3 km) from Disney Springs™ and 8.1 mi (13.1 km) from Walt Disney World® Resort.

Star Wars & Encanto Bunk Rooms + Pool @ Storeylake Facility and Service
This smoke-free cottage offers complimentary parking nearby.

Star Wars & Encanto Bunk Rooms + Pool @ Storeylake 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.

See details
Fully Booked
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Others

8990 Stinger Drive

Cottage

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Osceola
8990 Stinger Drive 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 Reunion Resort Golf Course. This family-friendly cottage is 11.2 mi (18 km) from Old Town and 12 mi (19.3 km) from ESPN Wide World of Sports Complex.

8990 Stinger Drive Facility and Service
Enjoy recreational amenities such as an outdoor pool and a waterslide. Additional features at this cottage include complimentary wireless internet access, an arcade/game room, and barbecue grills.

8990 Stinger Drive Rooms
Make yourself comfortable in this air-conditioned cottage, 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 dryer.

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

See details
Fully Booked
Let's check on other dates!
Interior

2050 E Irlo Bronson, 1bed

Cottage

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Osceola
2050 E Irlo Bronson, 1bed Location
With a stay at this cottage in Kissimmee, you'll be within a 5-minute drive of Osceola Heritage Park and Osceola Center for the Arts. This cottage is 12.4 mi (19.9 km) from Old Town and 16.3 mi (26.2 km) from Orange County Convention Center.

2050 E Irlo Bronson, 1bed 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).

See details
Fully Booked
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Exterior & Views

Margaritaville Cottages Orlando

Cottage

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Osceola
Margaritaville Cottages Orlando Location
When you stay at this cottage in Kissimmee, you'll be in a shopping district, a 5-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort. This cottage is 6.2 mi (9.9 km) from ESPN Wide World of Sports Complex and 6.6 mi (10.6 km) from Disney's Animal Kingdom® Theme Park.

Margaritaville Cottages Orlando Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and tour/ticket assistance.

Margaritaville Cottages Orlando Rooms
Make yourself comfortable in your cottage. Complimentary wireless internet access is available to keep you connected.

See details
3.3/5
Fully Booked
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Exterior & Views

1780spp New 7 Bedroom 5 Bathroom Solara Villa

Cottage

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Osceola
1780spp New 7 Bedroom 5 Bathroom Solara Villa Location
With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This spa cottage is 5.5 mi (8.9 km) from Disney Springs™ and 6.5 mi (10.5 km) from Walt Disney World® Resort.

1780spp New 7 Bedroom 5 Bathroom Solara Villa 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.

1780spp New 7 Bedroom 5 Bathroom Solara Villa 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.

See details
Fully Booked
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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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Fully Booked
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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.

See details
Fully Booked
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Cottages in Osceola

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