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Cottages in Osceola

Osceola
Wed, 18 Nov 2026 - Thu, 19 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 672 Cottages in Osceola
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Upstay Family Retreat w Pool, Theater & Games Room

Cottage

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Osceola
Upstay Family Retreat w Pool, Theater & Games 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 9.9 mi (16 km) from ESPN Wide World of Sports Complex and 10.1 mi (16.3 km) from Disney's Animal Kingdom® Theme Park.

Upstay Family Retreat w Pool, Theater & Games Room Facility and Service
Take advantage of recreational opportunities offered, including a complimentary water park, an outdoor pool, and a lazy river. Additional features at this cottage include complimentary wireless internet access and gas grills.

Upstay Family Retreat w Pool, Theater & Games Room Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with an oven and a stovetop. A 32-inch Smart television is provided, with digital programming available.

Restaurant and Cafe
At this cottage, enjoy a satisfying meal at the restaurant. Wrap up your day with a drink at the bar/lounge.

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Upstay Luxury Resort Home w Private Pool & Hot Tub

Cottage

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Osceola
Upstay Luxury Resort Home w Private Pool & Hot Tub 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 8.9 mi (14.3 km) from Disney Springs™ and 9.9 mi (15.9 km) from Walt Disney World® Resort.

Upstay Luxury Resort Home w Private Pool & Hot Tub 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 and barbecue grills.

Upstay Luxury Resort Home w Private Pool & Hot Tub Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with an oven and a stovetop. Conveniences include a microwave and a dryer.

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Interior

Top Rated 4BR Home

Cottage

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Osceola
Top Rated 4BR Home 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 7.5 mi (12.1 km) from Disney Springs™ and 8.6 mi (13.8 km) from Walt Disney World® Resort.

Top Rated 4BR Home Facility and Service
Take in the views from a garden and make use of amenities such as complimentary wireless internet access and barbecue grills.

Top Rated 4BR Home Rooms
Make yourself comfortable in this air-conditioned cottage, which features a fireplace. A kitchen is outfitted with an oven, a stovetop, and a microwave. Cable television is provided for your entertainment. Conveniences include a dryer and an iron/ironing board.

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Exterior & Views

8 Bdrm 5 Bath Villa

Cottage

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Osceola
8 Bdrm 5 Bath Villa 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 11.4 mi (18.4 km) from Old Town and 12.2 mi (19.7 km) from ESPN Wide World of Sports Complex.

8 Bdrm 5 Bath Villa Facility and Service
Take time to pamper yourself with a visit to the full-service spa. Additional amenities at this cottage include wireless internet access (surcharge) and an arcade/game room.

8 Bdrm 5 Bath Villa Rooms
Make yourself comfortable in this cottage, which has a kitchen. An LED television along with a video-game console are provided for your entertainment.

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Luxury Lakeview w/ Star Wars Gameroom & Themed Rms

Cottage

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Osceola
Luxury Lakeview w/ Star Wars Gameroom & Themed Rms Location
With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This cottage is 8 mi (12.9 km) from Walt Disney World® Resort and 9.7 mi (15.6 km) from Disney's Animal Kingdom® Theme Park.

Luxury Lakeview w/ Star Wars Gameroom & Themed Rms Facility and Service
This smoke-free cottage offers complimentary parking nearby.

Luxury Lakeview w/ Star Wars Gameroom & Themed Rms 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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Exterior & Views

Hzd9057

Cottage

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Osceola
Hzd9057 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 11.5 mi (18.5 km) from Old Town and 12.3 mi (19.7 km) from ESPN Wide World of Sports Complex.

Hzd9057 Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and barbecue grills.

Hzd9057 Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with an oven and a stovetop. Conveniences include a desk and a microwave.

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Exterior & Views

Spectacular Cottage with Private Pool Near Disney with Margaritaville Resort Access - 8026KD

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 Spectacular Cottage with Private Pool Near Disney with Margaritaville Resort Access - 8026KD, 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 Spectacular Cottage with Private Pool Near Disney with Margaritaville Resort Access - 8026KD through their distinctive delivery assistance.Indulge in the numerous pursuits available at Spectacular Cottage with Private Pool Near Disney with Margaritaville Resort Access - 8026KD.Eliminate those holiday calories by stopping by home and making use of their well-equipped exercise amenities.
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Room

Spacious 6-bedroom Home With Private Pool & Spa in Solara Resort Just 7 Miles to Disney!

Cottage

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Osceola
Spacious 6-bedroom Home With Private Pool & Spa in Solara Resort Just 7 Miles to Disney! Location
Located in Kissimmee, this cottage is within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This cottage is 10.1 mi (16.2 km) from Disney's Animal Kingdom® Theme Park and 11.3 mi (18.1 km) from ESPN Wide World of Sports Complex.

Spacious 6-bedroom Home With Private Pool & Spa in Solara Resort Just 7 Miles to 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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Chic 5bed Retreat, Perfect for Family Getaways

Cottage

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Osceola
Chic 5bed Retreat, Perfect for Family Getaways Location
With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This cottage is 12.5 mi (20.1 km) from Walt Disney World® Resort and 12.7 mi (20.4 km) from Old Town.

Chic 5bed Retreat, Perfect for Family Getaways Facility and Service
Dip into one of the 2 outdoor pools or enjoy other recreational amenities, which include a 24-hour fitness center. This cottage also features complimentary wireless internet access and gas grills.

Chic 5bed Retreat, Perfect for Family Getaways Rooms
Treat yourself to a stay in this individually decorated cottage, 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 dryer and an iron/ironing board.

Restaurant and Cafe
Wrap up your day with a drink at the poolside bar.

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Others

Sleeps 18! Family Retreat w/ Game Room, Pool, Resort Access Shadow Mountain

Cottage

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Osceola
Sleeps 18! Family Retreat w/ Game Room, Pool, Resort Access Shadow Mountain 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 (18.1 km) from Walt Disney World® Resort and 11.7 mi (18.9 km) from Old Town.

Sleeps 18! Family Retreat w/ Game Room, Pool, Resort Access Shadow Mountain Facility and Service
Take advantage of recreation opportunities such as an outdoor pool, or other amenities including complimentary wireless internet access and barbecue grills.

Sleeps 18! Family Retreat w/ Game Room, Pool, Resort Access Shadow Mountain Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with a refrigerator and a stovetop. Conveniences include a microwave and a washer/dryer.

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11br Familyhome/games @ Solara + Resort Access!

Cottage

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Osceola
11br Familyhome/games @ Solara + Resort Access! Location
Located in Kissimmee, this cottage is within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This cottage is 10.1 mi (16.2 km) from Disney's Animal Kingdom® Theme Park and 11.3 mi (18.1 km) from ESPN Wide World of Sports Complex.

11br Familyhome/games @ Solara + Resort Access! 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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Exterior & Views

1716 Lima Avenue

Cottage

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Osceola
1716 Lima Avenue 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 10.2 mi (16.4 km) from Disney's Animal Kingdom® Theme Park and 11.4 mi (18.4 km) from ESPN Wide World of Sports Complex.

1716 Lima Avenue Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a lazy river. Additional amenities at this cottage include complimentary wireless internet access, an arcade/game room, and barbecue grills.

1716 Lima Avenue Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with a refrigerator and an oven. 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.

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Sport & Beauty

Luxury 5 Bedroom Private Pool IHR 1019

Cottage

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Osceola
Luxury 5 Bedroom Private Pool IHR 1019 Location
Located in Kissimmee, this cottage is within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This spa cottage is 10.3 mi (16.6 km) from Disney's Animal Kingdom® Theme Park and 11.2 mi (18 km) from ESPN Wide World of Sports Complex.

Luxury 5 Bedroom Private Pool IHR 1019 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.

Luxury 5 Bedroom Private Pool IHR 1019 Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with a refrigerator and a microwave. There's a private balcony or patio. Complimentary wireless internet access keeps you connected, and a flat-screen television is provided for your entertainment.

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Sport & Beauty

1832 Tropical Palms Circle

Cottage

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Osceola
1832 Tropical Palms Circle Location
Located in Kissimmee, this cottage is within a 15-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This family-friendly cottage is 8.5 mi (13.7 km) from Walt Disney World® Resort and 10.2 mi (16.4 km) from Disney's Animal Kingdom® Theme Park.

1832 Tropical Palms Circle Facility and Service
Enjoy recreational amenities such as an outdoor pool and a waterslide. This cottage also features complimentary wireless internet access, an arcade/game room, and barbecue grills.

1832 Tropical Palms Circle 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 washing machine.

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

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Qj062n Imagination at Bear's Den

Cottage

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Osceola
Qj062n Imagination at Bear's Den Location
Located in Kissimmee (Reunion), this cottage is within a 10-minute drive of Reunion Resort Golf Course and Mystic Dunes Golf Club. This cottage is 7 mi (11.3 km) from Walt Disney World® Resort and 9 mi (14.6 km) from Old Town.

Qj062n Imagination at Bear's Den Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and barbecue grills.

Qj062n Imagination at Bear's Den Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with an oven and a stovetop. Conveniences include a microwave and a dryer, and you can also request a crib/infant bed (complimentary).

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Room

Ultimate Resort Retreat, Stunning 6-bedroom Haven

Cottage

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Osceola
Ultimate Resort Retreat, Stunning 6-bedroom Haven Location
Located in Kissimmee, this cottage is within a 15-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This cottage is 8.6 mi (13.9 km) from Walt Disney World® Resort and 10.4 mi (16.7 km) from Disney's Animal Kingdom® Theme Park.

Ultimate Resort Retreat, Stunning 6-bedroom Haven Facility and Service
Don't miss out on the many recreational opportunities, including an outdoor pool, a hot tub, and a 24-hour fitness center. Additional features at this cottage include complimentary wireless internet access and gas grills.

Ultimate Resort Retreat, Stunning 6-bedroom Haven Rooms
Treat yourself to a stay in this individually decorated cottage, 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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4.0/5
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2413-12-rd-famous World Cities Themed Bowling Home

Cottage

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Osceola
2413-12-rd-famous World Cities Themed Bowling Home Location
Located in Kissimmee, this cottage is within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This cottage is 7.4 mi (11.9 km) from Disney Springs™ and 8.4 mi (13.6 km) from Walt Disney World® Resort.

2413-12-rd-famous World Cities Themed Bowling Home Facility and Service
Take in the views from a garden and make use of amenities such as complimentary wireless internet access and barbecue grills.

2413-12-rd-famous World Cities Themed Bowling Home Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with an oven and a stovetop. Cable programming along with a video-game console are 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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Exterior & Views

Sea Breeze Cottage near Disney with Private Hot Tub Margaritaville Resort Access - 3016SR

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 private villa.Effortlessly plan your daily activities and travel requirements with concierge service, luggage storage and safety deposit boxes provided by the front desk services.The private villa 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 private villa, select rooms are equipped with linen service to improve your stay.At Sea Breeze Cottage near Disney with Private Hot Tub Margaritaville Resort Access - 3016SR, 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 feel revitalized using a hair dryer 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 Sea Breeze Cottage near Disney with Private Hot Tub Margaritaville Resort Access - 3016SR through their distinctive delivery assistance. Indulge in the numerous pursuits available at Sea Breeze Cottage near Disney with Private Hot Tub Margaritaville Resort Access - 3016SR. Eliminate those holiday calories by stopping by private villa and making use of their well-equipped exercise amenities.
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Interior

2820-5-rc-impeccable Corner lot Home

Cottage

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Osceola
2820-5-rc-impeccable Corner lot Home Location
With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Flamingo Crossings Town Center and Mystic Dunes Golf Club. This cottage is 6.8 mi (10.9 km) from Walt Disney World® Resort and 8.4 mi (13.5 km) from Disney's Animal Kingdom® Theme Park.

2820-5-rc-impeccable Corner lot Home 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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Exterior & Views

Key Lime Cabana Cottage near Disney with Margaritaville Resort Island H2O Access - 3062KL

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.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 Key Lime Cabana Cottage near Disney with Margaritaville Resort Island H2O Access - 3062KL, 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. Key Lime Cabana Cottage near Disney with Margaritaville Resort Island H2O Access - 3062KL offers a hair dryer and toiletries in the restrooms of specific accommodations. 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 Key Lime Cabana Cottage near Disney with Margaritaville Resort Island H2O Access - 3062KL through their distinctive delivery assistance. Indulge in the numerous pursuits available at Key Lime Cabana Cottage near Disney with Margaritaville Resort Island H2O Access - 3062KL.Eliminate those holiday calories by stopping by home and making use of their well-equipped exercise amenities.
See details
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Cottages in Osceola

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