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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
Living area

Windsor Hills Resort 5 Bedroom Home With Game Room 0851

Cottage

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Osceola
Windsor Hills Resort 5 Bedroom Home With Game Room 0851 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 5.6 mi (9 km) from ESPN Wide World of Sports Complex and 5.9 mi (9.4 km) from Old Town.

Windsor Hills Resort 5 Bedroom Home With Game Room 0851 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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Game room

Windsor Palms Resort 6 Bedroom With Pool Spa 0877

Cottage

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Osceola
Windsor Palms Resort 6 Bedroom With Pool Spa 0877 Location
Located in Kissimmee, this cottage is within a 15-minute drive of Walt Disney World® Resort and Old Town. This cottage is 7.1 mi (11.4 km) from ESPN Wide World of Sports Complex and 7.5 mi (12.1 km) from Disney's Hollywood Studios®.

Windsor Palms Resort 6 Bedroom With Pool Spa 0877 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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Exterior & Views

518mb New and Modern 8 Bedroom 5 Bathroom Villa

Cottage

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Osceola
518mb New and Modern 8 Bedroom 5 Bathroom Villa Location
Located in Kissimmee, this cottage is 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 9.8 mi (15.8 km) from ESPN Wide World of Sports Complex.

518mb New and Modern 8 Bedroom 5 Bathroom Villa Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

518mb New and Modern 8 Bedroom 5 Bathroom 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.

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Primary image

Chic 8BR All Suites With Pool and Game Room

Cottage

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Osceola
Chic 8BR All Suites With Pool and Game Room Location
With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Mystic Dunes Golf Club and ChampionsGate Golf Club. This cottage is 5.4 mi (8.7 km) from Walt Disney World® Resort and 7.6 mi (12.3 km) from ESPN Wide World of Sports Complex.

Chic 8BR All Suites With Pool and Game Room 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 cottage include complimentary wireless internet access, a picnic area, and gas grills.

Chic 8BR All Suites With Pool and Game Room Rooms
Make yourself comfortable in this air-conditioned cottage, which features a private pool and an outdoor private hot tub. There's a private furnished patio. A kitchen is outfitted with an oven, a stovetop, and a microwave. Cable television is provided for your entertainment.

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Room

Super Luxury Home, Private Pool, Premium Location

Cottage

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Osceola
Super Luxury Home, Private Pool, Premium Location 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 (13.9 km) from Walt Disney World® Resort.

Super Luxury Home, Private Pool, Premium Location Facility and Service
Take advantage of recreational opportunities offered, including an outdoor pool, a hot tub, and a 24-hour fitness center. Additional amenities at this cottage include complimentary wireless internet access and gas grills.

Super Luxury Home, Private Pool, Premium Location 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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5.0/5
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Sport & Beauty

8953 Candy Palm Road

Cottage

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Osceola
8953 Candy Palm Road 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 family-friendly cottage is 6.5 mi (10.5 km) from Walt Disney World® Resort and 8.2 mi (13.1 km) from Disney's Animal Kingdom® Theme Park.

8953 Candy Palm Road 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.

8953 Candy Palm Road 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.

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Interior

Kcc4749

Cottage

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Osceola
Kcc4749 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 cottage is 6.1 mi (9.8 km) from Disney Springs™ and 7 mi (11.2 km) from Walt Disney World® Resort.

Kcc4749 Rooms
Make yourself comfortable in this air-conditioned cottage, which has a kitchen.

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Others

Harry Potter~frozen Room 5BR w Game Room, Disney!

Cottage

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Osceola
Harry Potter~frozen Room 5BR w Game Room, Disney! Location
Located in Kissimmee, this cottage is within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This cottage is 7 mi (11.2 km) from Disney Springs™ and 8 mi (12.9 km) from Walt Disney World® Resort.

Harry Potter~frozen Room 5BR w Game Room, Disney! Facility and Service
This smoke-free cottage offers complimentary parking nearby.

Harry Potter~frozen Room 5BR w Game Room, 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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Disney Getaway w/ Private Pool & Spa

Cottage

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Osceola
Disney Getaway w/ Private Pool & Spa Location
With a stay at this cottage in Kissimmee (Windsor Hills), you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This cottage is 5.7 mi (9.2 km) from ESPN Wide World of Sports Complex and 6 mi (9.6 km) from Old Town.

Disney Getaway w/ Private Pool & Spa Facility and Service
This smoke-free cottage offers complimentary parking nearby.

Disney Getaway w/ Private Pool & Spa 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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Spacious Family Home w Pool, Hot Tub & BBQ

Cottage

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Osceola
Spacious Family Home w Pool, Hot Tub & BBQ 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 family-friendly cottage is 6.6 mi (10.6 km) from Walt Disney World® Resort and 8.3 mi (13.3 km) from Disney's Animal Kingdom® Theme Park.

Spacious Family Home w Pool, Hot Tub & BBQ Facility and Service
Don't miss out on the many recreational opportunities, including an outdoor pool, a waterslide, and a hot tub. This cottage also features complimentary wireless internet access, an arcade/game room, and gas grills.

Spacious Family Home w Pool, Hot Tub & BBQ Rooms
Make yourself comfortable in your air-conditioned cottage, which features a Smart TV. Digital television is provided for your entertainment.

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

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Windsor at Westside Resort 8 Bedroom Pool Spa Home 0956

Cottage

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Osceola
Windsor at Westside Resort 8 Bedroom Pool Spa Home 0956 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 10.3 mi (16.6 km) from Disney's Animal Kingdom® Theme Park and 11.4 mi (18.3 km) from ESPN Wide World of Sports Complex.

Windsor at Westside Resort 8 Bedroom Pool Spa Home 0956 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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Room

Getaway Delight-8 Bedrooms, Pool & Great Location

Cottage

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Osceola
Getaway Delight-8 Bedrooms, Pool & Great Location Location
With a stay at this cottage in Four Corners, you'll be within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This cottage is 11.9 mi (19.2 km) from Old Town and 12.7 mi (20.4 km) from ESPN Wide World of Sports Complex.

Getaway Delight-8 Bedrooms, Pool & Great Location Facility and Service
Be sure to enjoy recreational amenities, including an outdoor pool, a hot tub, and a 24-hour fitness center. This cottage also features complimentary wireless internet access and gas grills.

Getaway Delight-8 Bedrooms, Pool & Great Location Rooms
Make yourself comfortable in this air-conditioned 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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6br/themed Rooms, Loaded Games, Near Disney!

Cottage

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Osceola
6br/themed Rooms, Loaded Games, Near Disney! Location
With a stay at this cottage in Kissimmee (Windsor Hills), you'll be a 5-minute drive from Mystic Dunes Golf Club and 8 minutes from Walt Disney World® Resort. This cottage is 6.1 mi (9.8 km) from ESPN Wide World of Sports Complex and 6.3 mi (10.2 km) from Old Town.

6br/themed Rooms, Loaded Games, Near Disney! Facility and Service
This smoke-free cottage offers complimentary parking nearby.

6br/themed Rooms, Loaded Games, 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.

See details
Fully Booked
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Exterior & Views

8911sd Champions Gate 8 Bedroom Resort Villa

Cottage

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Osceola
8911sd Champions Gate 8 Bedroom Resort Villa 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 11.5 mi (18.5 km) from Old Town and 12.3 mi (19.7 km) from ESPN Wide World of Sports Complex.

8911sd Champions Gate 8 Bedroom Resort Villa 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.

8911sd Champions Gate 8 Bedroom Resort Villa 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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Pool

Tg220t Heritage Rock Spring

Cottage

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Osceola
Tg220t Heritage Rock Spring Location
With a stay at this cottage in Kissimmee (Champions Gate), you'll be within a 15-minute drive of Reunion Resort Golf Course and Mystic Dunes Golf Club. This cottage is 8.1 mi (13 km) from Walt Disney World® Resort and 10.1 mi (16.3 km) from Old Town.

Tg220t Heritage Rock Spring 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

SW & Frozen Rooms, Pool, Spa, 3 King Beds

Cottage

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Osceola
SW & Frozen Rooms, Pool, Spa, 3 King Beds 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 (11.7 km) from Disney Springs™ and 8.3 mi (13.4 km) from Walt Disney World® Resort.

SW & Frozen Rooms, Pool, Spa, 3 King Beds Facility and Service
This smoke-free cottage offers complimentary parking nearby.

SW & Frozen Rooms, Pool, Spa, 3 King Beds 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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Exterior & Views

8823inter

Cottage

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Osceola
8823inter 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 11.1 mi (17.9 km) from Old Town and 11.9 mi (19.2 km) from ESPN Wide World of Sports Complex.

8823inter Facility and Service
Take time to pamper yourself with a visit to the full-service spa.

8823inter Rooms
Make yourself comfortable in this air-conditioned villa, featuring a kitchen with a refrigerator and a microwave. Complimentary wireless internet access is available to keep you connected.

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Exterior & Views

Ground Floor Gathering up to 9 Guests Bl387

Cottage

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Osceola
Ground Floor Gathering up to 9 Guests Bl387 Location
Located in Kissimmee, this cottage is within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This cottage is 9 mi (14.4 km) from Disney Springs™ and 9.9 mi (16 km) from Walt Disney World® Resort.

Ground Floor Gathering up to 9 Guests Bl387 Facility and Service
Enjoy a range of recreational amenities, including an outdoor pool, a hot tub, and a 24-hour fitness center. This cottage also features complimentary wireless internet access and gas grills.

Ground Floor Gathering up to 9 Guests Bl387 Rooms
Make yourself comfortable in this air-conditioned 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 a ceiling fan.

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Others

1560 Tempo Lane

Cottage

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Osceola
1560 Tempo Lane 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 11.3 mi (18.3 km) from Old Town and 12.1 mi (19.5 km) from ESPN Wide World of Sports Complex.

1560 Tempo Lane 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.

1560 Tempo Lane 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.

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Bedroom

Emerald Resort 5 Bedroom 3 Bathroom Villa

Cottage

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Osceola
Emerald Resort 5 Bedroom 3 Bathroom Villa Location
Located in Kissimmee, this cottage is within a 15-minute drive of Walt Disney World® Resort and Old Town. This spa cottage is 7.4 mi (12 km) from ESPN Wide World of Sports Complex and 8.1 mi (13 km) from Disney's Hollywood Studios®.

Emerald Resort 5 Bedroom 3 Bathroom Villa Facility and Service
Take time to pamper yourself with a visit to the full-service spa. You can take advantage of recreational amenities such as an outdoor pool and a fitness center.

Emerald Resort 5 Bedroom 3 Bathroom Villa Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with a refrigerator and a microwave. There's a private lanai. Complimentary wireless internet access keeps you connected, and a flat-screen television is provided for your entertainment.

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Cottages in Osceola

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