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Cottages in Osceola

Osceola
Sat, 14 Nov 2026 - Sun, 15 Nov 2026 (1 night)
1 Adult, 0 Children
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Showing 660 Cottages in Osceola
Private kitchen

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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Lakeview 7BR Getaway, Pool, Great Location

Cottage

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Osceola
Lakeview 7BR Getaway, Pool, Great Location Location
With a stay at this cottage in Kissimmee (Crystal Cove), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This cottage is 8.3 mi (13.4 km) from Disney Springs™ and 8.6 mi (13.9 km) from Walt Disney World® Resort.

Lakeview 7BR Getaway, Pool, Great Location Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a hot tub. Additional features at this cottage include complimentary wireless internet access, a picnic area, and gas grills.

Lakeview 7BR Getaway, Pool, Great Location Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with an oven and a stovetop. There's a private furnished patio. Cable television is provided for your entertainment. Conveniences include a microwave and a dryer.

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Comfort 6BR Getaway, Private Pool, Great Location

Cottage

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Osceola
Comfort 6BR Getaway, Private Pool, Great Location 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 7.5 mi (12.1 km) from ESPN Wide World of Sports Complex and 8 mi (12.9 km) from Disney's Hollywood Studios®.

Comfort 6BR Getaway, Private Pool, Great 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. This cottage also features complimentary wireless internet access, a picnic area, and gas grills.

Comfort 6BR Getaway, Private Pool, Great Location Rooms
Make yourself comfortable in this air-conditioned cottage, 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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Fully Booked
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Upstay: 9BR Disney Retreat w Pool, BBQ & Hot Tub

Cottage

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Osceola
Upstay: 9BR Disney Retreat w Pool, BBQ & Hot Tub 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 (11.3 km) from Disney Springs™ and 7.7 mi (12.4 km) from Walt Disney World® Resort.

Upstay: 9BR Disney Retreat w Pool, BBQ & Hot Tub Facility and Service
Take advantage of recreational opportunities offered, including an outdoor pool, a hot tub, and a fitness center. Additional amenities at this cottage include complimentary wireless internet access and gas grills.

Upstay: 9BR Disney Retreat w Pool, BBQ & Hot Tub Rooms
Make yourself comfortable in this air-conditioned cottage, which features a private pool and an outdoor private hot tub. There's a private patio. A kitchen is outfitted with an oven, a microwave, and a kitchen island. Digital television is provided for your entertainment.

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Fully Booked
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Others

8925 Play Through Drive

Cottage

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Osceola
8925 Play Through Drive 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 family-friendly cottage is 12.5 mi (20.1 km) from Walt Disney World® Resort and 12.7 mi (20.4 km) from Old Town.

8925 Play Through 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.

8925 Play Through 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.

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Interior

6-bedroom 2505

Cottage

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Osceola
6-bedroom 2505 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.

6-bedroom 2505 Rooms
Make yourself comfortable in this air-conditioned cottage, which has a kitchen. Cable television is provided for your entertainment.

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Srl9004

Cottage

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Osceola
Srl9004 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.

Srl9004 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

Storey Lake Escape w/ Waterfront & Themed Rooms

Cottage

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Osceola
Storey Lake Escape w/ Waterfront & Themed Rooms 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 mi (9.6 km) from Disney Springs™ and 6.9 mi (11.1 km) from Walt Disney World® Resort.

Storey Lake Escape w/ Waterfront & Themed Rooms Facility and Service
This smoke-free cottage offers complimentary parking nearby.

Storey Lake Escape w/ Waterfront & Themed Rooms 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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Rc104p Fairway Bliss

Cottage

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Osceola
Rc104p Fairway Bliss Location
With a stay at this cottage in Kissimmee (Reunion), you'll be within a 15-minute drive of Reunion Resort Golf Course and Mystic Dunes Golf Club. This cottage is 7.5 mi (12 km) from Walt Disney World® Resort and 9.5 mi (15.3 km) from Old Town.

Rc104p Fairway Bliss Facility and Service
Take advantage of recreation opportunities such as an outdoor pool, or other amenities including complimentary wireless internet access and barbecue grills.

Rc104p Fairway Bliss 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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Fully Booked
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Interior

Upstay: Family Home w Pool, Cinema & Games Room

Cottage

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Osceola
Upstay: Family Home w Pool, Cinema & Games Room 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 (11.2 km) from Disney Springs™ and 8 mi (12.9 km) from Walt Disney World® Resort.

Upstay: Family Home w Pool, Cinema & Games Room Facility and Service
Take advantage of recreational opportunities offered, including an outdoor pool, a hot tub, and a fitness center. Additional amenities at this cottage include complimentary wireless internet access and gas grills.

Upstay: Family Home w Pool, Cinema & Games 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 patio. A kitchen is outfitted with an oven, a microwave, and a kitchen island. Digital television is provided for your entertainment.

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Fully Booked
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Exterior & Views

Tuttle Orlando Villa

Cottage

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Osceola
Tuttle Orlando Villa Location
With a stay at Tuttle Orlando Villa in Kissimmee, you'll be a 5-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort. This family-friendly hotel is 5 mi (8 km) from ESPN Wide World of Sports Complex and 5.3 mi (8.6 km) from Disney's Animal Kingdom® Theme Park.

Tuttle Orlando Villa Facility and Service
Dip into one of the 14 outdoor pools or 14 hot tubs and enjoy other recreational amenities, which include a complimentary water park. Additional amenities at this hotel include complimentary wireless internet access, concierge services, and an arcade/game room.

Tuttle Orlando Villa Rooms
Make yourself at home in one of the 3 guestrooms. Rooms have private balconies or patios. Prepare your meals in the shared/communal kitchen. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms with bathtubs or showers are provided.

Restaurant and Cafe
Grab a bite to eat at one of the hotel's many dining establishments, which include 2 restaurants and a coffee shop/cafe. Relax with a refreshing drink from the poolside bar or one of the 3 bars/lounges. Full breakfasts are available daily from 8:00 AM to 10:30 AM for a fee.

Important Information
This property is closed from January 1 2026 to December 31 2026 (dates subject to change).

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Fully Booked
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Exterior & Views

Upstay - 18-guest Mansion w Pool, Games, Cinema

Cottage

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Osceola
Upstay - 18-guest Mansion w Pool, Games, Cinema Location
Located in Kissimmee, this cottage is within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This cottage is 8.9 mi (14.4 km) from Disney Springs™ and 9.9 mi (15.9 km) from Walt Disney World® Resort.

Upstay - 18-guest Mansion w Pool, Games, Cinema Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. This cottage also features complimentary wireless internet access and barbecue grills.

Upstay - 18-guest Mansion w Pool, Games, Cinema 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
2.0/5
Fully Booked
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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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Serenity - Family & Pet Friendly, Amazing Location

Cottage

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Osceola
Serenity - Family & Pet Friendly, Amazing Location Location
With a stay at this cottage in Kissimmee (Crestwynd Bay), you'll be a 5-minute drive from Mystic Dunes Golf Club and 6 minutes from Walt Disney World® Resort. This cottage is 5.2 mi (8.4 km) from ESPN Wide World of Sports Complex and 5.5 mi (8.8 km) from Old Town.

Serenity - Family & Pet Friendly, Amazing Location Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. This cottage also features complimentary wireless internet access and gas grills.

Serenity - Family & Pet Friendly, Amazing Location Rooms
Make yourself comfortable in this air-conditioned cottage, which has a kitchen. Cable television is provided for your entertainment. Conveniences include a desk and a coffee/tea maker, and you can also request a crib/infant bed (complimentary).

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Interior

8939ad · Amazing Solara 7br/ Pool /spa /free Waterpark

Cottage

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Osceola
8939ad · Amazing Solara 7br/ Pool /spa /free Waterpark 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 mi (16.1 km) from Disney's Animal Kingdom® Theme Park and 11.2 mi (18 km) from ESPN Wide World of Sports Complex.

8939ad · Amazing Solara 7br/ Pool /spa /free Waterpark Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and barbecue grills.

8939ad · Amazing Solara 7br/ Pool /spa /free Waterpark 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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Game room

Windsor Westside Resort 7 Bedroom Home Game Room 0855

Cottage

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Osceola
Windsor Westside Resort 7 Bedroom Home Game Room 0855 Location
Located in Kissimmee, this cottage is within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This cottage is 10.2 mi (16.5 km) from Disney's Animal Kingdom® Theme Park and 10.6 mi (17 km) from ESPN Wide World of Sports Complex.

Windsor Westside Resort 7 Bedroom Home Game Room 0855 Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Windsor Westside Resort 7 Bedroom Home Game Room 0855 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

4701rrl

Cottage

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Osceola
4701rrl Location
With a stay at this cottage in Kissimmee (Crystal Cove), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This cottage is 8.3 mi (13.3 km) from Disney Springs™ and 8.5 mi (13.6 km) from ESPN Wide World of Sports Complex.

4701rrl Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center.

4701rrl Rooms
Make yourself comfortable in this air-conditioned cottage, which features a private pool and a flat-screen TV. A kitchen is outfitted with a refrigerator and a microwave. Complimentary wireless internet access is available to keep you connected.

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Family 6BR Home, Pool & Game Room

Cottage

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Osceola
Family 6BR Home, Pool & Game Room 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 7.8 mi (12.6 km) from Walt Disney World® Resort and 9.5 mi (15.3 km) from Disney's Animal Kingdom® Theme Park.

Family 6BR Home, Pool & Game Room 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.

Family 6BR Home, Pool & Game Room 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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5.0/5
Fully Booked
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Exterior & Views

6 BD 5 BH House Game Room Pool Spa

Cottage

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Osceola
6 BD 5 BH House 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 family-friendly 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.

6 BD 5 BH House 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), an arcade/game room, and barbecue grills.

6 BD 5 BH House Game Room Pool Spa Rooms
Make yourself comfortable in this cottage, which features a fireplace and a private pool. A kitchen makes it easy to prepare your meals. Complimentary wireless internet access keeps you connected, and an LED television is provided for your entertainment. Conveniences include a washer/dryer and an iron/ironing board.

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Bedroom

6 Bed 5 Ba Villa with Games, Pool & Spa

Cottage

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Osceola
6 Bed 5 Ba Villa with Games, Pool & Spa 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 6.1 mi (9.8 km) from Disney Springs™ and 6.8 mi (11 km) from ESPN Wide World of Sports Complex.

6 Bed 5 Ba 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.

6 Bed 5 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.

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Fully Booked
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Cottages in Osceola

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