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Cottages in Osceola

Osceola
Thu, 19 Nov 2026 - Fri, 20 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 658 Cottages in Osceola
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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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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Others

Lakeview/star Wars & Minions Rooms + Resort Access

Cottage

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Osceola
Lakeview/star Wars & Minions Rooms + Resort Access 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 12.3 mi (19.8 km) from Walt Disney World® Resort and 12.3 mi (19.9 km) from Old Town.

Lakeview/star Wars & Minions Rooms + Resort Access Facility and Service
This smoke-free cottage offers complimentary parking nearby.

Lakeview/star Wars & Minions Rooms + 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.

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Fully Booked
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Upstay Resort Home w Private Poolchampionsgate

Cottage

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Osceola
Upstay Resort Home w Private Poolchampionsgate 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 (18.2 km) from Old Town.

Upstay Resort Home w Private Poolchampionsgate Facility and Service
Take advantage of recreation opportunities such as an outdoor pool, or other amenities including complimentary wireless internet access and barbecue grills.

Upstay Resort Home w Private Poolchampionsgate 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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Sport & Beauty

9014 Sunshine Ridge Loop

Cottage

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Osceola
9014 Sunshine Ridge Loop 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 10.1 mi (16.2 km) from Disney's Animal Kingdom® Theme Park and 11.3 mi (18.2 km) from ESPN Wide World of Sports Complex.

9014 Sunshine Ridge Loop Facility and Service
Take advantage of recreation 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.

9014 Sunshine Ridge Loop 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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12br Bella Vida Pool Near Disney

Cottage

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Osceola
12br Bella Vida Pool Near Disney 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 10 mi (16 km) from Walt Disney World® Resort.

12br Bella Vida Pool Near Disney Facility and Service
This smoke-free cottage offers complimentary parking nearby.

12br Bella Vida Pool 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, and you can also request a crib/infant bed (complimentary).

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Lavish 4BR Home in Windsor Hills Resort

Cottage

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Osceola
Lavish 4BR Home in Windsor Hills Resort 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 6.4 mi (10.3 km) from Old Town.

Lavish 4BR Home in Windsor Hills Resort Rooms
Make yourself comfortable in this air-conditioned cottage, which has a kitchen.

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Interior

Wsb670

Cottage

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Osceola
Wsb670 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 12.3 mi (19.8 km) from Old Town and 13.1 mi (21.1 km) from ESPN Wide World of Sports Complex.

Wsb670 Facility and Service
Take in the views from a terrace and make use of amenities such as complimentary wireless internet access.

Wsb670 Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with an oven and a stovetop. There's a private patio. Conveniences include a microwave and a dryer.

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Fully Booked
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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.

See details
Fully Booked
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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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Fully Booked
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Interior

Og534d Homestead Cypress

Cottage

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Osceola
Og534d Homestead Cypress Location
With a stay at this cottage in Kissimmee (Reunion), you'll be within a 15-minute drive of Walt Disney World® Resort and Reunion Resort Golf Course. This cottage is 9.6 mi (15.4 km) from ESPN Wide World of Sports Complex and 10.1 mi (16.2 km) from Disney's Hollywood Studios®.

Og534d Homestead Cypress 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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Interior

Encore Swanky

Cottage

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Osceola
Encore Swanky 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 7.4 mi (12 km) from ESPN Wide World of Sports Complex and 7.9 mi (12.7 km) from Disney's Hollywood Studios®.

Encore Swanky 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 amenities at this cottage include an arcade/game room and barbecue grills.

Encore Swanky Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with a refrigerator and an oven. Satellite programming along with a video-game console are provided for your entertainment. Conveniences include a microwave and a dryer, and housekeeping is provided on a limited basis.

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Others

Heated Pool & Bathtub 4BR Near Disney

Cottage

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Osceola
Heated Pool & Bathtub 4BR Near Disney Location
With a stay at this cottage in Kissimmee (Indian Point), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This cottage is 9.2 mi (14.7 km) from Disney Springs™ and 10 mi (16 km) from ESPN Wide World of Sports Complex.

Heated Pool & Bathtub 4BR Near Disney Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Heated Pool & Bathtub 4BR Near Disney Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with an oven and a microwave. There's a private patio. Conveniences include a dryer and an iron/ironing board.

See details
Fully Booked
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4177 Paragraph Drive

Cottage

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Osceola
4177 Paragraph Drive Location
Located in Kissimmee, this cottage is within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This family-friendly cottage is 7.7 mi (12.3 km) from Disney Springs™ and 8.7 mi (14.1 km) from Walt Disney World® Resort.

4177 Paragraph Drive Facility and Service
Be sure to enjoy recreational amenities, including an outdoor pool, a lazy river, and a waterslide. Additional amenities at this cottage include complimentary wireless internet access and barbecue grills.

4177 Paragraph Drive 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.

See details
Fully Booked
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Kcc4741

Cottage

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Osceola
Kcc4741 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 (9.7 km) from Disney Springs™ and 7 mi (11.2 km) from Walt Disney World® Resort.

Kcc4741 Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and barbecue grills.

Kcc4741 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

It's A Wonderful Life Vacay Home

Cottage

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Osceola
It's A Wonderful Life Vacay Home Location
With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Old Town. This cottage is 6.6 mi (10.6 km) from ESPN Wide World of Sports Complex and 7.1 mi (11.4 km) from Disney's Hollywood Studios®.

It's A Wonderful Life Vacay Home Rooms
Make yourself comfortable in this individually decorated cottage, featuring a kitchen with a refrigerator and an oven. There's a private furnished patio. A 42-inch flat-screen television with digital programming provides entertainment, while complimentary wireless internet access keeps you connected. Conveniences include a separate sitting area and a microwave.

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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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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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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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Fully Booked
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Spacious 6 Bed Home With Pool in Storey Lake

Cottage

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Osceola
Spacious 6 Bed Home With Pool in Storey Lake 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.

Spacious 6 Bed Home With Pool in Storey Lake Facility and Service
Enjoy recreational amenities such as an outdoor pool and a 24-hour fitness center. Additional features at this cottage include complimentary wireless internet access and gas grills.

Spacious 6 Bed Home With Pool in Storey Lake 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.

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5.0/5
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Cottages in Osceola

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