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Cottages in Osceola

Osceola
Sat, 14 Nov 2026 - Sun, 15 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 647 Cottages in Osceola
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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
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Others

Disney Mansion With Hot Tub, Pool & Resort Access

Cottage

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Osceola
Disney Mansion With Hot Tub, Pool & Resort Access Location
When you stay at this cottage in Kissimmee, you'll be on a lake, within a 10-minute drive of ChampionsGate Golf Club and Flamingo Crossings Town Center. This family-friendly cottage is 7.9 mi (12.7 km) from Walt Disney World® Resort and 9.6 mi (15.4 km) from Disney's Animal Kingdom® Theme Park.

Disney Mansion With Hot Tub, Pool & Resort Access Facility and Service
Take advantage of recreational opportunities offered, including an outdoor pool, a lazy river, and a waterslide. Additional amenities at this cottage include complimentary wireless internet access and gas grills.

Disney Mansion With Hot Tub, Pool & Resort Access Rooms
Make yourself comfortable in this individually decorated cottage, featuring a kitchen with an oven and a stovetop. A 40-inch Smart television is provided, with digital programming available.

Restaurant and Cafe
At this cottage, enjoy a satisfying meal at the restaurant. Relax with your favorite drink at the bar/lounge or the poolside bar.

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Exterior & Views

3050 Pirate Way

Cottage

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Osceola
3050 Pirate Way Location
With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center. This cottage is 6.1 mi (9.9 km) from Disney's Animal Kingdom® Theme Park and 6.6 mi (10.5 km) from Old Town.

3050 Pirate Way Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with a refrigerator and an oven. There's a private balcony. 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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Fully Booked
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Interior

491-8-ld-private Pool With Game and Movie

Cottage

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Osceola
491-8-ld-private Pool With Game and Movie 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 7.4 mi (11.9 km) from ESPN Wide World of Sports Complex and 7.9 mi (12.7 km) from Disney's Hollywood Studios®.

491-8-ld-private Pool With Game and Movie 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

Westgate Vacation Villas Resort

Cottage

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Osceola
Westgate Vacation Villas Resort offers top-notch services and amenities, ensuring guests experience utmost comfort.Share your photos and respond to emails at your convenience, thanks to the free Wi-Fi internet access offered by resort.Experience the wonders of Orlando (FL) with ease by utilizing the services provided at car hire. Visitors can take advantage of complimentary parking directly at the resort.Reception services such as concierge service, express check-in or check-out, luggage storage and safety deposit boxes are available to accommodate your requirements. Should you desire access to the top entertainment in the city, assistance can be provided by the resort's ticket service. Traveling with minimal baggage is achievable at Westgate Vacation Villas Resort, as the resort's laundromat and dry cleaning service ensures your garments stay fresh.Room amenities feature room service, allowing you to unwind and make the most of your visit.Minor items you neglected to bring won't cause major issues! Simply visit convenience stores to acquire what's necessary.The resort maintains a completely smoke-free zone, providing a breathable atmosphere.Each accommodation at Westgate Vacation Villas Resort is thoughtfully created and adorned to provide visitors with a comfortable, home-like atmosphere.In certain rooms, the resort offers blackout curtains and air conditioning for guest convenience and satisfaction.At Westgate Vacation Villas Resort, uniquely crafted rooms provide various layout choices, featuring spaces equipped with separate living room and balcony or terrace.In select rooms, guests at the resort can enjoy top-notch in-room entertainment with television and cable TV available for their convenience. Rest assured, in a few chosen rooms, you will find the convenience of a refrigerator and a coffee or tea maker at your disposal. Understanding the significance of bathroom facilities in enhancing visitor contentment, resort offers a hair dryer and toiletries within a few chosen chambers. Embark on your holiday experience in the most ideal manner. Commence each morning of your visit with an on-site breakfast.Experience the delight of a fresh morning by savoring excellent coffee at the cafe situated within resort.Should you prefer not to venture out for a meal, the enticing culinary choices at resort are always available for your satisfaction.Experience an unforgettable evening with your fellow travelers just a short distance away, at resort's bar.Throughout the day and evening, grab a bite to eat from resort's self-service vending machines whenever you please.Should you be particularly discerning in your dining choices, you will surely appreciate having access to the on-site BBQ facilities provided at this location.Throughout the day, engage in the entertaining activities available at Westgate Vacation Villas Resort. Make certain to allocate time for discovering the shoreline, easily reachable right from the resort. Unwind after a long day by stopping by hot tub, spa and sauna to rejuvenate your senses.Each day at resort, immerse yourself in the invigorating waters of the pool, perfect for a rejuvenating plunge or a series of revitalizing laps. Bypass the formal attire and choose a laid-back mixed drink or brew at resort's waterside lounge.For individuals who don't want to skip their exercise routine, visiting the resort fitness center ensures you maintain your vitality and wellness.
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Interior

1370 Tuscana LN Davenport, 3bed

Cottage

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Osceola
1370 Tuscana LN Davenport, 3bed Location
With a stay at this cottage in Four Corners (Champions Gate), you'll be within a 15-minute drive of Old Town and ChampionsGate Golf Club. This cottage is 10.1 mi (16.3 km) from ESPN Wide World of Sports Complex and 10.2 mi (16.4 km) from Walt Disney World® Resort.

1370 Tuscana LN Davenport, 3bed Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and barbecue grills.

1370 Tuscana LN Davenport, 3bed 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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Upstay: Resort Retreat w/ Private Pool & BBQ Area

Cottage

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Osceola
Upstay: Resort Retreat w/ Private Pool & BBQ Area Location
Located in Kissimmee, this cottage is within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This cottage is 9.6 mi (15.5 km) from Disney Springs™ and 10.3 mi (16.6 km) from ESPN Wide World of Sports Complex.

Upstay: Resort Retreat w/ Private Pool & BBQ Area Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and barbecue grills.

Upstay: Resort Retreat w/ Private Pool & BBQ Area 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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Others

Luxe Home w Themed Rooms, Loaded Games, Disney

Private Cottage

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Osceola
Luxe Home w Themed Rooms, Loaded Games, 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 mi (9.7 km) from ESPN Wide World of Sports Complex and 6.3 mi (10.1 km) from Old Town.

Luxe Home w Themed Rooms, Loaded Games, Disney 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.

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Sport & Beauty

The Sea Shelter Sunny 4 BDR in Margaritaville!

Cottage

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Osceola
The Sea Shelter Sunny 4 BDR in Margaritaville! Location
When you stay at this cottage in Kissimmee, you'll be next to a golf course, a 4-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort. This golf cottage is 5.8 mi (9.3 km) from Old Town and 6 mi (9.7 km) from ESPN Wide World of Sports Complex.

The Sea Shelter Sunny 4 BDR in Margaritaville! Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

The Sea Shelter Sunny 4 BDR in Margaritaville! Rooms
Treat yourself to a stay in this individually decorated cottage, which features a private pool and a flat-screen TV. There's a private furnished balcony/patio. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Digital television is provided for your entertainment.

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5.0/5
Fully Booked
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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.

See details
Fully Booked
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Spectacular 7BR Home w Pool & Arcade Near Disney

Cottage

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Osceola
Spectacular 7BR Home w Pool & Arcade Near Disney 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 8.6 mi (13.9 km) from Walt Disney World® Resort and 10.4 mi (16.8 km) from Disney's Animal Kingdom® Theme Park.

Spectacular 7BR Home w Pool & Arcade Near Disney Facility and Service
Enjoy a range of recreational amenities, 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.

Spectacular 7BR Home w Pool & Arcade Near Disney Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with an oven and a microwave. Cable television is provided for your entertainment. Conveniences include an all-in-one washing machine and dryer and an iron/ironing board.

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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Mickey, Minions, & Poolside Family Getaway

Cottage

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Osceola
Mickey, Minions, & Poolside Family Getaway 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 (16.3 km) from Disney's Animal Kingdom® Theme Park and 11.3 mi (18.2 km) from ESPN Wide World of Sports Complex.

Mickey, Minions, & Poolside Family Getaway Facility and Service
This smoke-free cottage offers complimentary parking nearby.

Mickey, Minions, & Poolside Family Getaway 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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Cozy 5BR Townhome w/ Mickey Themed & Pool

Cottage

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Osceola
Cozy 5BR Townhome w/ Mickey Themed & Pool 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 8.2 mi (13.1 km) from Walt Disney World® Resort and 9.8 mi (15.8 km) from Disney's Animal Kingdom® Theme Park.

Cozy 5BR Townhome w/ Mickey Themed & Pool Facility and Service
This smoke-free cottage offers complimentary parking nearby.

Cozy 5BR Townhome w/ Mickey Themed & Pool 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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Star Wars Game Room+pool Near Disney Parks

Cottage

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Osceola
Star Wars Game Room+pool Near Disney Parks 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 (16.4 km) from Disney's Animal Kingdom® Theme Park and 11.4 mi (18.3 km) from ESPN Wide World of Sports Complex.

Star Wars Game Room+pool Near Disney Parks Facility and Service
This smoke-free cottage offers complimentary parking nearby.

Star Wars Game Room+pool Near Disney Parks 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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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.

See details
Fully Booked
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Greenview Retreat w/ Private Pool & Games

Cottage

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Osceola
Greenview Retreat w/ Private Pool & Games 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 11.2 mi (18 km) from Old Town and 11.9 mi (19.2 km) from ESPN Wide World of Sports Complex.

Greenview Retreat w/ Private Pool & Games Facility and Service
This smoke-free cottage offers complimentary parking nearby.

Greenview Retreat w/ Private Pool & Games 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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Upstay - Lively Mansion w Pool, Theater, Games

Cottage

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Osceola
Upstay - Lively Mansion w Pool, Theater, Games 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 8.8 mi (14.2 km) from Disney Springs™ and 9.6 mi (15.4 km) from ESPN Wide World of Sports Complex.

Upstay - Lively Mansion w Pool, Theater, Games 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 - Lively Mansion w Pool, Theater, Games 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.

See details
Fully Booked
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Beauty Home, Private Pool in Champions Gate

Cottage

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Osceola
Beauty Home, Private Pool in Champions Gate Location
With a stay at this cottage in Four Corners (Champions Gate), you'll be within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This cottage is 12.7 mi (20.4 km) from Old Town and 13.2 mi (21.3 km) from Walt Disney World® Resort.

Beauty Home, Private Pool in Champions Gate 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.

Beauty Home, Private Pool in Champions Gate Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen 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
Fully Booked
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Pool

Windsor Hills Resort 5 Bedroom Private Pool Home 0869

Cottage

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Osceola
Windsor Hills Resort 5 Bedroom Private Pool Home 0869 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 5.8 mi (9.3 km) from ESPN Wide World of Sports Complex and 6.1 mi (9.8 km) from Old Town.

Windsor Hills Resort 5 Bedroom Private Pool Home 0869 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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Mvd1506

Cottage

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Osceola
Mvd1506 Location
Located in Four Corners, this cottage is within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This cottage is 11.8 mi (18.9 km) from Old Town and 12.6 mi (20.2 km) from ESPN Wide World of Sports Complex.

Mvd1506 Rooms
Make yourself comfortable in this air-conditioned cottage, which has a kitchen. There's a private patio.

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Cottages in Osceola

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