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Cottages in Osceola

Osceola
Sun, 15 Nov 2026 - Mon, 16 Nov 2026 (1 night)
1 Adult, 0 Children
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Showing 652 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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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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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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Room

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

Last Minute Deal! Free Pool Heat! Encantada 87

Cottage

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Osceola
Last Minute Deal! Free Pool Heat! Encantada 87 Location
With a stay at this cottage in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and Old Town. This cottage is 7 mi (11.3 km) from Disney's Animal Kingdom® Theme Park and 8.2 mi (13.3 km) from ESPN Wide World of Sports Complex.

Last Minute Deal! Free Pool Heat! Encantada 87 Facility and Service
Take advantage of recreation opportunities such as an outdoor pool, or other amenities including complimentary wireless internet access and barbecue grills.

Last Minute Deal! Free Pool Heat! Encantada 87 Rooms
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with an oven and a stovetop. There's a private balcony. Conveniences include a microwave and a washer/dryer.

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Sp8136

Cottage

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Osceola
Sp8136 Location
With a stay at this cottage in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and Old Town. This cottage is 7.3 mi (11.7 km) from ESPN Wide World of Sports Complex and 7.8 mi (12.5 km) from Disney's Hollywood Studios®.

Sp8136 Facility and Service
Take in the views from a terrace and make use of amenities such as complimentary wireless internet access.

Sp8136 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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Room

Private Pool, Modern Elegance, Ideal Locale

Cottage

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Osceola
Private Pool, Modern Elegance, Ideal Locale 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 11.6 mi (18.6 km) from Old Town and 12.3 mi (19.9 km) from ESPN Wide World of Sports Complex.

Private Pool, Modern Elegance, Ideal Locale Facility and Service
Dip into one of the 2 outdoor pools or enjoy other recreational amenities, which include a 24-hour fitness center. Additional features at this cottage include complimentary wireless internet access and gas grills.

Private Pool, Modern Elegance, Ideal Locale 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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Exterior & Views

Blue Cascade Cottage near Disney with Margaritaville Resort Island H2O Access - 8064LS

Cottage

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Osceola
Great care is taken to ensure guests experience comfort through top-notch services and amenities. Stay connected with your associates, as complimentary Wi-Fi is available during your entire visit. The home offers car hire amenities to assist you in discovering your desired offerings in Orlando (FL). When arriving by car, take advantage of the home's convenient on-site parking facilities. The home offers reception amenities including concierge service, luggage storage and safety deposit boxes to ensure a comfortable stay for guests.To ensure the well-being and convenience of all visitors, smoking is strictly prohibited throughout the entire home.Smoking is permitted solely in the specified smoking zones allocated by home. In order to ensure the utmost level of relaxation, the guestrooms feature an inviting design and are equipped with all basic necessities, creating a delightful stay experience.To ensure your satisfaction, certain rooms in the home come fitted with linen service for a more pleasant stay.Several chosen accommodations at Blue Cascade Cottage near Disney with Margaritaville Resort Island H2O Access - 8064LS have a balcony or terrace incorporated into the room design.Selected rooms offer in-room amusement like television as a source of entertainment for guests to enjoy. Within specific rooms, a refrigerator and a coffee or tea maker is conveniently available for your use.Understanding the significance of bathroom facilities in enhancing visitor contentment, home offers a hair dryer and toiletries within a few chosen chambers. Upon your arrival, don't miss experiencing bar for enjoyable in-house evening entertainment.Visitors staying at Blue Cascade Cottage near Disney with Margaritaville Resort Island H2O Access - 8064LS have the option to receive groceries in their room for meal preparation, courtesy of the unique service provided by the home. Throughout the day, engage in the entertaining activities available at Blue Cascade Cottage near Disney with Margaritaville Resort Island H2O Access - 8064LS.Guests who enjoy maintaining their fitness regimen while on holiday can visit the fitness center provided by home.
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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

Exquisite 9bed 6.5ba Villa

Cottage

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Osceola
Exquisite 9bed 6.5ba Villa Location
With a stay at this cottage in Kissimmee (Indian Ridge), you'll be a 5-minute drive from Mystic Dunes Golf Club and 9 minutes from Walt Disney World® Resort. This family-friendly cottage is 6.8 mi (11 km) from ESPN Wide World of Sports Complex and 7.3 mi (11.7 km) from Old Town.

Exquisite 9bed 6.5ba Villa Facility and Service
Take time to pamper yourself with a visit to the full-service spa. This cottage also features wireless internet access (surcharge) and barbecue grills.

Exquisite 9bed 6.5ba Villa Rooms
Your cottage features a flat-screen TV. Conveniences include a dryer and an iron/ironing board.

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Interior

Mnl2678

Cottage

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Osceola
Mnl2678 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 (9.1 km) from ESPN Wide World of Sports Complex and 5.9 mi (9.5 km) from Old Town.

Mnl2678 Rooms
Make yourself comfortable in this air-conditioned cottage, which has a kitchen.

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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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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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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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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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Newly Renovated 6BR Family Homepool, BBQ & Games

Cottage

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Osceola
Newly Renovated 6BR Family Homepool, BBQ & Games Location
With a stay at this cottage in Kissimmee, you'll be within a 15-minute drive of Old Town and 192 Flea Market. This cottage is 9.6 mi (15.4 km) from Orlando Vineland Premium Outlets and 9.7 mi (15.6 km) from Disney Springs™.

Newly Renovated 6BR Family Homepool, BBQ & Games Facility and Service
Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. Additional amenities at this cottage include complimentary wireless internet access and barbecue grills.

Newly Renovated 6BR Family Homepool, BBQ & Games 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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Home 9 Bed Themed Rooms, Pool, Storey Lake

Cottage

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Osceola
Home 9 Bed Themed Rooms, Pool, 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 6.3 mi (10.1 km) from Disney Springs™ and 6.9 mi (11.1 km) from Walt Disney World® Resort.

Home 9 Bed Themed Rooms, Pool, Storey Lake Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a 24-hour fitness center. Additional amenities at this cottage include complimentary wireless internet access and gas grills.

Home 9 Bed Themed Rooms, Pool, 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 desk and a separate sitting area.

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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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Interior

Upstay Bella Vida Retreat w Pool, Cinema and Games

Cottage

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Osceola
Upstay Bella Vida Retreat w Pool, Cinema and Games 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 Bella Vida Retreat w Pool, Cinema and Games 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 Bella Vida Retreat w Pool, Cinema and 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.

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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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Cottages in Osceola

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