Hotels in Windward Cay

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20 Jul - 21 Jul
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Top 10 Hotels in Windward Cay

Hyatt Regency Orlando International Airport
Relax by the pool surrounded by palm trees and lounge chairs.

Hyatt Regency Orlando International Airport

4.0 star property
9.4 out of 10, Exceptional, (3393)
"Great location and stay "
The price is S$257
includes taxes & fees
22 Jul - 23 Jul
Hyatt Regency Orlando International Airport
Hyatt House Orlando Airport
Relax in style with a comfortable sofa and matching armchairs around a central table.

Hyatt House Orlando Airport

2.0 star property
9.6 out of 10, Exceptional, (2348)
"Great stay"
The price is S$172
includes taxes & fees
21 Jul - 22 Jul
Hyatt House Orlando Airport
Wingate by Wyndham - Orlando International Airport
Two single beds with white linens and a central nightstand.

Wingate by Wyndham - Orlando International Airport

3.0 star property
8.8 out of 10, Excellent, (3524)
"Great stay "
The price is S$124
includes taxes & fees
21 Jul - 22 Jul
Wingate by Wyndham - Orlando International Airport
Lake Nona Wave Hotel
Relax by the pool surrounded by colorful umbrellas and lounge chairs.

Lake Nona Wave Hotel

4.0 star property
9.6 out of 10, Exceptional, (1005)
"It was a good location and a fun looking hotel with some cool features."
The price is S$324
includes taxes & fees
31 Jul - 1 Aug
Lake Nona Wave Hotel
La Quinta Inn & Suites by Wyndham Orlando Airport North
Enjoy a fully equipped kitchenette with a microwave, toaster, coffee maker, and refrigerator.

La Quinta Inn & Suites by Wyndham Orlando Airport North

3.0 star property
7.8 out of 10, Good, (7161)
"Lo único que no nos gustó día la piscina estaba súper descuidada y sucia de ramas de palmas y hojas. Y verde el agua. Lo de más súper bien. "
The price is S$122
includes taxes & fees
22 Jul - 23 Jul
La Quinta Inn & Suites by Wyndham Orlando Airport North
Rosen Shingle Creek
Relax by the pool surrounded by lounge chairs and umbrellas, with a view of the resort's distinctive building in the background.

Rosen Shingle Creek

4.5 star property
9.4 out of 10, Exceptional, (3893)
"Great staff, great food, beautiful property"
The price is S$169
includes taxes & fees
26 Jul - 27 Jul
Rosen Shingle Creek
Hyatt House Orlando International Drive
Enjoy a delicious spread of scrambled eggs, casserole, and mixed vegetables at our buffet.

Hyatt House Orlando International Drive

4.0 star property
9.4 out of 10, Exceptional, (644)
"Great hotel."
The price is S$126
includes taxes & fees
17 Aug - 18 Aug
Hyatt House Orlando International Drive
Pestana Orlando Suites - Lake Buena Vista
Hypo-allergenic bedding, minibar, in-room safe, individually decorated

Pestana Orlando Suites - Lake Buena Vista

4.0 star property
9.4 out of 10, Exceptional, (1656)
"We had a nice stay"
The price is S$123
includes taxes & fees
27 Jul - 28 Jul
Pestana Orlando Suites - Lake Buena Vista
Hampton Inn Orlando-International Airport
Relax by the rectangular pool surrounded by lounge chairs and umbrellas.

Hampton Inn Orlando-International Airport

2.5 star property
9.0 out of 10, Wonderful, (1417)
"Good place, if you need to stay close to the airport."
The price is S$134
includes taxes & fees
28 Jul - 29 Jul
Hampton Inn Orlando-International Airport
Wyndham Garden Orlando Airport
Relax by the pool surrounded by lush greenery and comfortable lounge seating.

Wyndham Garden Orlando Airport

3.0 star property
9.0 out of 10, Wonderful, (3756)
"Great stay"
The price is S$144
includes taxes & fees
11 Aug - 12 Aug
Wyndham Garden Orlando Airport
Alhambra Villas
Stunning hotel with modern design, surrounded by lush landscaping and a serene atmosphere.

Alhambra Villas

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Enjoy my stay love this place"
The price is S$119
includes taxes & fees
21 Jul - 22 Jul
Alhambra Villas
Drury Plaza Hotel Orlando - Disney Springs Area
Relax by the pool surrounded by palm trees and lounge chairs.

Drury Plaza Hotel Orlando - Disney Springs Area

3.0 star property
9.8 out of 10, Exceptional, (4491)
"Great position and lovely hotel"
The price is S$197
includes taxes & fees
27 Jul - 28 Jul
Drury Plaza Hotel Orlando - Disney Springs Area
Country Inn & Suites by Radisson, Orlando Airport, FL
Classic hotel with a covered entrance and palm trees.

Country Inn & Suites by Radisson, Orlando Airport, FL

3.0 star property
7.8 out of 10, Good, (3931)
"Great stay!!"
The price is S$114
includes taxes & fees
18 Aug - 19 Aug
Country Inn & Suites by Radisson, Orlando Airport, FL
Sonesta Essential Orlando
Two single beds with white bedding and a flat-screen TV are featured in this stylish room.

Sonesta Essential Orlando

3.0 star property
7.2 out of 10, Good, (1711)
"Excellent, great hospitality from the staff"
The price is S$115
includes taxes & fees
21 Jul - 22 Jul
Sonesta Essential Orlando
Kompose Boutique Resort at Theme Parks
Relax in style with a view of the outdoor pool from our spacious lobby, featuring a stunning chandelier and unique sculpture.

Kompose Boutique Resort at Theme Parks

4.0 star property
9.6 out of 10, Exceptional, (725)
"Great stay "
The price is S$124
includes taxes & fees
10 Aug - 11 Aug
Kompose Boutique Resort at Theme Parks
Magic Moment Resort and Kids Club
Relax in this stylish living room with a large sofa, coffee table, and fireplace, perfect for unwinding.

Magic Moment Resort and Kids Club

3.0 star property
8.4 out of 10, Very good, (2362)
"Very nice with great breakfast "
Magic Moment Resort and Kids Club
Ramada by Wyndham Suites Orlando Airport
Relax in a cozy space with a neatly made bed, flat-screen TV, and workspace area.

Ramada by Wyndham Suites Orlando Airport

3.0 star property
8.2 out of 10, Very good, (4643)
"Excellent location, service and rooms!!"
The price is S$144
includes taxes & fees
4 Aug - 5 Aug
Ramada by Wyndham Suites Orlando Airport
Hyatt Place Orlando Airport
Enjoy cooking in this well-equipped kitchen with an oven, microwave, and ample storage.

Hyatt Place Orlando Airport

3.0 star property
8.8 out of 10, Excellent, (1225)
"Great place!"
The price is S$159
includes taxes & fees
4 Aug - 5 Aug
Hyatt Place Orlando Airport
Seasons Florida Resort
Relax in this serene outdoor seating area with a round table and comfortable chairs.

Seasons Florida Resort

2.0 star property
8.8 out of 10, Excellent, (2999)
"Very great spot for couples and families "
Seasons Florida Resort
Holiday Inn Orlando International Dr-ICON by IHG
Enjoy meals at the large dining table and stay productive at the computer desk, with a view of the outdoors through the large windows.

Holiday Inn Orlando International Dr-ICON by IHG

3.0 star property
9.0 out of 10, Wonderful, (2101)
"Property was very clean! It was just a very comfortable place to stay"
The price is S$148
includes taxes & fees
27 Jul - 28 Jul
Holiday Inn Orlando International Dr-ICON by IHG
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Where to stay in Windward Cay

Find the best Windward Cay areas for the activities you enjoy most.
International Drive District map

International Drive District

1 out of top 10 points of interest in this area

Visitors to International Drive District rave about its breathtaking beach views, exciting theme parks and popular shops. You might also want to make some time to see Aquatica or The Orlando Eye at ICON Park while you're exploring the neighbourhood.

Universal Studios Florida® featuring signage, a city and night scenes
Florida Center map

Florida Center

2 out of top 10 points of interest in this area

If you're spending some time in Florida Center, Universal Orlando Resort and Universal Studios Florida are top sights worth seeing.

Magic Kingdom® Theme Park which includes interior views and rides as well as a couple
Photo by ©Disney
Open Photo by ©Disney
Bay Lake map

Bay Lake

4 out of top 10 points of interest in this area

Exciting theme parks plentiful wildlife and top sights from Epcot® to Walt Disney World® Resort – discover Bay Lake, a destination also famous for its entertainment.

Downtown Orlando map

Downtown Orlando

Ample dining options, great live music, and fantastic lake views are just a few top things to explore in Downtown Orlando. A visit to The Social or Church Street Station might round out your trip, and you can jump aboard the metro at Church Street Station or Lynx Central Station to get around town.

Reunion map

Reunion

The top golf courses and fun-filled water parks are top of the list for many visitors to Reunion. A stop by Reunion Resort Golf Course or Jack Nicklaus Course might round out your trip.

Top Windward Cay Hotel Reviews

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings

10/10 Excellent
"Enjoyed my stay at Home2Suites. The staff was amazing and the hotel was very clean. "
Dellesha K 5-night trip
Posted 9 hours ago
Home2 Suites by Hilton Orlando at Flamingo Crossings

Frequently asked questions

What's it like in Windward Cay?

Travellers to the Windward Cay neighbourhood in Kissimmee will be sure to enjoy their stay.

What's a favourite hotel to stay in Windward Cay?

For your stay in Windward Cay, Windward Cay 4707 is one of the top choices based on our traveller data. Another good option for your stay in the area is Peaceful Windward Cay 3 Bedroom Home by Redawning.

How many hotels will I be able to find in Windward Cay?

Expedia has 28 hotels and other accommodation options in Windward Cay to choose from, making this an ideal home base for exploring the greater Kissimmee area.

If I need to cancel my hotel reservation in Windward Cay, will I receive a refund?

Yes! The majority of hotel reservations are fully refundable if you cancel before the hotel’s cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a non-refundable reservation, it might still be possible to cancel it and receive a refund within a 24-hour period of booking. Put your dates in and click on "Search", then you can filter by "fully refundable" to review the best options available in Windward Cay.

What is there to do around this Kissimmee neighbourhood?

A few places to visit in the area around Windward Cay include Old Town, Medieval Times and Wat Florida Dhammaram. While you're out sightseeing, Kissimmee Go-Karts and Capone's Dinner Show are a couple of additional sights to visit in Kissimmee.