What's it like in Windward Cay?

Travelers to the Windward Cay neighborhood in Kissimmee will be sure to enjoy their stay.

How many hotels will I find in Windward Cay?

Expedia has 33 hotels and other accommodations 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, most hotel reservations are refundable provided that you cancel before the hotel’s cancellation deadline, which in most cases is within 24 or 48 hours of your check-in date. If you booked a non-refundable reservation, you might be able to still cancel and be given a refund within a 24-hour period of booking. Plug in your dates, click on "Search", then use the "fully refundable" filter to get the best deals available in Windward Cay.

What is there to do around this Kissimmee neighborhood?

A few places to visit in the area around Windward Cay include Old Town, Medieval Times, and Kissimmee Go-Karts. While you're out sightseeing, Pioneer Village at Shingle Creek and 192 Flea Market are a couple of additional sights to visit in Kissimmee.

10 Best Hotels in Windward Cay, Orlando for 2026

A golf course with a large hotel and residential area.

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Our top choices for Windward Cay hotels

A spacious restaurant with high ceilings, hanging pendant lights, and a variety of seating arrangements.

1. Embassy Suites by Hilton Orlando Lake Buena Vista South

3 km from Windward Cay

Cassandra

CA $145 total

includes taxes & fees

Oct 18 - Oct 19

A hotel with a central entrance, palm trees, and a clear sky.

2. Comfort Suites Maingate East

4.6 km from Windward Cay

Diahiana

CA $115 total

includes taxes & fees

Nov 1 - Nov 2

A swimming pool with a blue slide, surrounded by palm trees and a fenced area.

3. Radisson Hotel Orlando Lake Buena Vista South

3 km from Windward Cay

Angela

CA $102 total

includes taxes & fees

Oct 12 - Oct 13

A modern hotel lobby with a reception desk, a round coffee table, a sofa, and a large window with curtains.

4. Seasons Florida Resort

1.6 km from Windward Cay

Antonio

CA $74 total

includes taxes & fees

Oct 12 - Oct 13

A hotel room with a large bed, a smaller bed, a desk, and a chair. There is a decorative item on the bed and a rug on the floor.

5. Palazzo Lakeside Hotel

2.7 km from Windward Cay

Joel

CA $91 total

includes taxes & fees

Oct 11 - Oct 12

A modern waiting area with two black chairs, a small table with a plant, and a large window offering a view of trees and buildings.

6. Travelodge by Wyndham Orlando Lake Buena Vista South

3.6 km from Windward Cay

Paola

CA $90 total

includes taxes & fees

Oct 7 - Oct 8

7. The Vietta Hotel

2.6 km from Windward Cay

Norris

CA $98 total

includes taxes & fees

Oct 11 - Oct 12

A spacious lobby with a large chandelier, a reception desk, and a view of the outside through large windows.

8. Star Island Resort and Club

2.4 km from Windward Cay

Shawn

CA $161 total

includes taxes & fees

Oct 29 - Oct 30

A modern living room with a large flat-screen TV, a white sofa, and a coffee table.

9. Magic Moment Resort & Kids Club, Dazzler Select by Wyndham

3.2 km from Windward Cay

Mirtha

CA $193 total

includes taxes & fees

Oct 7 - Oct 8

A swimming pool with people in the water, including a person in a green and red inflatable ring.

10. Buena Vista Suites Orlando

5.7 km from Windward Cay

Jana

CA $223 total

includes taxes & fees

Oct 7 - Oct 8

An aerial view of a resort with multiple swimming pools, landscaped gardens, and outdoor seating areas.

11. Rosen Shingle Creek

13.4 km from Windward Cay

Maria

CA $162 total

includes taxes & fees

Oct 17 - Oct 18

An aerial view of a curved swimming pool with lounge chairs and umbrellas around it.

12. Meliá Orlando Celebration

6.8 km from Windward Cay

David

CA $162 total

includes taxes & fees

Oct 19 - Oct 20

A multi-story hotel with a swimming pool, balconies, and outdoor seating areas.

13. Rosen Inn Lake Buena Vista

8.9 km from Windward Cay

Odett

CA $98 total

includes taxes & fees

Oct 26 - Oct 27

A multi-story hotel with a swimming pool, parking, and a landscaped area.

14. Holiday Inn Express & Suites Orlando - Lake Buena Vista by IHG

9.5 km from Windward Cay

Abi Carolina Fornino

CA $127 total

includes taxes & fees

Oct 6 - Oct 7

A hotel with a large pool, palm trees, and a waterfall feature.

15. Caribe Royale Orlando, WorldHotels Elite

5.7 km from Windward Cay

Brittany

CA $364 total

includes taxes & fees

Oct 10 - Oct 11

A water park with multiple slides and water features, surrounded by a multi-story building with balconies.

16. Holiday Inn Resort Orlando Suites - Waterpark by IHG

6.4 km from Windward Cay

Maylier

CA $202 total

includes taxes & fees

Oct 6 - Oct 7

A reception desk with a digital screen, a headset, and a sign for 'SPOT HOTEL ORLANDO THE COLLECTION'.

17. SPOT X Hotel Orlando/Intl Dr by The Red Collection

9 km from Windward Cay

Lisa

CA $118 total

includes taxes & fees

Oct 26 - Oct 27

A spacious lobby with a grand chandelier, modern seating, and a view of the outdoor area.

18. Kompose Boutique Resort at Theme Parks

11.5 km from Windward Cay

Nicolas

CA $122 total

includes taxes & fees

Oct 6 - Oct 7

A large hotel complex with multiple high-rise buildings, a central swimming pool, and surrounding greenery.

19. Vacation Village Orlando, Celebration

6.5 km from Windward Cay

Wilbert

CA $144 total

includes taxes & fees

Oct 25 - Oct 26

An aerial view of a resort with a large swimming pool surrounded by palm trees and lounge chairs.

20. Wyndham Grand Orlando Resort Bonnet Creek

8.1 km from Windward Cay

Carlos

CA $266 total

includes taxes & fees

Oct 29 - Oct 30

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Where to stay in Windward Cay

Find the best Windward Cay areas and neighborhoods for the activities you enjoy most.

The entrance to the Hollywood Studios area with a large sign and distinctive architecture.

Bay Lake

Home to all four Walt Disney World Resort theme parks and one water park, this city offers endless entertainment, including Disney's Fort Wilderness Resort & Campground and Magnolia and Palm Golf Courses.

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A large Ferris wheel with blue lights, surrounded by a cityscape with illuminated buildings and a tall green tower.

International Drive District

Adventure activities, iconic attractions, shopping and world-class dining destinations make this famous street one of Orlando’s most popular tourist attractions.

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A roller coaster at Universal Orlando Resort, featuring a tall palm tree and a clear blue sky.

Florida Center

While visiting Florida Center, you might make a stop by sights like Universal Orlando Resort and Universal Studios Florida.

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A large Ferris wheel with blue lighting, surrounded by a parking lot and buildings.

Champions Gate

Abundant dining options and pristine golf courses are well-reviewed features of Champions Gate. Make a stop by top sights like ChampionsGate Golf Club while you're exploring the area.

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Orlando downtown welcome sign with tropical scene; Shutterstock ID 99801884

Downtown Orlando

Orlando's historic core boasts art galleries, retail, restaurants, and nightclubs, with attractions like Lake Eola Park, Linton E. Allen Memorial Fountain, and performing arts theaters, all accessible via public transportation.

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Top Windward Cay Hotel Reviews

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent

"Very clean and easy to get around"

Rosen Inn Lake Buena Vista

10/10 Excellent

"Didn’t use the amenities as we only stayed for the weekend and we were out at the parks most of the time. We checked in late evening and when we got to the room the bathroom was missing the shower curtain but we were tired and decided to call next day and they brought in a new one. Other than that, the room shows its age but it was spacious, we liked that they had a desk with a mirror to get ready and the sink was separate from the shower so as a big family we could all get ready faster. Very much enjoyed our stay and felt safe while staying there. Also very close to all major attractions."

Hotels in Windward Cay, Orlando

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Our top choices for Windward Cay hotels

1. Embassy Suites by Hilton Orlando Lake Buena Vista South

2. Comfort Suites Maingate East

3. Radisson Hotel Orlando Lake Buena Vista South

4. Seasons Florida Resort

5. Palazzo Lakeside Hotel

6. Travelodge by Wyndham Orlando Lake Buena Vista South

7. The Vietta Hotel

8. Star Island Resort and Club

9. Magic Moment Resort & Kids Club, Dazzler Select by Wyndham

10. Buena Vista Suites Orlando

11. Rosen Shingle Creek

12. Meliá Orlando Celebration

13. Rosen Inn Lake Buena Vista

14. Holiday Inn Express & Suites Orlando - Lake Buena Vista by IHG

15. Caribe Royale Orlando, WorldHotels Elite

16. Holiday Inn Resort Orlando Suites - Waterpark by IHG

17. SPOT X Hotel Orlando/Intl Dr by The Red Collection

18. Kompose Boutique Resort at Theme Parks

19. Vacation Village Orlando, Celebration

20. Wyndham Grand Orlando Resort Bonnet Creek

Where to stay in Windward Cay

Bay Lake

International Drive District

Florida Center

Champions Gate

Downtown Orlando

Top Windward Cay Hotel Reviews

Westgate Lakes Resort & Spa Universal Studios Area

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