The Best Hotels in Windward Cay, Orlando - 2026 Updated Prices

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

Nguyen

฿4,173 total

includes taxes & fees

18 Oct - 19 Oct

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

2. Comfort Suites Maingate East

4.6 km from Windward Cay

Diahiana

฿2,871 total

includes taxes & fees

2 Nov - 3 Nov

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.

3. Palazzo Lakeside Hotel

2.7 km from Windward Cay

Darius

฿2,203 total

includes taxes & fees

11 Oct - 12 Oct

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

฿1,722 total

includes taxes & fees

11 Oct - 12 Oct

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

5. Radisson Hotel Orlando Lake Buena Vista South

3 km from Windward Cay

JORGE

฿2,573 total

includes taxes & fees

5 Nov - 6 Nov

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

6. Star Island Resort and Club

2.4 km from Windward Cay

Shawn

฿4,092 total

includes taxes & fees

24 Oct - 25 Oct

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

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

3.2 km from Windward Cay

Mirtha

฿3,514 total

includes taxes & fees

20 Oct - 21 Oct

A reception desk with two monitors, a printer, and a keyboard.

8. Drury Plaza Hotel Orlando - Disney Springs Area

8.4 km from Windward Cay

Brianne

฿6,092 total

includes taxes & fees

8 Nov - 9 Nov

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

9. Buena Vista Suites Orlando

5.7 km from Windward Cay

Jonathan

฿5,447 total

includes taxes & fees

25 Oct - 26 Oct

10. The Vietta Hotel

2.6 km from Windward Cay

Fakhar-ud-din

฿2,413 total

includes taxes & fees

11 Oct - 12 Oct

A swimming pool with a covered seating area and palm trees in the background.

11. Legacy Vacation Resorts - Kissimmee/Orlando

2.8 km from Windward Cay

Crystal

฿2,774 total

includes taxes & fees

19 Oct - 20 Oct

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

12. Caribe Royale Orlando, WorldHotels Elite

5.7 km from Windward Cay

Brittany

฿8,563 total

includes taxes & fees

30 Oct - 31 Oct

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

13. Wyndham Grand Orlando Resort Bonnet Creek

8.1 km from Windward Cay

Anthony

฿6,262 total

includes taxes & fees

29 Oct - 30 Oct

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

14. Holiday Inn Express & Suites Orlando at SeaWorld by IHG

11.3 km from Windward Cay

Roberto

฿3,584 total

includes taxes & fees

18 Oct - 19 Oct

15. Hyatt Regency Grand Cypress

9.2 km from Windward Cay

Elizabeth

฿7,959 total

includes taxes & fees

28 Oct - 29 Oct

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

16. Kompose Boutique Resort at Theme Parks

11.5 km from Windward Cay

Nicolas

฿2,481 total

includes taxes & fees

12 Oct - 13 Oct

A modern hotel with "La Quinta" signage, featuring a prominent entrance and a covered outdoor area.

17. La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks

9.8 km from Windward Cay

Mercedes

฿3,372 total

includes taxes & fees

20 Oct - 21 Oct

A breakfast bar with various food dispensers, a seating area with a table and chairs, and large windows with a view of greenery.

18. Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

16.4 km from Windward Cay

Lauren

฿2,854 total

includes taxes & fees

29 Oct - 30 Oct

An arcade with various gaming machines, including racing and motorcycle games.

19. Holiday Inn Resort Orlando - Lake Buena Vista by IHG

7.6 km from Windward Cay

Rosalinda

฿3,785 total

includes taxes & fees

13 Oct - 14 Oct

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

20. Rosen Inn Lake Buena Vista

8.9 km from Windward Cay

Odett

฿2,725 total

includes taxes & fees

26 Oct - 27 Oct

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Where to stay in Windward Cay

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

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

Bay Lake

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.

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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

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

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

Champions Gate

Ample dining options and top 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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A golf course with bunkers, water hazards, and a large lake.

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.

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Top Windward Cay Hotel Reviews

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent

"Room was very clean. Front desk staff were great! Will definitely return!"

The Grove Resort & Water Park Orlando

10/10 Excellent

"I had a wonderful stay! The room was incredibly clean and comfortable, making it easy to relax. The staff was friendly and always ready to help with anything I needed. The pool area was fantastic, and the whole place felt very family-friendly. I would definitely recommend this spot to other travelers!"

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent

"A wonderful property. The amenities were fantastic. Daily buffet breakfast and evening diner included was a pleasant surprise. Evening beverages as well. Salt water pool and hot tub were nice, but the shuttle buses to and from the parks were a great savings on gas and parking fees. No resort fees as well make the property a must stay and full value for families!"

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.

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

Expedia has 33 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 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.

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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. Palazzo Lakeside Hotel

4. Seasons Florida Resort

5. Radisson Hotel Orlando Lake Buena Vista South

6. Star Island Resort and Club

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

8. Drury Plaza Hotel Orlando - Disney Springs Area

9. Buena Vista Suites Orlando

10. The Vietta Hotel

11. Legacy Vacation Resorts - Kissimmee/Orlando

12. Caribe Royale Orlando, WorldHotels Elite

13. Wyndham Grand Orlando Resort Bonnet Creek

14. Holiday Inn Express & Suites Orlando at SeaWorld by IHG

15. Hyatt Regency Grand Cypress

16. Kompose Boutique Resort at Theme Parks

17. La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks

18. Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

19. Holiday Inn Resort Orlando - Lake Buena Vista by IHG

20. Rosen Inn Lake Buena Vista

Where to stay in Windward Cay

Bay Lake

International Drive District

Florida Center

Champions Gate

Reunion

Top Windward Cay Hotel Reviews

DoubleTree by Hilton at the Entrance to Universal Orlando

Frequently asked questions

Explore a world of travel with Expedia