Top Windward Cay Hotels

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

AED 457 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

AED 314 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

Joel

AED 236 total

includes taxes & fees

12 Oct - 13 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

AED 190 total

includes taxes & fees

12 Oct - 13 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

AED 282 total

includes taxes & fees

5 Nov - 6 Nov

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

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

3.2 km from Windward Cay

Mirtha

AED 384 total

includes taxes & fees

20 Oct - 21 Oct

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

7. Star Island Resort and Club

2.4 km from Windward Cay

Shawn

AED 448 total

includes taxes & fees

18 Oct - 19 Oct

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

8. Legacy Vacation Resorts - Kissimmee/Orlando

2.8 km from Windward Cay

Crystal

AED 303 total

includes taxes & fees

19 Oct - 20 Oct

9. The Vietta Hotel

2.6 km from Windward Cay

Fakhar-ud-din

AED 321 total

includes taxes & fees

2 Nov - 3 Nov

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

10. Caribe Royale Orlando, WorldHotels Elite

5.7 km from Windward Cay

Brittany

AED 938 total

includes taxes & fees

16 Oct - 17 Oct

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

11. Buena Vista Suites Orlando

5.7 km from Windward Cay

Jonathan

AED 595 total

includes taxes & fees

25 Oct - 26 Oct

A hotel pool area with lounge chairs and umbrellas, surrounded by tall buildings and a sunset sky.

12. Drury Plaza Hotel Orlando - Disney Springs Area

8.4 km from Windward Cay

Brianne

AED 667 total

includes taxes & fees

28 Oct - 29 Oct

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

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

11.3 km from Windward Cay

Roberto

AED 380 total

includes taxes & fees

19 Oct - 20 Oct

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

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

9.8 km from Windward Cay

Mercedes

AED 368 total

includes taxes & fees

20 Oct - 21 Oct

15. Hyatt Regency Grand Cypress

9.2 km from Windward Cay

Elizabeth

AED 872 total

includes taxes & fees

28 Oct - 29 Oct

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

16. Rosen Shingle Creek

13.4 km from Windward Cay

Maria

AED 448 total

includes taxes & fees

18 Oct - 19 Oct

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

17. Meliá Orlando Celebration

6.8 km from Windward Cay

David

AED 492 total

includes taxes & fees

4 Nov - 5 Nov

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

18. Wyndham Grand Orlando Resort Bonnet Creek

8.1 km from Windward Cay

Anthony

AED 686 total

includes taxes & fees

29 Oct - 30 Oct

A hotel reception desk with HP computers, a digital display, and a sign for the SPOT HOTEL ORLANDO.

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

9 km from Windward Cay

Lisa

AED 309 total

includes taxes & fees

27 Oct - 28 Oct

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

20. Kompose Boutique Resort at Theme Parks

11.5 km from Windward Cay

Nicolas

AED 262 total

includes taxes & fees

12 Oct - 13 Oct

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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

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 Orange County Convention Center or Orange County Convention Center North while you're exploring the neighborhood.

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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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A golf course with bunkers, water hazards, and a large lake.

Reunion

The waterparks and pristine golf courses 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

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

10/10 Excellent

"Very close to parks free breakfast was actually good place was clean and beds were comfortable"

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent

"We picked this hotel because it was right outside Universal Studios. We arrived early and they were able to accommodate us with our room, which included hot cookies and bottled water. The staff was very friendly. The room was clean and stocked with towels every day. We didn't use any amenities, since we were at the park the whole time. It was conveniently located near many restaurants for dinner. Parking was easy, but unfortunately, there was a daily fee. We definitely would stay again."

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent

"Room was clean and fresh. Check in was simple and they got us in early because a room was available. Beautiful pools and pool decks with multiple experiences. Easy property map and lots of parking. The grill restaurant on site was fresh and good tasting menu. Healthy options and American style cuisine options as well as a full bar (it’s pool side). Check out was easy as well, they gave me a 1,000 extra points for being a reward member and an offer to stay for more nights at a cheaper rate with in the next two years of travel (they don’t even take dates if you want to book) very non pressure and friendly staff. Have stayed at their other golf course style resort in Orlando as well. Also, the gate check in is a nice touch and very easy access."

Frequently asked questions

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.

Where can I learn more about changing or cancelling my trip to Windward Cay?

For more information about changing or cancelling your trip to Windward Cay, click here.

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.

Find 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. Palazzo Lakeside Hotel

4. Seasons Florida Resort

5. Radisson Hotel Orlando Lake Buena Vista South

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

7. Star Island Resort and Club

8. Legacy Vacation Resorts - Kissimmee/Orlando

9. The Vietta Hotel

10. Caribe Royale Orlando, WorldHotels Elite

11. Buena Vista Suites Orlando

12. Drury Plaza Hotel Orlando - Disney Springs Area

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

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

15. Hyatt Regency Grand Cypress

16. Rosen Shingle Creek

17. Meliá Orlando Celebration

18. Wyndham Grand Orlando Resort Bonnet Creek

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

20. Kompose Boutique Resort at Theme Parks

Where to stay in Windward Cay

Bay Lake

International Drive District

Florida Center

Champions Gate

Reunion

Top Windward Cay Hotel Reviews

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

Frequently asked questions