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

1. Seasons Florida Resort

1.6 km from Windward Cay

Stephen

AED 210 total

includes taxes & fees

18 Oct - 19 Oct

2. The Vietta Hotel

2.6 km from Windward Cay

Fakhar-ud-din

AED 252 total

includes taxes & fees

11 Oct - 12 Oct

In-room safe, laptop workspace, blackout drapes, iron/ironing board

3. Palazzo Lakeside Hotel

2.7 km from Windward Cay

Arcenio

AED 248 total

includes taxes & fees

20 Sep - 21 Sep

4. Embassy Suites by Hilton Orlando Lake Buena Vista South

3 km from Windward Cay

Luis

AED 375 total

includes taxes & fees

4 Oct - 5 Oct

5. Radisson Hotel Orlando Lake Buena Vista South

3 km from Windward Cay

Dustin

AED 263 total

includes taxes & fees

24 Sep - 25 Sep

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

3.2 km from Windward Cay

Teresa

AED 263 total

includes taxes & fees

30 Sep - 1 Oct

7. Travelodge by Wyndham Orlando Lake Buena Vista South

3.6 km from Windward Cay

Isandall

AED 222 total

includes taxes & fees

30 Sep - 1 Oct

8. Hilton Vacation Club Polynesian Isles Kissimmee

3.9 km from Windward Cay

MAHADEVAN

AED 470 total

includes taxes & fees

27 Sep - 28 Sep

Outdoor pool, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers

9. Buena Vista Suites Orlando

5.7 km from Windward Cay

gloria

AED 577 total

includes taxes & fees

27 Sep - 28 Sep

10. Caribe Royale Orlando, WorldHotels Elite

5.7 km from Windward Cay

Carnesha

AED 938 total

includes taxes & fees

18 Sep - 19 Sep

11. Vacation Village Orlando, Celebration

6.5 km from Windward Cay

Monica

AED 374 total

includes taxes & fees

20 Sep - 21 Sep

Outdoor pool, open 7:00 AM to 11:00 PM, cabanas (surcharge)

12. Meliá Orlando Celebration

6.8 km from Windward Cay

Juanita

AED 456 total

includes taxes & fees

27 Sep - 28 Sep

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

7.6 km from Windward Cay

juan

AED 417 total

includes taxes & fees

20 Sep - 21 Sep

14. Wyndham Grand Orlando Resort Bonnet Creek

8.1 km from Windward Cay

Kimberly

AED 719 total

includes taxes & fees

23 Sep - 24 Sep

15. Wyndham Garden Lake Buena Vista – Disney Springs® Area

8.2 km from Windward Cay

Pavel

AED 516 total

includes taxes & fees

20 Sep - 21 Sep

16. Drury Plaza Hotel Orlando - Disney Springs Area

8.4 km from Windward Cay

Keller

AED 579 total

includes taxes & fees

21 Sep - 22 Sep

17. Rosen Inn Lake Buena Vista

8.9 km from Windward Cay

Lisa

AED 270 total

includes taxes & fees

1 Oct - 2 Oct

18. Hilton Vacation Club Grand Beach Orlando

6.3 km from Windward Cay

Karla

AED 483 total

includes taxes & fees

20 Sep - 21 Sep

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

9 km from Windward Cay

Travis

AED 282 total

includes taxes & fees

21 Sep - 22 Sep

3 outdoor pools, open 7 AM to 10:00 PM, cabanas (surcharge)

20. Hyatt Regency Grand Cypress

9.2 km from Windward Cay

Stephanie Sarai

AED 864 total

includes taxes & fees

25 Sep - 26 Sep

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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 a blue light, surrounded by a water fountain display and palm trees.

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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent

"We had a one bedroom with kitchen, the room also had a jacuzzi. Our flight was delayed so didn’t get to utilise the apartment but were very happy the few hours we spent there and would recommend"

Universal's Cabana Bay Beach Resort

8/10 Good

"We had a great time. The shuttle to and from the parks was perfect for us. The resort needs some upgrades. Like paint and new carpets. I own a cleaning service and for the most part it was clean but didn’t smell clean and fresh like a resort should. I would probably stay again just for the convenience of restaurants, Starbucks, lazy river and the pools."

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

10/10 Excellent

"This hotel is the best around the Flamingo Crossing area. The fact that there are restaurants and a Target across the street is a plus. The hotel staff is extremely friendly and accommodating, they try to get you everything you need and help you with anything. The breakfast is great and they even have gluten free Mickey waffles. There’s a good size pool in the hotel and also a nice parking area next to the hotel. The rooms are very spacious and clean. Housekeeping comes every other day unlike some other hotels that are every 4-5 days. This is the second time I stayed with my sister at the property and we will continue to come to this hotel every time we come to Disney or universal. This is a must stay hotel"

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. Seasons Florida Resort

2. The Vietta Hotel

3. Palazzo Lakeside Hotel

4. Embassy Suites by Hilton Orlando Lake Buena Vista South

5. Radisson Hotel Orlando Lake Buena Vista South

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

7. Travelodge by Wyndham Orlando Lake Buena Vista South

8. Hilton Vacation Club Polynesian Isles Kissimmee

9. Buena Vista Suites Orlando

10. Caribe Royale Orlando, WorldHotels Elite

11. Vacation Village Orlando, Celebration

12. Meliá Orlando Celebration

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

14. Wyndham Grand Orlando Resort Bonnet Creek

15. Wyndham Garden Lake Buena Vista – Disney Springs® Area

16. Drury Plaza Hotel Orlando - Disney Springs Area

17. Rosen Inn Lake Buena Vista

18. Hilton Vacation Club Grand Beach Orlando

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

20. Hyatt Regency Grand Cypress

Where to stay in Windward Cay

Bay Lake

International Drive District

Florida Center

Champions Gate

Reunion

Top Windward Cay Hotel Reviews

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Frequently asked questions