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

Rp2.227.579 total

includes taxes & fees

18 Oct - 19 Oct

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.

2. Palazzo Lakeside Hotel

2.7 km from Windward Cay

Darius

Rp1.172.990 total

includes taxes & fees

13 Oct - 14 Oct

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

3. Comfort Suites Maingate East

4.6 km from Windward Cay

Diahiana

Rp1.527.716 total

includes taxes & fees

2 Nov - 3 Nov

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

4. Star Island Resort and Club

2.4 km from Windward Cay

Shawn

Rp2.184.235 total

includes taxes & fees

18 Oct - 19 Oct

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

5. Seasons Florida Resort

1.6 km from Windward Cay

Antonio

Rp926.992 total

includes taxes & fees

12 Oct - 13 Oct

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

6. Radisson Hotel Orlando Lake Buena Vista South

3 km from Windward Cay

JORGE

Rp1.373.317 total

includes taxes & fees

5 Nov - 6 Nov

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

7. Drury Plaza Hotel Orlando - Disney Springs Area

8.4 km from Windward Cay

Brianne

Rp3.251.823 total

includes taxes & fees

28 Oct - 29 Oct

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

8. Caribe Royale Orlando, WorldHotels Elite

5.7 km from Windward Cay

Brittany

Rp4.571.047 total

includes taxes & fees

16 Oct - 17 Oct

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

Rp1.869.730 total

includes taxes & fees

20 Oct - 21 Oct

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

10. Legacy Vacation Resorts - Kissimmee/Orlando

2.8 km from Windward Cay

Crystal

Rp1.475.773 total

includes taxes & fees

19 Oct - 20 Oct

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

11. Wyndham Grand Orlando Resort Bonnet Creek

8.1 km from Windward Cay

Anthony

Rp3.342.639 total

includes taxes & fees

29 Oct - 30 Oct

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

12. Buena Vista Suites Orlando

5.7 km from Windward Cay

Jonathan

Rp2.898.317 total

includes taxes & fees

25 Oct - 26 Oct

13. The Vietta Hotel

2.6 km from Windward Cay

Fakhar-ud-din

Rp1.561.846 total

includes taxes & fees

2 Nov - 3 Nov

14. Hyatt Regency Grand Cypress

9.2 km from Windward Cay

Elizabeth

Rp4.248.776 total

includes taxes & fees

28 Oct - 29 Oct

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

15. Kompose Boutique Resort at Theme Parks

11.5 km from Windward Cay

Nicolas

Rp1.320.296 total

includes taxes & fees

12 Oct - 13 Oct

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

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

16.4 km from Windward Cay

Lauren

Rp1.523.316 total

includes taxes & fees

27 Oct - 28 Oct

A hotel room with a bed, a desk, a chair, a sofa, and a TV.

17. Pestana Orlando Suites - Lake Buena Vista

9.6 km from Windward Cay

Tracy

Rp1.924.143 total

includes taxes & fees

28 Oct - 29 Oct

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

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

7.6 km from Windward Cay

Rosalinda

Rp2.013.638 total

includes taxes & fees

14 Oct - 15 Oct

A large hotel with multiple floors, a central courtyard, and a reflective water feature.

19. Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

16.3 km from Windward Cay

Camille

Rp1.660.245 total

includes taxes & fees

28 Oct - 29 Oct

A pool with a waterfall feature, lounge areas, and a building with a green roof in the background.

20. Hilton Vacation Club Mystic Dunes Orlando

11.6 km from Windward Cay

Juan

Rp2.364.710 total

includes taxes & fees

18 Oct - 19 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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent

"Loved the space inside. Disappointed the ceiling fan in screened in porch didn’t work. Staff all friendly. Close drive to attractions Loved back door with outside access right to pool."

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?

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. Palazzo Lakeside Hotel

3. Comfort Suites Maingate East

4. Star Island Resort and Club

5. Seasons Florida Resort

6. Radisson Hotel Orlando Lake Buena Vista South

7. Drury Plaza Hotel Orlando - Disney Springs Area

8. Caribe Royale Orlando, WorldHotels Elite

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

10. Legacy Vacation Resorts - Kissimmee/Orlando

11. Wyndham Grand Orlando Resort Bonnet Creek

12. Buena Vista Suites Orlando

13. The Vietta Hotel

14. Hyatt Regency Grand Cypress

15. Kompose Boutique Resort at Theme Parks

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

17. Pestana Orlando Suites - Lake Buena Vista

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

19. Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

20. Hilton Vacation Club Mystic Dunes Orlando

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

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