10 Best Hotels in Windward Cay, Orlando for 2026

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Our top choices for Windward Cay hotels

A spacious lobby with a reception desk, seating area, and a decorative flower arrangement.

1. Embassy Suites by Hilton Orlando Lake Buena Vista South

3 km from Windward Cay

Peterjohn

CA $171 total

includes taxes & fees

Nov 15 - Nov 16

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

2. Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort

1.6 km from Windward Cay

Viridiana

CA $78 total

includes taxes & fees

Nov 10 - Nov 11

A kitchen with wooden cabinets, a microwave, a refrigerator, and two bar stools.

3. Club Sevilla

0.7 km from Windward Cay

Eric

CA $89 total

includes taxes & fees

Nov 17 - Nov 18

A hotel pool area with a water slide, palm trees, and a bridge.

4. Radisson Hotel Orlando Lake Buena Vista South

3 km from Windward Cay

Wilfredo

CA $101 total

includes taxes & fees

Nov 19 - Nov 20

A modern interior with a white spiral staircase, a large Christmas tree, and a dining area with white furniture.

5. Palazzo Lakeside Hotel

2.7 km from Windward Cay

Juan

CA $82 total

includes taxes & fees

Dec 9 - Dec 10

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

Alfredo I

CA $84 total

includes taxes & fees

Nov 18 - Nov 19

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

Michelle

CA $156 total

includes taxes & fees

Dec 9 - Dec 10

A spacious lobby with a high ceiling, two exits, and comfortable seating areas with tables and chairs.

8. Hilton Vacation Club Polynesian Isles Kissimmee

3.9 km from Windward Cay

Steven

CA $162 total

includes taxes & fees

Nov 22 - Nov 23

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

9. Legacy Vacation Resorts - Kissimmee/Orlando

2.8 km from Windward Cay

Ionela

CA $107 total

includes taxes & fees

Dec 1 - Dec 2

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

10. Meliá Orlando Celebration

6.8 km from Windward Cay

Yong Pin

CA $146 total

includes taxes & fees

Nov 25 - Nov 26

A hotel room with two beds, a desk with a chair, a television, and large abstract paintings on the wall.

11. Buena Vista Suites Orlando

5.7 km from Windward Cay

Karen

CA $215 total

includes taxes & fees

Nov 29 - Nov 30

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

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

9 km from Windward Cay

Michelle Elis Onofre

CA $97 total

includes taxes & fees

Nov 30 - Dec 1

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

Yotuel

CA $99 total

includes taxes & fees

Nov 16 - Nov 17

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

Lilian

CA $134 total

includes taxes & fees

Nov 24 - Nov 25

A modern indoor patio with a fire pit table, seating, a bar area, and large windows.

15. SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista

9.5 km from Windward Cay

Holly

CA $126 total

includes taxes & fees

Nov 29 - Nov 30

16. Candlewood Suites Orlando - Lake Buena Vista by IHG

9.3 km from Windward Cay

Miguel

CA $113 total

includes taxes & fees

Nov 12 - Nov 13

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

17. Kompose Boutique Resort at Theme Parks

11.5 km from Windward Cay

Theresa

CA $102 total

includes taxes & fees

Nov 17 - Nov 18

A modern lobby with a neon sign, a large flat-screen TV, and a seating area with a sofa and chairs.

18. Aloft by Marriott Orlando Lake Buena Vista

9.5 km from Windward Cay

Carmine

CA $130 total

includes taxes & fees

Nov 12 - Nov 13

19. Rosen Shingle Creek

13.4 km from Windward Cay

Dominic

CA $176 total

includes taxes & fees

Nov 24 - Nov 25

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

20. Holiday Inn Resort Orlando Suites - Waterpark by IHG

6.4 km from Windward Cay

Nikisha

CA $221 total

includes taxes & fees

Nov 15 - Nov 16

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Compare popular hotels in Windward Cay

Property	Star rating	Guest rating
Embassy Suites by Hilton Orlando Lake Buena Vista South	4.0 star property	9.6 Exceptional 1,688 reviews	View
Drury Plaza Hotel Orlando - Disney Springs Area	4.0 star property	9.8 Exceptional 6,245 reviews	View
Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort	2.0 star property	9.0 Wonderful 4,108 reviews	View
Radisson Hotel Orlando Lake Buena Vista South	3.5 star property	8.8 Excellent 3,757 reviews	View
Hilton Vacation Club Polynesian Isles Kissimmee	3.0 star property	9.6 Exceptional 1,919 reviews	View

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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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

Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort

Kissimmee

10/10 Excellent

Noel

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

Comfort Suites Maingate East

Kissimmee

10/10 Excellent

Maria

Hilton Vacation Club Polynesian Isles Kissimmee

Kissimmee

10/10 Excellent

Ronald

Meliá Orlando Celebration

Celebration

10/10 Excellent

CHANTAL

Buena Vista Suites Orlando

Orlando

10/10 Excellent

Christine

SPOT X Hotel Orlando/Intl Dr by The Red Collection

Orlando

10/10 Excellent

Sarah

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

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

Bay Lake

10/10 Excellent

mercy

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

Drury Plaza Hotel Orlando - Disney Springs Area

Lake Buena Vista

10/10 Excellent

Jason N

A resort with multiple swimming pools, a large central pool, and a lake.

Embassy Suites By Hilton Orlando Sunset Walk

Kissimmee

10/10 Excellent

We recently stayed at The Embassy Suites on Sunset Walk and had a fantastic experience. The hotel offers great amenities, including a fitness center, free daily breakfast, and complimentary Wi-Fi. The rooms are spacious and feel luxurious, with modern furnishings and pretty views. Located close to restaurants on Sunset Walk, a water park, and shopping - it's perfect for walking around and exploring the area. The pool area is beautiful, ideal for relaxing, and the hotel staff are incredibly...

Dzenita

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.

Hotels in Windward Cay, Orlando from CA $29

Change your mind

Treat yourself

Be picky

Check prices for these dates

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Property class

Guest rating

Our top choices for Windward Cay hotels

1. Embassy Suites by Hilton Orlando Lake Buena Vista South

2. Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort

3. Club Sevilla

4. Radisson Hotel Orlando Lake Buena Vista South

5. Palazzo Lakeside Hotel

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

7. Star Island Resort and Club

8. Hilton Vacation Club Polynesian Isles Kissimmee

9. Legacy Vacation Resorts - Kissimmee/Orlando

10. Meliá Orlando Celebration

11. Buena Vista Suites Orlando

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

13. Rosen Inn Lake Buena Vista

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

15. SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista

16. Candlewood Suites Orlando - Lake Buena Vista by IHG

17. Kompose Boutique Resort at Theme Parks

18. Aloft by Marriott Orlando Lake Buena Vista

19. Rosen Shingle Creek

20. Holiday Inn Resort Orlando Suites - Waterpark by IHG

Compare popular hotels in Windward Cay

Where to stay in Windward Cay

Bay Lake

International Drive District

Florida Center

Champions Gate

Reunion

Top Windward Cay Hotel Reviews

Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort

10/10 Excellent

Frequently Asked Questions

What's it like in Windward Cay?

How many hotels will I find in Windward Cay?

If I need to cancel my hotel reservation in Windward Cay, will I receive a refund?

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

What is there to do around this Kissimmee neighborhood?

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