A golf course with a large hotel and residential area.

Find hotels in Windward Cay, Orlando from $54

Dates

November 2026

December 2026

Upfront pricing
Our total price for your stay includes taxes and fees
Treat yourself
Save 10% or more on over 100,000 hotels worldwide with Member Prices
Learn about One Key
Be picky
Search almost a million properties worldwide

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

Top Windward Cay Hotel Reviews

A spacious restaurant with high ceilings, hanging pendant lights, and a variety of seating arrangements.

Embassy Suites by Hilton Orlando Lake Buena Vista South

Kissimmee

10/10 Excellent

Chris

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

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

Kissimmee

10/10 Excellent

I don’t want to leave a good review because this place is a hidden gem and I don’t want the secret to get out! We stayed for a week, the main purpose was to go to Disney. From hotel door to Magic Kingdom gate was 15-20 minutes. There is a Target 3 minutes driving distance and the cleanest Waffle House with the nicest staff is across the street. You will need a car to access either of these. The staff for this hotel could not have been nicer. This is a very very basic no frills hotel. If...

Michelle

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

Radisson Hotel Orlando Lake Buena Vista South

Kissimmee

10/10 Excellent

Luis

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

Magic Moment Resort & Kids Club, Dazzler Select by Wyndham

Kissimmee

10/10 Excellent

Randall

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

Palazzo Lakeside Hotel

Kissimmee

10/10 Excellent

Lorraine

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

Kompose Boutique Resort at Theme Parks

Kissimmee

10/10 Excellent

Patrik

Rosen Shingle Creek

Orlando

10/10 Excellent

Narciso

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

Star Island Resort and Club

Kissimmee

10/10 Excellent

Tyronda

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

Buena Vista Suites Orlando

Orlando

10/10 Excellent

Juan

A wooden pier leading to a gazebo by a lake with trees and a clear sky.

Hilton Vacation Club Grand Beach Orlando

Orlando

10/10 Excellent

Our stay was only one night as we were heading down for a week long cruise. We ended up not getting to the resort until 3:00 am as we sat on the interstate behind a bad wreck for hours! I was worried we would not even be able to check in. I was so wrong to worry! The girl at the front desk was so sweet and even offered us an extra hour so we could sleep a little longer. The resort is beautiful! The space is great! Everything was clean! We really enjoyed our short amount of time here and we will...

Amanda

SPOT X Hotel Orlando/Intl Dr by The Red Collection

Orlando

10/10 Excellent

MICHALE

Candlewood Suites Orlando - Lake Buena Vista by IHG

Orlando

10/10 Excellent

Venessa

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

Bharat

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

Rosen Inn Lake Buena Vista

Orlando

10/10 Excellent

Annie

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

Amy Dawn

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

Embassy Suites By Hilton Orlando Sunset Walk

Kissimmee

10/10 Excellent

This property gave me international resort vibes in Florida. It really was an oasis. I had a two bedroom and our party was five, three were children. The entire property is clean. The staff from the front desk to the support staff were polite and professional. Great location, if you only want to drive a couple of minutes for access to restaurants, you're in a perfect location. It's also not too far out from the theme parks. TIP: There is a $40 daily resort fee that will be deducted from your...

Serene

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.

Explore a world of travel with Expedia

Lodging

Find hotels in Windward Cay, Orlando from $54

Upfront pricing

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

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

6. Palazzo Lakeside Hotel

7. Star Island Resort and Club

8. Legacy Vacation Resorts - Kissimmee/Orlando

9. Hilton Vacation Club Polynesian Isles Kissimmee

10. Meliá Orlando Celebration

11. Kompose Boutique Resort at Theme Parks

12. Candlewood Suites Orlando - Lake Buena Vista by IHG

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

14. Rosen Inn Lake Buena Vista

15. Buena Vista Suites Orlando

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

17. Aloft by Marriott Orlando Lake Buena Vista

18. Holiday Inn Resort Orlando Suites - Waterpark by IHG

19. Rosen Shingle Creek

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

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

Embassy Suites by Hilton Orlando Lake Buena Vista South

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?

Explore a world of travel with Expedia