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.

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.

10 Best Hotels in Windward Cay, Orlando for 2026

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

Cassandra

CA $145 total

includes taxes & fees

Oct 25 - Oct 26

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

2. Comfort Suites Maingate East

4.6 km from Windward Cay

Diahiana

CA $115 total

includes taxes & fees

Nov 1 - Nov 2

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

3. Radisson Hotel Orlando Lake Buena Vista South

3 km from Windward Cay

Angela

CA $102 total

includes taxes & fees

Oct 8 - Oct 9

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

CA $62 total

includes taxes & fees

Oct 20 - Oct 21

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.

5. Palazzo Lakeside Hotel

2.7 km from Windward Cay

Joel

CA $92 total

includes taxes & fees

Oct 11 - Oct 12

A modern waiting area with two black chairs, a small table with a plant, and a large window offering a view of trees and buildings.

6. Travelodge by Wyndham Orlando Lake Buena Vista South

3.6 km from Windward Cay

Paola

CA $88 total

includes taxes & fees

Oct 4 - Oct 5

7. The Vietta Hotel

2.6 km from Windward Cay

Norris

CA $97 total

includes taxes & fees

Oct 11 - Oct 12

A spacious lobby with a high ceiling, wooden beams, and a central round table surrounded by chairs. There are potted plants, a reception desk, and a wall with a welcome sign.

8. Hilton Vacation Club Polynesian Isles Kissimmee

3.9 km from Windward Cay

Danielle

CA $168 total

includes taxes & fees

Oct 5 - Oct 6

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

CA $192 total

includes taxes & fees

Nov 1 - Nov 2

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

10. Buena Vista Suites Orlando

5.7 km from Windward Cay

Laura

CA $222 total

includes taxes & fees

Oct 7 - Oct 8

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

11. Meliá Orlando Celebration

6.8 km from Windward Cay

Juanita

CA $164 total

includes taxes & fees

Oct 8 - Oct 9

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

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

11.3 km from Windward Cay

Fernanda

CA $139 total

includes taxes & fees

Oct 5 - Oct 6

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

Odett

CA $98 total

includes taxes & fees

Oct 27 - Oct 28

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

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

7.6 km from Windward Cay

Rosalinda

CA $168 total

includes taxes & fees

Oct 4 - Oct 5

A hotel room with two beds, a desk with a chair, and a wall-mounted artwork.

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

9 km from Windward Cay

Lisa

CA $112 total

includes taxes & fees

Oct 26 - Oct 27

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

CA $162 total

includes taxes & fees

Oct 18 - Oct 19

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

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

9.8 km from Windward Cay

Jessica

CA $137 total

includes taxes & fees

Oct 5 - Oct 6

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

18. Caribe Royale Orlando, WorldHotels Elite

5.7 km from Windward Cay

Brittany

CA $362 total

includes taxes & fees

Oct 3 - Oct 4

A modern kitchen with dark wood cabinets, stainless steel appliances, a tiled backsplash, and a dining area with a bar stool.

19. Staybridge Suites Orlando at SeaWorld by IHG

10.8 km from Windward Cay

Timothy

CA $157 total

includes taxes & fees

Oct 4 - Oct 5

A reception desk area with a neon sign reading "TRYP Orlando" and a modern wooden ceiling.

20. TRYP by Wyndham Orlando

9.9 km from Windward Cay

Regina

CA $142 total

includes taxes & fees

Oct 5 - Oct 6

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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

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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Orlando downtown welcome sign with tropical scene; Shutterstock ID 99801884

Downtown Orlando

Orlando's historic core boasts art galleries, retail, restaurants, and nightclubs, with attractions like Lake Eola Park, Linton E. Allen Memorial Fountain, and performing arts theaters, all accessible via public transportation.

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Top Windward Cay Hotel Reviews

Avanti International Resort

10/10 Excellent

"Spacious room, super clean, staff friendly for sure we will be back!"

Universal's Cabana Bay Beach Resort

8/10 Good

"We really enjoyed the amenities - the pools, waterslide, firepit, games, bowling, dining, all of it! We were disappointed that we had to purchase our own tubes for the lazy river, so we did not get to enjoy that. Seems like the tubes should be complimentary. Our room was clean, but one hallway was dirty and we saw roaches. Overall, we loved our stay!"

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. Radisson Hotel Orlando Lake Buena Vista South

4. Seasons Florida Resort

5. Palazzo Lakeside Hotel

6. Travelodge by Wyndham Orlando Lake Buena Vista South

7. The Vietta Hotel

8. Hilton Vacation Club Polynesian Isles Kissimmee

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

10. Buena Vista Suites Orlando

11. Meliá Orlando Celebration

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

13. Rosen Inn Lake Buena Vista

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

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

16. Rosen Shingle Creek

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

18. Caribe Royale Orlando, WorldHotels Elite

19. Staybridge Suites Orlando at SeaWorld by IHG

20. TRYP by Wyndham Orlando

Where to stay in Windward Cay

Bay Lake

International Drive District

Florida Center

Champions Gate

Downtown Orlando

Top Windward Cay Hotel Reviews

Avanti International Resort

Frequently asked questions

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