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.

Windward Cay hotels, Orlando, United States of America: Orlando Hotel Guide

A golf course with a large hotel and residential area.

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Our top choices for Windward Cay hotels

A pool area with lounge chairs and palm trees, surrounded by a building with a tiled roof.

1. Club Sevilla

0.7 km from Windward Cay

Emilie

includes taxes & fees

15 Nov - 16 Nov

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

includes taxes & fees

16 Nov - 17 Nov

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

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

3.2 km from Windward Cay

Alfredo I

includes taxes & fees

15 Nov - 16 Nov

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

Sandra

includes taxes & fees

29 Nov - 30 Nov

A spacious lobby with a leather sofa, a bar area with stools, and a seating area with tables and chairs.

5. Embassy Suites by Hilton Orlando Lake Buena Vista South

3 km from Windward Cay

Peterjohn

includes taxes & fees

24 Nov - 25 Nov

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

6. Palazzo Lakeside Hotel

2.7 km from Windward Cay

Ilse

includes taxes & fees

29 Nov - 30 Nov

An indoor swimming pool with clear glass walls, a hot tub, and a patio area with lounge chairs.

7. Legacy Vacation Resorts - Kissimmee/Orlando

2.8 km from Windward Cay

Ionela

includes taxes & fees

15 Dec - 16 Dec

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

8. Star Island Resort and Club

2.4 km from Windward Cay

Michelle

includes taxes & fees

30 Nov - 1 Dec

A hotel with a pool area, lounge chairs, and a restaurant.

9. Meliá Orlando Celebration

6.8 km from Windward Cay

Yong Pin

includes taxes & fees

30 Nov - 1 Dec

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.

10. Hilton Vacation Club Polynesian Isles Kissimmee

3.9 km from Windward Cay

Steven

includes taxes & fees

15 Dec - 16 Dec

A resort pool area with a winding pool design, lounge chairs, and palm trees.

11. Kompose Boutique Resort at Theme Parks

11.5 km from Windward Cay

ivan

includes taxes & fees

17 Nov - 18 Nov

A spacious lobby with a pool table, comfortable seating areas, and a reception desk.

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

9 km from Windward Cay

Daryl

includes taxes & fees

30 Nov - 1 Dec

A large indoor swimming pool surrounded by lounge chairs and umbrellas, with a hotel building in the background.

13. Rosen Shingle Creek

13.4 km from Windward Cay

Dominic

includes taxes & fees

24 Nov - 25 Nov

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

14. Rosen Inn Lake Buena Vista

8.9 km from Windward Cay

Clayton

includes taxes & fees

7 Dec - 8 Dec

A hotel entrance with a pool, palm trees, and a fountain.

15. Ramada by Wyndham Kissimmee Gateway

11.4 km from Windward Cay

Shantall

includes taxes & fees

12 Dec - 13 Dec

A hotel sign with "BUENA VISTA SUITES" and a building with multiple floors and windows.

16. Buena Vista Suites Orlando

5.7 km from Windward Cay

Karen

includes taxes & fees

16 Nov - 17 Nov

A hotel with a central swimming pool surrounded by lounge chairs and palm trees, overlooking a body of water.

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

7.6 km from Windward Cay

Jesus

includes taxes & fees

22 Nov - 23 Nov

A hotel with multiple swimming pools, a landscaped garden, and a large building with balconies.

18. Vacation Village Orlando, Celebration

6.5 km from Windward Cay

Jonatan

includes taxes & fees

17 Nov - 18 Nov

A hotel pool area with lounge chairs, a water fountain, and a building with multiple floors and windows.

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

9.5 km from Windward Cay

Holly

includes taxes & fees

29 Nov - 30 Nov

A hammock on a sandy beach with a wooden structure and a wooden deck over water.

20. Hilton Vacation Club Grand Beach Orlando

6.3 km from Windward Cay

Angel

includes taxes & fees

13 Dec - 14 Dec

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Compare popular hotels in Windward Cay

Property	Property class	Guest rating
Club Sevilla	3.5 star property	9.0 Wonderful 1,003 reviews	View
Embassy Suites by Hilton Orlando Lake Buena Vista South	4.0 star property	9.6 Exceptional 1,698 reviews	View
Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort	2.0 star property	9.0 Wonderful 4,119 reviews	View
Magic Moment Resort & Kids Club, Dazzler Select by Wyndham	3.0 star property	8.6 Excellent 3,231 reviews	View
Radisson Hotel Orlando Lake Buena Vista South	3.5 star property	8.8 Excellent 3,733 reviews	View

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

Universal's Endless Summer Resort - Dockside Inn and Suites

10/10 Excellent

"Second time we stayed in this hotel. Still great experience, will definitely come back again."

The Grove Resort & Water Park Orlando

10/10 Excellent

"Came to Orlando for family vacation and this is our 2nd time to book here at The Grove. My expectation still the same… Wonderful stay from start to finish! The room was spotless, the bed was super comfortable, and the staffs were very friendly and accommodating."

Fairfield Inn & Suites Lake Buena Vista in Marriott Village

10/10 Excellent

"The staff were amazing. Ismael at the front desk was training, but was doing a wonderful job. All other front desk staff were also very helpful and very friendly. I truly appreciated that. Breakfast was good, although my partner wanted the diced potatoes every day and they switched out certain items each day."

Evermore Orlando Resort

10/10 Excellent

"We came to celebrate my husband's 60th birthday, just the two of us, and stayed in a beautiful four-bedroom flat. At check-in, I had booked the Bayfront online and initially received a city view we didn't understand the mishap., however the staff let us know there was a complimentary upgrade to the Bayfront, which was wonderful💕 My husband was delighted with the experience. We did need some air freshener in the apartment but otherwise it was clean.👌 The service was excellent. 🥰The staff made my husband feel amazing. surprising him with champagne, and a few appetizers.. They were all so kind and made us feel special. We will definitely return.🌟💕❤️💕"

Orlando Hotel Guide. Hotels in Windward Cay, Orlando, United States of America

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Filter by

Property class

Guest rating

Our top choices for Windward Cay hotels

1. Club Sevilla

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

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

4. Radisson Hotel Orlando Lake Buena Vista South

5. Embassy Suites by Hilton Orlando Lake Buena Vista South

6. Palazzo Lakeside Hotel

7. Legacy Vacation Resorts - Kissimmee/Orlando

8. Star Island Resort and Club

9. Meliá Orlando Celebration

10. Hilton Vacation Club Polynesian Isles Kissimmee

11. Kompose Boutique Resort at Theme Parks

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

13. Rosen Shingle Creek

14. Rosen Inn Lake Buena Vista

15. Ramada by Wyndham Kissimmee Gateway

16. Buena Vista Suites Orlando

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

18. Vacation Village Orlando, Celebration

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

20. Hilton Vacation Club Grand Beach Orlando

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

Universal's Endless Summer Resort - Dockside Inn and Suites

Frequently asked questions