Windward Cay Hotels: 37,849 Cheap Accommodation in Windward Cay

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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

Peterjohn

includes taxes & fees

25 Nov - 26 Nov

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

2. 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.

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

1.6 km from Windward Cay

Viridiana

includes taxes & fees

16 Nov - 17 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 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

Ilse

includes taxes & fees

29 Nov - 30 Nov

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

includes taxes & fees

18 Nov - 19 Nov

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

includes taxes & fees

15 Nov - 16 Nov

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

includes taxes & fees

8 Dec - 9 Dec

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

includes taxes & fees

15 Dec - 16 Dec

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

Karen

includes taxes & fees

29 Nov - 30 Nov

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

Yong Pin

includes taxes & fees

30 Nov - 1 Dec

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

12. Rosen Inn Lake Buena Vista

8.9 km from Windward Cay

Clayton

includes taxes & fees

9 Dec - 10 Dec

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

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

9 km from Windward Cay

Daryl

includes taxes & fees

30 Nov - 1 Dec

A hotel with a swimming pool surrounded by lounge chairs and palm trees.

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

11.3 km from Windward Cay

Maria

includes taxes & fees

14 Dec - 15 Dec

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

includes taxes & fees

29 Nov - 30 Nov

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

Melodina

includes taxes & fees

15 Dec - 16 Dec

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

ivan

includes taxes & fees

17 Nov - 18 Nov

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

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

9.8 km from Windward Cay

Anup

includes taxes & fees

18 Nov - 19 Nov

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

19. Hilton Vacation Club Grand Beach Orlando

6.3 km from Windward Cay

Angel

includes taxes & fees

15 Dec - 16 Dec

A poolside area with lounge chairs and umbrellas, a fire pit, and a pool.

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

7.6 km from Windward Cay

Jesus

includes taxes & fees

22 Nov - 23 Nov

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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

Hotels recommended for families in Windward Cay

A modern living room with a black leather sectional sofa, a teal rug, and white orchids.

Beautiful pool home 20 minutes from Disney!

Windward Cay

Our guide on 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

Embassy Suites by Hilton Orlando Lake Buena Vista South

Kissimmee

10/10 Excellent

Kerryn

Radisson Hotel Orlando Lake Buena Vista South

Kissimmee

8/10 Good

Andrew

Hilton Vacation Club Polynesian Isles Kissimmee

Kissimmee

10/10 Excellent

Fantastic place for our 3 weeks for 4 in a 2 bed place. Had 2 bathrooms and excellent kitchen with dishwasher and own laundry. Great staff and easy location to all Disney and Universal at a fraction of the cost of their properties. Apartment was huge and plenty of space. Only cleaned once a week but this was fine as we are used to doing it ourselves and also felt much less intrusive and could just "feel at home". Thanks Polynesian team!

Mark

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

Jade

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

Bay Lake

10/10 Excellent

Vincent

Hilton Vacation Club Grand Beach Orlando

Orlando

10/10 Excellent

Dian

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

Pestana Orlando Suites - Lake Buena Vista

Orlando

10/10 Excellent

Megan

Holiday Inn Express & Suites Orlando at SeaWorld by IHG

International Drive District

10/10 Excellent

tawhai

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

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Bay Lake

10/10 Excellent

Amiel

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.

Windward Cay Hotels, Kissimmee

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for Windward Cay hotels

1. Embassy Suites by Hilton Orlando Lake Buena Vista South

2. Club Sevilla

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

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. Buena Vista Suites Orlando

11. Meliá Orlando Celebration

12. Rosen Inn Lake Buena Vista

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

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

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

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

17. Kompose Boutique Resort at Theme Parks

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

19. Hilton Vacation Club Grand Beach Orlando

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

Compare popular hotels in Windward Cay

Hotels recommended for families in Windward Cay

Beautiful pool home 20 minutes from Disney!

Our guide on 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 be able to find in Windward Cay?

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

What is there to do around this Kissimmee neighbourhood?