A golf course with a large hotel and residential area.

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

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Check prices for these dates

Next weekend
11 Sept - 13 Sept
In two weeks
18 Sept - 20 Sept

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Our top choices for Windward Cay hotels

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

1. Seasons Florida Resort

Seasons Florida Resort
2.0 star property
1.6 km from Windward Cay
9.0 out of 10, Wonderful, (3,875 reviews)
"Nice and a good place to stay."
United States
Joel
The price is €50
includes taxes & fees
13 Sept - 14 Sept
Seasons Florida Resort
A spacious restaurant with high ceilings, hanging pendant lights, and a variety of seating arrangements.

2. Embassy Suites by Hilton Orlando Lake Buena Vista South

Embassy Suites by Hilton Orlando Lake Buena Vista South
4.0 star property
3 km from Windward Cay
9.6 out of 10, Exceptional, (1,549 reviews)
"Excellent service and breakfast"
United States
Ivandra
The price is €88
includes taxes & fees
4 Oct - 5 Oct
Embassy Suites by Hilton Orlando Lake Buena Vista South
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.

3. Palazzo Lakeside Hotel

Palazzo Lakeside Hotel
3.0 star property
2.7 km from Windward Cay
8.4 out of 10, Very good, (5,314 reviews)
"The hotel was beautiful, we had a great time."
United States
LILLIAN
The price is €49
includes taxes & fees
7 Sept - 8 Sept
Palazzo Lakeside Hotel
A modern living room with a large flat-screen TV, a white sofa, and a coffee table.

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

Magic Moment Resort & Kids Club, Dazzler Select by Wyndham
3.0 star property
3.2 km from Windward Cay
8.6 out of 10, Excellent, (3,217 reviews)
"It was very family friendly!"
United States
Jose
The price is €55
includes taxes & fees
7 Sept - 8 Sept
Magic Moment Resort & Kids Club, Dazzler Select by Wyndham
A swimming pool with a blue slide, surrounded by palm trees and a fenced area.

5. Radisson Hotel Orlando Lake Buena Vista South

Radisson Hotel Orlando Lake Buena Vista South
3.5 star property
3 km from Windward Cay
8.8 out of 10, Excellent, (3,859 reviews)
"The hotel building and staff are great and friendly. The breakfast is okay. Continental.. simple but filling.. the pool and lazy river are awesome."
United States
yesenia
The price is €63
includes taxes & fees
27 Sept - 28 Sept
Radisson Hotel Orlando Lake Buena Vista South
An aerial view of a curved swimming pool with lounge chairs and umbrellas around it.

6. Meliá Orlando Celebration

Meliá Orlando Celebration
4.0 star property
6.8 km from Windward Cay
8.8 out of 10, Excellent, (1,614 reviews)
"Great place to stay"
United States
Juanita
The price is €107
includes taxes & fees
15 Sept - 16 Sept
Meliá Orlando Celebration
A modern reception desk with a logo, a computer, and a glass door leading outside.

7. The Vietta Hotel

The Vietta Hotel
2.0 star property
2.6 km from Windward Cay
7.8 out of 10, Good, (1,002 reviews)
"It was nice and clean Hotel with all anemities close by."
Canada
Fakhar-ud-din
The price is €72
includes taxes & fees
7 Sept - 8 Sept
The Vietta Hotel
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.

8. Travelodge by Wyndham Orlando Lake Buena Vista South

Travelodge by Wyndham Orlando Lake Buena Vista South
2.0 star property
3.6 km from Windward Cay
7.6 out of 10, Good, (1,004 reviews)
"This place is close too all amenities you will need for this vacation or business. Close to all restaurants. Minutes away"
United States
Isandall
The price is €51
includes taxes & fees
10 Sept - 11 Sept
Travelodge by Wyndham Orlando Lake Buena Vista South
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.

9. Hilton Vacation Club Polynesian Isles Kissimmee

Hilton Vacation Club Polynesian Isles Kissimmee
3.0 star property
3.9 km from Windward Cay
9.6 out of 10, Exceptional, (1,901 reviews)
"Good place for a family."
Canada
MAHADEVAN
The price is €106
includes taxes & fees
7 Sept - 8 Sept
Hilton Vacation Club Polynesian Isles Kissimmee
A modern indoor patio with a fire pit table, seating, a bar area, and large windows.

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

SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista
3.0 star property
9.5 km from Windward Cay
8.8 out of 10, Excellent, (3,602 reviews)
"Great stay, will definitely be back."
United States
Shander Aria
The price is €75
includes taxes & fees
10 Sept - 11 Sept
SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista
A swimming pool with people in the water, including a person in a green and red inflatable ring.

11. Buena Vista Suites Orlando

Buena Vista Suites Orlando
4.0 star property
5.7 km from Windward Cay
9.2 out of 10, Wonderful, (2,523 reviews)
"Clean, friendly staff, breakfast very good"
United States
Jose
The price is €152
includes taxes & fees
7 Sept - 8 Sept
Buena Vista Suites Orlando
A large outdoor swimming pool with multiple water features and lounge areas.

12. Wyndham Garden Lake Buena Vista – Disney Springs® Area

Wyndham Garden Lake Buena Vista – Disney Springs® Area
3.5 star property
8.2 km from Windward Cay
8.4 out of 10, Very good, (4,155 reviews)
"Great location to Disney Springs."
United States
Samon
The price is €102
includes taxes & fees
7 Sept - 8 Sept
Wyndham Garden Lake Buena Vista – Disney Springs® Area
A hotel reception area with a marble counter, a Mickey Mouse decoration, and surfboards on the wall.

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

Holiday Inn Resort Orlando - Lake Buena Vista by IHG
3.5 star property
7.6 km from Windward Cay
8.6 out of 10, Excellent, (4,023 reviews)
"Great service pool and pool bar are great rooms are nice and big great place to stay"
United States
juan
The price is €90
includes taxes & fees
10 Sept - 11 Sept
Holiday Inn Resort Orlando - Lake Buena Vista by IHG
A large outdoor swimming pool with multiple lanes, surrounded by lounge chairs and umbrellas.

14. Wyndham Lake Buena Vista – Disney Springs® Area

Wyndham Lake Buena Vista – Disney Springs® Area
4.0 star property
8.2 km from Windward Cay
8.8 out of 10, Excellent, (2,918 reviews)
"Always a great stay"
United States
tracy
The price is €121
includes taxes & fees
7 Sept - 8 Sept
Wyndham Lake Buena Vista – Disney Springs® Area
A large hotel complex with multiple high-rise buildings, a central swimming pool, and surrounding greenery.

15. Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
6.5 km from Windward Cay
8.6 out of 10, Excellent, (4,969 reviews)
"Enjoyed the stay booked again"
United States
Joseph
The price is €87
includes taxes & fees
7 Sept - 8 Sept
Vacation Village Orlando, Celebration
A multi-story hotel with a central courtyard, parking area, and a view of the surrounding cityscape at night.

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

SPOT X Hotel Orlando/Intl Dr by The Red Collection
3.0 star property
9 km from Windward Cay
8.6 out of 10, Excellent, (3,652 reviews)
"Everything great including location!"
United States
Travis
The price is €68
includes taxes & fees
13 Sept - 14 Sept
SPOT X Hotel Orlando/Intl Dr by The Red Collection
A spacious lobby with a grand chandelier, modern seating, and a view of the outdoor area.

17. Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks
3.0 star property
11.5 km from Windward Cay
9.4 out of 10, Exceptional, (5,628 reviews)
"Such a wonderful stay"
United States
ivan
The price is €76
includes taxes & fees
29 Sept - 30 Sept
Kompose Boutique Resort at Theme Parks
A hotel pool area with lounge chairs and umbrellas, surrounded by tall buildings and a sunset sky.

18. Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area
4.0 star property
8.4 km from Windward Cay
9.8 out of 10, Exceptional, (6,046 reviews)
"Amazing hotel!"
United States
Samantha
The price is €136
includes taxes & fees
21 Sept - 22 Sept
Drury Plaza Hotel Orlando - Disney Springs Area
A hotel with a swimming pool, blue lounge chairs, and palm trees.

19. Hilton Vacation Club Grand Beach Orlando

Hilton Vacation Club Grand Beach Orlando
3.0 star property
6.3 km from Windward Cay
9.4 out of 10, Exceptional, (1,750 reviews)
"Wonderful resort beautiful rooms"
United States
Luis
The price is €113
includes taxes & fees
13 Sept - 14 Sept
Hilton Vacation Club Grand Beach Orlando
A modern kitchen with a central island, built-in shelves, and a variety of appliances and utensils.

20. AC Hotel by Marriott Orlando Lake Buena Vista

AC Hotel by Marriott Orlando Lake Buena Vista
3.5 star property
8.4 km from Windward Cay
9.2 out of 10, Wonderful, (1,952 reviews)
"great place!"
United States
Alexandra
The price is €96
includes taxes & fees
7 Sept - 8 Sept
AC Hotel by Marriott Orlando Lake Buena Vista
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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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.
Photo by Gary Burke
Open Photo by Gary Burke

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.

The entrance to Aquatica with colorful signage and a water slide.

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.

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.

A roller coaster at Universal Orlando Resort, featuring a tall palm tree and a clear blue sky.
Photo by Peter Sutton
Open Photo by Peter Sutton

Florida Center

If you're spending some time in Florida Center, Universal Orlando Resort and Universal Studios Florida are top sights worth seeing.

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.

Top Windward Cay Hotel Reviews

Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent
"The best off property place to stay."
Leslie 3-night trip
Posted less than an hour ago
Drury Plaza Hotel Orlando - Disney Springs Area

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.