Windward Cay Hotels, Orlando

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Our top choices for Windward Cay hotels

4716-4-ww-blend of Relaxation and Convenience

4716-4-ww-blend of Relaxation and Convenience
2.0 star property
Windward Cay
The price is AU$4,322
includes taxes & fees
14 Feb - 15 Feb
4716-4-ww-blend of Relaxation and Convenience

Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area
3.0 star property
8.4 km from Windward Cay
9.8 out of 10, Exceptional, (5,574 reviews)
"Great hotel"
United States
Gary
The price is AU$275
includes taxes & fees
10 Feb - 11 Feb
Drury Plaza Hotel Orlando - Disney Springs Area

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
8.2 out of 10, Very good, (3,963 reviews)
"Great hotel"
United States
Jose Carlos
The price is AU$234
includes taxes & fees
22 Feb - 23 Feb
Wyndham Garden Lake Buena Vista – Disney Springs® Area

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
16.3 km from Windward Cay
9.2 out of 10, Wonderful, (5,209 reviews)
"great place to stay nearest to all location ."
Canada
VIMAL
The price is AU$178
includes taxes & fees
10 Feb - 11 Feb
Home2 Suites by Hilton Orlando at Flamingo Crossings

Holiday Inn Express Hotel & Suites Ocoee East by IHG

Holiday Inn Express Hotel & Suites Ocoee East by IHG
2.5 star property
26.8 km from Windward Cay
8.4 out of 10, Very good, (1,006 reviews)
"The check in process was easy and friendly "
United States
Luisa
The price is AU$208
includes taxes & fees
1 Feb - 2 Feb
Holiday Inn Express Hotel & Suites Ocoee East by IHG

Aloft Orlando Lake Buena Vista

Aloft Orlando Lake Buena Vista
3.0 star property
9.5 km from Windward Cay
8.8 out of 10, Excellent, (1,953 reviews)
"Super nice hotel at a great price."
United States
Terry
The price is AU$145
includes taxes & fees
8 Feb - 9 Feb
Aloft Orlando Lake Buena Vista

The Delaney Hotel

The Delaney Hotel
3.5 star property
25.9 km from Windward Cay
9.6 out of 10, Exceptional, (1,052 reviews)
"Always love staying here. "
United States
Cate
The Delaney Hotel

Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
16.4 km from Windward Cay
9.4 out of 10, Exceptional, (2,232 reviews)
"Great place to stay "
United States
ALTON
The price is AU$224
includes taxes & fees
24 Feb - 25 Feb
Homewood Suites by Hilton Orlando at Flamingo Crossings

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, (1,457 reviews)
"Loved everything about this hotel "
United States
Giselle
The price is AU$243
includes taxes & fees
22 Feb - 23 Feb
Hilton Vacation Club Grand Beach Orlando

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

La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks
3.0 star property
9.8 km from Windward Cay
8.6 out of 10, Excellent, (2,474 reviews)
"Everything was great, clean and breakfast included and pet friendly. Will definitely stay there again "
United States
Rosalba
The price is AU$151
includes taxes & fees
8 Feb - 9 Feb
La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
3.0 star property
16.3 km from Windward Cay
9.6 out of 10, Exceptional, (1,996 reviews)
"Always love staying here when visiting Orlando!"
United States
Bethany L
The price is AU$228
includes taxes & fees
2 Mar - 3 Mar
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Candlewood Suites Orlando - Lake Buena Vista by IHG

Candlewood Suites Orlando - Lake Buena Vista by IHG
2.5 star property
9.3 km from Windward Cay
9.0 out of 10, Wonderful, (2,346 reviews)
"Room was very nice it even had a recliner chair which my other half needs to sleep . I would stay here again."
United States
Lisa
The price is AU$150
includes taxes & fees
9 Feb - 10 Feb
Candlewood Suites Orlando - Lake Buena Vista by IHG

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
8.6 out of 10, Excellent, (3,558 reviews)
"Loved the pool area, very clean, good location, breakfast is decent, staff is great! "
Canada
Jordana
The price is AU$179
includes taxes & fees
23 Feb - 24 Feb
SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista

Holiday Inn Resort Orlando Suites - Waterpark by IHG

Holiday Inn Resort Orlando Suites - Waterpark by IHG
3.5 star property
6.2 km from Windward Cay
7.2 out of 10, Good, (4,715 reviews)
"Excellent for a quick Stay!"
United States
Matthew
The price is AU$163
includes taxes & fees
3 Feb - 4 Feb
Holiday Inn Resort Orlando Suites - Waterpark by IHG

avid hotel Orlando International Airport by IHG

avid hotel Orlando International Airport by IHG
2.5 star property
21.2 km from Windward Cay
9.2 out of 10, Wonderful, (2,128 reviews)
"Great quick stay for a good value!"
United States
Pamela
The price is AU$207
includes taxes & fees
3 Mar - 4 Mar
avid hotel Orlando International Airport by IHG

Hyatt Place Orlando/Lake Buena Vista

Hyatt Place Orlando/Lake Buena Vista
3.0 star property
9.1 km from Windward Cay
8.4 out of 10, Very good, (1,471 reviews)
"Nice hotel, fast check-in love it"
United States
Yuberka
The price is AU$152
includes taxes & fees
10 Feb - 11 Feb
Hyatt Place Orlando/Lake Buena Vista

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

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
2.5 star property
16.4 km from Windward Cay
9.4 out of 10, Exceptional, (4,483 reviews)
"Amazing room and great breakfasts for the price "
United States
Christian
The price is AU$185
includes taxes & fees
3 Mar - 4 Mar
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Element Orlando Universal Blvd.

Element Orlando Universal Blvd.
3.0 star property
15.1 km from Windward Cay
9.2 out of 10, Wonderful, (2,035 reviews)
"Great staff, clean rooms and great location."
Canada
Lynne
The price is AU$150
includes taxes & fees
8 Feb - 9 Feb
Element Orlando Universal Blvd.

Hampton Inn & Suites Orlando Airport @ Gateway Village

Hampton Inn & Suites Orlando Airport @ Gateway Village
3.0 star property
22.8 km from Windward Cay
9.4 out of 10, Exceptional, (2,521 reviews)
"Great stay "
United States
Nancy
The price is AU$237
includes taxes & fees
23 Feb - 24 Feb
Hampton Inn & Suites Orlando Airport @ Gateway Village

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
4.0 star property
7.2 km from Windward Cay
9.4 out of 10, Exceptional, (4,460 reviews)
"Room was very nice, staff helpful and great location for travelers. "
United States
Nancy
The price is AU$184
includes taxes & fees
26 Feb - 27 Feb
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
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.

Our guide on where to stay in Windward Cay

Find the best Windward Cay areas for the activities you enjoy most.

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.

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.

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.

Florida Center

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

Downtown Orlando

One of the most popular neighborhoods in Florida, this bustling area is full of art galleries, shops, bars and restaurants.

Top Windward Cay Hotel Reviews

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 31 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, Capone's Dinner Show and Pirate's Island Adventure Golf are a couple of additional sights to visit in Kissimmee.

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