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 NZ$5,002
includes taxes & fees
28 Feb - 1 Mar
4716-4-ww-blend of Relaxation and Convenience

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, (2,801 reviews)
"Friendly, excellent staff, easy to access to Disney world!"
United States
Yukari
The price is NZ$299
includes taxes & fees
22 Feb - 23 Feb
Wyndham 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, (5,254 reviews)
"great place to stay nearest to all location ."
Canada
VIMAL
The price is NZ$209
includes taxes & fees
2 Mar - 3 Mar
Home2 Suites by Hilton Orlando at Flamingo Crossings

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, (5,609 reviews)
"Great hotel"
United States
Gary
The price is NZ$350
includes taxes & fees
2 Mar - 3 Mar
Drury Plaza Hotel Orlando - Disney Springs Area

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, (1,007 reviews)
"The check in process was easy and friendly "
United States
Luisa
The price is NZ$279
includes taxes & fees
26 Feb - 27 Feb
Holiday Inn Express Hotel & Suites Ocoee East by IHG

The Delaney Hotel

The Delaney Hotel
3.5 star property
25.9 km from Windward Cay
9.6 out of 10, Exceptional, (1,061 reviews)
"Always love staying here. "
United States
Cate
The Delaney Hotel

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, (2,004 reviews)
"We loved this hotel everything was great! The breakfast, location and amenities "
United States
Catalina
The price is NZ$267
includes taxes & fees
23 Feb - 24 Feb
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

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, (1,967 reviews)
"Super nice hotel at a great price."
United States
Terry
The price is NZ$168
includes taxes & fees
10 Feb - 11 Feb
Aloft Orlando Lake Buena Vista

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, (1,465 reviews)
"Great room and clean amenities "
United States
Myra
The price is NZ$281
includes taxes & fees
22 Feb - 23 Feb
Hilton Vacation Club Grand Beach Orlando

Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
16.3 km from Windward Cay
9.4 out of 10, Exceptional, (2,256 reviews)
"Great place to stay "
United States
ALTON
The price is NZ$244
includes taxes & fees
23 Feb - 24 Feb
Homewood Suites by Hilton Orlando at Flamingo Crossings

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, (2,352 reviews)
"Staff very nice..room and property clean well maintained "
United States
Natalie
The price is NZ$174
includes taxes & fees
23 Feb - 24 Feb
Candlewood Suites Orlando - Lake Buena Vista by IHG

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, (3,090 reviews)
"Great location and so friendly staff."
United States
Emel
The price is NZ$163
includes taxes & fees
23 Feb - 24 Feb
SPOT X Hotel Orlando/Intl Dr by The Red Collection

Courtyard by Marriott Orlando Downtown

Courtyard by Marriott Orlando Downtown
3.0 star property
28.8 km from Windward Cay
9.6 out of 10, Exceptional, (1,006 reviews)
"Room was nice clean Great staff "
United States
John
The price is NZ$269
includes taxes & fees
15 Feb - 16 Feb
Courtyard by Marriott Orlando Downtown

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
4.0 star property
18.5 km from Windward Cay
8.8 out of 10, Excellent, (4,087 reviews)
"Great hotel, Wonderful amenities and location!"
United States
William
The price is NZ$245
includes taxes & fees
3 Mar - 4 Mar
Hilton Vacation Club Aqua Sol Orlando West

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, (2,500 reviews)
"Everything was great, clean and breakfast included and pet friendly. Will definitely stay there again "
United States
Rosalba
The price is NZ$182
includes taxes & fees
24 Feb - 25 Feb
La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks

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, (2,145 reviews)
"Great quick stay for a good value!"
United States
Pamela
The price is NZ$234
includes taxes & fees
23 Feb - 24 Feb
avid hotel Orlando International Airport by IHG

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, (4,769 reviews)
"Staff was friendly, room was spacious and enjoyed food court area with kids activities. "
United States
Jamie
The price is NZ$194
includes taxes & fees
10 Feb - 11 Feb
Holiday Inn Resort Orlando Suites - Waterpark by IHG

Bryan’s Spanish Cove

Bryan’s Spanish Cove
3.0 star property
6.5 km from Windward Cay
9.4 out of 10, Exceptional, (1,002 reviews)
"Everything about this resort was beyond amazing. "
United States
Ermilo
The price is NZ$307
includes taxes & fees
8 Mar - 9 Mar
Bryan’s Spanish Cove

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, (3,563 reviews)
"Loved the pool area, very clean, good location, breakfast is decent, staff is great! "
Canada
Jordana
The price is NZ$208
includes taxes & fees
23 Feb - 24 Feb
SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista

Days Inn by Wyndham Orlando Conv. Center/International Dr

Days Inn by Wyndham Orlando Conv. Center/International Dr
2.0 star property
12.6 km from Windward Cay
8.2 out of 10, Very good, (2,607 reviews)
"Great staff, clean room, and in a great place!"
United States
Eva
The price is NZ$126
includes taxes & fees
9 Feb - 10 Feb
Days Inn by Wyndham Orlando Conv. Center/International Dr
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 30 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.