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Our top choices for Windward Cay hotels

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, (4,021 reviews)
"Clean room/ very kind staff/ location was amazing! "
Canada
Michael
The price is ฿2,870
฿4,538 total
includes taxes & fees
12 Apr - 13 Apr
Wyndham Garden Lake Buena Vista – Disney Springs® Area

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, (2,802 reviews)
"Loved this hotel! Was clean,wonderful staff the breakfast was always delicious!"
United States
Kari
The price is ฿3,846
฿5,636 total
includes taxes & fees
22 Mar - 23 Mar
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
16.2 km from Windward Cay
9.2 out of 10, Wonderful, (5,322 reviews)
"Great breakfast and nice property."
United States
Christopher
The price is ฿4,017
฿4,519 total
includes taxes & fees
15 Apr - 16 Apr
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, (5,700 reviews)
"amazing stay highly recommend "
United States
Christian
The price is ฿5,220
฿5,872 total
includes taxes & fees
2 Apr - 3 Apr
Drury Plaza Hotel Orlando - Disney Springs Area

The Delaney Hotel

The Delaney Hotel
3.5 star property
25.9 km from Windward Cay
9.6 out of 10, Exceptional, (1,058 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, (2,012 reviews)
"Clean rooms and great location"
United States
Alexis
The price is ฿4,622
฿5,200 total
includes taxes & fees
5 Apr - 6 Apr
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

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, (2,304 reviews)
"Friendly staff, clean rooms , good customer service and the location was close to Disney parkes."
Canada
Amir
The price is ฿4,279
฿4,814 total
includes taxes & fees
5 Apr - 6 Apr
Homewood Suites by Hilton Orlando at Flamingo Crossings

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, (1,955 reviews)
"Great staff and clean rooms "
United States
Tara Lynn
The price is ฿2,909
฿3,273 total
includes taxes & fees
22 Mar - 23 Mar
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, (1,471 reviews)
"Great place!!"
United States
Richard
The price is ฿4,509
฿5,982 total
includes taxes & fees
25 Mar - 26 Mar
Hilton Vacation Club Grand Beach Orlando

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, (2,389 reviews)
"Very clean, comfortable and located near everything you need. "
Canada
Sabrina
The price is ฿2,295
฿2,945 total
includes taxes & fees
22 Mar - 23 Mar
Candlewood Suites Orlando - Lake Buena Vista by IHG

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, (4,084 reviews)
"Great place for family"
United States
Lane
The price is ฿3,709
฿5,082 total
includes taxes & fees
13 Apr - 14 Apr
Hilton Vacation Club Aqua Sol Orlando West

Holiday Inn & Suites Orlando I-Drive Theme Parks by IHG

Holiday Inn & Suites Orlando I-Drive Theme Parks by IHG
3.0 star property
9.1 km from Windward Cay
9.0 out of 10, Wonderful, (1,714 reviews)
"The check in staff were great, rooms were clean and hotel is close to everything."
Canada
Kenton
The price is ฿3,394
฿3,818 total
includes taxes & fees
5 Apr - 6 Apr
Holiday Inn & Suites Orlando I-Drive Theme Parks by IHG

Meliá Orlando Celebration

Meliá Orlando Celebration
4.0 star property
6.8 km from Windward Cay
8.8 out of 10, Excellent, (1,568 reviews)
"Love the hotel The staff is outstanding!"
United States
Deborah
The price is ฿2,812
฿4,366 total
includes taxes & fees
30 Mar - 31 Mar
Meliá Orlando Celebration

Bryan’s Spanish Cove

Bryan’s Spanish Cove
3.0 star property
6.5 km from Windward Cay
9.4 out of 10, Exceptional, (1,003 reviews)
"Everything about this resort was beyond amazing. "
United States
Ermilo
The price is ฿5,207
฿6,404 total
includes taxes & fees
12 Apr - 13 Apr
Bryan’s Spanish Cove

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, (2,181 reviews)
"Great stay"
United States
Nicole
The price is ฿3,749
฿4,218 total
includes taxes & fees
31 Mar - 1 Apr
avid hotel Orlando International Airport 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, (3,192 reviews)
"Clean rooms, comfy beds, staff was great! "
United States
Rebecca
The price is ฿2,330
฿3,203 total
includes taxes & fees
6 Apr - 7 Apr
SPOT X Hotel Orlando/Intl Dr by The Red Collection

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, (2,695 reviews)
"Excellent stay , clean , ihop is in the same building , close to the highway , old hotel but kept up well "
United States
James
The price is ฿2,308
฿2,596 total
includes taxes & fees
29 Mar - 30 Mar
Days Inn by Wyndham Orlando Conv. Center/International Dr

Element Orlando Universal Blvd.

Element Orlando Universal Blvd.
3.0 star property
15.1 km from Windward Cay
9.2 out of 10, Wonderful, (2,105 reviews)
"The property is in a great location nice places to eat and great staff"
United States
janett
The price is ฿2,857
฿3,215 total
includes taxes & fees
22 Mar - 23 Mar
Element Orlando Universal Blvd.

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, (2,584 reviews)
"Great location "
United States
Henry
The price is ฿3,132
฿3,524 total
includes taxes & fees
29 Mar - 30 Mar
La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks

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

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
3.0 star property
16.4 km from Windward Cay
9.4 out of 10, Exceptional, (4,602 reviews)
"Would love to stay here again "
United States
Ropheline
The price is ฿3,749
฿4,218 total
includes taxes & fees
13 Apr - 14 Apr
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
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.

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 32 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.