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Mar 18 - Mar 19
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Mar 19 - Mar 20
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Mar 20 - Mar 22
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Our top choices for Windward Cay hotels

Aerial view

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 NT$2,835
NT$4,482 total
includes taxes & fees
Apr 12 - Apr 13
Wyndham Garden Lake Buena Vista – Disney Springs® Area
Front of property

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)
"Excellent stay, we really enjoyed ourselves. Would absolutely come again. "
United States
ashley
The price is NT$3,798
NT$5,566 total
includes taxes & fees
Mar 22 - Mar 23
Wyndham Lake Buena Vista – Disney Springs® Area
Exterior

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 NT$3,967
NT$4,463 total
includes taxes & fees
Apr 15 - Apr 16
Home2 Suites by Hilton Orlando at Flamingo Crossings
Outdoor pool, sun loungers

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 NT$5,155
NT$5,799 total
includes taxes & fees
Apr 2 - Apr 3
Drury Plaza Hotel Orlando - Disney Springs Area
Terrace/patio

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
Exterior

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 NT$4,565
NT$5,135 total
includes taxes & fees
Apr 5 - Apr 6
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
BBQ/picnic area

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 NT$4,162
NT$4,683 total
includes taxes & fees
Apr 13 - Apr 14
Homewood Suites by Hilton Orlando at Flamingo Crossings
Lobby lounge

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 NT$2,873
NT$3,232 total
includes taxes & fees
Mar 22 - Mar 23
Aloft Orlando Lake Buena Vista
Exterior

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 NT$4,453
NT$5,907 total
includes taxes & fees
Mar 25 - Mar 26
Hilton Vacation Club Grand Beach Orlando
Exterior

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, (2,391 reviews)
"Very clean, comfortable and located near everything you need. "
Canada
Sabrina
The price is NT$2,266
NT$2,909 total
includes taxes & fees
Mar 22 - Mar 23
Candlewood Suites Orlando - Lake Buena Vista by IHG
2 outdoor pools, pool umbrellas, sun loungers

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 NT$3,663
NT$5,019 total
includes taxes & fees
Apr 13 - Apr 14
Hilton Vacation Club Aqua Sol Orlando West
Meeting facility

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 NT$3,352
NT$3,771 total
includes taxes & fees
Apr 5 - Apr 6
Holiday Inn & Suites Orlando I-Drive Theme Parks by IHG
Outdoor wedding area

Meliá Orlando Celebration

Meliá Orlando Celebration
4.0 star property
6.8 km from Windward Cay
8.8 out of 10, Excellent, (1,567 reviews)
"Love the hotel The staff is outstanding!"
United States
Deborah
The price is NT$2,777
NT$4,311 total
includes taxes & fees
Mar 30 - Mar 31
Meliá Orlando Celebration
Exterior

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 NT$5,142
NT$6,324 total
includes taxes & fees
Apr 12 - Apr 13
Bryan’s Spanish Cove
Exterior

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 NT$3,703
NT$4,166 total
includes taxes & fees
Apr 1 - Apr 2
avid hotel Orlando International Airport by IHG
Property grounds

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, (3,191 reviews)
"Clean rooms, comfy beds, staff was great! "
United States
Rebecca
The price is NT$2,301
NT$3,163 total
includes taxes & fees
Mar 31 - Apr 1
SPOT X Hotel Orlando/Intl Dr by The Red Collection
Exterior

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 NT$2,279
NT$2,564 total
includes taxes & fees
Mar 29 - Mar 30
Days Inn by Wyndham Orlando Conv. Center/International Dr
Outdoor pool

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 NT$2,822
NT$3,174 total
includes taxes & fees
Mar 22 - Mar 23
Element Orlando Universal Blvd.
Front of property - evening/night

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 NT$3,066
NT$3,449 total
includes taxes & fees
Apr 12 - Apr 13
La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks
Free daily buffet breakfast

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 NT$3,703
NT$4,166 total
includes taxes & fees
Apr 13 - Apr 14
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.
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Where to stay in Windward Cay

Find the best Windward Cay areas and neighborhoods for the activities you enjoy most.
Visiting Aquatica water park in Orlando, Florida, enjoying thrilling water slides and attractions

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.

This is the third park built at the Walt Disney World Resort, opening on May 1, 1989 as Disney-MGM Studios. Today, it's known as Disney's Hollywood Studios.
Photo by Gary Burke
Open Photo by Gary Burke

Bay Lake

Home to all four Walt Disney World Resort theme parks and one water park, this city offers endless entertainment, including Disney's Fort Wilderness Resort & Campground and Magnolia and Palm Golf Courses.

Champions Gate

Abundant dining options and pristine 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.

Hollywood Rip Ride Rock it at Universal Studios, Orlando. Taken on a Sony a6000 with a 16 mm Sony lens. # TroveonTuesday
Photo by Peter Sutton
Open Photo by Peter Sutton

Florida Center

While visiting Florida Center, you might make a stop by sights like Universal Orlando Resort and Universal Studios Florida.

Orlando downtown welcome sign with tropical scene; Shutterstock ID 99801884

Downtown Orlando

Orlando's historic core boasts art galleries, retail, restaurants, and nightclubs, with attractions like Lake Eola Park, Linton E. Allen Memorial Fountain, and performing arts theaters, all accessible via public transportation.

Top Windward Cay Hotel Reviews

Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

10/10 Excellent
"I was able to bring my two dogs and I didn’t even had to use my waste bags. They have everything accessible for you to clean after your pets outside building E."
Rosana 3-night trip
Posted 1 hour ago
Rosen Inn at Pointe Orlando

Frequently asked questions

What's it like in Windward Cay?
Travelers to the Windward Cay neighborhood in Kissimmee will be sure to enjoy their stay.
How many hotels will I find in Windward Cay?
Expedia has 32 hotels and other accommodations 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, most hotel reservations are refundable provided that you cancel before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your check-in date. If you booked a non-refundable reservation, you might be able to still cancel and be given a refund within a 24-hour period of booking. Plug in your dates, click on "Search", then use the "fully refundable" filter to get the best deals available in Windward Cay.
Where can I learn more about changing or cancelling my trip to Windward Cay?
For more information about changing or cancelling your trip to Windward Cay, click here.
What is there to do around this Kissimmee neighborhood?
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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