Windward Cay Vacations from $237

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Your Windward Cay Vacation

Take all the hassle out of organizing your next break with a Windward Cay vacation package. Soak in the sights and sounds of this captivating neighborhood and enjoy what it has to offer. Kick start your trip to Windward Cay by checking out nearby attractions such as Old Town, Give Kids the World Village and Medieval Times. Expedia can help you turn your ideal Windward Cay vacation into reality, whatever your budget or travel plans.

The Latest Windward Cay Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $516, price is now $237 per person
$237
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.8/10 Excellent! (3,062 reviews)
Clean room and friendly staff

Reviewed on Sep 1, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was $1,175, price is now $434 per person
$434
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.8/10 Excellent! (1,008 reviews)
Being able to text the front desk for my needs was very helpful! Staff was friendly and the Universal shuttles were convenient.

Reviewed on Aug 30, 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was $850, price is now $358 per person
$358
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.2/10 Very Good! (5,275 reviews)
It was a good stay here for a couple days, been to this resort before and it was amazing

Reviewed on Sep 2, 2025

ette hotel

ette hotel

5 out of 5
Price was $1,581, price is now $715 per person
$715
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
9.8/10 Exceptional! (330 reviews)
Excellent service, food, location and staff! Thank you

Reviewed on Aug 11, 2025

Reunion Resort & Golf Club

Reunion Resort & Golf Club

5 out of 5
Reunion
Save 100% on your flight
Price was $1,014, price is now $497 per person
$497
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.8/10 Excellent! (1,377 reviews)
Staff was amazing and accommodating.

Reviewed on Sep 1, 2025

Where to stay in Windward Cay

Find the best Windward Cay areas and neighborhoods for the activities you enjoy most. Learn more about Windward Cay
International Drive showing landscape views

International Drive District

1 out of top 10 points of interest in this area

Adventure activities, iconic attractions, shopping and world-class dining destinations make this famous street one of Orlando’s most popular tourist attractions.

Find hotels in International Drive District

Windward Cay Hotel Deals

Marriott's Grande Vista

Marriott's Grande Vista

4 out of 5
5925 Avenida Vista, Orlando, FL
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $98 total per night from Sep 23 to Sep 24
$98 total
Sep 23 - Sep 24
Total with taxes and fees
Marriott's Grande Vista
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

3.5 out of 5
6550 Adventure Way, Orlando, FL
Fully refundableReserve now, pay when you stay
$140 nightly
The price is $158 total per night from Sep 29 to Sep 30
$158 total
Sep 29 - Sep 30
Total with taxes and fees
Universal's Cabana Bay Beach Resort
Holiday Inn Resort Kissimmee by the Parks by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG

3.5 out of 5
3011 Maingate Ln, Kissimmee, FL
Fully refundable
$73 nightly
The price is $83 total per night from Sep 7 to Sep 8
$83 total
Sep 7 - Sep 8
Total with taxes and fees
Holiday Inn Resort Kissimmee by the Parks by IHG
See all 52,784 properties in Windward Cay
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Windward Cay

Walt Disney World® Resort

Walt Disney World® Resort

Walt Disney World® Resort is part of Orlando. It makes up part of bustling metropolis that is home to 240,000 inhabitants. Walt Disney World® Resort is approximately 15 miles (24 kilometers) from Orlando’s city center. If you are flying in, Walt Disney World® Resort is approximately 15 miles (24 kilometers) from Orlando International Airport.

Walt Disney World® Resort
Universal Studios Florida™

Universal Studios Florida

Thrill rides based on your favorite movies create this internationally acclaimed theme park.

Universal Studios Florida
Universal Studios Orlando showing street scenes, a city and rides

Universal Orlando Resort

Make your Florida vacation one to remember with a stay at this hotel and theme park complex.

Universal Orlando Resort

Things to do

Universal Orlando Resort Express Passes

Universal Orlando Resort Express Passes

$149
per traveler
84% of travellers recommend
Universal Orlando Resort Express Passes
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

$27
per adult
90% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

$76
per traveler
84% of travellers recommend
LEGOLAND® Florida Tickets
See all activities in Orlando
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.