Windward Cay Vacation Packages

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Top Holiday Package Deals in Windward Cay

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

Seasons Florida Resort

2 out of 5
per person
Sep 29 - Oct 6
found 2 days ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.8/10 Excellent! (2,970 reviews)
Staff was very friendly, joyous as well as helpful and room was clean, neat, well kept.

Reviewed on Jul. 28, 2025

ette hotel

ette hotel

5 out of 5
per person
Sep 29 - Oct 6
found 2 days ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
9.8/10 Exceptional! (313 reviews)
Fantastic hotel. Beautiful room, great food, exceptional staff and the smell was phenomenal

Reviewed on Jul. 27, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8.6/10 Excellent! (1,006 reviews)
Awesome stay! Pool is amazing and staff is friendly!

Reviewed on Jul. 27, 2025

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8/10 Very Good! (1,277 reviews)
The only thing that was a problem was the fact that I wasn't told that I couldn't use the water park unless I was a owner, other than that I love The place

Reviewed on Jul. 27, 2025

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
International Drive District
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
7/10 Good! (1,959 reviews)
The staff were friendly. Thanks! The elevator was very old. And we had to scan the room card every single time to take the elevator, and I had problems with my card many times with the elevator. My entry light turned on by itself in my room few times for two nights. Also the AC was very loud. :(

Reviewed on Jul. 25, 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
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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

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

4 out of 5
5780 Major Blvd, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Aug 14 to Aug 15
CA $139
CA $156 total
Aug 14 - Aug 15
includes taxes & fees
8.2/10 Very Good! (6,524 reviews)
"I absolutely love the staff. Very helpful and so very sweet! The location is perfect for a universal studios trip. I would stay here again."

Reviewed on Jul. 27, 2025

DoubleTree by Hilton at the Entrance to Universal Orlando
Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

4 out of 5
9300 Jeff Fuqua Boulevard, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is CA $243 per night from Jul 29 to Jul 30
CA $243
CA $274 total
Jul 29 - Jul 30
includes taxes & fees
9.4/10 Exceptional! (3,417 reviews)
Great Hotel
"This Hotel is Great. Clean rooms. Spacious king bed. Quiet and wonderful staff. Loved it."

Reviewed on Jul. 27, 2025

Hyatt Regency Orlando International Airport
Marriott's Grande Vista

Marriott's Grande Vista

4 out of 5
5925 Avenida Vista, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is CA $119 per night from Aug 17 to Aug 18
CA $119
CA $134 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (2,695 reviews)
"Great place to stay when visiting Disney. Only thing to be aware of is Marriott charges a $25 per day parking charge."

Reviewed on Jul. 27, 2025

Marriott's Grande Vista
See all 52,748 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.
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Frequently asked questions

How much does a Windward Cay vacation package cost?
Tailor make your Windward Cay vacation package from just CA $585. Pick from any combination of flights, hotels and rental cars to pull together the trip of your dreams. Don't forget to add on a few experiences or activities!
How do I get a cheap travel package to Windward Cay?
Bundle your bookings with Expedia to save big on your next getaway. With more than 550 air carriers and 1,000,000 hotels throughout the world, your Windward Cay vacation package can be tailored exactly to suit your budget. With all those extra dollars, why not add one or more interesting experiences and tours? It's an easy way to unlock even more savings. Your dream vacation in Windward Cay is much closer than you thought!
Where should I stay in Windward Cay?
A trip to Windward Cay isn't complete without stopping by Old Town, Fun Spot America and Give Kids the World Village. Spend your evenings near these popular attractions and make sightseeing a breeze.
What are the top hotels in Windward Cay?
Make a reservation at Ref 43 Family Villa With Own Pool Near Disney. It's one of the neighborhood's most in-demand properties. Another top-rated option in Windward Cay is Lakeside Villa With Perfect Views From Your Private Pool In A Peaceful Community.
How far in advance should I book my Windward Cay vacation?
Reserving your spot early with Expedia means one less thing to worry about. Most air carriers advertise prices up to 12 months prior to departure dates. Usually, this is the cheapest time to book. If circumstances have left you booking late, great deals to Windward Cay will sometimes occur just a few weeks before departure.
What does an Expedia Windward Cay travel package include?
Much of that is up to you. You can select from a variety of Windward Cay packages, such as a rental car, flight and hotel. You can also book a flight and a hotel, or a flight with a rental car. Once you've made your booking, you can add on the fun stuff like experiences and tours. Whatever your perfect Windward Cay trip looks like, get set to save!
What should I know before booking a Windward Cay travel package?
Bundling your bookings into a Windward Cay vacation package is the easiest way to organize your trip. Not only that, you'll save when you combine your hotels, flights and car rentals. Once you've booked, why not add on a tour or an activity?
If I'm not able to travel, can I cancel my Windward Cay vacation package?
Your situation can change unexpectedly, so yes, you can. You may be able to change or cancel your Windward Cay vacation package for free within 24 hours of booking. For bookings made more than 24 hours ago, you can still make changes, but your car rental company, airline or hotel may impose a charge. Need more information? Take a look at our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.

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

Movie sets and thrill rides combine to create this internationally acclaimed theme park.

Universal Studios Florida
Universal Studios Orlando which includes 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

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Aquatica Orlando

CA $74
per traveller
82% of travellers recommend
Aquatica Orlando
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

CA $108
per traveller
84% of travellers recommend
LEGOLAND® Florida Tickets
Indoor Karting

Andretti Indoor Karting & Games in Orlando

CA $42
per adult
80% of travellers recommend
Andretti Indoor Karting & Games in Orlando
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.