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.
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was CA $1,322, price is now CA $716 per person
CA $716
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Orlando (MCO)
8.2/10 Very good! (1,979 reviews)
It should be noted that you have to pay an extra fee to go to the waterpark there, but the staff was very helpful and we enjoyed our stay.

Reviewed on Jul 9, 2026

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was CA $1,622, price is now CA $765 per person
CA $765
per person
Oct 2 - Oct 7
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
9/10 Wonderful! (1,275 reviews)
Dryer and washer had hair in them poor Internet connection needs extra parking spaces for customers

Reviewed on Jul 8, 2026

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was CA $1,744, price is now CA $1,000 per person
CA $1,000
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Orlando (MCO)
8.2/10 Very good! (1,806 reviews)
The room was very clean and all the amenities were family friendly. We had a great stay!!

Reviewed on Jul 10, 2026

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was CA $1,297, price is now CA $772 per person
CA $772
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.4/10 Very good! (6,621 reviews)
Great place with lots to do. Home away from home

Reviewed on Jul 10, 2026

Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Price was CA $1,244, price is now CA $760 per person
CA $760
per person
Aug 24 - Aug 30
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.6/10 Excellent! (1,000 reviews)
Family friendly

Reviewed on Jul 7, 2026

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
A traditional Japanese torii gate with a dragon sculpture in front, overlooking a calm lake with a distant view of a spherical building.

Bay Lake

3 out of top 10 points of interest in this area
4.5/5(198 area reviews)

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.

Find hotels in Bay Lake

Windward Cay Hotel Deals

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

4 out of 5
8800 Vistana Centre Dr Orlando FL
Fully refundableReserve now, pay when you stay
The price is CA $194 per night from Aug 6 to Aug 7
CA $194
CA $218 total
Aug 6 - Aug 7
includes taxes & fees
9.2/10 Wonderful! (6,058 reviews)
"The location was perfect the ease of checking in was a breeze. The room was spacious and very clean there was enough towels in there for me and my wife we never had to ask for any extra towels. The three days we spent in there were perfect love the stay! The staff was really friendly . And I love ..."

Reviewed on Jul 10, 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue Winter Garden FL
Fully refundableReserve now, pay when you stay
The price is CA $261 per night from Aug 10 to Aug 11
CA $261
CA $371 total
Aug 10 - Aug 11
includes taxes & fees
8/10 Very good! (10,398 reviews)
"Checking in took us 1 hour & 52 minutes. This is not a joke. The lines were going out the front doors. Others in line joked the flight was shorter than the line to check in. We got locked out of our room at 8:30pm with twin infants. Everything to feed them was locked inside our room. It was not a ..."

Reviewed on Jul 10, 2026

The Grove Resort & Water Park 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 $265 per night from Aug 3 to Aug 4
CA $265
CA $298 total
Aug 3 - Aug 4
includes taxes & fees
9.4/10 Exceptional! (4,313 reviews)
"Ok"

Reviewed on Jul 9, 2026

Hyatt Regency Orlando International Airport
See all 52,486 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
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Family Vacations

Frequently asked questions

How much does a Windward Cay vacation package cost?
Tailor make your Windward Cay vacation package from just CA $716. 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.

Things to do

Universal Orlando Resort Theme Park Tickets

Universal Orlando Resort Theme Park Tickets (US & Canada)

CA $247
per adult
86% of travellers recommend
Universal Orlando Resort Theme Park Tickets (US & Canada)
Aquatica Orlando

Aquatica Orlando

CA $82
per traveller
86% of travellers recommend
Aquatica Orlando
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

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

CA $48
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
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.