Windward Cay Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Price found within the past 48 hours. Click for updated prices.
  • Outdoor pool, pool umbrellas
    Jul 3 - Jul 6

    Westgate Palace Hotel / Universal / I-Drive + Flight

    International Drive District
    3 nights
    4.0 star property
    8.8/10 - Excellent (1,253 reviews)
    "Our room was extremely clean and quiet. It was very close to Universal Studios. Highly recommend!"
    Reviewed May 16, 2026
    Roundtrip • Toronto (YYZ) - Orlando (MCO)
    YYZ - MCO • 1 stop MCO - YYZ • 1 stop
    CA $1,379
    CA $795
    per traveller
    found 1 day ago
    Westgate Palace Hotel / Universal / I-Drive
  • Water park
    Jul 26 - Aug 9

    Westgate Town Center Resort + Flight

    Kissimmee
    14 nights
    4.0 star property
    8.2/10 - Very good (1,729 reviews)
    "This family friendly resort offers first class amenities and hospitality at a budget friendly price. The accommodations were clean and had everything we needed already there."
    Reviewed May 18, 2026
    Roundtrip • St. John's (YYT) - Orlando (MCO)
    YYT - MCO • 2 stops MCO - YYT • 2 stops
    CA $2,904
    CA $1,603
    per traveller
    found 1 day ago
    Westgate Town Center Resort
  • Exterior
    Jun 28 - Jul 5

    Boardwalk Inn and Suites + Flight

    Davis
    7 nights
    2.5 star property
    8.4/10 - Very good (1,838 reviews)
    "Staff was very helpful. Clean room. Dining within walking distance. Oceanfront very nice."
    Reviewed May 16, 2026
    Roundtrip • Toronto (YYZ) - Orlando (MCO)
    YYZ - MCO • 1 stop MCO - YYZ • 1 stop
    CA $1,408
    CA $900
    per traveller
    found 2 hours ago
    Boardwalk Inn and Suites
  • Front of property
    Jul 29 - Aug 5

    Palazzo Lakeside Hotel + Flight

    Kissimmee
    7 nights
    3.0 star property
    8.2/10 - Very good (5,149 reviews)
    "Todos muy amables y gentiles"
    Reviewed May 17, 2026
    Roundtrip • Montreal (YUL) - Orlando (MCO)
    YUL - MCO • 1 stop MCO - YUL • 1 stop
    CA $1,274
    CA $831
    per traveller
    found 11 hours ago
    Palazzo Lakeside Hotel
  • Sundeck
    Aug 3 - Aug 7

    Westgate Cocoa Beach Resort + Flight

    Cocoa Beach
    4 nights
    4.0 star property
    8.6/10 - Excellent (548 reviews)
    "Everuthing was perfect"
    Reviewed May 17, 2026
    Roundtrip • Toronto (YYZ) - Orlando (MCO)
    YYZ - MCO • 1 stop MCO - YYZ • 1 stop
    CA $2,064
    CA $1,360
    per traveller
    found 1 day ago
    Westgate Cocoa Beach Resort

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 District

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.

Find hotels in International Drive District

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 $197 per night from Jun 16 to Jun 17
CA $197
CA $221 total
Jun 16 - Jun 17
includes taxes & fees
9.2/10 Wonderful! (5,513 reviews)
"Me gustó mucho mi estadía y la limpieza muy bien me encantó volvería a hospedarme 10/10"

Reviewed on May 18, 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/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 $279 per night from May 25 to May 26
CA $279
CA $314 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (4,172 reviews)
"Grea TY"

Reviewed on May 18, 2026

Hyatt Regency Orlando International Airport
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue Winter Garden FL
The price is CA $227 per night from May 21 to May 22
CA $227
CA $331 total
May 21 - May 22
includes taxes & fees
8/10 Very Good! (9,921 reviews)
"Very extremely clean. One of the best resorts I’ve stayed in. Staff was good, some could have better attitudes but other than that I loved it here. Will be recommending"

Reviewed on May 18, 2026

The Grove Resort & Water Park Orlando
See all 53,369 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
Family Vacations
Family Vacations

Frequently asked questions

How much does a Windward Cay vacation package cost?
Tailor make your Windward Cay vacation package from just . 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 Orlando Resort

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 Theme Park Tickets

Universal Orlando Resort Theme Park Tickets (US & Canada)

CA $221
per adult
86% of travellers recommend
Universal Orlando Resort Theme Park Tickets (US & Canada)
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 $37
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

CA $53
per traveller
86% 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.