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.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Save 100% on your flight
per person
Aug. 11 - Aug. 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8/10 Very Good! (4,086 reviews)
Second time staying at this property and it meets my expectations. Very helpful and kind staff. Conveniently located around restaurants, retail, grocery stores, and theme parks

Reviewed on Jun. 20, 2024

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Florida Center
Save 100% on your flight
per person
Aug. 11 - Aug. 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8.4/10 Very Good! (999 reviews)
Property was very nice

Reviewed on Jun. 16, 2024

ette hotel

ette hotel

4.5 out of 5
Save 100% on your flight
per person
Aug. 12 - Aug. 16
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Orlando (MCO)
9.8/10 Exceptional! (151 reviews)
There are no words to express my experience! It was fantastic to spend my birthday at this Hotel! Thanks thanks thanks

Reviewed on Jun. 16, 2024

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
per person
Aug. 11 - Aug. 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
7.8/10 Good! (3,733 reviews)
2 bedroom suite was perfect for 4 people. Plenty of space and everything you need for a vacation. Great property. Didn’t like that you needed to pay $20 per person per day to use their water park (and it was really small and not worth it). Overall I would recommend especially for families with older kids.

Reviewed on Jun. 19, 2024

Seasons Florida Resort

Seasons Florida Resort

2 out of 5
per person
Aug. 11 - Aug. 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8.8/10 Excellent! (1,894 reviews)
Staff was friendly and helpful

Reviewed on Jun. 19, 2024

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
Downtown Orlando

Downtown Orlando

3.5/5(17 area reviews)

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.

Find hotel + flight trips in Downtown Orlando

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 Jul. 3 to Jul. 4
CA $139
CA $156 total
includes taxes & fees
Jul 3 - Jul 4
8.2/10 Very Good! (6,285 reviews)
"Great piece of property"

Reviewed on Jun. 20, 2024

DoubleTree by Hilton at the Entrance to Universal 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 $333 per night from Jun. 24 to Jun. 25
CA $333
CA $443 total
includes taxes & fees
Jun 24 - Jun 25
8.2/10 Very Good! (5,593 reviews)
"Enjoyed staying at the Grove the only thing i can say is make sure you are aware of additional fees that you will have to pay on top of the overall booking. After checking in we had to pay an additional $40 per night for resort fees and also parking is $25 per night even though the parking is attached ..."

Reviewed on Jun. 18, 2024

The Grove Resort & Water Park Orlando
Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel
Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel
3.5 out of 5
14500 Continental Gateway, Orlando, FL
Fully refundable
The price is CA $125 per night from Jun. 26 to Jun. 27
CA $125
CA $208 total
includes taxes & fees
Jun 26 - Jun 27
7.2/10 Good! (23 reviews)
"Great"

Reviewed on Jun. 19, 2024

Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel
See all 52,728 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

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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 $439. 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

Image for Walt Disney World® Resort

Walt Disney World® Resort

4.5/5(226 reviews)

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
Image for Universal Studios Florida

Universal Studios Florida

4.5/5(988 reviews)

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

Universal Studios Florida
Image for Universal Orlando Resort

Universal Orlando Resort

4.5/5(399 reviews)

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

Universal Orlando Resort

Things to do

Image for Aquatica Orlando

Aquatica Orlando

CA $65
Per adult
82% of travellers recommend
Aquatica Orlando
Image for Orlando: Museum of Illusions Admission Ticket

Orlando: Museum of Illusions Admission Ticket

CA $42
Per adult
86% of travellers recommend
Orlando: Museum of Illusions Admission Ticket
Image for I-RIDE Trolley Pass

I-RIDE Trolley Pass

CA $9
Per adult
84% of travellers recommend
I-RIDE Trolley Pass
See all activities in Orlando

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.