Windward Cay Holidays

Book a Hotel + Flight or Car together to unlock savings

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

Visitors to International Drive District rave about its breathtaking beach views, exciting theme parks and popular shops. You might also want to make some time to see Aquatica or The Orlando Eye at ICON Park while you're exploring the neighbourhood.

Find hotels in International Drive District

Top hotels in Windward Cay

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 2.441.883 ₫ per night from 10 Sept to 11 Sept
2.441.883 ₫
2.747.118 ₫ total
10 Sept - 11 Sept
includes taxes & fees
DoubleTree by Hilton at the Entrance to Universal Orlando
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 2.297.284 ₫ per night from 21 Sept to 22 Sept
2.297.284 ₫
2.584.445 ₫ total
21 Sept - 22 Sept
includes taxes & fees
8.8/10 Excellent! (2,948 reviews)
"Onsite 9 hole golf course was nice. The rooms were simple but clean. We had a nice view of hole 5 on the course. I liked the screened in back patio . The pools were clean and refreshing in the 100 degree days we were there . My son especially liked the pool that played movies. The food was good. ..."

Reviewed on 27 Aug 2025

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
The price is 3.742.552 ₫ per night from 3 Sept to 4 Sept
3.742.552 ₫
4.210.371 ₫ total
3 Sept - 4 Sept
includes taxes & fees
Universal's Cabana Bay Beach Resort
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.

Frequently asked questions

How much does a Windward Cay holiday package cost?
Tailor make your Windward Cay holiday 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 1null000null000 hotels throughout the world, your Windward Cay holiday 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 holiday 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 neighbourhood'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 holiday?
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 holiday package is the easiest way to organise 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 holiday package?
Your situation can change unexpectedly, so yes, you can. You may be able to change or cancel your Windward Cay holiday 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.

Popular places to visit

Walt Disney World® Resort

Walt Disney World® Resort

Enjoy the rides and games at Walt Disney World® Resort and find out why this is a popular theme park in Lake Buena Vista. Discover the top-notch restaurants and entertainment choices in this family-friendly area.

Walt Disney World® Resort
Universal Studios Florida® showing rides, a city and street scenes

Universal Orlando Resort

Enjoy the excitement at Universal Orlando Resort and find out why this is a popular theme park in Orlando. Visit the shops and top-notch restaurants in this family-friendly area.

Universal Orlando Resort
Disney Springs™

Disney Springs™

You can find the perfect gifts to bring home when you visit Disney Springs™, a favourite shopping spot in Lake Buena Vista. Experience the entertainment choices and acclaimed theatre scene in this family-friendly area.

Disney Springs™