Windward Cay Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ฿27,000 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Plan, book, and manage your trip all in one place

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 theme park with a large rock formation, Old-Town sign, and various food and restaurant signs.

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

Top hotels in Windward Cay

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 ฿5,624 per night from 14 Jul to 15 Jul
฿5,624
฿6,327 total
14 Jul - 15 Jul
includes taxes & fees
9.2/10 Wonderful! (6,031 reviews)
"Amazing rooms amazing pool! Checking was easy only a few minutes rooms are very spacious all the amenities are great! No complaints that was very friendly"

Reviewed on 7 Jul 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
The price is ฿6,456 per night from 3 Aug to 4 Aug
฿6,456
฿9,098 total
3 Aug - 4 Aug
includes taxes & fees
8/10 Very good! (10,361 reviews)
"Family friendly. I would definitely stay there agian."

Reviewed on 7 Jul 2026

The Grove Resort & Water Park Orlando
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 ฿4,992 per night from 19 Jul to 20 Jul
฿4,992
฿5,616 total
19 Jul - 20 Jul
includes taxes & fees
9/10 Wonderful! (7,148 reviews)
"The staff were extremely helpful and friendly and rooms were clean. I’d definitely stay here again"

Reviewed on 7 Jul 2026

Universal's Cabana Bay Beach Resort
See all 52,387 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 1,000,000 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.

Things to do

Universal Orlando Resort Theme Park Tickets

Universal Orlando Resort Theme Park Tickets

฿5,388
per adult
78% of travellers recommend
Universal Orlando Resort Theme Park Tickets
"Drawn to Life" presented by Cirque du Soleil and Disney

Drawn to Life presented by Cirque du Soleil and Disney

฿2,791
per adult
96% of travellers recommend
Drawn to Life presented by Cirque du Soleil and Disney
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

฿1,265
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.