Windward Cay Holidays from AU$2,756

Book a Hotel + Flight or Car together to unlock savings

Your Windward Cay Holiday

Take all the hassle out of organising your next break with a Windward Cay holiday package. Soak in the sights and sounds of this captivating neighbourhood and enjoy what it has to offer. Kick start your trip to Windward Cay by checking out nearby attractions such as Old Town, Give Kids the World Village and Medieval Times. Expedia can help you turn your ideal Windward Cay holiday into reality, whatever your budget or travel plans.

Top Holiday Package Deals in Windward Cay

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Orlando Airport

Courtyard by Marriott Orlando Airport

3 out of 5
Airport North
Price was AU$2,846, price is now AU$2,756 per person
AU$2,756
per person
21 June - 25 June
found 1 hour ago
Return flight included
Sydney (SYD) to Orlando (MCO)
8.6/10 Excellent! (1,008 reviews)
Everything was amazing except for not having a jacuzzi.

Reviewed on 13 May 2026

Mission to Mars

Mission to Mars

4 out of 5
Loughman
Price was AU$11,667, price is now AU$10,820 per person
AU$10,820
per person
21 June - 25 June
found 1 hour ago
Return flight included
Sydney (SYD) to Orlando (MCO)
No reviews
Residentas Citrus Ridge

Residentas Citrus Ridge

4 out of 5
Price was AU$3,220, price is now AU$3,004 per person
AU$3,004
per person
21 June - 25 June
found 1 hour ago
Return flight included
Sydney (SYD) to Orlando (MCO)
No reviews
Avanti International Resort

Avanti International Resort

4 out of 5
International Drive District
Price was AU$2,982, price is now AU$2,800 per person
AU$2,800
per person
21 June - 25 June
found 1 hour ago
Return flight included
Sydney (SYD) to Orlando (MCO)
7.8/10 Good! (4,517 reviews)
The room was clean and updated. The pool was really nice. Location was convenient and close to many restaurants annd shopping. Really close to the parks. We really enjoyed our stay.

Reviewed on 18 May 2026

DoubleTree by Hilton Orlando Airport

DoubleTree by Hilton Orlando Airport

4 out of 5
Airport North
Price was AU$2,971, price is now AU$2,815 per person
AU$2,815
per person
21 June - 25 June
found 1 hour ago
Return flight included
Sydney (SYD) to Orlando (MCO)
8.6/10 Excellent! (2,337 reviews)
Last time I stayed I got fee breakfast buffet for Expedia gold. I didn’t receive any perks this visit at all.

Reviewed on 17 May 2026

Our guide on 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

Our pick of the best 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 AU$225 per night from 17 June to 18 June
AU$225
17 June - 18 June
includes taxes & fees
9.2/10 Wonderful! (5,507 reviews)
"Clean room. The room was so spacious and well maintained. I do recommend it to others."

Reviewed on 18 May 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 AU$313 per night from 25 May to 26 May
AU$313
25 May - 26 May
includes taxes & fees
9.4/10 Exceptional! (4,169 reviews)
"So convenient! We had super early flights and we just took the elevator down and we were right there at the TSA line."

Reviewed on 18 May 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
Fully refundableReserve now, pay when you stay
The price is AU$337 per night from 21 May to 22 May
AU$337
21 May - 22 May
includes taxes & fees
8/10 Very Good! (9,909 reviews)
"Everything was accurate to the photos, just have to pay an 300$ incidental fee that wasn’t shared on the website but they give it back quick once you check out."

Reviewed on 18 May 2026

The Grove Resort & Water Park Orlando
See all 53,207 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.
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beach holidays
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Frequently asked questions

How much does a Windward Cay holiday package cost?
Tailor make your Windward Cay holiday package from just AU$2,756. 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.

Discover the most popular places to visit in Windward Cay

Walt Disney World® Resort

Walt Disney World® Resort

4.5/5(9 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
Universal Studios Florida

Universal Studios Florida

4.5/5(49 reviews)

Exhilarating rides and world class film sets are brought together to create this outstanding world-renowned theme park.

Universal Studios Florida
Universal Orlando Resort

Universal Orlando Resort

4.5/5(30 reviews)

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

Universal Orlando Resort

Activities

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

AU$53
per traveller
86% of travellers recommend
LEGOLAND® Florida Tickets
Walt Disney World® Resort Theme Park Tickets

Walt Disney World® Resort Theme Park Tickets

AU$260
per adult
Walt Disney World® Resort Theme Park Tickets
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

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

AU$38
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.