Windward Cay Holidays from AU$2,191

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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.
Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Price was AU$3,439, price is now AU$2,191 per person
AU$2,191
per person
24 Feb - 3 Mar
found 6 hours ago
Return flight included
Sydney (SYD) to Orlando (MCO)
9.2/10 Wonderful! (2,232 reviews)
The room was spotless, the staff was wonderful and the location was so convenient. We had a toddler with us so being attached to the mall made it so easy for us to spend the evening outside the hotel room but not having to drive around either. The hotel was so nice, if we find ourselves back in Orlando we will stay here again

Reviewed on 11 Dec 2025

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

4 out of 5
Price was AU$4,707, price is now AU$2,996 per person
AU$2,996
per person
24 Feb - 3 Mar
found 21 hours ago
Return flight included
Sydney (SYD) to Orlando (MCO)
9.2/10 Wonderful! (1,001 reviews)
Hot tub didn’t work. Called and a person came and solved the running problem. But the next day it didn’t work again. Very poor since we rented because of the hot tub was included.

Reviewed on 9 Dec 2025

Reunion Resort & Golf Club

Reunion Resort & Golf Club

5 out of 5
Reunion
Price was AU$3,374, price is now AU$2,460 per person
AU$2,460
per person
24 Feb - 3 Mar
found 6 hours ago
Return flight included
Sydney (SYD) to Orlando (MCO)
8.8/10 Excellent! (1,422 reviews)
Staff were lovely at check in and was VERY happy with the spacious accommodations for our family. However, simple and cheap updates to room and restaurants could really be used - I.e. paint refreshing, cleaning pictures hanging in hallways that have splatter marks of something on them, caulking replacement, fixing cabinets not closing or terribly askew, making sure TVs and remotes work, etc

Reviewed on 1 Dec 2025

Embassy Suites by Hilton Orlando International Dr Conv Ctr

Embassy Suites by Hilton Orlando International Dr Conv Ctr

3.5 out of 5
International Drive District
Price was AU$3,549, price is now AU$2,616 per person
AU$2,616
per person
24 Feb - 3 Mar
found 6 hours ago
Return flight included
Sydney (SYD) to Orlando (MCO)
8.4/10 Very Good! (1,008 reviews)
Yes yes the room was great, the view was fantastic and the staff were very polite.

Reviewed on 6 Dec 2025

WorldQuest Orlando Resort

WorldQuest Orlando Resort

4 out of 5
Price was AU$3,201, price is now AU$2,374 per person
AU$2,374
per person
24 Feb - 3 Mar
found 6 hours ago
Return flight included
Sydney (SYD) to Orlando (MCO)
8.4/10 Very Good! (4,017 reviews)
Kitchen was full of kitchen item’s I like a lot

Reviewed on 10 Dec 2025

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
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International Drive District

1 out of top 10 points of interest in this area

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

DoubleTree by Hilton Hotel Orlando at SeaWorld

DoubleTree by Hilton Hotel Orlando at SeaWorld

4 out of 5
10100 International Drive Orlando FL
Fully refundableReserve now, pay when you stay
The price is AU$153 per night from 18 Dec to 19 Dec
AU$153
18 Dec - 19 Dec
includes taxes & fees
7.4/10 Good! (6,227 reviews)
Great location friendly staff

Reviewed on 9 Dec 2025

DoubleTree by Hilton Hotel Orlando at SeaWorld
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 AU$225 per night from 15 Dec to 16 Dec
AU$225
15 Dec - 16 Dec
includes taxes & fees
8.8/10 Excellent! (5,714 reviews)
Room in very good shape as was the common space. Food is pretty good for the price.

Reviewed on 10 Dec 2025

Universal's Cabana Bay Beach Resort
Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

3 out of 5
9000 International Drive Orlando FL
Fully refundableReserve now, pay when you stay
The price is AU$112 per night from 18 Dec to 19 Dec
AU$112
18 Dec - 19 Dec
includes taxes & fees
8.4/10 Very Good! (5,367 reviews)
Convenient, clean and friendly staff

Reviewed on 9 Dec 2025

Rosen Inn at Pointe Orlando
See all 53,973 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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Frequently asked questions

How much does a Windward Cay holiday package cost?
Tailor make your Windward Cay holiday package from just AU$2,191. 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(48 reviews)

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

Universal Studios Florida
Universal Studios Florida® which includes a city, street scenes and rides

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

Scenic 30 Minute Airboat Tour

Scenic 30 Minute Airboat Tour

AU$59
per adult
100% of travellers recommend
Scenic 30 Minute Airboat Tour
Walt Disney World® Resort Theme Park Tickets

Walt Disney World® Resort Theme Park Tickets

AU$299
per adult
Walt Disney World® Resort Theme Park Tickets
WonderWorks All Access After Dark

WonderWorks All Access After Dark

AU$43
per traveller
84% of travellers recommend
WonderWorks All Access After Dark
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.