Windward Cay Holidays from AU$2,186

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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.
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
per person
22 Apr - 28 Apr
found 4 hours ago
Return flight included
Sydney (SYD) to Orlando (MCO)
7.8/10 Good! (1,482 reviews)
The only thing that I was not too fond of was the water pressure and the hot water. The water pressure was absolutely terrible and with the water being hot it wasn’t. The water wasn’t even like warm

Reviewed on 27 Jan. 2025

Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
per person
22 Apr - 28 Apr
found 4 hours ago
Return flight included
Sydney (SYD) to Orlando (MCO)
8.4/10 Very Good! (1,001 reviews)
A last minute reservation at a great price and a great location.

Reviewed on 30 Jan. 2025

Reunion Resort & Golf Club

Reunion Resort & Golf Club

5 out of 5
Reunion
per person
22 Apr - 28 Apr
found 4 hours ago
Return flight included
Sydney (SYD) to Orlando (MCO)
8.6/10 Excellent! (1,210 reviews)
So luxurious and very well decorated! We enjoyed feeling so comfortable and it was super clean! Staff was so knowledgeable and very accommodating. Definitely coming back!!!

Reviewed on 10 Jan. 2025

ette hotel

ette hotel

5 out of 5
per person
22 Apr - 28 Apr
found 1 day ago
Return flight included
Sydney (SYD) to Orlando (MCO)
9.8/10 Exceptional! (249 reviews)
This hotel is amazing for family

Reviewed on 7 Jan. 2025

Margaritaville Cottages Orlando by VStays

Margaritaville Cottages Orlando by VStays

4 out of 5
per person
22 Apr - 28 Apr
found 1 day ago
Return flight included
Sydney (SYD) to Orlando (MCO)
9/10 Wonderful! (1,007 reviews)
Very nice area, quiet, and beautiful villas. Villas could be cleaner and staff could be friendlier. Overall had a nice and relaxing stay.

Reviewed on 29 Jan. 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
Universal Studios Florida® featuring night scenes, a city and signage

Florida Center

2 out of top 10 points of interest in this area

If you're spending some time in Florida Center, Universal Orlando Resort and Universal Studios Florida are top sights worth seeing.

Find hotels in Florida Center

Our pick of the best Windward Cay Hotel Deals

Rosen Inn Lake Buena Vista
Rosen Inn Lake Buena Vista
3.5 out of 5
8442 Palm Parkway, Orlando, FL
The price is AU$124 per night from 23 Feb to 24 Feb
AU$124
includes taxes & fees
23 Feb - 24 Feb
8.2/10 Very Good! (4,630 reviews)
"Nice place at a reasonable price."

Reviewed on 30 Jan. 2025

Rosen Inn Lake Buena Vista
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$369 per night from 9 Feb to 10 Feb
AU$369
includes taxes & fees
9 Feb - 10 Feb
8/10 Very Good! (6,814 reviews)
"Hello my name is Juan Triana I was staying from Friday the 24th to Sunday the 26 th in room 3531 where everything was excellent, I left some sunglasses in the room , I could keep them to pick them up Let me know please thanks"

Reviewed on 29 Jan. 2025

The Grove Resort & Water Park 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$505 per night from 12 Feb to 13 Feb
AU$505
includes taxes & fees
12 Feb - 13 Feb
9.2/10 Wonderful! (3,147 reviews)
"Pre flight excellent"

Reviewed on 28 Jan. 2025

Hyatt Regency Orlando International Airport
See all 52,082 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Windward Cay holiday package cost?
Tailor make your Windward Cay holiday package from just AU$2,186. 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® 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
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

Activities

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

AU$128
per traveller
84% of travellers recommend
LEGOLAND® Florida Tickets
Orlando: Train Transfer to Miami

Orlando: Train Transfer to Miami

AU$79
per adult
100% of travellers recommend
Orlando: Train Transfer to Miami
2014_AQ_KatasKookaburraCove_D4D_0772.jpg

Aquatica Orlando

AU$87
per traveller
82% of travellers recommend
Aquatica Orlando
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.