Windward Cay Holidays

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Price found within the past 48 hours. Click for updated prices.
Hilton Orlando Buena Vista Palace - Disney Springs® Area

Hilton Orlando Buena Vista Palace - Disney Springs® Area

4 out of 5
Price was HK$5,890, price is now HK$5,004 per person
HK$5,004
per person
15 Aug - 19 Aug
found 11 hours ago
Return direct flight included
Toronto (YTO) to Orlando (MCO)
8.6/10 Excellent! (1,878 reviews)
Ese hotel es magnífico para vacacionar muy buen servicio limpieza y muy cerca de los parques

Reviewed on 14 Jun 2026

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was HK$7,684, price is now HK$5,546 per person
HK$5,546
per person
15 Aug - 19 Aug
found 11 hours ago
Return direct flight included
Toronto (YTO) to Orlando (MCO)
9.6/10 Exceptional! (1,131 reviews)
Clean room, nice staff

Reviewed on 21 Jun 2026

AC Hotel by Marriott Orlando Downtown

AC Hotel by Marriott Orlando Downtown

2.5 out of 5
Downtown Orlando
Price was HK$6,630, price is now HK$5,430 per person
HK$5,430
per person
15 Aug - 19 Aug
found 11 hours ago
Return direct flight included
Toronto (YTO) to Orlando (MCO)
9.2/10 Wonderful! (1,255 reviews)
The staff was amazing and helpful! Great place to stay if you are attending an event at the Kia Center!

Reviewed on 21 Jun 2026

Wyndham Grand Orlando Resort Bonnet Creek

Wyndham Grand Orlando Resort Bonnet Creek

4 out of 5
Price was HK$6,179, price is now HK$5,211 per person
HK$5,211
per person
15 Aug - 19 Aug
found 11 hours ago
Return direct flight included
Toronto (YTO) to Orlando (MCO)
8.8/10 Excellent! (2,980 reviews)
Decent property, with well appointed rooms. Somewhat pushy time-share salesman in reception, which felt horribly out of place. Shower in the bathroom was either stone cold or boiling hot and would literally be a danger to small children. A good resort that could be great with some minor tweaks.

Reviewed on 20 Jun 2026

Landing Furnished Apartments near Lake Apopka

Landing Furnished Apartments near Lake Apopka

4 out of 5
Price was HK$6,321, price is now HK$5,438 per person
HK$5,438
per person
15 Aug - 19 Aug
found 11 hours ago
Return direct flight included
Toronto (YTO) to Orlando (MCO)
No reviews

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

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 HK$1,324 per night from 14 Jul to 15 Jul
HK$1,324
HK$1,490 total
14 Jul - 15 Jul
includes taxes & fees
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
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 refundable
The price is HK$769 per night from 12 Jul to 13 Jul
HK$769
HK$865 total
12 Jul - 13 Jul
includes taxes & fees
8.6/10 Excellent! (6,935 reviews)
"Perfection"

Reviewed on 20 Jun 2026

DoubleTree by Hilton at the Entrance to Universal Orlando
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 HK$1,560 per night from 24 Jun to 25 Jun
HK$1,560
HK$2,187 total
24 Jun - 25 Jun
includes taxes & fees
8/10 Very Good! (10,232 reviews)
"Abitaciones muy amplias la pasamos bien volveria"

Reviewed on 21 Jun 2026

The Grove Resort & Water Park Orlando
See all 52,356 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 vacation package cost?
Tailor make your Windward Cay vacation package from just HK$5,004. 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.

Popular places to visit

Walt Disney World® Resort

Walt Disney World® Resort

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

Movie sets and thrill rides combine to create this internationally acclaimed theme park.

Universal Studios Florida
Universal Orlando Resort

Universal Orlando Resort

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

Universal Orlando Resort

Things to do

Universal Orlando Resort Express Passes

Universal Orlando Resort Express Passes

HK$1,669
per traveller
80% of travellers recommend
Universal Orlando Resort Express Passes
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

HK$302
per traveller
86% of travellers recommend
LEGOLAND® Florida 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

HK$242
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.