Windward Cay Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 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
Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was €998, price is now €659 per person
€659
per person
17 Sept - 24 Sept
found 7 hours ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
9/10 Wonderful! (3,664 reviews)
Air conditioning was great along with the shower. Would stay again!

Reviewed on 11 Jul 2026

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Save 100% on your flight
Price was €1,609, price is now €816 per person
€816
per person
17 Sept - 24 Sept
found 7 hours ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
9/10 Wonderful! (1,275 reviews)
Family oriented

Reviewed on 10 Jul 2026

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was €1,102, price is now €673 per person
€673
per person
17 Sept - 24 Sept
found 7 hours ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
8.2/10 Very good! (1,979 reviews)
Everything was great thanks

Reviewed on 12 Jul 2026

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was €1,191, price is now €740 per person
€740
per person
17 Sept - 24 Sept
found 7 hours ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
8.4/10 Very good! (6,621 reviews)
.

Reviewed on 12 Jul 2026

Lake Buena Vista Resort Village & Spa

Lake Buena Vista Resort Village & Spa

4 out of 5
Price was €1,198, price is now €896 per person
€896
per person
17 Sept - 24 Sept
found 7 hours ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
8.4/10 Very good! (10,103 reviews)
Loved the condo and spa services. Did have to talk with a lady trying to sell time shares. She was nice until I declined and had to decline multiple times, she was very pushy. After about the 4th time I politely declined the time share meeting she became very rude and short. I was no longer anyone she wanted to have in her presence. I’m just glad I didn’t have to deal with her long, I probably would have looked for another place to stay had that been the case.

Reviewed on 11 Jul 2026

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 traditional Japanese torii gate with a dragon sculpture in front, overlooking a calm lake with a distant view of a spherical building.

Bay Lake

3 out of top 10 points of interest in this area
4.5/5(64 area reviews)

Exciting theme parks plentiful wildlife and top sights from Epcot® to Walt Disney World® Resort – discover Bay Lake, a destination also famous for its entertainment.

Find hotels in Bay Lake

Top hotels in Windward Cay

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 €184 per night from 3 Aug to 4 Aug
€184
3 Aug - 4 Aug
includes taxes & fees
9.4/10 Exceptional! (4,326 reviews)
"Super convenient for early morning flights and helpful staff."

Reviewed on 12 Jul 2026

Hyatt Regency Orlando International Airport
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 €167 per night from 15 Jul to 16 Jul
€167
15 Jul - 16 Jul
includes taxes & fees
9.2/10 Wonderful! (6,082 reviews)
"One of my best experiences, staff was quick to respond to my family needs. The room is the size of 2 bedroom apt, with all the nesscary items avaliable."

Reviewed on 12 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
Fully refundableReserve now, pay when you stay
The price is €225 per night from 10 Aug to 11 Aug
€225
10 Aug - 11 Aug
includes taxes & fees
8/10 Very good! (10,423 reviews)
"Review: Building 1 Stay - Spacious but Poorly Maintained ​My overall stay was just okay. While there were a few bright spots, I would not stay here again due to major cleanliness and noise issues. ​Regarding the positives, the two-bedroom suite was very roomy and comfortable. The customer service ..."

Reviewed on 12 Jul 2026

The Grove Resort & Water Park Orlando
See all 52,177 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 €659. 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

Walt Disney World® Resort Theme Park Tickets

Walt Disney World® Resort Theme Park Tickets

€158
per adult
88% of travellers recommend
Walt Disney World® Resort Theme Park Tickets
Magic Kingdom® Park

Walt Disney World® Theme Park Tickets

€684
per adult
88% of travellers recommend
Walt Disney World® 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

€29
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.