Windward Cay Holidays from £584
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Your Windward Cay Holiday
Book a Windward Cay holiday package and discover the atmosphere and rhythm of this interesting neighbourhood. With all your travel plans taken care of, the only thing you need to worry about here is having a good time. Wondering where to go during your trip to Windward Cay? Nearby attractions such as Old Town, Fun Spot America and Medieval Times are good places to start. No matter what your dream Windward Cay holiday looks like, you can make it a reality with Expedia.
Price found within the past 48 hours. Click for updated prices.
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
£968
per person
22 Nov - 28 Nov
found 1 day ago
Return direct flight included
London (LHR) to Orlando (MCO)
9.2/10 Wonderful! (1,003 reviews)
We stayed in one of the cottages and it was just perfect. The fully equipped kitchen downstairs with a master suite was perfect for my parents. I appreciated having the laundry upstairs with the other bedrooms.
The staff at the main building were so helpful with our packages and printing documents for us.
Unfortunately we had a very busy week and could not enjoy the wonderful amenities of the resort.
Overall, a great selection and would start again!
Reviewed on 25 Sept 2026
Westgate Palace Hotel / Universal / I-Drive
International Drive District
£660
per person
2 Dec - 8 Dec
found 1 day ago
Return flight included
London (LGW) to Orlando (MCO)
9/10 Wonderful! (1,330 reviews)
Got charged $200 and change for an 8 day stay for resort fees. No housekeeping in 8 days, bar closed all day every day, 2 food outlets closed by 3pm along with Starbucks so no resort facilities
Reviewed on 29 Sept 2026
The Delaney Hotel
South Orange
£794
per person
2 Dec - 8 Dec
found 1 day ago
Return flight included
London (LGW) to Orlando (MCO)
9.6/10 Exceptional! (1,214 reviews)
Super happy with our stay. Parking garage has Tesla chargers, plus! Staff was very friendly. Room and hotel were clean. We did not visit the restaurant/bar. I will be staying again and highly recommend!
Reviewed on 29 Sept 2026
Seasons Florida Resort
£601
per person
22 Nov - 28 Nov
found 1 day ago
Return direct flight included
London (LHR) to Orlando (MCO)
9/10 Wonderful! (3,949 reviews)
The staff was absolutely wonderful, we had a week at Disney and we loved the hotel. A lot of restaurants and everything was in close range. My wife and I will be back in February for The Daytona 500 and we can’t wait to already go back!
Reviewed on 29 Sept 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
Bay Lake
3 out of top 10 points of interest in this area
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.
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.
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.
Champions Gate
Ample dining options and top golf courses are well-reviewed features of Champions Gate. Make a stop by top sights like ChampionsGate Golf Club while you're exploring the area.
Downtown Orlando
One of the most popular neighborhoods in Florida, this bustling area is full of art galleries, shops, bars and restaurants.
Top hotels in Windward Cay
Hyatt Regency Orlando International Airport
9300 Jeff Fuqua Boulevard Orlando FL
Fully refundableReserve now, pay when you stay
£186
26 Oct - 27 Oct
includes taxes & fees
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr Orlando FL
Fully refundableReserve now, pay when you stay
£116
20 Oct - 21 Oct
includes taxes & fees
9.2/10 Wonderful! (6,890 reviews)
"Love it"
Reviewed on 29 Sept 2026
Marriott's Grande Vista
5925 Avenida Vista Orlando FL
Fully refundableReserve now, pay when you stay
£81
20 Oct - 21 Oct
includes taxes & fees
9/10 Wonderful! (5,067 reviews)
"Food was to expensive! Hardly no smoking areas outside. Alcohol was very high priced also."
Reviewed on 29 Sept 2026
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 travel package cost?
Get set to book, because a trip to Windward Cay starts from an enticing £584. When you bundle your hotels, flights and car rentals into a travel package, you'll enjoy the best prices.
If I'm not able to travel, can I cancel my Windward Cay travel package?
Because we understand life can throw you a few curveballs, the answer is yes. To learn more, check out our Customer Service Portal. But generally speaking, if you've booked your Windward Cay travel package in the last 24 hours, you may be able to change or cancel it for free. Your airline, hotel or car rental company may charge a fee if your booking is older than that.
How do I get a cheap travel package to Windward Cay?
It's easy. Just bundle everything together. Flights, rental cars and hotels — combine whatever you need into a Windward Cay travel package to save loads of cash. Score even more deals when you add extras such as experiences or tours to your booking. But that's not the only impressive part. You have the flexibility to tailor your trip your way. We offer over 550 airlines and 1,000,000 hotels across the world, so that everyone has a chance to travel and fulfil those holiday fantasies.
Does Expedia offer Book Now, Pay Later Windward Cay holidays?
Expedia has partnered with online lender Klarna to make your next break easier on your wallet. Paying in instalments means you can spread the costs of your next big holiday, leaving you with more cash to spend while you're travelling. Klarna has several payment plans to choose from, so you're sure to find one that suits your budget. Browse these flexible payment options:
- Pay monthly holidays: If paying bite-sized amounts each month is what works best for you, Klarna offers just that! Paying in convenient monthly instalments will make your getaway dreams come true.
- Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay for your holiday in multiple transactions.
- Low deposit holidays: If paying a small percentage of your getaway (rather than the total upfront) makes it easier to hit that "book now" button, consider a low deposit holiday payment plan with Klarna.
Where should I stay in Windward Cay?
Book a room just around the corner from ChampionsGate Golf Club, one of this neighbourhood's most well-known attractions. It's the perfect place for those eager to check out the local sights.
What are the top hotels in Windward Cay?
Get your trip off to a great start by reserving a room at Magic Moment Resort and Kids Club. It's one of most sought-after hotels in Windward Cay. Another cosy option is Red Lion Hotel Orlando Lake Buena Vista South.
How far in advance should I book my Windward Cay holiday?
While prices do change, we generally recommend booking your seats as early as possible. Many international airfares are found on Expedia up to 12 months in advance. If you're booking late, you may still get lucky. Cheaper tickets to Windward Cay sometimes appear in the weeks prior to departure.
What does an Expedia Windward Cay travel package include?
Packages include flights, rental cars and hotels, but you can combine any of them to create your dream Windward Cay getaway. You can also add on a few experiences and activities once you've made your booking. You're in charge! When you combine your bookings with Expedia, you'll get access to discounts you won't find elsewhere.
What should I know before booking a Windward Cay travel package?
So many places to go, so many things to see. With a travel package, you can check more of them off your list. Bundle your hotels, rental cars and flights and make big savings.
Can I choose my airline with a Windward Cay Expedia travel package?
Yes, and with more than 550 airlines to pick from across the globe, it's all about choice. Scroll through the available options and find out which airline suits your needs and budget.
Things to do
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
£23
per adult
92% of travellers recommend
Drawn to Life presented by Cirque du Soleil and Disney
£63
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.