Windward Cay Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Windward Cay Vacation Packages
- Westgate Town Center Resort
Jan 9 - Jan 14Westgate Town Center Resort + Flight
Kissimmee5 nights4.0 star property8.4/10 - Very good (2,078 reviews)"Great"Reviewed November 9, 2026Roundtrip • Toronto (YYZ) - Orlando (MCO)YYZ - MCO • Nonstop MCO - YYZ • Nonstop - Margaritaville Cottages Orlando by Vstays with H2O Waterpark
Dec 18 - Dec 23Margaritaville Cottages Orlando by Vstays with H2O Waterpark + Flight
Kissimmee5 nights4.0 star property9.2/10 - Wonderful (1,000 reviews)Roundtrip • Hamilton (YHM) - Orlando (MCO)YHM - MCO • Nonstop MCO - YHM • Nonstop - Westgate Cocoa Beach Resort
Jan 24 - Jan 28Westgate Cocoa Beach Resort + Flight
Cocoa Beach4 nights4.0 star property8.6/10 - Excellent (578 reviews)"The beaches across the street. The pools are nice however I had a room right next to the pool and they play music up until 9:00pm at night. So if you just trying to rest that will not happen. The music just kept playing all day long."Reviewed November 8, 2026Roundtrip • Toronto (YYZ) - Orlando (MCO)YYZ - MCO • Nonstop MCO - YYZ • NonstopCA $1,703CA $966found 1 day agoper traveller - Meliá Orlando Celebration
Jan 15 - Jan 21Meliá Orlando Celebration + Flight
Celebration6 nights4.0 star property8.8/10 - Excellent (1,645 reviews)Roundtrip • Toronto (YTO) - Orlando (MCO)YYZ - MCO • Nonstop MCO - YYZ • NonstopCA $1,659CA $974found 1 day agoper traveller - Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort
Jan 31 - Feb 5Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort + Flight
Kissimmee5 nights2.0 star property9.0/10 - Wonderful (4,108 reviews)Roundtrip • Halifax (YHZ) - Orlando (MCO)YHZ - MCO • Nonstop MCO - YHZ • NonstopCA $1,524CA $946found 18 hours agoper traveller
Where to stay in Windward Cay
Bay Lake
International Drive District
Florida Center
Champions Gate
Reunion
Windward Cay Hotel Deals
Embassy Suites by Hilton Orlando Lake Buena Vista South
Embassy Suites by Hilton Orlando Lake Buena Vista South"Ok"
Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort
Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort"Estuvo excelente"
"It's clean, quiet and the pool and hot tub is very clean and open 24/7"
Radisson Hotel Orlando Lake Buena Vista South
Radisson Hotel Orlando Lake Buena Vista South"No complaints"
Magic Moment Resort & Kids Club, Dazzler Select by Wyndham
Magic Moment Resort & Kids Club, Dazzler Select by Wyndham"I’m not entirely sure how this hotel is classified as 4-stars. It does have nicely renovated lobby. But everything else is a 2-star motel. Our room was very old. Only the sink got renovated. One of two very old ice machines wasn’t working. They did have a fun looking pool area that was about it."
"I only stayed one night but my AC didn’t work and it was so hot in my room. Also my patio door didn’t open. The property was otherwise nice. Being bombarded at check-in about timeshare opportunities was a bit obnoxious. And I know this is an unpopular opinion but the overly, in your face marketing and positive affirmations was a bit much. It was an extremely busy check-in day and I was definitely tired and cranky so take my review with a grain of salt."
"Really nice hotel"
Legacy Vacation Resorts - Kissimmee/Orlando
Legacy Vacation Resorts - Kissimmee/Orlando"I was in a renovated room with poor furniture, leather couches scratched up and table had a piece of cardboard holding up one side of the leg. No breakfast despite what Expedia says"
Frequently Asked Questions
How much does a Windward Cay vacation package cost?
Tailor make your Windward Cay vacation package from just CA $522. 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 vacation 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 vacation 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 neighborhood'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 vacation?
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 vacation package is the easiest way to organize 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 vacation package?
Your situation can change unexpectedly, so yes, you can. You may be able to change or cancel your Windward Cay vacation 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.