--- title: "Windward Cay Holidays 2026 from £775 | Expedia.co.uk" description: "Book your ATOL protected Windward Cay holiday today! Enjoy flexibility with our interest-free instalments & book now pay later option. Fully refundable rates on most hotels." canonical: "https://www.expedia.co.uk/Windward-Cay.d553248635976481817.Holidays-City-Breaks" language: en-GB market: GB currency: GBP prices_as_of: 2026-11-14T06:51:48Z --- # Windward Cay Holidays from £775 ![A golf course with a large hotel and residential area.](https://images.trvl-media.com/place/553248635976471221/cd629767-bf91-4c89-9796-72eb15af2f55.jpg?impolicy=fcrop&w=1200&h=300&q=medium) ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to £750 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 Packages with flights are ATOL protected ### 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](https://www.expedia.co.uk/Old-Town-Orlando.d6128179.Attraction), [Fun Spot America](https://www.expedia.co.uk/Fun-Spot-America-Orlando.d553248621532654181.Attraction) and [Medieval Times](https://www.expedia.co.uk/Medieval-Times-Orlando.d6153643.Attraction) are good places to start. No matter what your dream Windward Cay holiday looks like, you can make it a reality with Expedia. ## The Latest Windward Cay Holiday Packages Price found within the past 48 hours. Click for updated prices. Trip length 3 nights4 nights5 nights6-7 nights Stars 5 star4 star & up3 star & up2 star & up Flight class EconomyPremium economyBusinessFirst class Remove all filters - ![A hotel with a pool area, lounge chairs, and a restaurant.](https://images.trvl-media.com/lodging/2000000/1760000/1759600/1759572/24c143e1.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A rooftop bar with outdoor seating, artificial grass, and colorful umbrellas overhead.](https://images.trvl-media.com/lodging/2000000/1760000/1759600/1759572/2ab817e2.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **5 Feb - 10 Feb** ### [Meliá Orlando Celebration + Flight](https://www.expedia.co.uk/go/package/search/FlightHotel/2027-02-05/2027-02-10/?FromAirport=DUB&Destination=MCO&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1759572&dealMarker=&paandie=true&cabinClass=e) Celebration 5 nights **8.8/10** \- Excellent (1,645 reviews) "Clean and quiet" Reviewed November 13, 2026 Return • Dublin (DUB) - Orlando (MCO) DUB - MCO • 1 stop MCO - DUB • 1 stop [~~£1,197~~](https://www.expedia.co.uk/) **£775** per traveller found 1 day ago - ![A resort with multiple buildings, a central pool area, a beach, and a dock with a boat.](https://images.trvl-media.com/lodging/36000000/35110000/35109100/35109061/f3a6676e.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A two-story building with a balcony, a door, and a sign indicating private residence.](https://images.trvl-media.com/lodging/36000000/35110000/35109100/35109061/163bc88f.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **5 Feb - 10 Feb** ### [Margaritaville Cottages Orlando by Vstays with H2O Waterpark + Flight](https://www.expedia.co.uk/go/package/search/FlightHotel/2027-02-05/2027-02-10/?FromAirport=DUB&Destination=MCO&NumRoom=1&NumAdult=2&NumChild=0&hotelId=35109061&dealMarker=&paandie=true&cabinClass=e) Kissimmee 5 nights **9.2/10** \- Wonderful (1,001 reviews) Return • Dublin (DUB) - Orlando (MCO) DUB - MCO • 1 stop MCO - DUB • 1 stop Save 100% on your flight [~~£1,626~~](https://www.expedia.co.uk/) **£810** per traveller found 1 day ago - ![A stone wall, a brown sofa with orange and yellow cushions, a glass table with a fire feature, and a wooden door with decorative glass panels.](https://images.trvl-media.com/lodging/20000000/19390000/19389600/19389598/ceba7f1d.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A reception desk with a dark wooden panel and illuminated letters spelling "BELAN HOTEL".](https://images.trvl-media.com/lodging/20000000/19390000/19389600/19389598/b671dcdf.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **5 Feb - 10 Feb** ### [The Delaney Hotel + Flight](https://www.expedia.co.uk/go/package/search/FlightHotel/2027-02-05/2027-02-10/?FromAirport=DUB&Destination=MCO&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19389598&dealMarker=&paandie=true&cabinClass=e) South Orange 5 nights **9.6/10** \- Exceptional (1,251 reviews) "Very pretty hotel. The room was clean. The parking was easy. Was very cozy." Reviewed November 12, 2026 Return • Dublin (DUB) - Orlando (MCO) DUB - MCO • 1 stop MCO - DUB • 1 stop Save 100% on your flight [~~£1,301~~](https://www.expedia.co.uk/) **£793** per traveller found 1 day ago - ![A modern hotel lobby with a reception desk, a round coffee table, a sofa, and a large window with curtains.](https://images.trvl-media.com/lodging/2000000/1820000/1813900/1813900/c5ff34ca.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![An outdoor seating area with wicker furniture, a central wooden table, and a red brick wall with potted plants.](https://images.trvl-media.com/lodging/2000000/1820000/1813900/1813900/1492ecfb.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **22 Dec - 28 Dec** ### [Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort + Flight](https://www.expedia.co.uk/go/package/search/FlightHotel/2026-12-22/2026-12-28/?FromAirport=LGW&Destination=MCO&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1813900&dealMarker=&paandie=true&cabinClass=e) Kissimmee 6 nights **9.0/10** \- Wonderful (4,117 reviews) Return • London (LGW) - Orlando (MCO) LGW - MCO • 2 stops MCO - LGW • 2 stops [~~£1,480~~](https://www.expedia.co.uk/) **£990** per traveller found 1 day ago - ![A resort with multiple swimming pools, lounge areas, and a modern building with balconies.](https://images.trvl-media.com/lodging/91000000/90610000/90603800/90603710/9dffefcc.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A rooftop lounge with wicker furniture, round tables, and potted plants.](https://images.trvl-media.com/lodging/91000000/90610000/90603800/90603710/3b75aa5f.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **26 Dec - 31 Dec** ### [Conrad Orlando at Evermore + Flight](https://www.expedia.co.uk/go/package/search/FlightHotel/2026-12-26/2026-12-31/?FromAirport=DUB&Destination=MCO&NumRoom=1&NumAdult=2&NumChild=0&hotelId=90603710&dealMarker=&paandie=true&cabinClass=e) Orlando 5 nights **9.6/10** \- Exceptional (620 reviews) "Perfection! Staff was incredible, felt VIP with every interaction. Beautiful and pristine property." Reviewed November 13, 2026 Return • Dublin (DUB) - Orlando (MCO) DUB - MCO • 2 stops MCO - DUB • 2 stops [~~£2,257~~](https://www.expedia.co.uk/) **£1,590** per traveller found 1 day ago ## Where to stay in Windward Cay Find the best Windward Cay areas for the activities you enjoy most. - [Bay Lake](#) - [International Drive District](#) - [Florida Center](#) - [Champions Gate](#) - [Reunion](#) ![The entrance to the Hollywood Studios area with a large sign and distinctive architecture.](https://images.trvl-media.com/place/6034611/0651c460-1c16-4875-9d82-c8176180500d.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) Photo by Gary Burke [View properties in map for Bay Lake](https://www.expedia.co.uk/Hotel-Search?pwaOverlay=map®ionId=6034611) ### Bay Lake 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. [See properties](https://www.expedia.co.uk/Hotel-Search?regionId=6034611) ![A large Ferris wheel with blue lights, surrounded by a cityscape with illuminated buildings and a tall green tower.](https://images.trvl-media.com/place/619865273516826624/613109b3-69fe-460f-a790-86303e0a5a6f.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [View properties in map for International Drive District](https://www.expedia.co.uk/Hotel-Search?pwaOverlay=map®ionId=6034244) ### 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. [See properties](https://www.expedia.co.uk/Hotel-Search?regionId=6034244) ![A roller coaster at Universal Orlando Resort, featuring a tall palm tree and a clear blue sky.](https://images.trvl-media.com/place/2693/a38bf836-943a-4d3e-a7bb-827a9190adfc.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) Photo by Peter Sutton [View properties in map for Florida Center](https://www.expedia.co.uk/Hotel-Search?pwaOverlay=map®ionId=553248635976479235) ### Florida Center If you're spending some time in Florida Center, Universal Orlando Resort and Universal Studios Florida are top sights worth seeing. [See properties](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976479235) ![A large Ferris wheel with blue lighting, surrounded by a parking lot and buildings.](https://images.trvl-media.com/place/6070422/bf48d0dc-da44-41f0-8b5f-3d3081658aec.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [View properties in map for Champions Gate](https://www.expedia.co.uk/Hotel-Search?pwaOverlay=map®ionId=6070422) ### 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. [See properties](https://www.expedia.co.uk/Hotel-Search?regionId=6070422) ![A golf course with bunkers, water hazards, and a large lake.](https://images.trvl-media.com/place/6126579/e29f47dd-eca6-4743-9733-8e92df605127.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [View properties in map for Reunion](https://www.expedia.co.uk/Hotel-Search?pwaOverlay=map®ionId=6126579) ### Reunion The top golf courses and fun-filled water parks are top of the list for many visitors to Reunion. A stop by Reunion Resort Golf Course or Jack Nicklaus Course might round out your trip. [See properties](https://www.expedia.co.uk/Hotel-Search?regionId=6126579) ## Windward Cay Hotel Deals ### [Embassy Suites by Hilton Orlando Lake Buena Vista South](https://www.expedia.co.uk/Orlando-Hotels-Embassy-Suites-By-Hilton-Orlando-Lake-Buena-Vista-South.h4836993.Hotel-Information) ![A spacious lobby with a leather sofa, a bar area with stools, and a seating area with tables and chairs.](https://images.trvl-media.com/lodging/5000000/4840000/4837000/4836993/8454b71a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 4955 Kyngs Heath Rd, Kissimmee, FL, 34746, US - Location: 1.9 mi from Windward Cay - Star rating: 4/5 - Guest rating: 9.6/10 (Exceptional, 1697 reviews) - Price: £101, includes taxes & fees, 22 Nov - 23 Nov - Review: Breakfast was amazing. The food was hot and fresh. I loved the omelet bar. The public areas were well-maintained. ### [Club Sevilla](https://www.expedia.co.uk/Orlando-Hotels-Club-Sevilla.h8404136.Hotel-Information) ![A pool area with lounge chairs and palm trees, surrounded by a building with a tiled roof.](https://images.trvl-media.com/lodging/9000000/8410000/8404200/8404136/5659a869.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 4646 W Irlo Bronson Memorial Hwy, Kissimmee, FL, 34746, US - Location: 0.5 mi from Windward Cay - Star rating: 3.5/5 - Guest rating: 9/10 (Wonderful, 1001 reviews) - Price: £39, includes taxes & fees, 15 Nov - 16 Nov - Review: We've stayed here multiple times, room is great, clean and in a good location. ### [Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort](https://www.expedia.co.uk/Orlando-Hotels-Seasons-Florida-Resort.h1813900.Hotel-Information) ![A modern hotel lobby with a reception desk, a round coffee table, a sofa, and a large window with curtains.](https://images.trvl-media.com/lodging/2000000/1820000/1813900/1813900/c5ff34ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 4736 W Irlo Bronson Hwy Memorial, Kissimmee, FL, 34746, US - Location: 1 mi from Windward Cay - Star rating: 2/5 - Guest rating: 9/10 (Wonderful, 4117 reviews) - Price: £34, includes taxes & fees, 16 Nov - 17 Nov ### [Radisson Hotel Orlando Lake Buena Vista South](https://www.expedia.co.uk/Orlando-Hotels-Red-Lion-Hotel-Orlando-Lake-Buena-Vista-South.h7622.Hotel-Information) ![A hotel pool area with a water slide, palm trees, and a bridge.](https://images.trvl-media.com/lodging/1000000/10000/7700/7622/28e8f5ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 5150 West Irlo Bronson Memorial Highway, Kissimmee, FL, 34746, US - Location: 1.9 mi from Windward Cay - Star rating: 3.5/5 - Guest rating: 8.8/10 (Excellent, 3732 reviews) - Price: £56, includes taxes & fees, 23 Nov - 24 Nov - Review: No pregunte si llevan comida a la habitación? ### [Comfort Suites Maingate East](https://www.expedia.co.uk/Orlando-Hotels-Comfort-Suites-Maingate-East.h460421.Hotel-Information) ![A hotel with a swimming pool, multiple floors, and a parking lot.](https://images.trvl-media.com/lodging/1000000/470000/460500/460421/c5d7caed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 2775 Florida Plaza Blvd, Kissimmee, FL, 34746, US - Location: 2.8 mi from Windward Cay - Star rating: 3/5 - Guest rating: 8.4/10 (Very good, 2605 reviews) - Price: £68, includes taxes & fees, 13 Dec - 14 Dec ### [Magic Moment Resort & Kids Club, Dazzler Select by Wyndham](https://www.expedia.co.uk/Orlando-Hotels-Magic-Moment-Resort-And-Kids-Club.h13313558.Hotel-Information) ![A modern living room with a large flat-screen TV, a white sofa, and a coffee table.](https://images.trvl-media.com/lodging/14000000/13320000/13313600/13313558/96d0f52c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 5200 West Irlo Bronson Memorial Highway, Kissimmee, FL, 34746, US - Location: 2 mi from Windward Cay - Star rating: 3/5 - Guest rating: 8.6/10 (Excellent, 3230 reviews) - Price: £45, includes taxes & fees, 18 Nov - 19 Nov - Review: It is a dirty motel. The pictures on Expedia doesn’t match actual rooms. Refused to return my money. We did not fit in the room because advertised different and wouldn’t stay there how dirty it was. Yikes. ### [Palazzo Lakeside Hotel](https://www.expedia.co.uk/Orlando-Hotels-Palazzo-Lakeside.h14701.Hotel-Information) ![A modern interior with a white spiral staircase, a large Christmas tree, and a dining area with white furniture.](https://images.trvl-media.com/lodging/1000000/20000/14800/14701/f253be82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 4944 W. Irlo Bronson Memorial Highway, Kissimmee, FL, 34746, US - Location: 1.7 mi from Windward Cay - Star rating: 3/5 - Guest rating: 8.4/10 (Very good, 5392 reviews) - Price: £44, includes taxes & fees, 29 Nov - 30 Nov - Review: Beautiful and peaceful hotel love it ### [Star Island Resort and Club](https://www.expedia.co.uk/Orlando-Hotels-Star-Island-Resort-And-Club.h198051.Hotel-Information) ![A spacious lobby with a large chandelier, a reception desk, and a view of the outside through large windows.](https://images.trvl-media.com/lodging/1000000/200000/198100/198051/229ee8a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 5000 Avenue Of The Stars, Kissimmee, FL, 34746, US - Location: 1.5 mi from Windward Cay - Star rating: 3.5/5 - Guest rating: 8.4/10 (Very good, 1512 reviews) - Price: £83, includes taxes & fees, 14 Dec - 15 Dec - Review: Clean room 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. [See all properties in Windward Cay](https://www.expedia.co.uk/Hotel-Search?startDate=2026-11-28&endDate=2026-11-29®ionId=553248635976481817&adults=2&sort=RECOMMENDED&openPlayBack=true) ## 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 £775\. 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](https://www.expedia.co.uk/service/?langid=1033). 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](https://www.expedia.co.uk/Orlando-Hotels-Magic-Moment-Resort-And-Kids-Club.h13313558.Hotel-Information). It's one of most sought-after hotels in Windward Cay. Another cosy option is [Red Lion Hotel Orlando Lake Buena Vista South](https://www.expedia.co.uk/Orlando-Hotels-Red-Lion-Hotel-Orlando-Lake-Buena-Vista-South.h7622.Hotel-Information). ### 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. \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.