Title: All inclusive Vacations in Windley Key 2025/2026 | Expedia.ca ![](https://images.trvl-media.com/place/6282211/9f8e583b-bc9a-4a16-b731-daa0b5c7f87b.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Windley Key All inclusive Vacations ## Book a Hotel + Flight or Car together to unlock savings Stay added Flight added Car - Economy - Premium economy - Business class - First class Leaving from Going to Dates Travellers ## Room 1 Adults ChildrenAges 2 to 17 InfantsYounger than 2 I only need accommodation for part of my trip - ## Plan, book, travel with confidence ### Better together Save up to CA $1,096 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 ## Flight and All inclusive hotel deals in Windley Key Price found within the past 48 hours. Click for updated prices. ![Pelican Grand Beach Resort - A Noble House Resort](https://images.trvl-media.com/lodging/1000000/50000/49900/49851/12ee1484_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pelican Grand Beach Resort - A Noble House Resort East Fort Lauderdale CA $1,052 per person Nov 30 - Dec 5 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8.8/10 Excellent! (1,238 reviews) The hotel needs significant maintenance Reviewed on Sep 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-30/2025-12-05/?FromAirport=YTO&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=49851&paandie=true&HotelClass=40&dealMarker=SrTTAdiOVbDJkkvCXH940r4tatKc1687z7OtQYR1stzgSlqAam7vFAMitIKAVgM2) ![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/dffb9d2c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Retreat Collection at 1 Hotel & Homes South Beach South Beach CA $13,098 per person Nov 7 - Nov 12 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8/10 Very Good! (1 review) [](https://expedia.ca/go/package/search/FlightHotel/2025-11-07/2025-11-12/?FromAirport=YTO&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12316590&paandie=true&HotelClass=40&dealMarker=bYeZ0zNbyuTEHYoqBgyX515ttUCEtJpmAVu2SqVXWS8mbzGeD32_GsQ-aNLyPq7r) ![Winslow's Bungalows - Key West Historic Inns](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/7cf7d263_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Winslow's Bungalows - Key West Historic Inns Old Town Key West CA $1,944 per person Dec 13 - Dec 20 found 14 hours ago Roundtrip non-stop flight included Ottawa (YOW) to Key West (EYW) 9.2/10 Wonderful! (1,005 reviews) Excellent hotel in every way, the gardens, the room, the breakfast, the location, we will definitely return. Reviewed on Sep 25, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-13/2025-12-20/?FromAirport=YOW&Destination=EYW&NumRoom=1&NumAdult=2&NumChild=0&hotelId=529611&paandie=true&HotelClass=40&dealMarker=D5_BV1nef-O-1MviosFT9B0gXuubV8rkQeKoPUUNwdFErLim5-2jigdA2Jf85XGH) ![EAST Miami Residences](https://images.trvl-media.com/lodging/79000000/78580000/78570600/78570563/dca879fa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### EAST Miami Residences Downtown Miami CA $1,556 per person Dec 5 - Dec 8 found 1 day ago Roundtrip flight included Toronto (YYZ) to Miami (MIA) 9/10 Wonderful! (77 reviews) Convenient for shopping and food. Reviewed on Sep 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-05/2025-12-08/?FromAirport=YYZ&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=78570563&paandie=true&HotelClass=40&dealMarker=SPEG3OnDpNAsdTGCSpuDudDdOPYVfM3SbB5mjJqyJfVljhImRguAwWj_1bFk73fq) ![Carillon Miami Wellness Resort](https://images.trvl-media.com/lodging/12000000/11350000/11344400/11344361/1345796e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Carillon Miami Wellness Resort North Beach CA $2,176 per person Nov 9 - Nov 14 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8.8/10 Excellent! (756 reviews) Few issues but fixed after check in - amazing place to relax - recharge. Reviewed on Sep 25, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-09/2025-11-14/?FromAirport=YTO&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=11344361&paandie=true&HotelClass=40&dealMarker=c7sPKcxJ5bY79ep1okRjaaK3FkgpvGale26-WyuNIeAZp_8zJGogHArS3l38T6Jb) Don't see what you're looking for? See all available trips from Columbus to Windley Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-10-28/2025-11-04/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* All inclusive holidays in Windley Key Price found within the past 48 hours. Click for updated prices. ![EAST Miami Residences](https://images.trvl-media.com/lodging/79000000/78580000/78570600/78570563/dca879fa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### EAST Miami Residences Downtown Miami CA $1,556 per person Dec 5 - Dec 8 found 1 day ago Roundtrip flight included Toronto (YYZ) to Miami (MIA) 9/10 Wonderful! (77 reviews) Convenient for shopping and food. Reviewed on Sep 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-05/2025-12-08/?FromAirport=YYZ&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=78570563&paandie=true&HotelClass=50&dealMarker=SPEG3OnDpNAsdTGCSpuDudDdOPYVfM3SbB5mjJqyJfVljhImRguAwWj_1bFk73fq) ![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/dffb9d2c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Retreat Collection at 1 Hotel & Homes South Beach South Beach CA $13,098 per person Nov 7 - Nov 12 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8/10 Very Good! (1 review) [](https://expedia.ca/go/package/search/FlightHotel/2025-11-07/2025-11-12/?FromAirport=YTO&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12316590&paandie=true&HotelClass=50&dealMarker=bYeZ0zNbyuTEHYoqBgyX515ttUCEtJpmAVu2SqVXWS8mbzGeD32_GsQ-aNLyPq7r) ![Carillon Miami Wellness Resort](https://images.trvl-media.com/lodging/12000000/11350000/11344400/11344361/1345796e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Carillon Miami Wellness Resort North Beach CA $2,176 per person Nov 9 - Nov 14 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8.8/10 Excellent! (756 reviews) Few issues but fixed after check in - amazing place to relax - recharge. Reviewed on Sep 25, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-09/2025-11-14/?FromAirport=YTO&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=11344361&paandie=true&HotelClass=50&dealMarker=c7sPKcxJ5bY79ep1okRjaaK3FkgpvGale26-WyuNIeAZp_8zJGogHArS3l38T6Jb) Don't see what you're looking for? See all available trips from Columbus to Windley Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-10-28/2025-11-04/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night All inclusive holidays in Windley Key Price found within the past 48 hours. Click for updated prices. ![The Shelborne By Proper, a Member of Design Hotels](https://images.trvl-media.com/lodging/1000000/30000/25500/25451/e49031f1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Shelborne By Proper, a Member of Design Hotels South Beach CA $1,107 per person Dec 15 - Dec 18 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 9.8/10 Exceptional! (31 reviews) Lovely beach view. Beautiful small terrace. Nice color story in the rooms. Love the pool and the staff. Please make slippers or flip flops to wear. The floors are marble. Soft slippers or flip flops would be cozy and great for the branding. Reviewed on Sep 27, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-15/2025-12-18/?FromAirport=YTO&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=25451&paandie=true&HotelClass=40&dealMarker=SPEG3OnDpNAsdTGCSpuDuYzTKta1LGddA8F4rvPkhiG-43loGi4SHP3CyeD1zQJP) ![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/dffb9d2c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Retreat Collection at 1 Hotel & Homes South Beach South Beach CA $6,589 per person Nov 3 - Nov 6 found 4 hours ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8/10 Very Good! (1 review) [](https://expedia.ca/go/package/search/FlightHotel/2025-11-03/2025-11-06/?FromAirport=YTO&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12316590&paandie=true&HotelClass=40&dealMarker=EJcZ_mrSrkWeNUdTT7h25_T2XuwtIusIuovM5ldP8ln5oLJItmAkqWHZUs3CbmPt) ![EAST Miami Residences](https://images.trvl-media.com/lodging/79000000/78580000/78570600/78570563/dca879fa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### EAST Miami Residences Downtown Miami CA $1,556 per person Dec 5 - Dec 8 found 1 day ago Roundtrip flight included Toronto (YYZ) to Miami (MIA) 9/10 Wonderful! (77 reviews) Convenient for shopping and food. Reviewed on Sep 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-05/2025-12-08/?FromAirport=YYZ&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=78570563&paandie=true&HotelClass=40&dealMarker=SPEG3OnDpNAsdTGCSpuDudDdOPYVfM3SbB5mjJqyJfVljhImRguAwWj_1bFk73fq) Don't see what you're looking for? See all available trips from Columbus to Windley Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-10-28/2025-11-04/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night All inclusive holidays in Windley Key Price found within the past 48 hours. Click for updated prices. ![Cavalier Hotel South Beach](https://images.trvl-media.com/lodging/1000000/20000/13600/13579/a2036d80_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cavalier Hotel South Beach South Beach CA $1,614 per person Dec 4 - Dec 8 found 1 day ago Roundtrip non-stop flight included Ottawa (YOW) to Miami (MIA) 8.4/10 Very Good! (1,000 reviews) The staff greeted us wonderfully. The room is clean. The VIP perk was pleasant. Would definitely stay here again. Reviewed on Sep 25, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-08/?FromAirport=YOW&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=13579&paandie=true&dealMarker=EACBH2Vc90sAGsE0s4KuCbRFGtrKtsUf1YFY-OiQ6dEWRezgofzV_itnU1048_3k) ![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/dffb9d2c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Retreat Collection at 1 Hotel & Homes South Beach South Beach CA $9,915 per person Nov 8 - Nov 12 found 21 hours ago Roundtrip non-stop flight included Vancouver (YVR) to Miami (MIA) 8/10 Very Good! (1 review) [](https://expedia.ca/go/package/search/FlightHotel/2025-11-08/2025-11-12/?FromAirport=YVR&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12316590&paandie=true&dealMarker=EJcZ_mrSrkWeNUdTT7h255sl80QCMXldd9dh7hOtzT9yIF4-cKKjHf4iuvjWBOyv) ![Bentley Hotel South Beach](https://images.trvl-media.com/lodging/1000000/130000/120300/120299/8ae6370c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Bentley Hotel South Beach South Beach CA $2,091 per person Dec 4 - Dec 8 found 1 day ago Roundtrip non-stop flight included Ottawa (YOW) to Miami (MIA) 9.2/10 Wonderful! (334 reviews) We had a very pleasant stay at this hotel. The property was clean and comfortable, and everything we needed was easily available. The highlight of our experience was the staff — they were extremely responsive, helpful, and made sure we felt well taken care of throughout our stay. Their attention and professionalism truly added to the overall experience. I would gladly stay here again and recommend it to others. Reviewed on Sep 28, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-08/?FromAirport=YOW&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=120299&paandie=true&dealMarker=EACBH2Vc90sAGsE0s4KuCehbHUyi80xrPfBoOKLvWzRFnTGepIlbLIYrYiLSvMbI) Don't see what you're looking for? See all available trips from Columbus to Windley Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-10-28/2025-11-04/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Embark on an unforgettable all-inclusive trip to Windley Key including airfare with Expedia #### What are some benefits of booking an all-inclusive vacation? When you opt for an all-inclusive vacation to Windley Key, you can have everything you want to do planned out in advance. That means you get to simply coast through your vacation knowing exactly what's coming next. Plus, this helps you get a final tally on the costs beforehand, so it's much easier on your budget. #### Can I book all-inclusive packages with airfare and meals? Yes, all-inclusive vacation packages are readily available for Windley Key, and you can search for them simply by using the search filter for all-inclusivity. When you book your flight along with your accommodations, you may even find some savings, with the potential to save up to 43. #### Why should I book Windley Key vacations that are all inclusive and adults only? Adults-only stays in Windley Key are good for travellers who are looking to relax in laid-back and easygoing surroundings. Everyone in the area will be looking to do much of the same without any kids to worry about, so you can truly take in some time for yourself in pampered bliss. Plus, you can filter for adults-only stays specifically in your search, so they're easy to find. #### Can I book all-inclusive packages? Yes, all-inclusive packages are fairly standard in Windley Key. You can easily find all-inclusive options by using the search filters, but that's just the beginning. If you're booking at the last minute, you may even find additional discounts as properties try to fill their last remaining spots for cheap vacations that are all inclusive. #### Can I book cheap all-inclusive trips to Windley Key? If you're looking to save, you'll find a wide range of prices available, ranging from CA $1,052. By booking your accommodations and flight together, you may be able to enjoy savings of up to 43. Be sure to sort your search results by price to list the cheapest options first. #### What should I look for when booking a 5-star all-inclusive vacation in Windley Key? If you've implemented the 5-star filter when searching for your all-inclusive vacation in Windley Key, there are a few factors to keep an eye out for. Spa access is particularly popular, as it's one of the best features you'll find in luxury accommodation options. Additionally, you should consider opting for an infinity pool and a luxury suite, especially if you're travelling with a relatively large group. #### What should I consider when booking Windley Key vacation packages that are all inclusive for the family? The most important thing to consider for all-inclusive family vacations to Windley Key is what your family is interested in. If your kids need access to a pool, you'll want to implement the search filter for that amenity. Kids' clubs can also be perfect for your family, as can babysitting services if the adults in your group plan on enjoying Windley Key's nightlife. #### How can I find the best deals on all-inclusive vacations in Windley Key? You can always sort your search results by price to automatically put the cheapest options at the top of your search while still considering all your implemented search filters. #### Can I book an all-inclusive package that is fully refundable? Yes, reservations that are fully refundable are available on some all-inclusive packages in . You can explore each package's cancellation policy in the policy section of their page, where you'll learn exactly how you can qualify. Sometimes, nothing is required to qualify. #### Why should I book an all-inclusive vacation with Expedia? Booking with Expedia makes it easy to find the ultimate all-inclusive vacation package. By offering accommodations and flights together, all-inclusive packages are easy for us to create and for you to enjoy. With benefits like being fully refundable and flexible dates on some packages, you can enjoy a more stree-free booking process. Expedia Rewards members can take that even further with the possibility of additional discounts. ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Top All inclusive Vacation Destinations > - 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[All inclusive vacations in Sosúa](https://www.expedia.ca/lp/theme-vacations/all-inclusive-vacations/601998/Sosua) > - [All inclusive vacations in the Dominican Republic](https://www.expedia.ca/lp/theme-vacations/all-inclusive-vacations/50/Dominican-Republic) ## More Vacations Ideas [Flights to Windley Key](https://expedia.ca/Cheap-Flights-To-Windley-Key.d553248635976197663.Travel-Guide-Flights)[Windley Key Hotels](https://expedia.ca/Windley-Key-Hotels.d553248635976197663.Travel-Guide-Hotels)[Windley Key Vacation Rentals](https://expedia.ca/Windley-Key-Vacation-Rentals.d553248635976197663.Travel-Guide-VacationRentals)[Windley Key Car Rentals](https://expedia.ca/Car-Rentals-In-Windley-Key.d553248635976197663.Car-Rental-Guide)[Windley Key Vacations](https://expedia.ca/Windley-Key.d553248635976197663.Destination-Travel-Guides)[Things to do in Windley Key](https://expedia.ca/Things-To-Do-In-Windley-Key.d553248635976197663.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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