Title: All inclusive Vacations in Windley Key 2025/2026 | Expedia.ca ![](https://images.trvl-media.com/place/553248635997958830/30b22f53-286f-436b-ae7a-d035c9062e6c.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. ![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 $931 per person Nov 24 - Nov 28 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 9.8/10 Exceptional! (31 reviews) Great hotel. Clearly freshly refurbished and excellent facilities. Staff were extremely attentive - everyone we bumped into in the lift, for example, even junior team members, asked how we were and whether there was anything that they could do to improve our stay. Shows a great culture! Only downsides are a bar that shuts very early (10pm) and a LOT of mosquitoes in the outdoor pool area - they give bug spray it we had to retreat late afternoon or after rain. Reviewed on Oct 6, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-24/2025-11-28/?FromAirport=YTO&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=25451&paandie=true&HotelClass=40&dealMarker=dOFjm76SFJtsdaLmLTKA33cLiwF3x9CcN9gxT5oUaC5wQ-fadKSVDZNJGvsYueAY) ![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 $19,795 per person Dec 29 - Jan 3 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Miami (MIA) 8/10 Very Good! (1 review) [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-03/?FromAirport=YMQ&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12316590&paandie=true&HotelClass=40&dealMarker=AHInqYT5nUKkZuSpv67nuRNUwhO9pTk9O5gMykooskHmYm31zO-OgYQSnMK7nUQZ) ![Park Central South Beach](https://images.trvl-media.com/lodging/1000000/10000/1200/1168/280efeed_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Central South Beach South Beach CA $2,925 per person Dec 26 - Jan 2 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Miami (MIA) 8.6/10 Excellent! (217 reviews) Everyone was nice but the room definitely felt “used”. It was clean but paint pealing and the door was damaged, and there was a $300 deposit required for one night stay that I was unaware of until check in. Especially given the state of the room, $300 out of no where was a bit much. Now waiting for it to be released. The restaurants attached were okay. I wish breakfast had been available before 7am. Reviewed on Oct 17, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2026-01-02/?FromAirport=YMQ&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1168&paandie=true&HotelClass=40&dealMarker=0zFYPZw5veQEBQKr5c-7sSwm_ABHNBDtI102P-GWKLPX3uZGlKOHsC-4VlQLNIlI) ![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 $2,997 per person Dec 26 - Jan 2 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Miami (MIA) 9.4/10 Exceptional! (390 reviews) Clean Room Beach View Reviewed on Oct 17, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2026-01-02/?FromAirport=YMQ&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=120299&paandie=true&HotelClass=40&dealMarker=0zFYPZw5veQEBQKr5c-7scjWSWjVt5igRgHNqhuyKdIWUwc8O68Na5OgKAuzHgMK) ![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 $1,456 per person Nov 18 - Nov 25 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Miami (MIA) 8.6/10 Excellent! (1,273 reviews) The beach access was top tier. The amenities and service provided on the beach was immaculate. Will return Reviewed on Oct 18, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-18/2025-11-25/?FromAirport=YMQ&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=49851&paandie=true&HotelClass=40&dealMarker=eQ41785sc6bOv5L8pbLHTiZouVcZn_QYjNaFupmHHaEMLZm9PowSCcbQSY5-IZmV) 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/2025-11-18/2025-11-25/?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. ![1 Hotel South Beach](https://images.trvl-media.com/lodging/2000000/1800000/1790100/1790087/w4800h3297x0y3-ab24f575_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel South Beach South Beach CA $1,816 per person Nov 25 - Nov 28 found 1 day ago Roundtrip flight included Montreal (YMQ) to Miami (MIA) 9.4/10 Exceptional! (1,307 reviews) I did not had view from my room but I had very good service Reviewed on Oct 16, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-25/2025-11-28/?FromAirport=YMQ&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1790087&paandie=true&HotelClass=50&dealMarker=VFrCK3WKSueRXlUYG9jyCRdgmoDKi2vhnvYTBBYmHJZqH-rTRB1I_08smjMEeeF_) ![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 $19,795 per person Dec 29 - Jan 3 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Miami (MIA) 8/10 Very Good! (1 review) [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-03/?FromAirport=YMQ&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12316590&paandie=true&HotelClass=50&dealMarker=AHInqYT5nUKkZuSpv67nuRNUwhO9pTk9O5gMykooskHmYm31zO-OgYQSnMK7nUQZ) ![Kimpton EPIC Hotel by IHG](https://images.trvl-media.com/lodging/3000000/2240000/2237200/2237168/bd3b03e4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kimpton EPIC Hotel by IHG Downtown Miami CA $2,994 per person Dec 29 - Jan 3 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Miami (MIA) 9/10 Wonderful! (2,068 reviews) The room was clean the pool area was nice. And the staff is always wonderful. Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-03/?FromAirport=YMQ&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2237168&paandie=true&HotelClass=50&dealMarker=tFMtCMF6NxyHIGv-n_rqeaWPUkHl1G8kejW3yP5aWLXdRPhfMx-PtXphm8WeFP-e) 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/2025-11-18/2025-11-25/?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 $1,067 per person Nov 27 - Nov 30 found 13 hours ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 9.8/10 Exceptional! (31 reviews) Great hotel. Clearly freshly refurbished and excellent facilities. Staff were extremely attentive - everyone we bumped into in the lift, for example, even junior team members, asked how we were and whether there was anything that they could do to improve our stay. Shows a great culture! Only downsides are a bar that shuts very early (10pm) and a LOT of mosquitoes in the outdoor pool area - they give bug spray it we had to retreat late afternoon or after rain. Reviewed on Oct 6, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-27/2025-11-30/?FromAirport=YTO&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=25451&paandie=true&HotelClass=40&dealMarker=8UMz_NWRt5IPA-CAJMBkY7mV2BB8o8ec4x6lgXQH-SVyTbCXjYmDscC36LJ3pM7c) ![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 $6,567 per person Jan 4 - Jan 7 found 1 day ago Roundtrip flight included Toronto (YYZ) to Miami (MIA) 8/10 Very Good! (1 review) [](https://expedia.ca/go/package/search/FlightHotel/2026-01-04/2026-01-07/?FromAirport=YYZ&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12316590&paandie=true&HotelClass=40&dealMarker=AHInqYT5nUKkZuSpv67nuYsZdMRMWV9d9WCWtDZ8GSDA_F-0BN4T6OuoA5Ojhn2n) ![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 $1,590 per person Dec 5 - Dec 8 found 1 day ago Roundtrip flight included Toronto (YYZ) to Miami (MIA) 9/10 Wonderful! (78 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=b7yB_45JWJobUDFCyrW0wAC2HJNVbXBV9n2V1JvzbRxZmt30cgMIG5Fzh_4MMn8y) 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/2025-11-18/2025-11-25/?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 $504 per person Nov 24 - Nov 28 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8.4/10 Very Good! (1,000 reviews) Fantastic service, great restaurant downstairs, super convenient for beach access, shopping and dining! Reviewed on Oct 13, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-24/2025-11-28/?FromAirport=YTO&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=13579&paandie=true&dealMarker=dOFjm76SFJtsdaLmLTKA3_yBKyiufD_eMQiGbSnJaJ1WCq-KfVEMAihM6M5YS-Ba) ![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 $1,416 per person Jan 7 - Jan 11 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 9.8/10 Exceptional! (31 reviews) Great hotel. Clearly freshly refurbished and excellent facilities. Staff were extremely attentive - everyone we bumped into in the lift, for example, even junior team members, asked how we were and whether there was anything that they could do to improve our stay. Shows a great culture! Only downsides are a bar that shuts very early (10pm) and a LOT of mosquitoes in the outdoor pool area - they give bug spray it we had to retreat late afternoon or after rain. Reviewed on Oct 6, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-07/2026-01-11/?FromAirport=YTO&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=25451&paandie=true&dealMarker=AHInqYT5nUKkZuSpv67nuXwmmtS5Lk3RviORwLTGLJSXf5S53L5n_38hGCQE82LD) ![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 $10,452 per person Dec 20 - Dec 24 found 13 hours ago Roundtrip non-stop flight included Montreal (YUL) to Miami (MIA) 8/10 Very Good! (1 review) [](https://expedia.ca/go/package/search/FlightHotel/2025-12-20/2025-12-24/?FromAirport=YUL&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12316590&paandie=true&dealMarker=AHInqYT5nUKkZuSpv67nufgad1mXwvSTAE9FacBLnvtqeP6RadjGlCFLQ5mMTaNR) 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/2025-11-18/2025-11-25/?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 52. #### 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 $504. By booking your accommodations and flight together, you may be able to enjoy savings of up to 52. 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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