Title: Adventure 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 Adventure 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 Adventure hotel deals in Windley Key Price found within the past 48 hours. Click for updated prices. ![Pelican Hotel](https://images.trvl-media.com/lodging/1000000/60000/55100/55046/22b81b04_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pelican Hotel South Beach CA $1,157 per person Dec 13 - Dec 20 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Miami (MIA) 9.2/10 Wonderful! (383 reviews) This was quite an unexpected little gem! Oscar was so incredibly nice and each day seemed to almost look for us coming off the elevator to suggest things to do in the area. He gave us recommendations on shopping and where to eat, which did not disappoint! The Mojitos that we got for free happy hour were absolutely amazing! We will definitely stay here again! Oh, and the speakeasy upstairs super cute! Reviewed on Oct 11, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-13/2025-12-20/?FromAirport=YUL&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=55046&paandie=true&HotelClass=40&dealMarker=HFE5z3wBQ9agr8JvJqS5MyswjyutKLT47pTPBevphtCP3hK9qhaC310uC1amGjuN) ![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 $16,421 per person Dec 14 - Dec 21 found 1 day ago Roundtrip flight included Montreal (YMQ) to Miami (MIA) 8/10 Very Good! (1 review) [](https://expedia.ca/go/package/search/FlightHotel/2025-12-14/2025-12-21/?FromAirport=YMQ&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12316590&paandie=true&HotelClass=40&dealMarker=NdFnuoRmI-uCae-shPb_qPWrMoJhXYtJNbg9S93To_ymz1KPmw4Rt54hK5w2Pmia) ![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 $1,996 per person Jan 4 - Jan 11 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) 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/2026-01-04/2026-01-11/?FromAirport=YHM&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=120299&paandie=true&HotelClass=40&dealMarker=INqQEB--Kkvoi62J-R0bQQ4XxJ4f1b32APi0BY2TMcpejAip6bM55kEnvJ4riZdY) ![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 $1,790 per person Jan 4 - Jan 11 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Miami (MIA) 8.6/10 Excellent! (217 reviews) The staff was simply the best! Everyone was so friendly and attentive. The complimentary bikes, beach towels and beach chairs were everything. The location is walkable and convenient to some of the best eateries. An overall excellent experience!!! Reviewed on Oct 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-04/2026-01-11/?FromAirport=YHM&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1168&paandie=true&HotelClass=40&dealMarker=INqQEB--Kkvoi62J-R0bQQ6_HhO9ZYg9XRhPs7HdSrDpAJ2ErYDtlywv1AhjUbaQ) ![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 $4,319 per person Jan 4 - Jan 11 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Miami (MIA) 9.4/10 Exceptional! (1,333 reviews) I had an awesome view…. Got upgraded on check in so that I could see the ocean from my room… excellent service from everyone Reviewed on Oct 21, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-04/2026-01-11/?FromAirport=YHM&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1790087&paandie=true&HotelClass=40&dealMarker=INqQEB--Kkvoi62J-R0bQWScwOOsPyxGwJd7oXYI19PNjY0pliViI8RBPIB1mqlQ) 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/2025-11-22/2025-11-29/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Adventure holidays in Windley Key Price found within the past 48 hours. Click for updated prices. ![EAST Miami](https://images.trvl-media.com/lodging/13000000/12080000/12079000/12078999/e1fc0c39_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### EAST Miami Downtown Miami CA $2,059 per person Jan 4 - Jan 11 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Miami (MIA) 9.2/10 Wonderful! (3,480 reviews) It is just an overall 5 star experience and hotel. Reviewed on Oct 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-04/2026-01-11/?FromAirport=YHM&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12078999&paandie=true&HotelClass=50&dealMarker=INqQEB--Kkvoi62J-R0bQbW774n7yP2Uc3yyDadD_wEFMsH4gU5d9tPIEwLfCJoC) ![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 $16,421 per person Dec 14 - Dec 21 found 1 day ago Roundtrip flight included Montreal (YMQ) to Miami (MIA) 8/10 Very Good! (1 review) [](https://expedia.ca/go/package/search/FlightHotel/2025-12-14/2025-12-21/?FromAirport=YMQ&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12316590&paandie=true&HotelClass=50&dealMarker=NdFnuoRmI-uCae-shPb_qPWrMoJhXYtJNbg9S93To_ymz1KPmw4Rt54hK5w2Pmia) ![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 $4,319 per person Jan 4 - Jan 11 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Miami (MIA) 9.4/10 Exceptional! (1,333 reviews) I had an awesome view…. Got upgraded on check in so that I could see the ocean from my room… excellent service from everyone Reviewed on Oct 21, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-04/2026-01-11/?FromAirport=YHM&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1790087&paandie=true&HotelClass=50&dealMarker=INqQEB--Kkvoi62J-R0bQWScwOOsPyxGwJd7oXYI19PNjY0pliViI8RBPIB1mqlQ) 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/2025-11-22/2025-11-29/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Adventure holidays in Windley Key Price found within the past 48 hours. Click for updated prices. ![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 $1,487 per person Dec 5 - Dec 8 found 1 day ago Roundtrip flight included Toronto (YTO) 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/2025-12-05/2025-12-08/?FromAirport=YTO&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=120299&paandie=true&HotelClass=40&dealMarker=VQOyAN7p_xUUaMfVEk5jczJzM15DPt7x2szDXqS7-8lTwXSZtpVb88GC4O1fJ6Xj) ![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 $16,093 per person Dec 27 - Dec 30 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/2025-12-27/2025-12-30/?FromAirport=YYZ&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12316590&paandie=true&HotelClass=40&dealMarker=zsdb7AqbqTyQd7e-XzjFS_QjlT0HzmYBo3SG6IDDPdkrY4In7LvOoFZj_EEdtGrX) ![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 $1,871 per person Dec 25 - Dec 28 found 23 hours ago Roundtrip non-stop flight included Toronto (YTO) 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/2025-12-25/2025-12-28/?FromAirport=YTO&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=78570563&paandie=true&HotelClass=40&dealMarker=Cbw3zlj7-zIj6-GHS0UyoN1N59JiYM8ajAbzncMR-UIzf4iXzRhSSA_OpxEFUIdw) 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/2025-11-22/2025-11-29/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Adventure holidays in Windley Key Price found within the past 48 hours. Click for updated prices. ![The Local House](https://images.trvl-media.com/lodging/3000000/2640000/2630300/2630242/483f19c4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Local House South Beach CA $1,116 per person Jan 15 - Jan 19 found 1 day ago Roundtrip flight included Toronto (YYZ) to Miami (MIA) 9.2/10 Wonderful! (1,002 reviews) A wonderful small boutique hotel with a great restaurant for brunch and beach takeaway. Attentive, polite staff, great vibe. Reviewed on Oct 15, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-15/2026-01-19/?FromAirport=YYZ&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2630242&paandie=true&dealMarker=XItW3S9IEX475_X9-Ca14ddFe2wEHmQ8YJ0HBd75LiOox7ZG8lEGybaLdqm89nCY) ![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 $1,724 per person Dec 22 - Dec 26 found 20 hours ago Roundtrip non-stop flight included Montreal (YMQ) to Miami (MIA) 9.8/10 Exceptional! (39 reviews) Really great stay, big thanks to Crispy and team! Hotel has a great atmosphere and location. I’ll be sure to visit again! Reviewed on Oct 21, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-22/2025-12-26/?FromAirport=YMQ&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=25451&paandie=true&dealMarker=Z1kMevP7eAQq5xTvKgbZMZYPgbnylNJFYjVXbgStLx_zYrjpTmd-q8dQpnMA12J-) ![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 $1,215 per person Dec 22 - Dec 26 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Miami (MIA) 8.6/10 Excellent! (1,273 reviews) Nice hotel with direct beach access. Far enough from busy downtown beach that it’s quiet, but also further from restaurants, could be a pro or con depending on the person. Hotel food was good and pool was a good time. Made friends with some iguanas as well. Reviewed on Oct 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-22/2025-12-26/?FromAirport=YTO&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=49851&paandie=true&dealMarker=krzFBWmUET-KznEBhREJutsEFHnTKduiesE2EJlNh6PI09tanSTiXfseu7jPgcFZ) 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/2025-11-22/2025-11-29/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 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) ## 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. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAyAAAAMgAQAAAADzCzvFAAAFNklEQVR4Xu3cMXIjOQxAUaoUKJwj9FF0tNbR+ig6woYKVMYOQJBgtyiPUbOzgef/xBZE8nXGlTy1Rf6HynHwJwJJBZIKJBVIKpBUIKlAUoGkAkkFkgokFUgqkFQgqUBSgaQCSQWSCiQVSCqQVCCpQFKBpAJJBZIKJBVIqgF5lkNLHf2QDx8Mq04i27BqlX98TW+Nk0FAQEBqILU1TgYBsbWRbrds+7WN48Tj6NRet1EPZDICsaYnTkYg1vTEyQjEmp44GYFY0xMnIxBreuJk9HXEtpdyqUis3XTqC28l7niRu/5wxEb7jRoICIj+AAEpICDe54joiT/0x1ZHpZwrUvSOf4DUZSD1HRAQC6SAgJTfQ3x0aotb5vbRWX8BAQHxxS0QkAIC8lUk0rWWu5G7W3318igaSASigYBoIBZIBKI9dycdtm/lUt33o0NrnAwyGR1a42SQyejQGieDTEaH1jgZZDI6tMbJIJPRoTVOBpmMDq1x8oBMsu2TUSB99FkgIJMm20HeN9kO8r7JdpD3TbaDvG+y/T9EHvWOl/oH5g//a7J2fh3ZhR6ubty7ICBjICAga5wGAiK63f/h9EVf3duJY77dENETR9fyjUMgIAICAgICMjQgT1+kXXT7otNbcdeLE6+xdTfyVUMgICB1Fcii01sBiUBADPG1j35V9+0x8jZ9FB1ZsQoExAMREBAQkCzia2/F7nhpo6Ifscd/zLXom7cSq/ystZ0LAgICAuKr/Ky1nQsC4tnfiSdr/UL3AhG566P46NoWgIAICIgHAiIg8mukrS1l0bV67VuPeqqfeHJXV/nGNupuDwTEAgEBAdFAZIbE2p596rbuVbLP031VPMrW3i6/uONB9LetvV1AtHs7AsQCAYlAWt8SefY3bHspS31lrt/xS13lo30fumD/dB4ICEgLxAKJQEBE/05sV7WdKLL/pGyIpUjZX/vTUQ/k5cTJqAfycuJk1AN5OXEy6oG8nDgZ9UBeTpyMeiAvJ05GvQGJ29vv+PFEu7195F2be9anG0f+XwI9kAICAgICArLGyUdkX4y2eoqdKIMrctff+qN4tqoHYoHsAwHZbQcB+ZsR72rvlKUh8d31XX/bjyz9bG6jop/Njw8MAgKigYCAgLReEfuIHWtL236pruiJYzbaX/vHQCIbgfQRSAQS2Qikj0Ci74qsYt9wizzqdneLX/t6x/uHZ3OtpQ5sZKt0+NlHbJA2slU6BLFAeiB1AAJS/ibEusS4jq7Nfam7VjzdGkOQCAREQEBAQA7IsXP/PH1E7I63R7m3xdb4dD0QEJC22AKxQCwQkEnPflVvw/Zb+9K79O/Bj6tipIGATJpsF5C3TbYLyNsm2wXkbZPtAvK2yXb5PeTp+3pLvPdze9ET73rtax967f9MV9mJ9tW4rdJ8lQcCAgJSW+I9kBoIiK2NfHsp9r/78Nv73k4pijz6775xa69BQATEAlnjFUgNBERekfgDsyKW3d6iJypi22PUH8WLR1nrbg0EBAQEBAQkjRS90HVxG9lH7H7ief+lt7trWwoCAgICAqKBtKVfQHS79dA73lZpJ/883XdbW3MLCAgICMguEJDPkMgRqe5VER050ka++FbMtUfpG3sgICAaCAgISGuP7Ft0qnf8h56oi2Mkxwt9/NK76KfuIRABGc63Fp2CjIEIyHC+tegUZOxbIn8ukFQgqUBSgaQCSQWSCiQVSCqQVCCpQFKBpAJJBZIKJBVIKpBUIKlAUoGkAkkFkgokFUgqkFQgqUBSgaT6Psi/CQQ9tURxEkUAAAAASUVORK5CYII=)