Title: Windley Key Vacation Packages & Trips 2026 from CA $783 | Expedia.ca [Windley Key Travel Guide](https://expedia.ca/Windley-Key.dx553248635976197663)[Hotels in Windley Key](https://expedia.ca/Windley-Key-Hotels.d553248635976197663.Travel-Guide-Hotels)[Vacation Rentals in Windley Key](https://expedia.ca/Windley-Key-Vacation-Rentals.d553248635976197663.Travel-Guide-VacationRentals)[Flights to Windley Key](https://expedia.ca/Cheap-Flights-To-Windley-Key.d553248635976197663.Travel-Guide-Flights)[Things to do in Windley Key](https://expedia.ca/Things-To-Do-In-Windley-Key.d553248635976197663.Travel-Guide-Activities)[Windley Key Car Rentals](https://expedia.ca/Car-Rentals-In-Windley-Key.d553248635976197663.Car-Rental-Guide) ![](https://images.trvl-media.com/place/553248635997958830/30b22f53-286f-436b-ae7a-d035c9062e6c.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Windley Key Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## 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 ## Top Windley Key Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Beach Park Hotel](https://images.trvl-media.com/lodging/1000000/800000/796500/796471/d7b06f17_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Beach Park Hotel South Beach CA $783 per person Feb 14 - Feb 19 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Miami (MIA) 6.6/10 (1,001 reviews) Room was good. Vibe of hotel was strange Reviewed on Jan 6, 2026 ![Miami Downtown Condos](https://images.trvl-media.com/lodging/110000000/109790000/109784700/109784697/w2048h1535x0y1-af4622e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Miami Downtown Condos Downtown Miami CA $2,019 per person Mar 25 - Mar 30 found 18 hours ago Roundtrip non-stop flight included Hamilton (YHM) to Miami (MIA) 8.6/10 Excellent! (72 reviews) The room wasn’t cleaned when we arrived about 30 minutes after the check in time. It took about 2 hours to finally have the room cleaned and ready. I wished a smooth check in process and parking information before arriving. Reviewed on Jan 8, 2026 ![Creekside Inn](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/5e43c05b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Creekside Inn CA $1,265 per person Feb 18 - Feb 25 found 15 hours ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8/10 Very Good! (1,004 reviews) Staff good Room with problems: toilet, safe vault, tv, no closet, no chair, too small Reviewed on Jan 6, 2026 ![Cavalier Hotel South Beach](https://images.trvl-media.com/lodging/1000000/20000/13600/13579/c0c3faa8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cavalier Hotel South Beach South Beach CA $1,178 per person Feb 14 - Feb 19 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Miami (MIA) 8.4/10 Very Good! (1,001 reviews) Main road in front of hotel was closed. When we arrived, the concierge had no idea where to tell us to park. If they were transparent about it, ok. I would be ok. Then they said they are out of the 'free' wine, but could charge me $8 for a Heineken. Then couldn't get the elevator to work (we were on the 2nd floor thank God) The room was in good shape. The parking is what set off the chain for me. It's not hard to update a website. Or at least tell your staff what to say. Ended up parking in the City parking garage. I'd give it like a 75/100. Reviewed on Jan 6, 2026 ![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 $15,493 per person Mar 12 - Mar 17 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Miami (MIA) 8/10 Very Good! (1 review) ## Ready to book your vacation to Windley Key? Choose your dates ## Windley Key Hotel Deals ![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/d10a018b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort 84001 Overseas Hwy Islamorada FL Fully refundableReserve now, pay when you stay CA $423 CA $568 total Jan 28 - Jan 29 includes taxes & fees 8.8/10 Excellent! (124 reviews) Amazing place - so much variety Reviewed on Jan 6, 2026 [](https://expedia.ca/Hotel-Search?startDate=28%2F01%2F2026&endDate=29%2F01%2F2026&selected=11864&PinnedHotelID=11864&HadPinnedHotel=true®ionId=553248635976197663) ![Fisher Inn Resort & Marina](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/9ae0ece9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Fisher Inn Resort & Marina 84951 Overseas Hwy Islamorada FL Fully refundable CA $224 CA $298 total Jan 12 - Jan 13 includes taxes & fees 8.2/10 Very Good! (1,006 reviews) Beautiful view Reviewed on Jan 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=12%2F01%2F2026&endDate=13%2F01%2F2026&selected=3274374&PinnedHotelID=3274374&HadPinnedHotel=true®ionId=553248635976197663) ![Coconut Cove Resort and Marina](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/667446d9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Coconut Cove Resort and Marina 84801 Overseas Highway Islamorada FL CA $298 CA $335 total Jan 12 - Jan 13 includes taxes & fees 9/10 Wonderful! (164 reviews) Staff was amazing! Two couples manage this property, and they go above and beyond to make sure you enjoy this cute, old style Florida resort. Upon check in Crystal seemed like an old friend. Reviewed on Jan 2, 2026 [](https://expedia.ca/Hotel-Search?startDate=12%2F01%2F2026&endDate=13%2F01%2F2026&selected=4182524&PinnedHotelID=4182524&HadPinnedHotel=true®ionId=553248635976197663) [See all 2,744 properties in Windley Key](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=10%2F01%2F2026&endDate=11%2F01%2F2026®ionId=553248635976197663) 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. ![](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) ### Discover the most popular places to visit in Windley Key ![Windley Key Fossil Reef Geological State Park](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/340000/340296-Windley-Key-Fossil-Reef-Geological-State-Park.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Windley Key Fossil Reef Geological State Park Explore the fossilized reef of a former quarry in this island park, as you learn about the history and ecology from the interpretive trails. [](https://expedia.ca/Windley-Key-Fossil-Reef-Geological-State-Park-Islamorada.d6282211.Vacation-Attraction) ### What to do in Windley Key ![Explore the Mangrove Creeks with an All Day Kayak Rental ](https://mediaim.expedia.com/localexpert/677736/f5836570-8b49-49af-a667-33b8a8596ab7.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Explore Mangrove Creeks with an All Day SUP/single kayak Rental CA $67 per adult [](https://expedia.ca/things-to-do/explore-mangrove-creeks-with-an-all-day-supsingle-kayak-rental.a677736.activity-details) ![Ft. Lauderdale to Key West Bus Tour w/ 6 hours of free time in KW](https://mediaim.expedia.com/localexpert/46991024/43dad7c4-b2cc-4a13-8eb8-76d57d8a8a1e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Ft. Lauderdale to Key West Day Trip Quality Day Tours CA $308 per adult [](https://expedia.ca/things-to-do/ft-lauderdale-to-key-west-day-trip-quality-day-tours.a46991024.activity-details) ![Ft Lauderdale to Islamorada Tour with Boat Ride and Lunch](https://mediaim.expedia.com/localexpert/48978354/1bad22a6-2206-44c7-8ad9-68a1197fea7d.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Ft Lauderdale to Islamorada Tour with Boat Ride and Lunch CA $340 per adult [](https://expedia.ca/things-to-do/ft-lauderdale-to-islamorada-tour-with-boat-ride-and-lunch.a48978354.activity-details) [See all activities in Windley Key](https://expedia.ca/things-to-do/search?rid=553248635976197663) ## Frequently asked questions ### Can I cancel my flight booking to Windley Key due to COVID-19? ### What's the best way to find cheap flights to Windley Key that have flexible change policies? ### What are some of the general tips for travelers to Windley Key during the COVID-19 outbreak? > - Look into what rules and restrictions apply to both your origin and destination. It may not be possible to travel depending on local circumstances, so be sure to check in advance. > - When you pass through airport checkpoints, do not remove your face mask. You will be asked to briefly lower it for ID purposes. Passengers who refuse to wear a face mask may face civil penalties and may also be denied boarding. > - Rather than handing a TSA agent your boarding pass, position it straight on the scanner yourself. Then, hold it up for inspection. > - One liquid hand sanitizer container is now permitted in your carry-on bag. It must not be larger than 12 oz (350 ml), and you'll need to take it out of your bag for scanning. > - Place any personal items (phone, keys and wallet) in your carry-on rather than a bin to minimize handling during the screening process. > - Separate any food you're carrying for screening. Placing it in a clear plastic bag and into a bin reduces the need for a TSA officer to handle and inspect your belongings. ### Which airlines fly to Windley Key? ### How can I find cheap tickets to Windley Key? ### How much is a flight to Windley Key? ### What are the most popular airports to fly into in Windley Key? ### When is the cheapest time to fly to Windley Key? ### How much is a plane ticket to Windley Key? ### Which airlines with flights to Windley Key employ COVID-19 cleanliness policies? > - American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant. > - Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant. > - United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - [2 Star Hotels in Plantation Key ](https://www.expedia.ca/2Star-Plantation-Key-Hotels.s20-0-d553248635083898347.Travel-Guide-Filter-Hotels) - 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