Title: Beach Vacations in Windley Key 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 Beach Vacations ## 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 ## Flight and Beach hotel deals in Windley Key Price found within the past 48 hours. Click for updated prices. ![Miami Downtown Condos](https://images.trvl-media.com/lodging/110000000/109790000/109784700/109784697/c533f3d5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Miami Downtown Condos Downtown Miami CA $945 per person Jun 15 - Jun 18 found 3 hours ago Roundtrip flight included Montreal (YMQ) to Miami (MIA) 8.2/10 Very Good! (124 reviews) good location! the property was in good condition. typical size of a condo-good size for 2-3 people. clean. the app to assess amenities and the door was a bit finicky but other than that i would recommend it to others Reviewed on Mar 31, 2026 ![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/18023e21_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### La Siesta Resort & Villas Matecumbe CA $1,356 per person Jun 1 - Jun 6 found 19 hours ago Roundtrip flight included Montreal (YMQ) to Miami (MIA) 8.8/10 Excellent! (1,004 reviews) Everything was great. We enjoyed the complimentary water activities and access to sister resorts. Reviewed on Mar 28, 2026 ![Carillon Miami Wellness Resort](https://images.trvl-media.com/lodging/12000000/11350000/11344400/11344361/75c6ca53_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Carillon Miami Wellness Resort North Beach CA $3,051 per person Jun 14 - Jun 20 found 1 day ago Roundtrip flight included Montreal (YMQ) to Miami (MIA) 8.8/10 Excellent! (787 reviews) The staff were so so nice! The hotel was so clean and so green and so cool and I loved every minute of it Reviewed on Feb 5, 2026 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/2026-04-30/2026-05-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Beach holidays in Windley Key Price found within the past 48 hours. Click for updated prices. ![Miami Downtown Condos](https://images.trvl-media.com/lodging/110000000/109790000/109784700/109784697/c533f3d5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Miami Downtown Condos Downtown Miami CA $945 per person Jun 15 - Jun 18 found 3 hours ago Roundtrip flight included Montreal (YMQ) to Miami (MIA) 8.2/10 Very Good! (124 reviews) good location! the property was in good condition. typical size of a condo-good size for 2-3 people. clean. the app to assess amenities and the door was a bit finicky but other than that i would recommend it to others Reviewed on Mar 31, 2026 ![Carillon Miami Wellness Resort](https://images.trvl-media.com/lodging/12000000/11350000/11344400/11344361/75c6ca53_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Carillon Miami Wellness Resort North Beach CA $3,051 per person Jun 14 - Jun 20 found 1 day ago Roundtrip flight included Montreal (YMQ) to Miami (MIA) 8.8/10 Excellent! (787 reviews) The staff were so so nice! The hotel was so clean and so green and so cool and I loved every minute of it Reviewed on Feb 5, 2026 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/2026-04-30/2026-05-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Beach holidays in Windley Key Price found within the past 48 hours. Click for updated prices. ![Miami Downtown Condos](https://images.trvl-media.com/lodging/110000000/109790000/109784700/109784697/c533f3d5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Miami Downtown Condos Downtown Miami CA $945 per person Jun 15 - Jun 18 found 3 hours ago Roundtrip flight included Montreal (YMQ) to Miami (MIA) 8.2/10 Very Good! (124 reviews) good location! the property was in good condition. typical size of a condo-good size for 2-3 people. clean. the app to assess amenities and the door was a bit finicky but other than that i would recommend it to others Reviewed on Mar 31, 2026 ![Carillon Miami Wellness Resort](https://images.trvl-media.com/lodging/12000000/11350000/11344400/11344361/75c6ca53_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Carillon Miami Wellness Resort North Beach CA $1,906 per person Jun 22 - Jun 25 found 21 hours ago Roundtrip non-stop flight included Montreal (YMQ) to Miami (MIA) 8.8/10 Excellent! (787 reviews) The staff were so so nice! The hotel was so clean and so green and so cool and I loved every minute of it Reviewed on Feb 5, 2026 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/2026-04-30/2026-05-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Beach holidays in Windley Key Price found within the past 48 hours. Click for updated prices. ![President Hotel Villa](https://images.trvl-media.com/lodging/11000000/10620000/10612900/10612810/5a873fda_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### President Hotel Villa South Beach CA $1,769 per person Jun 23 - Jun 27 found 1 day ago Roundtrip flight included Montreal (YMQ) to Miami (MIA) 8.2/10 Very Good! (1,003 reviews) Check-in was confusing this is the Reviewed on Mar 28, 2026 ![Carillon Miami Wellness Resort](https://images.trvl-media.com/lodging/12000000/11350000/11344400/11344361/75c6ca53_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Carillon Miami Wellness Resort North Beach CA $2,661 per person Jun 23 - Jun 27 found 1 day ago Roundtrip flight included Montreal (YMQ) to Miami (MIA) 8.8/10 Excellent! (787 reviews) The staff were so so nice! The hotel was so clean and so green and so cool and I loved every minute of it Reviewed on Feb 5, 2026 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/2026-04-30/2026-05-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Find the best beach vacations in Windley Key #### What are some benefits when booking beach vacations in Windley Key? When you travel to the beach in Windley Key, soft sands and inviting waters, warm sun and gentle breezes will help you relax. This applies to the whole family, as kids and adults can find something fun to do, so family beach vacations are the quintessential family trip. #### How can I book the best beach vacations in Windley Key? To find the best beach vacation, you'll need to book the right accommodations for your family. What the best is depends on what you want from your Windley Key trip. Fortunately, you can use various filters combined with the beach filter to sort for what you want. Additionally, you'll need to consider the time of year you visit. #### Can I book cheap beach vacations in Windley Key? There are quite a few things you can do to get cheap beach vacations in Windley Key. Prices range from CA $945, and if you want to keep yours on the lower side, you may want to consider just how close to the beach you are. If you don't mind a bit of a walk, further away is typically cheaper. Additionally booking something with a kitchen can help you save by avoiding dining out. #### Can I book beach packages? Yes, and you'll find quite a few beach packages available in Windley Key. These package deals let you save by booking your accommodation and your flight together with savings of up to 42\. #### Why should I book family beach vacations? When you're travelling with the family to Windley Key, booking your vacation by the beach is one of the best ways to keep everyone happy. There's a reason why some of the most memorable family trips for kids are family beach vacations. You'll be just steps away from the water, and you can often enjoy stunning views of the shore from your room. #### How can I find a beachfront vacation in Windley Key? It's easy to find a beachfront vacation accommodation in Windley Key using the search filter. You can filter for waterfront properties specifically that will only show you results that have beautiful views of the shoreline. #### How can I book last-minute beach vacations? Travelling at the last minute doesn't mean you're out of luck to have a dream beach vacation. Last-minute beach vacations may even offer a nice discount as the owners of hotels or other accommodations try to fill their remaining vacancies. All you have to do is input your travel dates and Windley Key as your destination and see what's available. #### Can I find all-inclusive beach vacations ? Yes, all you have to do to find all-inclusive beach vacations in Windley Key is to use the search filter. It will automatically restrict your results to all-inclusive deals that allow you to plan the entire trip in advance. #### Can I book a beach trip that's fully refundable? Any fully refundable booking can bring peace of mind, and we're happy to offer this feature in several packages and locations throughout Islamorada. All you have to do to find them is check the policies section on each accommodation page. Of course, you can filter for fully-refundable results specifically, too. #### Why should I book beach vacations with Expedia? When you book with Expedia, you'll find a one-stop shop for all your planning needs. You can book your flight and accommodation at the same place and potentially get a discount for booking these together. You can also take advantage of the Expedia Rewards program. Becoming a member is free, and when you do, you'll earn points with every booking will add discounts on subsequent trips. ## Beach Hotels in Windley Key ![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 - 2 min walk from Theater of the Sea Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free parking, and a marina. Our guests praise the pool and the helpful staff in our reviews. ... 9/10 Wonderful! (229 reviews) Wow this is a hidden gem in Islamorada. We stayed for only 1 night but we regret not staying longer. The service is great. Upon arrival the lady in the reception is super kind and sweet. Was always smiling and attentive. The rooms were clean, the beds were comfortable. We stayed in a cottage and ... Reviewed on Mar 26, 2026 [](https://expedia.ca/Islamorada-Hotels-Coconut-Cove-Resort-And-Marina.h4182524.Hotel-Information) ![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/4671ebc2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort 84001 Overseas Hwy Islamorada FL - 10 min walk from Theater of the Sea Book a stay at this beach resort in Islamorada. Enjoy free WiFi, 3 outdoor pools, and 4 restaurants. Our guests praise the helpful staff and the clean rooms ... 9/10 Wonderful! (179 reviews) No breakfast bar at this resort. Many onsite options for purchase. I did miss having a microwave. Reviewed on Mar 27, 2026 [](https://expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information) ![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 - 5 min walk from Theater of the Sea Book a stay at this beach motel in Islamorada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ... 8.2/10 Very Good! (1,002 reviews) Súper Reviewed on Mar 24, 2026 [](https://expedia.ca/Islamorada-Hotels-Fisher-Inn-Resort-Marina.h3274374.Hotel-Information) [See all 2,722 properties in Windley Key](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®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. ## 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 Beach Vacation Destinations > - [Myrtle beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/601685/Myrtle-Beach) > - [Miami beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/8833/Miami-Beach) > - [Florida beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/211/Florida) > - [Barbados beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/16/Barbados) > - [South beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6138745/South-Beach) > - [Palm beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/9061/Palm-Beach) > - [Daytona beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6023995/Daytona-Beach) > - [Newport beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/8111/Newport-Beach) > - [Vero beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6023660/Vero-Beach) > - [India beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/80/India) > - [Laguna beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6298668/Laguna-Beach) > - [Ontario beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/2680/Ontario) > - [Canada beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/31/Canada) > - [Barcelona beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/179992/Barcelona) > - [Fort Myers beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/7194/Fort-Myers-Beach) > - [Portugal beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/147/Portugal) > - [Italy beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/86/Italy) > - [Thailand beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/178/Thailand) > - [France beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/59/France) ## 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