Title: Windley Key Scuba Diving Vacations 2026/2027 | Expedia.com ![](https://images.trvl-media.com/place/553248635997958830/30b22f53-286f-436b-ae7a-d035c9062e6c.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Windley Key Scuba Diving Vacations ## Book a Scuba Diving Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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 Scuba Diving vacation packages in Windley Key Price found within the past 48 hours. Click for updated prices. ![The Sunny](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145283/edbd844f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Sunny Ocean Four Save 100% on your flight $545 per person May 4 - May 8 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.2/10 Very Good! (81 reviews) Everything was beautiful. I have been here before and it is so much better than the first time I came here. The only issue we had was the walls seem so thin. We heard our neighbors all night and it was frustrating trying to sleep. It was as if they were in our room with us. That’s how clear we could hear them. Other than that what an amazing place to stay for a getaway. I will def stay there again. The hospitality and cleanliness was amazing. Reviewed on Mar 16, 2026 ![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/e518a34f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Retreat Collection at 1 Hotel & Homes South Beach South Beach $11,589 per person May 24 - May 31 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1 review) ![Tranquility Bay Beachfront Hotel and Resort](https://images.trvl-media.com/lodging/1000000/120000/117100/117099/854776a0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Tranquility Bay Beachfront Hotel and Resort Save 100% on your flight $1,389 per person Jun 8 - Jun 15 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.8/10 Excellent! (1,000 reviews) We stayed in a villa and enjoyed the water activities, plus Publix is nearby! We rested, recharged in a secure and peaceful environment… truly magical. Reviewed on Mar 16, 2026 ![Villas At Hawks Cay Resort](https://images.trvl-media.com/lodging/100000000/99930000/99920100/99920083/8638cc9f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Villas At Hawks Cay Resort Save 100% on your flight $954 per person May 5 - May 8 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.4/10 Very Good! (174 reviews) Property was clean and staff were helpful. Would stay again. Reviewed on Mar 11, 2026 ![Hotel Riu Plaza Miami Beach](https://images.trvl-media.com/lodging/1000000/80000/74600/74574/3532c352_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Miami Beach Mid Beach Save 100% on your flight $1,302 per person May 23 - May 30 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1,165 reviews) Perfectly located, friendly staff Reviewed on Mar 15, 2026 Don't see what you're looking for? See all available trips from Columbus to Windley Key [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-17/2026-04-24/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Scuba Diving vacations in Windley Key Price found within the past 48 hours. Click for updated prices. ![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/4608d7e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cheeca Lodge & Spa Matecumbe Save 100% on your flight $1,103 per person Jun 2 - Jun 7 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 9.2/10 Wonderful! (1,308 reviews) We did not use the spa services, we may have been able to barely see a small portion of the ocean out a window Reviewed on Mar 12, 2026 ![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/e518a34f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Retreat Collection at 1 Hotel & Homes South Beach South Beach $11,589 per person May 24 - May 31 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1 review) ![1 Hotel South Beach](https://images.trvl-media.com/lodging/2000000/1800000/1790100/1790087/5c0d327a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel South Beach South Beach Save 100% on your flight $1,749 per person May 22 - May 25 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Miami (MIA) 9.4/10 Exceptional! (1,455 reviews) This hotel is so beautiful and the staff is so kind and accommodating. The pool and beach areas are stunning, the food is delicious, the rooms are spacious, the beds are so comfortable, and the location is perfect. It’s the best hotel experience I’ve ever had, and I can’t wait to go back again! Reviewed on Mar 7, 2026 Don't see what you're looking for? See all available trips from Columbus to Windley Key [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-17/2026-04-24/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Scuba Diving vacations in Windley Key Price found within the past 48 hours. Click for updated prices. ![Villas At Hawks Cay Resort](https://images.trvl-media.com/lodging/100000000/99930000/99920100/99920083/8638cc9f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Villas At Hawks Cay Resort Save 100% on your flight $987 per person May 28 - May 31 found 1 day ago Roundtrip flight included Newark Liberty Intl. Airport (EWR) to Miami (MIA) 8.4/10 Very Good! (174 reviews) Property was clean and staff were helpful. Would stay again. Reviewed on Mar 11, 2026 ![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/e518a34f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Retreat Collection at 1 Hotel & Homes South Beach South Beach $5,132 per person Apr 20 - Apr 23 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1 review) ![Kimpton Surfcomber Hotel by IHG](https://images.trvl-media.com/lodging/1000000/20000/16000/15996/93c84cb9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kimpton Surfcomber Hotel by IHG South Beach Save 100% on your flight $1,004 per person May 29 - Jun 1 found 18 hours ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.2/10 Very Good! (1,007 reviews) Smallish rooms but very clean and fabulous outdoor amenities including pool and restaurant bar. Reviewed on Mar 10, 2026 Don't see what you're looking for? See all available trips from Columbus to Windley Key [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-17/2026-04-24/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Scuba Diving vacations in Windley Key Price found within the past 48 hours. Click for updated prices. ![Casablanca Miami Beach](https://images.trvl-media.com/lodging/32000000/31660000/31652200/31652150/f54c02bb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Casablanca Miami Beach North Beach Save 100% on your flight $515 per person Apr 17 - Apr 21 found 1 day ago Roundtrip flight included Philadelphia (PHL) to Miami (MIA) 5.8/10 (320 reviews) Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great. It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it. Reviewed on Feb 22, 2026 ![Creekside Inn](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/4743fa46_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Creekside Inn Save 100% on your flight $683 per person Apr 23 - Apr 27 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 7.8/10 Good! (1,027 reviews) Older, but near our kayaking. On the canal & near several restaurants- walkable. Quiet, cool Reviewed on Mar 16, 2026 ![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/e518a34f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Retreat Collection at 1 Hotel & Homes South Beach South Beach $7,038 per person May 4 - May 8 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1 review) Don't see what you're looking for? See all available trips from Columbus to Windley Key [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-17/2026-04-24/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Find amazing scuba diving vacations in Windley Key #### What are the main highlights of scuba diving in Windley Key? One of the main highlights of scuba diving vacation packages to Windley Key is the spectacular marine life. The clear waters and abundant wildlife only enhance the experience. In Windley Key, you'll also encounter a wide range of places to dive and many facilities and guides available. Take your pick from a vast array of Windley Key accommodations on Expedia. There's everything from luxury hotels to inviting guest houses for you to choose from. #### Can I expect guided tours or excursions for scuba diving in Windley Key? As a destination renowned worldwide for its scuba diving, you'll encounter a plethora of excursions and guided tours for your Windley Key vacation. You can even guarantee your space by reserving them in advance on Expedia. Before making your booking, on the trip details page, scroll down and you'll see a selection of popular tours and activities in Windley Key. In case your 2026 plans change, many allow for free cancellation, too. #### How to find special deals for scuba diving vacations in Windley Key? You'll often find juicy deals for Windley Key vacation packages from $515 by booking in advance when early-bird deals may be available. That said, you may score [last-minute deals](https://www.expedia.com/lp/b/vacations/last-minute-deals) when traveling during low season. On Expedia, the green label indicates you've scored an exclusive saving. It's wise to be flexible with your dates, as different departure days may be cheaper. You can also score member-only discounts on select hotels by joining the [One Key](https://www.expedia.com/welcome-one-key) rewards program. Best of all, it's free to join. #### How to book a Windley Key scuba diving vacation with Expedia? Pop your dates into the search wizard to start booking your Windley Key vacation package with Expedia. It lets you compare hundreds of some of the best deals at the click of a button. You can easily view all the packages that meet your preferences by using the handy search filters, too. These include things like ocean view, beachfront, and eco-certified. When you've pinned down the right Windley Key vacation package, click through to book in a few easy steps. #### What does a scuba diving vacation package in Windley Key typically include? Windley Key scuba diving vacation packages from $515 include return flights, accommodation and relevant taxes. Some may even include breakfast, too. If you book an all-inclusive vacation package to Windley Key, you'll enjoy all meals and drinks included. Keep in mind that each Windley Key resort is different, so be sure to scan over the inclusions before confirming your trip. These will be clearly displayed before you reach the checkout page on Expedia. #### Why book my scuba diving trip with Expedia? Thanks to exclusive deals you won't find anywhere else, you'll score some of the best prices when booking your 2026 Windley Key scuba diving vacation on Expedia. From luxury 5-star hotels to quaint bed and breakfasts, the vast variety means you'll easily find your dream trip. Expedia's 24/7 support and booking protection gives you peace of mind before and during your trip. You don't need to save up or wait until payday to book your vacation package to Windley Key, either. Expedia's vacation [payment plans](https://www.expedia.com/lp/b/vacations/payment-plans) let you spread the cost of your trip over 3, 6, or 12 months. #### Can I cancel my scuba diving vacation booking easily? Yes, many of Expedia's Windley Key vacation packages are flexible, meaning you can often cancel for free. Just be sure to double-check the cancellation policy before booking, as each deal is different. The free cancellation' search filter is especially helpful. It lets you narrow down your search to view only flexible Windley Key vacation packages. Book one of these on Expedia and if your 2026 plans change, you'll be able to easily modify or cancel your trip. #### How to plan for a scuba diving vacation in Windley Key? The best way to start planning your Windley Key scuba diving vacation is by choosing what time of year to go. The high season typically offers the best conditions for scuba diving, but you may find more crowds and higher prices than in low season. Next, decide what type of accommodation you'd like to stay in. On Expedia, you'll encounter everything from high-end oceanfront resorts to inviting boutiques and guest houses. Take a look at the [vacation planning page](https://www.expedia.com/lp/b/vacations/planning) for more tips and ideas. ## 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.com/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.com/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) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) 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](https://www.expedia.com/lp/theme-vacations/scuba-diving-vacations/8369/Key-Largo) > - [Bonaire Scuba Diving Vacations ](https://www.expedia.com/lp/theme-vacations/scuba-diving-vacations/182193/Bonaire) > - [Grand Cayman Scuba Diving Vacations ](https://www.expedia.com/lp/theme-vacations/scuba-diving-vacations/602874/Grand-Cayman) ## More Vacation Ideas [Flights to Windley Key ](https://expedia.com/Cheap-Flights-To-Windley-Key.d553248635976197663.Travel-Guide-Flights)[ Windley Key Hotels ](https://expedia.com/Windley-Key-Hotels.d553248635976197663.Travel-Guide-Hotels)[ Vacation Rentals in Windley Key ](https://expedia.com/Windley-Key-Vacation-Rentals.d553248635976197663.Travel-Guide-VacationRentals)[ Car Rentals in Windley Key ](https://expedia.com/Car-Rentals-In-Windley-Key.d553248635976197663.Car-Rental-Guide)[ Windley Key Vacations ](https://expedia.com/Windley-Key.d553248635976197663.Destination-Travel-Guides)[ Things to do in Windley Key ](https://expedia.com/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 even more - get up to 20% on select hotels 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