Title: Windley Key Vacation Packages 2026 from $385 | Expedia.com [Windley Key Travel Guide](https://expedia.com/Windley-Key.dx553248635976197663)[Hotels in Windley Key](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)[Flights to Windley Key](https://expedia.com/Cheap-Flights-To-Windley-Key.d553248635976197663.Travel-Guide-Flights)[Things to do in Windley Key](https://expedia.com/Things-To-Do-In-Windley-Key.d553248635976197663.Travel-Guide-Activities)[Car Rentals in Windley Key](https://expedia.com/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 Vacations from $385 ## Book a 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 ## The Latest Windley Key vacation packages Price found within the past 48 hours. Click for updated prices. ![The Penguin Hotel](https://images.trvl-media.com/lodging/1000000/70000/62900/62824/d4ab7ebb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Penguin Hotel South Beach Save 100% on your flight $385 per person May 14 - May 18 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.2/10 Very Good! (1,491 reviews) We had a terrific time and we are pretty sure we will be coming back around the same time next year! Reviewed on Feb 23, 2026 ![President Hotel](https://images.trvl-media.com/lodging/1000000/580000/575900/575859/5a013cab_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### President Hotel South Beach Save 100% on your flight $436 per person May 14 - May 18 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.4/10 Very Good! (1,775 reviews) Clean space. Easy checkin. Central location in South Beach. Reviewed on Feb 23, 2026 ![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 $842 per person Apr 27 - May 2 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 9.2/10 Wonderful! (394 reviews) Staff was top notch!! They were helpful and kind and always happy to interact with us. Reviewed on Feb 18, 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 Save 100% on your flight $1,241 per person Apr 17 - Apr 24 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1,004 reviews) This hotel is old but we'll maintained. The room was clean and beds were comfortable and passed my rigorous bedbug check. The staff was friendly and we were even able to check in early. Our room was facing the canal on the first floor and it was gorgeous. We saw a momma manatee and her baby right in front of our room! Boats go by ..kayaks...well worth the price. Reviewed on Feb 23, 2026 ![Nobu Hotel Miami Beach](https://images.trvl-media.com/lodging/17000000/16260000/16256600/16256597/06483b1e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Nobu Hotel Miami Beach Mid Beach $1,100 per person May 15 - May 20 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.6/10 Excellent! (1,266 reviews) The room was clean and the bed was comfortable. We were not pleased with the functionality of the bathroom. It looked very nice but the shower glass doors did not prevent water from coming out both under the door and where the door closes. After my husband took tge 1st shower, the water flooded the bathroom floor and out into the hallway. I had to shower standing in the corner of the shower up against the wall to keep the water from flooding the bathroom again. The sink and faucet design splashes water all over the vanity no mater how soft you run the water. So I spent time sopping up water each time we used the shower and sink. Then the toilet paper holder came apart off the wall so my husband fixed it. The staff were very nice and professiinal. Would have liked a breakfast buffet but no breakfast restaurant in the hotel. Reviewed on Feb 24, 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/2026-03-24/2026-03-31/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_553248635976197663) ### Discover the most popular places to visit in Windley Key ![Windley Key Fossil Reef Geological State Park](https://images.trvl-media.com/place/6282211/9f8e583b-bc9a-4a16-b731-daa0b5c7f87b.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Windley Key Fossil Reef Geological State Park 4.5/5(20 reviews) 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.com/Windley-Key-Fossil-Reef-Geological-State-Park-Islamorada.d6282211.Vacation-Attraction) ## 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 $424 nightly $477 total Mar 4 - Mar 5 Total with taxes and fees 9/10 Wonderful! (157 reviews) All was fantastic. Very nice staff. Clean room. Highly recommended Reviewed on Feb 23, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F4%2F2026&endDate=3%2F5%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 $316 nightly $356 total Mar 1 - Mar 2 Total with taxes and fees 8.4/10 Very Good! (1,004 reviews) The room was clean but tired. The location is good but highway noise. The staff were OK. The food truck was very good. Reviewed on Feb 22, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F1%2F2026&endDate=3%2F2%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 $358 nightly $403 total Mar 2 - Mar 3 Total with taxes and fees 9.2/10 Wonderful! (199 reviews) Cool place, definitely not a first class experience, but we loved it. Room clean, grounds nice, the animals running around were great. Best part was staff.the Lady at the desk was fantastic, and everyone we came across were very polite and friendly. I would 100% return. Reviewed on Feb 23, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F2%2F2026&endDate=3%2F3%2F2026&selected=4182524&PinnedHotelID=4182524&HadPinnedHotel=true®ionId=553248635976197663) [See all 2,741 properties in Windley Key](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F25%2F2026&endDate=2%2F26%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. ## Find the Best Windley Key Vacation Packages ## Windley Key Essential Information | Language | English | | --------------- | ---------------------------- | | Currency | U.S dollars | | Closest Airport | Key West Intl. 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