Title: Windley Key Vacation Packages 2026 from $483 | 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 $483 ## 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. ![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 $483 per person May 5 - May 9 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.4/10 Very Good! (1,775 reviews) I really liked the location — it was very convenient. The room was pretty big and very clean, which made the stay comfortable. The staff was friendly and welcoming. The breakfast was okay, nothing special, but it was fine. Reviewed on Mar 1, 2026 ![Casablanca Miami Beach](https://images.trvl-media.com/lodging/32000000/31660000/31652200/31652150/628e521a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Casablanca Miami Beach North Beach $2,064 per person May 18 - May 22 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 5.8/10 (311 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 ![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 $1,569 per person May 14 - May 21 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.6/10 Excellent! (1,266 reviews) The rooms are nice and large, amenities such as toiletries and free water bottle were great, and the easy access to the beach was perfect - you get chairs and an umbrella as part of your stay. Dining was also amazing - between the Nobu restaurant, the Inez Cafe, and tasty breakfast, you're covered! We did have issues, however, related to housekeeping - they were really kind and helpful, however, I don't know if it was due to miscommunication or mismanagement, but they skipped cleaning our room one day, and on another, took items but didn't replace with new ones, so had to call for towels, etc. On top of this, I had asked for items to be removed from the fridge days before our stay - received confirmation that it would be done. Got to the room - the items were not removed. I texted using their text system to ask if someone could remove the items, and received confirmation - twice over the time of our stay- but it never happened. This was frustrating. I could tell we weren't the only ones experiencing similar issues. Also, it took a couple tries of showering to understand the reason why water was pouring out onto the floor - the shower/glass door was missing a rubber cover at the bottom, so had to report that. Outside of these areas, the stay was really nice/relaxing. Reviewed on Mar 1, 2026 ![Flow Fort Lauderdale Hotel](https://images.trvl-media.com/lodging/71000000/70340000/70330700/70330603/w8183h5464x9y0-3a9d82ba_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Flow Fort Lauderdale Hotel Downtown Fort Lauderdale Save 100% on your flight $586 per person May 23 - May 29 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Miami (MIA) 9/10 Wonderful! (560 reviews) The 2-bedroom suite in East wing was just ok. Quite small with no table for eating. There was quite a bit of mold in the shower around the tiles near the ground. Stark appearance. West wing room was better, large, clean and dining table was appreciated. Waits for the elevator on west side is crazy! The amount of dogs in this building is problematic for people with fear of dogs or allergies. The tenants of the building don’t always clean up after their dogs and came down to feces in the hallway on ground level one morning. It is a condo building, not a hotel. Problem with west side of hotel is the train tracks right behind the building! The trains are loud and frequent and the dinging of the railway safety arms are a complete and utter annoyance. Overall, I suggest you understand what you are looking for and what you’re willing to put up with before booking here. Reviewed on Mar 2, 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 $599 per person Apr 2 - Apr 5 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1,004 reviews) The room was very small. The whole resort needed updating. There is no accommodations for seniors on the first floor. They said they could guarantee the room size, but they could not guarantee first floor access to those with disabilities. Other than the manager who is all business and not very sympathetic to anything, the staff that I met was very nice. To me it wasn’t worth the price we paid for it. Reviewed on Mar 2, 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/2026-04-03/2026-04-10/?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 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 $478 nightly $538 total Mar 5 - Mar 6 Total with taxes and fees 9/10 Wonderful! (160 reviews) i paid over 7 thousand dollars for 2 rooms for 4 nights..800 a night to get a view of a parking lot. i am a gold member of Marriott. The room was so small, no latch on door and the drawers were broken. HIGHLY DISAPPOINTED Reviewed on Mar 2, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F5%2F2026&endDate=3%2F6%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 refundableReserve now, pay when you stay $339 nightly $381 total Apr 2 - Apr 3 Total with taxes and fees 8.4/10 Very Good! (1,003 reviews) Great location. Room was clean and updated. Enjoyed the balcony. Reviewed on Mar 1, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F2%2F2026&endDate=4%2F3%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 $366 nightly $412 total Mar 29 - Mar 30 Total with taxes and fees 9.2/10 Wonderful! (205 reviews) It was wonderful Reviewed on Mar 2, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=4182524&PinnedHotelID=4182524&HadPinnedHotel=true®ionId=553248635976197663) [See all 2,738 properties in Windley Key](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F4%2F2026&endDate=3%2F5%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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