
Windley Key Vacations from $521
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The Latest Windley Key vacation packages
Price found within the past 48 hours. Click for updated prices.

Flow Fort Lauderdale Hotel
Downtown Fort Lauderdale
Price was $1,175, price is now $521 per person
$521
per person
Feb 22 - Feb 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9/10 Wonderful! (560 reviews)
No signage out front or anyone to welcome you. It’s a hotel mixed with mostly residential so the hospitality isn’t there. When I finally found what I thought the check in counter was, there was a rep at the counter on her computer, attending no one physical there and I waited 5 mins to be greeted. No welcome or I’ve reached the right place. Once I told her I was there to check in, the room wasn’t ready and I asked if I can leave the bags and use amenities until ready and she said of course with no direction. Said once I bring the bags she will tell me everything and when I returned she was out to lunch. Didn’t tell us where the parking was or elevators nothing. The building is clearly catered to residents and not so much as a hotel. There were two lovely gentlemen to assist when I returned and were extremely nice and finally explained the amenities and area . The pool was not heated and tiles are extremely slippery and dangerous when walking on them wet.
Reviewed on Dec 14, 2025

Bay Breeze Premium Apartments By Eskape Collection
Price was $1,219, price is now $540 per person
$540
per person
Mar 4 - Mar 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (189 reviews)
From the very efficient and effective check in, courteous customer service, and spotless room, our stay was great from the beginning. The place was spacious and modern. There was a big wrap around balcony (we had the two bedroom), and large kitchen. Even a washer and dryer. The only cons were the water pressure in the bathroom sink, and after a certain time, you cannot get more towels. House cleaning is "ask if you want", its not every day. For us we liked our privacy, so this worked for us. Another thing we loved was the quiet. The views were ok. Go ahead and book, you will not regret.
Reviewed on Dec 8, 2025

Hawks Cay Resort
Price was $1,832, price is now $829 per person
$829
per person
Feb 28 - Mar 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1,003 reviews)
The resort was beautiful, the room was nice and clean although the day after we arrived housekeeping did not come to our room to empty garbages and give us fresh towels and had to ask at front desk. But after that it was not a problem. Also 1 morning we woke up to no water in our room and had to call front desk and eventually was turned back on. Other than those things we had a nice time.
Reviewed on Dec 14, 2025


Pelican Hotel
South Beach
Price was $1,582, price is now $728 per person
$728
per person
Mar 4 - Mar 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (394 reviews)
Staff was friendly, room was clean, bed was comfortable, and everything looked as pictured, but down-rated slightly because a couple of little wall fixtures were broken in the room and the chairs in the room were uncomfortable. BEWARE there is a daily resort fee hiding in the fine print that increases the cost of the room and there was no major amenity like a swimming pool or spa that seemed to justify this. Breakfast was not included in the price of stay.
Reviewed on Dec 8, 2025
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See all available trips from Columbus to Windley Key
View all tripsDiscover the most popular places to visit in Windley Key

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.
Windley Key Hotel Deals

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$288 nightly
The price is $324 total per night from Dec 17 to Dec 18
$324 total
Dec 17 - Dec 18
Total with taxes and fees
9/10 Wonderful! (114 reviews)
Beautiful room, stunning views
Reviewed on Nov 19, 2025

Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $163 total per night from Dec 18 to Dec 19
$163 total
Dec 18 - Dec 19
Total with taxes and fees
8/10 Very Good! (1,002 reviews)
Great location, room was spotless and perfectly met my needs. I plan to return next year.
Reviewed on Dec 11, 2025

Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
$146 nightly
The price is $165 total per night from Dec 17 to Dec 18
$165 total
Dec 17 - Dec 18
Total with taxes and fees
8.8/10 Excellent! (149 reviews)
Great place to stay! Clean, great location and great customer service. Very easy to check in, front desk was so sweet! Highly recommended!!! Had a great experience overall
Reviewed on Dec 5, 2025
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. Airport (EYW) |
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



















