
Windley Key Vacations from $331
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The Latest Windley Key vacation packages
Price found within the past 48 hours. Click for updated prices.

Cavalier Hotel South Beach
South Beach
Save 100% on your flight
Price was $682, price is now $331 per person
$331
per person
May 9 - May 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Loved the location, room was nice, bathroom very small, very friendly staff, slow service at restaurant in the morning. Will go back
Reviewed on Feb 24, 2026

Casablanca Miami Beach
North Beach
Price was $5,039, price is now $2,053 per person
$2,053
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



President Hotel
South Beach
Save 100% on your flight
Price was $711, price is now $354 per person
$354
per person
May 9 - May 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,775 reviews)
Location is great, the rest is average or below average
Reviewed on Feb 26, 2026
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View all tripsDiscover the most popular places to visit in Windley Key

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.
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
$500 nightly
The price is $563 total per night from Mar 22 to Mar 23
$563 total
Mar 22 - Mar 23
Total with taxes and fees
9/10 Wonderful! (158 reviews)
Fun outdoor tiki bar. Beautiful beach access. Nice room.
Reviewed on Feb 27, 2026

Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$299 nightly
The price is $336 total per night from Mar 1 to Mar 2
$336 total
Mar 1 - Mar 2
Total with taxes and fees
8.4/10 Very Good! (1,002 reviews)
The room was spacious and clean with a nice view of the ocean. Unfortunately, our weeks stay was marred by the arctic freeze up and down the east coast. We were unable to access the "heated pool" nor go into the ocean. The clerk at the desk is very friendly. The pillows in our unit were dead. There ...
Reviewed on Feb 25, 2026

Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
$355 nightly
The price is $399 total per night from Mar 4 to Mar 5
$399 total
Mar 4 - Mar 5
Total with taxes and fees
9.2/10 Wonderful! (201 reviews)
Staff are wonderful, rooms are clean and well kept, nice small resort and great atmosphere. The BYOB Tiki Bar is a real hit in my book.
Reviewed on Feb 25, 2026
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.




















