
Windley Key Vacations from $523
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The Latest Windley Key vacation packages
Price found within the past 48 hours. Click for updated prices.

Fort Lauderdale Beach Resort by Vacatia
East Fort Lauderdale
Price was $921, price is now $523 per person
$523
per person
May 20 - May 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (525 reviews)
Nice clean rooms, nice location loved the view
Reviewed on Mar 10, 2026

Casablanca Miami Beach
North Beach
Price was $6,898, price is now $2,800 per person
$2,800
per person
May 2 - May 7
found 1 day ago
Roundtrip flight included
Boston (BOS) 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



1 Hotel South Beach
South Beach
Save 100% on your flight
Price was $2,670, price is now $1,505 per person
$1,505
per person
May 14 - May 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.4/10 Exceptional! (1,451 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
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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
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
$398 nightly
The price is $448 total per night from Mar 23 to Mar 24
$448 total
Mar 23 - Mar 24
Total with taxes and fees
9/10 Wonderful! (166 reviews)
Overpriced for a view of the parking lot on the ground floor.
Reviewed on Mar 7, 2026

Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
$299 nightly
The price is $336 total per night from Mar 11 to Mar 12
$336 total
Mar 11 - Mar 12
Total with taxes and fees
9/10 Wonderful! (215 reviews)
Very good experience. Managers were very pleasant. Older buildings but kept up and all was clean. Nice pool, nice chairs to view ocean.
Reviewed on Mar 10, 2026

Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$288 nightly
The price is $324 total per night from Mar 11 to Mar 12
$324 total
Mar 11 - Mar 12
Total with taxes and fees
8.4/10 Very Good! (1,009 reviews)
No. The pool was closed 2 days we were there. There weren’t many chairs in pool area for a property its size. The pool was not heated as was indicated on website. We asked three times to have the room cleaned. They came once and made the bed, threw out trash and gave clean towels. They did not sweep ...
Reviewed on Mar 10, 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.




















