Windley Key Vacations from $655
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The Latest Windley Key vacation packages
Price found within the past 48 hours. Click for updated prices.
Casablanca Miami Beach
North Beach
Price was $2,877, price is now $1,267 per person
$1,267
per person
Jun 23 - Jun 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
5.8/10 (322 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 Villa
South Beach
Price was $2,531, price is now $1,136 per person
$1,136
per person
Jun 23 - Jun 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (1,001 reviews)
Breakfast buffet was amazing but make sure to get there at 7:30am because around 9am it gets packed and it’s hard to find seats. There’s additional seating outside and in the patio but if there's rain you have to sit inside
Reviewed on Apr 16, 2026
ABAE Hotel by Eskape Collection
South Beach
Save 100% on your flight
Price was $2,176, price is now $1,198 per person
$1,198
per person
Jun 23 - Jun 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.8/10 Excellent! (1,001 reviews)
I LOVED THE AREA , THE ROOFTOP VIEWS , THE CLEANINESS OF EVERYTHING,
I DIDNT LIKE HOW THE POOL AREA CLOSED AT 8PM
Reviewed on Apr 19, 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
$305 nightly
The price is $343 total per night from May 4 to May 5
$343 total
May 4 - May 5
Total with taxes and fees
9/10 Wonderful! (185 reviews)
We loved everthing about this resort! We just wish we had stayed longer! We stayed in The Cove. It was secluded and quiet! A perfect get away!
Reviewed on Apr 16, 2026
Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$173 nightly
The price is $194 total per night from May 6 to May 7
$194 total
May 6 - May 7
Total with taxes and fees
8.2/10 Very Good! (1,005 reviews)
It was great location and loved the private porch off our room. Was the perfect place to relax after long days of fishing.
Reviewed on Apr 19, 2026
Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
$289 nightly
The price is $325 total per night from Apr 21 to Apr 22
$325 total
Apr 21 - Apr 22
Total with taxes and fees
9/10 Wonderful! (245 reviews)
Customer service was excellent
Reviewed on Apr 18, 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.
