
Windley Key Vacations from $524
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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 $5,507, price is now $2,165 per person
$2,165
per person
Jun 17 - Jun 21
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) 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



Cavalier Hotel South Beach
South Beach
Save 100% on your flight
Price was $1,211, price is now $649 per person
$649
per person
May 22 - May 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.6/10 Excellent! (1,000 reviews)
Its my fourth time there and i loved it
Reviewed on Apr 6, 2026
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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
$322 nightly
The price is $362 total per night from May 4 to May 5
$362 total
May 4 - May 5
Total with taxes and fees
9/10 Wonderful! (181 reviews)
Pool staff great. Too windy to do beach activities our trip unfortunately. Hotel room was great. Beautiful views. Check in was an unfortunate process. We were hoping for an early check in, instead didn’t get checked in till after our guaranteed 4PM.
Reviewed on Apr 4, 2026

Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
$280 nightly
The price is $315 total per night from May 3 to May 4
$315 total
May 3 - May 4
Total with taxes and fees
9/10 Wonderful! (234 reviews)
Rooms are very clean
Reviewed on Apr 4, 2026

Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $207 total per night from May 6 to May 7
$207 total
May 6 - May 7
Total with taxes and fees
8.2/10 Very Good! (1,002 reviews)
I loved the fact we had 2 king beds, the room was above average in size and we weren't far from the marina to go fishing. Will be staying here again!
Reviewed on Apr 8, 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.



















