
Windley Key Vacations from $753
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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 $1,374, price is now $753 per person
$753
per person
May 24 - May 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (1,007 reviews)
Everything was perfect . I would stay there again
Reviewed on Mar 16, 2026

Creekside Inn
Price was $1,887, price is now $791 per person
$791
per person
Jun 4 - Jun 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
7.8/10 Good! (1,027 reviews)
Older, but near our kayaking. On the canal & near several restaurants- walkable. Quiet, cool
Reviewed on Mar 16, 2026

Casablanca Miami Beach
North Beach
Price was $4,355, price is now $1,998 per person
$1,998
per person
May 21 - May 24
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


La Siesta Resort & Villas
Matecumbe
Save 100% on your flight
Price was $2,519, price is now $1,341 per person
$1,341
per person
Apr 25 - May 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.8/10 Excellent! (1,004 reviews)
Grrat view from room and location is awesome.
Reviewed on Mar 4, 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
$347 nightly
The price is $391 total per night from Apr 15 to Apr 16
$391 total
Apr 15 - Apr 16
Total with taxes and fees
9/10 Wonderful! (171 reviews)
Ocean view was very nice from the the 2nd floor. We were just off one of the beach areas, so very happy we weren't in front the
Reviewed on Mar 17, 2026

Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
$389 nightly
The price is $438 total per night from Mar 22 to Mar 23
$438 total
Mar 22 - Mar 23
Total with taxes and fees
9/10 Wonderful! (218 reviews)
The room has a mold issue, should have complained the night of. The smell was overwhelming and I woke up the next morning nacious. Low water pressure. Would not waste your time.
Reviewed on Mar 16, 2026

Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$294 nightly
The price is $330 total per night from Apr 16 to Apr 17
$330 total
Apr 16 - Apr 17
Total with taxes and fees
8.4/10 Very Good! (1,004 reviews)
Needs to remodel a bit. Staff was nice and rooms were clean. No place to put supplies in shower and water pressure was weak. Couch sunk to ground. View was good. Room was large.
Reviewed on Mar 15, 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.



















