
Windley Key Vacations from $747
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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 $4,356, price is now $1,839 per person
$1,839
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop 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

Solé Miami, A Noble House Resort
Ocean Four
Price was $1,923, price is now $950 per person
$950
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (2,052 reviews)
Location was great, right on the beach. The only thing is elevators- wait time is too long! Other that that was a nice place to stay.
Reviewed on Mar 9, 2026


EAST Miami Residences
Brickell
Save 100% on your flight
Price was $2,581, price is now $1,473 per person
$1,473
per person
May 24 - May 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9/10 Wonderful! (107 reviews)
We loved staying here and will definitely be back! Yes, it is very expensive, but compared to other Miami hotels this one is the best overall deal for what you get.
Reviewed on Mar 1, 2026
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View all tripsDiscover the most popular places to visit in Windley Key

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
$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
$389 nightly
The price is $438 total per night from Mar 12 to Mar 13
$438 total
Mar 12 - Mar 13
Total with taxes and fees
9/10 Wonderful! (214 reviews)
The grounds, room, pool/pool area and "beach" were very well kept. The property had almost everything we needed for our last night in the Keys. While the property is oceanfront, you cannot go in the water because of the seawall and coral, which was really disappointing but an oversight on our part ...
Reviewed on Mar 9, 2026

Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$308 nightly
The price is $347 total per night from Mar 11 to Mar 12
$347 total
Mar 11 - Mar 12
Total with taxes and fees
8.4/10 Very Good! (1,008 reviews)
We came here for a quiet night away. This place did not disappoint. Hotel was calm and peaceful. We enjoyed walking the dock and seeing all the different fish. The afternoon we arrived we had parrots outside our balcony which was amazing. Definitely our best night of our trip.
Reviewed on Mar 6, 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.




















