
Windley Key Vacations from $1,059
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The Latest Windley Key vacation packages
Price found within the past 48 hours. Click for updated prices.

Creekside Inn
Price was $2,306, price is now $1,059 per person
$1,059
per person
Apr 16 - Apr 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
7.8/10 Good! (1,007 reviews)
Room was clean. I recommend washing down the walls in the bathroom and around light fixtures. Staff was excellent. Pool was good.
Reviewed on Mar 6, 2026

Casablanca Miami Beach
North Beach
Price was $3,740, price is now $1,622 per person
$1,622
per person
May 11 - May 14
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


Cheeca Lodge & Spa
Matecumbe
Save 100% on your flight
Price was $3,007, price is now $1,783 per person
$1,783
per person
May 23 - May 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (1,298 reviews)
Simone and Aisha at the front desk were amazing! The staff were kind, friendly and helpful. A little island gem!
Reviewed on Mar 5, 2026

Villas At Hawks Cay Resort
Price was $2,924, price is now $1,749 per person
$1,749
per person
May 17 - May 23
found 14 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (145 reviews)
The staff were all great and very responsive.
Staying over by the adult only pool vs the main pool with all the kids is like being at 2 different resorts.
We really enjoyed our dinner at the Salt and Ash
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
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
$466 nightly
The price is $524 total per night from Mar 23 to Mar 24
$524 total
Mar 23 - Mar 24
Total with taxes and fees
9/10 Wonderful! (163 reviews)
Room was small despite being an upgrade
Reviewed on Mar 5, 2026

Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$303 nightly
The price is $341 total per night from Mar 11 to Mar 12
$341 total
Mar 11 - Mar 12
Total with taxes and fees
8.4/10 Very Good! (1,006 reviews)
We had an excellent day at this place. Rooms were modern and spotless. It was in walking distance to several great places some with live music. It was a very chill atmosphere and not overcrowded. We were able to take advantage of the kayaks and able to go out on the calm waters. All in all this place ...
Reviewed on Mar 5, 2026

Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
$339 nightly
The price is $381 total per night from Mar 8 to Mar 9
$381 total
Mar 8 - Mar 9
Total with taxes and fees
9.2/10 Wonderful! (209 reviews)
We only stayed one night. Staff was very friendly and accommodating. Property was very nice. Our mattress could’ve used an upgrade. Overall, a very good stay.
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.




















