Windley Key Vacations from $331

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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
Casablanca Miami Beach
The Retreat Collection at 1 Hotel & Homes South Beach
Creekside Inn
President Hotel
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Windley Key Hotel Deals

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

3.5 out of 5
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$500 nightly
The price is $563 total per night from Mar 22 to Mar 23
$563 total
Mar 22 - Mar 23
Total with taxes and fees
9/10 Wonderful! (158 reviews)
Fun outdoor tiki bar. Beautiful beach access. Nice room.

Reviewed on Feb 27, 2026

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

3.5 out of 5
84951 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$299 nightly
The price is $336 total per night from Mar 1 to Mar 2
$336 total
Mar 1 - Mar 2
Total with taxes and fees
8.4/10 Very Good! (1,002 reviews)
The room was spacious and clean with a nice view of the ocean. Unfortunately, our weeks stay was marred by the arctic freeze up and down the east coast. We were unable to access the "heated pool" nor go into the ocean. The clerk at the desk is very friendly. The pillows in our unit were dead. There ...

Reviewed on Feb 25, 2026

Fisher Inn Resort & Marina
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

3 out of 5
84801 Overseas Highway Islamorada FL
$355 nightly
The price is $399 total per night from Mar 4 to Mar 5
$399 total
Mar 4 - Mar 5
Total with taxes and fees
9.2/10 Wonderful! (201 reviews)
Staff are wonderful, rooms are clean and well kept, nice small resort and great atmosphere. The BYOB Tiki Bar is a real hit in my book.

Reviewed on Feb 25, 2026

Coconut Cove Resort and Marina
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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