Windley Key Vacations from $638

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The Latest Windley Key vacation packages

Price found within the past 48 hours. Click for updated prices.
Beach House Fort Lauderdale, a Hilton Resort
Casablanca Miami Beach
The Retreat Collection at 1 Hotel & Homes South Beach
President Hotel Villa
President Hotel
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Discover the most popular places to visit in Windley Key

Windley Key Hotel Deals

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

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

4 out of 5
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$313 nightly
The price is $352 total per night from May 4 to May 5
$352 total
May 4 - May 5
Total with taxes and fees
9/10 Wonderful! (187 reviews)
They hit you with a $65 per day resort fee…. Not the end of the world but not a good surprise after you leave.

Reviewed on Apr 21, 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
$173 nightly
The price is $194 total per night from May 6 to May 7
$194 total
May 6 - May 7
Total with taxes and fees
8.2/10 Very Good! (1,009 reviews)
Amazing hotel

Reviewed on Apr 20, 2026

Fisher Inn Resort & Marina
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

3 out of 5
84801 Overseas Highway Islamorada FL
$179 nightly
The price is $201 total per night from Apr 23 to Apr 24
$201 total
Apr 23 - Apr 24
Total with taxes and fees
9/10 Wonderful! (248 reviews)
Customer service was excellent

Reviewed on Apr 18, 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.