
Windley Key Vacation Packages
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Top Windley Key Vacation Deals
Price found within the past 48 hours. Click for updated prices.




Park Central South Beach
South Beach
per person
Oct 25 - Nov 1
found 21 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.2/10 Very Good! (911 reviews)
Perfectly situated. Right on the strip. Walking distance to the beach and night life. We had an ocean view room, but even with windows closed, it could get pretty noisy in the evening.
Reviewed on Aug. 11, 2025

Pelican Grand Beach Resort - A Noble House Resort
East Fort Lauderdale
per person
Oct 25 - Nov 1
found 19 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.8/10 Excellent! (1,156 reviews)
It's a very quaint hotel. The rooms are spacious with a living area. The pool is small, but it's a good thing there were not too many people. Great happy hours even during the weekend. I didn't like that they only have valet parking. Albert was the best server at Ocean 2000. And Jennifer and Melissa at the O2K Lounge.
Reviewed on Aug. 10, 2025
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
The price is CA $268 per night from Sep 8 to Sep 9
CA $268
CA $393 total
Sep 8 - Sep 9
includes taxes & fees
8.8/10 Excellent! (56 reviews)
"Great resort, excellent staff and customer service, I'll definitely coming back"
Reviewed on Aug. 7, 2025

Fisher Inn Resort & Marina
84951 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is CA $141 per night from Aug 12 to Aug 13
CA $141
CA $204 total
Aug 12 - Aug 13
includes taxes & fees
8/10 Very Good! (1,002 reviews)
"Great vibe. Very helpful. Great scenery and location!"
Reviewed on Aug. 10, 2025

Coconut Cove Resort and Marina
84801 Overseas Highway, Islamorada, FL
The price is CA $173 per night from Sep 8 to Sep 9
CA $173
CA $195 total
Sep 8 - Sep 9
includes taxes & fees
7.6/10 Good! (812 reviews)
The most relaxing night
"Amazing group of people works in this hotel ! Super friendly can’t wait to come back again"
Reviewed on Aug. 1, 2025
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.
Discover 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.
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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.