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

Cavalier Hotel South Beach
South Beach
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
A Perfect Stay on Ocean Drive
I had a wonderful stay at this hotel right on Ocean Drive in South Beach. The location is unbeatable—just steps from the beach and in the heart of all the action. The customer service was attentive and friendly, always ready to help with a smile. The on-site restaurant was a pleasant surprise—great food, good vibes, and drinks. The decor throughout the hotel is stylish and inviting, with that classic South Beach charm. Highly recommend for anyone looking to soak up the Miami vibe in comfort and style!
Reviewed on Jul. 31, 2025

Park Central South Beach
South Beach
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.2/10 Very Good! (906 reviews)
The property had just gone under new management, and things were a bit hectic. Unfortunately, we didn’t have TV service during our entire stay. However, the manager, Eric, went above and beyond to make up for the inconvenience—providing $15 food vouchers throughout our visit and waiving the resort fees. What a fantastic way to turn things around and keep a guest happy! Superb team and a perfect location. Be sure to go see Eric and his staff—they’re truly amazing individuals!
Reviewed on Jul. 31, 2025



Pelican Grand Beach Resort - A Noble House Resort
East Fort Lauderdale
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.6/10 Excellent! (1,119 reviews)
Needs new sheets
They felt like they had small balls from being super used
Place need new bed with prosper new linen
I stayed at a TownePlace for three nights that had better mattress and linen
Reviewed on Aug. 1, 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 $245 per night from Aug 19 to Aug 20
CA $245
CA $367 total
Aug 19 - Aug 20
includes taxes & fees
9/10 Wonderful! (53 reviews)
Three Waters is a beautiful place to vacation.
"Three Waters Resort was wonderful. We stayed in the Cove and it was very relaxing. The accommodations were spacious and clean."
Reviewed on Jul. 27, 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! (999 reviews)
"The property was prestine with a nice pool overlooking the water and a beautiful beach. I like the music they played on speaker in the recreational areas. They have dim lights at night the reflect on the water..so relaxing. The staff was excellent and manager, Thomas, was outstanding."
Reviewed on Jul. 27, 2025

Coconut Cove Resort and Marina
84801 Overseas Highway, Islamorada, FL
The price is CA $178 per night from Sep 2 to Sep 3
CA $178
CA $201 total
Sep 2 - Sep 3
includes taxes & fees
7.6/10 Good! (809 reviews)
Very Relaxing
"Beautiful setting with nice pool as well! The staff is very friendly and helpful, especially Clancy!!"
Reviewed on Jul. 30, 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.
What to do in Windley Key

Explore Mangrove Creeks with an All Day SUP/single kayak Rental
CA $64
per adult

Ft. Lauderdale to Key West Day Trip Quality Day Tours
CA $308
per adult

Ft Lauderdale to Islamorada Tour with Boat Ride and Lunch
CA $341
per adult
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