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

Pelican Grand Beach Resort - A Noble House Resort
East Fort Lauderdale
Price was CA $1,922, price is now CA $972 per person
CA $972
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.8/10 Excellent! (1,224 reviews)
I have been visiting pelican grand for well over a decade on and off and I hadnt been back in a few years and I thought the property looked much more run down! There were rust stains on walls near the pool and it just didnt feel as luxurious as it used to. I do think it might be time for a facelift for the pool area. Overall I do love this hotel and the room was comfortable and quiet. I love that the beach is right there and the dining options are nice.
Reviewed on Sep. 8, 2025


Ella's Cottages - Key West Historic Inns
Old Town Key West
Price was CA $4,595, price is now CA $2,225 per person
CA $2,225
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Key West (EYW)
9.4/10 Exceptional! (369 reviews)
This property is absolutely adorable! Room was clean and spacious. Front desk person was very nice and personable. The breakfast baskets that are delivered to your room are top notch! Will definitely be staying here again!
Reviewed on Aug. 31, 2025

Ridley House - Key West Historic Inns
Key West Historic District
Price was CA $3,366, price is now CA $1,680 per person
CA $1,680
per person
Oct 12 - Oct 19
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (815 reviews)
The staff were wonderful and we loved the breakfast and sangria hour and how walkable the area was! We walked everywhere during our stay. The only downsides were it is very noisy, since you can hear everything outside from in the room, and the AC in our room took about 2 days to cool down enough to be comfortable after the previous guests apparently had left the AC off and the windows open during their stay.
Reviewed on Sep. 3, 2025

Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Price was CA $2,796, price is now CA $1,454 per person
CA $1,454
per person
Oct 12 - Oct 19
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9/10 Wonderful! (781 reviews)
Pros: We loved the location. It's so easy to walk to any downtown place via Duval Street with tons of restaurant options. Since this is a hotel and no AirBnB, you gotta go eat somewhere.
You can also rent a golf cart or take an Uber to Fort Zachary Taylor Historic State Park Beach (best beach in Key West, except for overpriced bad food options).
A golf cart is the best mode of transportation with 2 kids in tow. Walking 30+min in this humid heat, including beach gear, snacks and etc..., is just no fun.
Parking around your hotel may be tricky and make sure you know the rules. We went off-season, so it was easy, but during high season-we have been told-it can be a challenge.
If you book a sunset, snorkeling, sandbar or fishing trip on a boat, which I highly recommend, it only takes 20min to walk to the harbor or you simply book a cab/Uber/Lyft.
The housekeepers were amazing and always made sure that we had enough clean towels.
Beach towels are never in shortage and available to pick up by the pool area 24/7.
Cons: The pool is very small, but then we didn't go to Key West to spend time at a pool. We prefer the beach and what nature has to offer. The marine life is just too amazing to dwell in a pool for us.
Reviewed on Sep. 8, 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 Sep 18 to Sep 19
CA $245
CA $367 total
Sep 18 - Sep 19
includes taxes & fees

Fisher Inn Resort & Marina
84951 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is CA $133 per night from Sep 21 to Sep 22
CA $133
CA $195 total
Sep 21 - Sep 22
includes taxes & fees

Coconut Cove Resort and Marina
84801 Overseas Highway, Islamorada, FL
The price is CA $161 per night from Sep 16 to Sep 17
CA $161
CA $182 total
Sep 16 - Sep 17
includes taxes & fees
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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