Florida Keys Fishing Vacations
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Flight and Fishing hotel deals in Florida Keys
Price found within the past 48 hours. Click for updated prices.
Hawks Cay Resort
CA $1,170
per person
Oct 14 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Miami (MIA)
8.2/10 Very good! (1,006 reviews)
Just returned from Hawks Cay, we loved the property in general. The big pool, the lagoon, the outdoor spaces all well maintained. It was our first time here and we appreciated the modern decoration of the lobby and all the areas around it, the breakfast cafe and the restaurant .
We stayed at the Pool Cabana room, perfect location in front of the main pool. The room was spacious , with a mini fridge and a coffee maker. Good lighting and space to store your things. My only suggestion would be to improve the beddings and mattresses.
Overall I got the feeling of a good old time American resort. Perfect for families since the kids can be at the pool, or kayaking at the lagoon or even fishing. We recommend it 👍
Reviewed on Sep 14, 2026
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View all trips5* Fishing holidays in Florida Keys
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View all trips3 Night Fishing holidays in Florida Keys
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Hawks Cay Resort
CA $915
per person
Nov 1 - Nov 4
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Miami (MIA)
8.2/10 Very good! (1,006 reviews)
Just returned from Hawks Cay, we loved the property in general. The big pool, the lagoon, the outdoor spaces all well maintained. It was our first time here and we appreciated the modern decoration of the lobby and all the areas around it, the breakfast cafe and the restaurant .
We stayed at the Pool Cabana room, perfect location in front of the main pool. The room was spacious , with a mini fridge and a coffee maker. Good lighting and space to store your things. My only suggestion would be to improve the beddings and mattresses.
Overall I got the feeling of a good old time American resort. Perfect for families since the kids can be at the pool, or kayaking at the lagoon or even fishing. We recommend it 👍
Reviewed on Sep 14, 2026
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View all trips4 Night Fishing holidays in Florida Keys
Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Sunset Harbor, Key West
Old Town Key West
CA $1,913
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
8.6/10 Excellent! (419 reviews)
Great location. Near everything. Walking distance to Duval. Quiet area near the water. Lots of activities around - rooms were spacious and pool area was nice. Staff was friendly. Kathy at the front was very nice and helpful.
Reviewed on Sep 13, 2026
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View all tripsFishing Hotels in Florida Keys
Islander Resort
82100 Overseas Highway Islamorada FL
- 3 hours drive from Duval Street
Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
9.4/10 Exceptional! (1,120 reviews)
"Great location. Very good CLEANING staff and FRONT DESK staff are excellent"
Reviewed on Sep 14, 2026
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
- 3 hours drive from Duval Street
Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
9.2/10 Wonderful! (1,439 reviews)
"Excellent hotel to spend good time with friends and family, just amazing."
Reviewed on Sep 14, 2026
Captain Pips Marina & Hideaway
1480 Overseas Hwy Marathon FL
- 2 hours drive from Duval Street
Stay at this hotel in Marathon. Enjoy free WiFi, a marina, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. ...
9/10 Wonderful! (1,005 reviews)
"Spacious clean room . Beautiful view from room. Convenient to local activities and restaurants. Looking forward to future stays."
Reviewed on Sep 14, 2026
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.
Things to do
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
CA $59
per adult
94% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
CA $77
per adult
88% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
CA $109
per adult
94% of travellers recommend
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