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.
Islander Resort
Matecumbe
Save 100% on your flight
Price was CA $2,624, price is now CA $1,940 per person
CA $1,940
per person
Jan 8 - Jan 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9.4/10 Exceptional! (1,147 reviews)
Great place! Chris at the pool bar was awesome! Will go back just to have his hospitality!
Reviewed on Oct 30, 2026
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Price was CA $2,694, price is now CA $2,347 per person
CA $2,347
per person
Dec 31 - Jan 2
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
9/10 Wonderful! (296 reviews)
The view from our room was outstanding. However, there was a horrible smell that kept floating on the wind from another part of the property- it smelled like sewage. The cleaning staff weren't great, and the woman who checked us in didn't give us any info on how to find our room. The rest of the staff were very helpful.
The room itself didn't have enough lighting. There was a full length mirror outside the bathroom, but there wasn't any light to see yourself in.
Reviewed on Oct 29, 2026
Casa Marina Key West, Curio Collection by Hilton
Old Town Key West
Price was CA $2,065, price is now CA $1,984 per person
CA $1,984
per person
Jan 10 - Jan 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
8.4/10 Very good! (979 reviews)
Beautiful property with private beach.
Reviewed on Oct 30, 2026
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View all trips5* Fishing holidays in Florida Keys
Price found within the past 48 hours. Click for updated prices.
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View all trips3 Night Fishing holidays in Florida Keys
Price found within the past 48 hours. Click for updated prices.
Hawks Cay Resort
Price was CA $1,333, price is now CA $1,170 per person
CA $1,170
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
8.2/10 Very good! (1,007 reviews)
Lots of amenities and great staff will be coming back to this location
Reviewed on Oct 28, 2026
Islander Resort
Matecumbe
Price was CA $1,847, price is now CA $1,618 per person
CA $1,618
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
9.4/10 Exceptional! (1,147 reviews)
Great place! Chris at the pool bar was awesome! Will go back just to have his hospitality!
Reviewed on Oct 30, 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 Centric Key West Resort and Spa
Key West Historic District
Price was CA $3,304, price is now CA $2,840 per person
CA $2,840
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9/10 Wonderful! (1,008 reviews)
This is a perfect property to stay at. Every person who worked there was courteous, helpful, responsive… just downright excellent. Room with partial Gulf view and balcony made morning coffee and general relaxing time enjoyable. Shopping close. Places to eat too but resort has great restaurant and bar has good food as well. Not far from Duval Street and other places of interest.
Reviewed on Oct 29, 2026
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View all tripsFishing Hotels in Florida Keys
Islander Resort
82100 Overseas Highway Islamorada FL
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! (1,154 reviews)
"Great place! Chris at the pool bar was awesome! Will go back just to have his hospitality!"
Reviewed on Oct 30, 2026
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
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 ...
Captain Pips Marina & Hideaway
1480 Overseas Hwy Marathon FL
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! (1,000 reviews)
"Our place was among several homes painted in wonderful bright colors. Ours was purple with yellow shutters and a bight blue door. Our room had a full kitchen, dinette, bathroom, and rear window over looking the marina. So fun and how great!"
Reviewed on Oct 28, 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 $63
per adult
94% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
CA $79
per adult
88% of travellers recommend
Champagne and Sunsets: A Key West Catamaran Adventure
CA $83
per adult
94% of travellers recommend
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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.
