
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
Price was CA $1,466, price is now CA $1,077 per person
CA $1,077
per person
Jun 25 - Jun 28
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
8/10 Very Good! (1,020 reviews)
We had a very good stay at the Hawks Cay villa we stayed in. The main pool, lagoon, Sunset Village pool, and fitness center were great. Our first night there, we stopped in Angler & Ale after a long day of travel. The service was SLOW and the food was likely bland Sysco basic options; nothing special.
Our villa (Sunset Villas), was ok. The showers had mildewy curtains and translucent shower knobs that allowed for us to see through to lots of mildew. Also, the shampoo, conditioner, and body wash didn't seem to get refilled before us. Mattresses could use replacing. But overall, it was ok. The unit needs more wall hooks; travelers need places to hang towels, toiletry bags, hangers, etc.
We were pleasantly surprised to see that laundry was available in our villa, which we didn't know would be the case. 3 detergent packs were provided, which was nice.
If staying in the villas, I'd recommend you stop at a grocery store to purchase your own: coffee grounds, dishwasher pods, kitchen sponge, dish soap, shampoo, conditioner, body wash/soap. Maybe additional laundry detergent if you plan to do a lot of laundry.
All in all, Hawks Cay is a great resort that allowed us to have the best of both the hotel and rental home experiences.
Reviewed on Apr 20, 2026

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Price was CA $2,045, price is now CA $1,262 per person
CA $1,262
per person
Jun 3 - Jun 7
just found
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
9/10 Wonderful! (181 reviews)
The Spray Watersports were awesome. Mary took us on a great wave runner expedition. The entire staff were amazing and cool. Fun times.
Reviewed on Apr 21, 2026

Cheeca Lodge & Spa
Matecumbe
Price was CA $1,848, price is now CA $1,310 per person
CA $1,310
per person
Jun 28 - Jul 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
9.2/10 Wonderful! (1,318 reviews)
We had a wonderful stay at this hotel beautiful scenery, excellent staff and wonderful food. Everyone was so welcoming. The amenities were my favorite. We took the bikes and went for a long ride, played tennis swam and drink by the pool.
Reviewed on Apr 19, 2026

Casa Marina Key West, Curio Collection by Hilton
Old Town Key West
Price was CA $2,007, price is now CA $1,439 per person
CA $1,439
per person
Jun 5 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Key West (EYW)
8.4/10 Very Good! (614 reviews)
Beautiful location. Great staff. Wonderful pool. Great beach view although rocky.
Reviewed on Apr 20, 2026

La Siesta Resort & Villas
Matecumbe
Price was CA $2,533, price is now CA $1,882 per person
CA $1,882
per person
Jun 28 - Jul 4
found 23 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
8.6/10 Excellent! (1,009 reviews)
It was simply stunning. Beautiful location, great facilities, spacious apartment and for a family of 5 the door key card being on the wristband is genius. Thank you for a wonderful stay
Reviewed on Apr 21, 2026
Don't see what you're looking for?
See all available trips from Columbus to Florida Keys
View all trips5* Fishing holidays in Florida Keys
Price found within the past 48 hours. Click for updated prices.

Cheeca Lodge & Spa
Matecumbe
Price was CA $1,848, price is now CA $1,310 per person
CA $1,310
per person
Jun 28 - Jul 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
9.2/10 Wonderful! (1,318 reviews)
We had a wonderful stay at this hotel beautiful scenery, excellent staff and wonderful food. Everyone was so welcoming. The amenities were my favorite. We took the bikes and went for a long ride, played tennis swam and drink by the pool.
Reviewed on Apr 19, 2026
Don't see what you're looking for?
See all available trips from Columbus to Florida Keys
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 $1,466, price is now CA $1,077 per person
CA $1,077
per person
Jun 25 - Jun 28
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
8/10 Very Good! (1,020 reviews)
We had a very good stay at the Hawks Cay villa we stayed in. The main pool, lagoon, Sunset Village pool, and fitness center were great. Our first night there, we stopped in Angler & Ale after a long day of travel. The service was SLOW and the food was likely bland Sysco basic options; nothing special.
Our villa (Sunset Villas), was ok. The showers had mildewy curtains and translucent shower knobs that allowed for us to see through to lots of mildew. Also, the shampoo, conditioner, and body wash didn't seem to get refilled before us. Mattresses could use replacing. But overall, it was ok. The unit needs more wall hooks; travelers need places to hang towels, toiletry bags, hangers, etc.
We were pleasantly surprised to see that laundry was available in our villa, which we didn't know would be the case. 3 detergent packs were provided, which was nice.
If staying in the villas, I'd recommend you stop at a grocery store to purchase your own: coffee grounds, dishwasher pods, kitchen sponge, dish soap, shampoo, conditioner, body wash/soap. Maybe additional laundry detergent if you plan to do a lot of laundry.
All in all, Hawks Cay is a great resort that allowed us to have the best of both the hotel and rental home experiences.
Reviewed on Apr 20, 2026

Casa Marina Key West, Curio Collection by Hilton
Old Town Key West
Price was CA $2,163, price is now CA $1,948 per person
CA $1,948
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Key West (EYW)
8.4/10 Very Good! (614 reviews)
Beautiful location. Great staff. Wonderful pool. Great beach view although rocky.
Reviewed on Apr 20, 2026

Hyatt Centric Key West Resort and Spa
Key West Historic District
Price was CA $2,223, price is now CA $2,070 per person
CA $2,070
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9/10 Wonderful! (1,009 reviews)
Friendly staff, clean rooms, good pool and hot tub.
Reviewed on Apr 20, 2026
Don't see what you're looking for?
See all available trips from Columbus to Florida Keys
View all trips4 Night Fishing holidays in Florida Keys
Price found within the past 48 hours. Click for updated prices.

Creekside Inn
Price was CA $2,020, price is now CA $1,108 per person
CA $1,108
per person
May 28 - Jun 1
found 23 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
7.8/10 Good! (1,011 reviews)
I stayed 4 nights in this hotel with my husband and we have an amazing time. The room needs a little update but I was clean and that is what is matters to me. The AC worked fine in my room but I see one guy working on the AC on other room. The staff was amazing and we really enjoyed our stay and I will love to be back soon
Reviewed on Apr 21, 2026

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Price was CA $2,045, price is now CA $1,262 per person
CA $1,262
per person
Jun 3 - Jun 7
just found
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
9/10 Wonderful! (181 reviews)
The Spray Watersports were awesome. Mary took us on a great wave runner expedition. The entire staff were amazing and cool. Fun times.
Reviewed on Apr 21, 2026

Hyatt Vacation Club at Sunset Harbor, Key West
Old Town Key West
Price was CA $3,424, price is now CA $2,360 per person
CA $2,360
per person
Jul 1 - Jul 5
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
8.6/10 Excellent! (354 reviews)
Location was great. Near most of Key West Attractions. Parked the car and walked everywhere.
Reviewed on Apr 14, 2026
Don't see what you're looking for?
See all available trips from Columbus to Florida Keys
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. ...
9.2/10 Wonderful! (1,005 reviews)
Ate breakfast outside the hotel
Reviewed on Apr 19, 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 ...
9.2/10 Wonderful! (1,318 reviews)
For the price per night you would think the rooms would look better than a standard hotel room.
Reviewed on Apr 20, 2026

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! (1,012 reviews)
We had a great time, the amenities were excellent, the room was spacious with a full kitchen, we look forward to going back.
Reviewed on Apr 21, 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.
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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.







