
Raccoon Key Fishing Vacations
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Flight and Fishing hotel deals in Raccoon Key
Price found within the past 48 hours. Click for updated prices.

Blue Flamingo Resort Key West
New Town
Price was CA $2,637, price is now CA $1,970 per person
CA $1,970
per person
May 16 - May 23
found 8 hours ago
Roundtrip flight included
Halifax (YHZ) to Key West (EYW)
8.2/10 Very Good! (1,980 reviews)
From the moment you enter, the lobby feels like a clean hotel. You are immediately welcomed by the front desk staff, making the check-in process quick and easy. The room wasn't ready, and although upgrades were offered, I declined. Shortly after, while sitting at the pool bar with a drink, I received a text message and soon afterward a call informing me that the room was available. The hotel staff is very well-trained and friendly. The room smells clean and was indeed cleaned; it is very well maintained. All amenities were working perfectly, and everything we needed was in the room. I find the breakfast at the pool bar in the morning was not the best; the location and food options were limited the coffee was not the best. The pool view room is spacious and comfortable.
Reviewed on Apr 1, 2026

Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Price was CA $3,479, price is now CA $2,339 per person
CA $2,339
per person
May 16 - May 23
found 8 hours ago
Roundtrip flight included
Halifax (YHZ) to Key West (EYW)
9.2/10 Wonderful! (1,194 reviews)
Second time we have stayed here.Staff is excellent, accommodating. The property is very well maintained and a great location.
Reviewed on Apr 1, 2026

The Marker Key West Harbor Resort
Key West Historic District
Price was CA $4,940, price is now CA $3,604 per person
CA $3,604
per person
May 16 - May 23
found 8 hours ago
Roundtrip flight included
Halifax (YHZ) to Key West (EYW)
9.2/10 Wonderful! (1,011 reviews)
We stayed at the Marker for our anniversary in a Harbor View room. Room was very nice and we looked out over a marina and had a nice balcony to sit out and enjoy a glass of wine. Breakfast was good at the bar by the pool but not great. Staff very friendly and helpful. Good enough fitness room to get a decent workout in but no universal machines.
Close enough to walk to just about anything you need. If you do stay in the Herbirview room be aware that the Schooner Bar across the path plays music til around 11 am or later each night and you can hear it from your room though it’s muffled. The first night we were there the band playing was way too loud and I could hear the words of the songs inside my room while the door was closed.
But if you want a very nice hotel with 3 pools and attentive staff in a great location whilst having the Key West vibe all around you the Marker is very good.
Reviewed on Apr 1, 2026

The Perry Hotel & Marina Key West
Price was CA $2,812, price is now CA $2,072 per person
CA $2,072
per person
May 16 - May 23
found 8 hours ago
Roundtrip flight included
Halifax (YHZ) to Key West (EYW)
9.4/10 Exceptional! (1,226 reviews)
great variety on the menus. we enjoyed our stay. My only negative comment is related to the loud conversations of our neighbors on the balcony two days and also a couple were sitting by the fire pits while they were on a phone call that they put on speaker. These incidents made our time relaxing on the balcony less enjoyable.
Reviewed on Mar 28, 2026

The Reach Key West, Curio Collection by Hilton
Old Town Key West
Price was CA $3,718, price is now CA $2,810 per person
CA $2,810
per person
May 16 - May 23
found 8 hours ago
Roundtrip flight included
Halifax (YHZ) to Key West (EYW)
8.6/10 Excellent! (1,013 reviews)
The beach was perfect except when a wedding was going on it was limited and no warnings for this. There was only 1 waitress fir beach and pool orders. Also waitress didnt even knowledge us over 10 when we tried to go for breakfast so we left . The culture is wonderful except wasnt informed roosters would wake u at 4am so earplugs would have been nice . Other than that It was beautiful and enjoyable
Reviewed on Mar 29, 2026
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Price found within the past 48 hours. Click for updated prices.

The Perry Hotel & Marina Key West
Price was CA $1,594, price is now CA $1,266 per person
CA $1,266
per person
Jun 4 - Jun 7
found 10 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Key West (EYW)
9.4/10 Exceptional! (1,226 reviews)
great variety on the menus. we enjoyed our stay. My only negative comment is related to the loud conversations of our neighbors on the balcony two days and also a couple were sitting by the fire pits while they were on a phone call that they put on speaker. These incidents made our time relaxing on the balcony less enjoyable.
Reviewed on Mar 28, 2026

The Marker Key West Harbor Resort
Key West Historic District
Price was CA $1,932, price is now CA $1,506 per person
CA $1,506
per person
Jun 4 - Jun 7
found 10 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Key West (EYW)
9.2/10 Wonderful! (1,011 reviews)
We stayed at the Marker for our anniversary in a Harbor View room. Room was very nice and we looked out over a marina and had a nice balcony to sit out and enjoy a glass of wine. Breakfast was good at the bar by the pool but not great. Staff very friendly and helpful. Good enough fitness room to get a decent workout in but no universal machines.
Close enough to walk to just about anything you need. If you do stay in the Herbirview room be aware that the Schooner Bar across the path plays music til around 11 am or later each night and you can hear it from your room though it’s muffled. The first night we were there the band playing was way too loud and I could hear the words of the songs inside my room while the door was closed.
But if you want a very nice hotel with 3 pools and attentive staff in a great location whilst having the Key West vibe all around you the Marker is very good.
Reviewed on Apr 1, 2026
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View all trips4 Night Fishing holidays in Raccoon Key
Price found within the past 48 hours. Click for updated prices.

Hyatt Vacation Club at Windward Pointe, Key West
Price was CA $2,525, price is now CA $1,798 per person
CA $1,798
per person
Jun 22 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Key West (EYW)
9.4/10 Exceptional! (1,020 reviews)
Room was very spacious and clean!
Reviewed on Mar 30, 2026

The Key West Hotel
Key West Historic District
Price was CA $2,936, price is now CA $1,986 per person
CA $1,986
per person
Jun 22 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Key West (EYW)
9.2/10 Wonderful! (536 reviews)
The tag line of the hotel is "Come Hide" which was appropriate as it is hidden from plain view of the hustle and bustle of Duval St. The entrance is mysterious as it is set back and the pathway leading to the reception office is filled with green ferns/palms. Loved it! The center of the property is highlighted the bar and the permanent stage for the daily entertainment. Great place to stay and close to everything!
Reviewed on Mar 30, 2026

Hyatt Vacation Club at Beach House, Key West
Price was CA $2,676, price is now CA $1,903 per person
CA $1,903
per person
Jun 22 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Key West (EYW)
9.4/10 Exceptional! (1,019 reviews)
These are recently renovated “condos” with 2 beds/2 baths, full kitchen, dining, and living area. Master bath is very nicely done with a giant shower for two. Very large deck/porch off each unit. The A/C went out but the friendly front desk and maintenance crew repaired it quickly. Resort has a large pool and large sand beach area with plenty of chairs and cabanas. New gas grills are near the pool area. There is a tiki bar on site with food. No complaints about this property whatsoever. There is a kayak tour guide right next door and I highly recommend their night kayak tour. The property is at the opposite end of the island to Old town/Duvall street. It’s about a 20 min bike ride to Duvall, and a 9 minute bike ride to Publix.
Reviewed on Apr 1, 2026
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