
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.

Oceans Edge Key West Resort, Hotel & Marina
Price was CA $1,781, price is now CA $1,391 per person
CA $1,391
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Key West (EYW)
9/10 Wonderful! (1,862 reviews)
El lugar muy bonito, la vegetación del lugar es espectacular, las habitaciones son espaciosas y limpias con vista al mar, el parking hay que pagarlo pero está bien. Diez de diez
Reviewed on May 23, 2026

The Perry Hotel & Marina Key West
Price was CA $1,958, price is now CA $1,432 per person
CA $1,432
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Key West (EYW)
9.4/10 Exceptional! (1,276 reviews)
Clean, comfortable, friendly, helpful staff. Pool area is convenient and well maintained. Love the shuttle service to and from town
Reviewed on May 20, 2026

Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Price was CA $2,027, price is now CA $1,552 per person
CA $1,552
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Key West (EYW)
9.2/10 Wonderful! (1,284 reviews)
Winslow
Arrival and grounds-arrived early about 2pm. It appeared based on the luggage in the front office that rooms are not ready prior to 4pm. But to be fair that is when check in is stated to be. We were able to keep our luggage in the lobby and they also gave us two free drink tokens to use at the bar. They texted us when the room was ready at exactly 4:02pm. The property is very beautiful. Lush and well maintained. The bungalows look to be in historic buildings and are charming. There are 2 pools. Small in size. Not many loungers. There is an outdoor bar with ample seating and shaded. There is also a breakfast area right next to the bar that is enclosed and air conditioned that is open at all times. After breakfast you can get ice and cold water as well as some fruit 24/7. We found this out on our own, we didn’t really get a run down of the property from anyone. We were given instructions to our room which was Bungalow 44. It’s was in a building that appeared to be an old historic home which is part of the Key West appeal. We were on the second floor, there is no elevator. They did not offer any bell hop service which was fine and we were able to get our luggage up and down the two times with minimal issues.
The room- again we stayed in Bungalow 44. It was on the second floor front of the building facing Truman Street. It was small. It was modern, fresh, and clean. The a/c was excellent, the ceiling fan was also a nice touch. Queen bed, very comfortable, one small side
Reviewed on May 23, 2026

The Gardens Hotel
Old Town Key West
Price was CA $2,329, price is now CA $1,794 per person
CA $1,794
per person
Jul 10 - Jul 15
just found
Roundtrip non-stop flight included
Halifax (YHZ) to Key West (EYW)
9.8/10 Exceptional! (1,006 reviews)
The hotel is situated in the middle of the Dual St, where I can go to either the west end (for seeing sunset) or east end (for seeing sunrise) of the street with almost the same distance. The buildings of the hotel have some history and in the colonial style, which I like very much. The garden provides an excellent place for breakfast and wine tasting.
Reviewed on May 21, 2026

Southernmost Beach Resort and Guesthouses
Old Town Key West
Price was CA $2,052, price is now CA $1,585 per person
CA $1,585
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Key West (EYW)
8.8/10 Excellent! (3,304 reviews)
Everything was great and relaxing
Reviewed on May 24, 2026
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Price found within the past 48 hours. Click for updated prices.

The Gardens Hotel
Old Town Key West
Price was CA $1,101, price is now CA $903 per person
CA $903
per person
Aug 4 - Aug 7
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Key West (EYW)
9.8/10 Exceptional! (1,006 reviews)
The hotel is situated in the middle of the Dual St, where I can go to either the west end (for seeing sunset) or east end (for seeing sunrise) of the street with almost the same distance. The buildings of the hotel have some history and in the colonial style, which I like very much. The garden provides an excellent place for breakfast and wine tasting.
Reviewed on May 21, 2026

Southernmost House - Adult Exclusive
Old Town Key West
Price was CA $2,659, price is now CA $1,689 per person
CA $1,689
per person
Jun 26 - Jun 29
found 16 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
Beautiful property. Excellent service.
Reviewed on May 15, 2026

The Marker Key West Harbor Resort
Key West Historic District
Price was CA $1,159, price is now CA $956 per person
CA $956
per person
Aug 4 - Aug 7
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Key West (EYW)
9.2/10 Wonderful! (1,007 reviews)
Best part of this hotel was the location. My husband was fishing this trip and it was a 2 minute walk to the boat. Beds were comfortable and I slept well. The amenities that you pay a resort fee of $54 a night were meh. My husband did go to the pool one day but none of the other offerings were interesting. We had friends that stayed as well and they paid an additional $44 a day for parking. We got breakfast every morning and that was good but the best part was our server Nelson. Always a smile and by the second morning I didn’t even need to ask for coffee, he just had it ready. The rooms were fine and they were clean. Bring your own shampoo and conditioner. What they provide is not great. Location was the best part of our stay.
Reviewed on May 20, 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.

Caribbean House
Old Town Key West
Price was CA $1,855, price is now CA $1,591 per person
CA $1,591
per person
Jun 30 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9/10 Wonderful! (360 reviews)
Room was very clean but very small, Not a resort with no pool or extra amenities but they charge you a destination free that is a hidden charge.
Reviewed on May 23, 2026


Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool
Old Town Key West
Price was CA $2,739, price is now CA $2,378 per person
CA $2,378
per person
Jul 20 - Jul 24
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (5 reviews)
Staff were awesome. Loved the trees and foliage and privacy.
Reviewed on Feb 17, 2026
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