My wife and I were on Key West at Christmas time back in 1985 we hired a guide name of Jan Easley he was very professional and we had a wonderful time. It was much colder than the locals were used to but coming from Sitka Alaska we were both very happy with the weather.
However the fish were reacting to the cooler weather and the Bones were off the edge of the flats but the Barracuda saved the day those were a real hoot from demonic grab to blistering run. We encountered one Permit but it did not want to play.
While the catching was not spectacular we both will never forget the fishing! (great bird watching too).
There were hardly any tourist in Key West when we were there so that I gather was a real bonus as the locals were all real friendly and the better night spots were easily accesible.
Hope you as much fun as we did good luck.