Tarmach,
October is still the hurricane season. Still can be quite hot and muggy. Maybe the end of October. If you want calm atmosphere and cool temperatures I would go for mid to late Novemeber and Early December. The end of December, January, and February can be cold and blustery. The reason for this is the very strong cold fronts that push down into Florida. Often referred to as an Alberta Clipper or some such thing. Even Miami can be uncomfortable at these times of year if by uncomfortable you mean shorts and Tshirt weather all day and night. January and February usually have clear skies day and night. This of course means heat loss due to radiation heat loss. There are exceptions to every rule of course.
Florida is experiencing a severe drought at this time for example.