I'm in what i guess you'd call north central FL, in Suwannee County. I live in a very rural area and hunt my own 5 acre lot. Each lot around me is the same long rectangular 5 acre size, and while others make their homes here it is all very heavily wooded. In fact, the lots surrounding my place are owned but undeveloped, so all year long I watch the local herd pass through my property in front and back of the house, going either roughly east or west. The front acre is cleared and the back 4 are for hunting. I have two food plots set up that are visible from the same blind.
i have yet to see any real trophies pass through, but that does not concern me as I hunt to fill my freezer, not wall space. Even so, I have averaged two deer harvested per year, but mainly because we have a large doe population here, so I'm pretty much guaranteed at least one during the three antlerless days I get in November. This year has been outstanding so far, with two average sized bucks and a doe in the freezer with 3 weeks left in the season.
There have been times when groups of 8 or 10 come through, and there may have been more than one male in the group, but I've noticed around here that the bucks start to stake their claim around October, driving off the other males. However, it's only been the last week or two that their pattern has changed, and I've seen a few does being chased late at night in the last week or so. Their activity may have started sooner but I can only say what I've seen myself.
I have to agree with the map/chart someone posted above. Northern Florida's rut can run anywhere from late December to early March depending on the region. Time will help you see the patterns in your area and familiarize yourself with roughly when the deer "change modes" from feeding to breeding.
Learn your woods well, give them a place to eat that they feel safe in, and come hunting season leave your woods as undisturbed as possible. The deer will soon tell you everything you need to know.
Good luck!
Joe