For the past couple of years, I have been traveling to Florida each winter to spend about two months there. I drive by car from Boston, and travel around Florida - visiting Miami, Tampa, Fort Lauderdale and Orlando.
Usually I wind up spending most of my time in the Orlando area since I own Disney Vacation Club, so I usually spend a couple of weeks there. Then I try and rent with RCI points. For Christmas and New Year's weeks, those are extremely busy Florida travel weeks so I will book those in as far in advance as possible. This most recent New Year's I spent my week on the beach, enjoying the Gulf shore's pleasant waters.
But for the rest of the time, I try and book inside RCI's Last Minute travel window. Florida travel is at its busiest in February, but January isn't too bad at all. I guess most of the senior snowbirds don't really head down to Key West and places like that until the first week of January. So for the most part I can pick up an Florida timeshare for between $200 and $250 a week, just by using RCI's last minute rentals.
So after spending a couple of weeks at Walt Disney World, I will usually move over to Wyndham, or I will go down to Miami for a few weeks. The drive down there isn't too bad at all. I usually take the Florida turnpike, which is a decent drive.
So if you are making Florida travel plans for the winter, you will need to plan well ahead for Christmas, New Years and February, but if you are going in January, November and the first three weeks of December you should be just fine.