Buongiorno,
My suggestion would be either to look at Florence or Siena for a "central" position. I would also suggest that you stay in the city centers because there will most probably be more activity in the evenings in the larger cities during that time period. Things are open in the small cities as well, but having Florence or Siena as a base will permit you to enjoy a happy hour (apricena) at sunset at a cozy cafe table. Be sure to ask about their parking situation wherever you consider staying - some will have free parking or if not, an arrangement with a local garage. Take a look for example at these rooms in front of Palazzo Pitti: http://www.florenceaccommodation.com...oscanelli.html
It is more likely in this time of the year that you will find B&B open or hotels. Villas and apartments have a tendency to close in the colder months... sometimes just because the heating alone is a bit pricey.
Having said that - dress warm!! Layers are suggested but sometimes you will find even museums and attractions are a bit chilly. Definitely bring gloves, a hat and a scarf (though all those things are fun to buy at the local markets ;-)!! )
Buon Viaggio,
Donna Denise
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