Tony:
Our favorite Tuscan village is Panzano. It is exactly between Florence and Siena on the Chianti Road. It is a wonderful hill town with some great restaurants, Italy's most famous butcher (Dario Cecchini) and lots of great wineries nearby (Panzanello and Volpaia are two favorites).
On our three trips there we have rented a villa about 1Km from the village. It is called Il Palagio. It is run by Monia who is very helpful - speaks wonderful English - and keeps the villa absolutely spotless. The individual apartments in the villa are quite comfortable and the outdoor areas (and the views) are spectacular. The website for the villa is www.infochianti.com.
I am an early riser - and it was such a treat for me to get up and walk into the village as it was waking up - have a little coffee - read the Int'l Herald Tribune and maybe pick up some pastry for the sleepy heads back at the villa.
Have fun.