Bobb,
Parking can often be challenging in Siena, so you might want to choose a hotel that provides parking.
If you haven't been to or driven in Italy before, note that each driver listed on the rental form must have the compulsory International Driver's Permit, which is used in conjunction with your home D.L. These are valid for one year, and easily obtained at any CAA/AAA office (two Passport-sized photos required, which may be provided by the issuing office).
You may also want to have a look at some of the other posts here concerning the dreaded Zona Traffico Limitato areas that are becoming increasingly prevalent in many Italian towns & cities especially Florence, which is almost saturated with automated ZTL cameras. EACH PASS through one of the automated Cameras will result in a €100+ ticket, which you won't know about until several months after you return home! This website provides more information - http://www.slowtrav.com/italy/driving/traffic_cameras_speeding.htm . There's also the issue of parking tickets, high fuel costs, tolls and automated speed cameras including the devious Traffic Tutor system which measures not only instantaneous speed but also average between two points. Violate either or both parameter and expensive tickets will follow.
You may find this recent thread to be interesting - https://community.ricksteves.com/travel-forum/italy/unsatisfied-judgment