The best place to rent a car from Florence to Siena

All the car rental agencies have offices near the SM Novella train station which is walking distance from the Ufizzi.

We always rent our cars thru AutoEurope.com
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It's just 45 miles from Florence to Siena--and all 4 lane highway. Most people take the bus down there--and the buses are staged across the street from the Florence train station to the right of the McDonalds. We found Siena a very difficult city to take a car in because it's very congested.

When we were in Tuscany, we rented from Hertz in Florence, and we turned the car in at Orvieto. The Hertz office is across the street from the train station. Then we took a 70 minute train into Rome Termini.

We always have rented our cars in Florence with pick up on Borgo Ognosanti, easy to get out of the city and onto the autostrada from there.
Our car rentals in Europe have always been done through AutoEurope.
In Siena we drive to the top of the hill, and park in the big lot on the right. It may be connected to a stadium. We have always found a parking space, even during The Palio.

We have rented through Autoeurope, picking up at a Hertz location in Florence that has since closed (closer to SR222). We will be picking up a car at the Hertz downtown Florence location (near the SMN rail station) in September…we’ll be driving down the SR222 to Siena as well. It does look a bit more convoluted from the new location, but the people at Hertz have always been very helpful with directions, so we’ll be good. You will want to be specific about taking the SR222 as opposed to the larger, faster highway. It’s a beautiful little journey!

Hope this helps a bit.