I have a question: if I want to stay a month in Tuscany, is there a Airbnb - like service that rents out properties by the month? Siena would be great but I'm assuming it would be cheaper further out. Any help appreciated.
Hi. I don't have a certain period in mind. I am flexible. Ideally April - May. Will I have a car? Yes, possibly, if the monthly apartment is somewhere far, as opposed to Florence central or Siena central.
Actually, a place like Airbnb or even a site like https://www.florenceaccommodation.com/ are great places to start looking for your stay, both have you dealing directly with the owner, instead of a middle man, and they can often offer you the better deals for a long stay. In fact, a few places have "extra" apartments that they don't advertise but are available to rent for longer periods of time.
Real estate sites are normally looking at a long stay as anywhere from 4 - 12 months.
April would probably give you better prices and more availability as opposed to May when the tourist season really starts to come into full swing.
The question regarding your type of transport is valid - Tuscany is lovely but the public transport system, the further you go outside the main cities, is dramatically reduced and could seriously leave you stranded. The major cities like Lucca, Florence, Pisa and even Arezzo, which have national train service, defiitely will help you in making itineraries all over Tuscany giving you a certain flexibility. Siena has a train and bus station - but it connects to Florence for many of its travels.
Agree with Donna Denise that florenceaccommodation.com is a good start. For location choose Florence Outskirts.
I do recommend a car as with a longer stay you have the time to do a bit of driving around. Some of my very best experiences have come from not having any particular plan apart from getting off the main thoroughfares. So often you come across a fascinating small village you would never have planned to visit, a beautiful country church, an exceptional view, a superb local trattoria etc.