Tuscany for a month--Where to stay June 2024?

What a great trip this will be!
Welcome to the forum!

I would want to be somewhere on the train line for easy access day trips and big enough to have enough of interest for a whole month

Lucca
Siena
Arezzo

For car rental
AutoEurope
Do a search here for car rental in Tuscany -there are many threads-some very recent

If you wanted a car for the whole month consider leasing

What an amazing trip! We spent a month in Italy a few years ago with our 2 teens. Part of that time we spent in Cortona, which is beautiful and relaxing. We used https://togethertuscany.com/en/ to rent our villa. They offer a variety of villas (and experiences) throughout Tuscany. We had an Italian cooking class at our villa for the 4 of us, which was fantastic. It's worth checking them out to see if they offer any place that meets your requirements.

Thank you both so much for the feedback and information. This gives us some focus on our planning.

Just a suggestion, you may not want to mention the work-from-home aspect when you inquire about lodging, as Italy does not allow digital nomads and working while visiting as a tourist is prohibited (assuming you are from the US and do not have EU passports). It's unclear exactly how this is being enforced, but you should be aware it is against the law. Wishing you a great vacation.

Given your requirements, and the fact you have four 20+ y.o. I suggest any of the following 3 locations in Tuscany:
1. Florence
2. Florence
3. Florence

All other places are ok for a few days getaways or for day trips from the aforementioned 3 cities, but not for people in their 20s for a full month.

Remote work for prolonged periods (over 6 months) is subject to a specific legislation passed with law decree 4/2022. For the occasional work during your short length of stay there will be no problems, just be aware that small villages may have slower internet speed. That will not be an issue in mid to large size towns.

None of the 3 locations I suggested requires to have a car full time. But you may want to rent one if planning to take short trips to rural areas.

If you can find an Airbnb in the San Frediano neighborhood it will be a bit less crowded with tourists and close enough to the station and rental car agencies for the occasional trips.

I agree with Roberto Florence is a great base for Tuscany especially with that long of a stay. All your daily necessities will be right outside your front door with enough rich history and walkability for each person to discover their own passion and interests. Think about your grocery/hygene/laundry needs and you could just walk to a well-stocked grovery store for that, or a farmers market for fruit and veg and the local butcher for meats. It is truely one of our favorite places in the world with a major train station to get you anywhere you want. Renting a car is a must for exploring the rest of Tuscany.

Maybe your preferred day trips will help decide your location. If you have people who love go to the water often, you might want Lucca. If you want to visit Rome, then Arezzo & Florence would be handier. If you’re thinking more of countryside Tuscany, then Siena & Arezzo are convenient.

Personally, for an extended stay, I would want to be very convenient to a larger city. Florence gets you to several fairly quickly by train besides being a nice city itself.

Consider staying in Siena or Panzano. Use Chianti and More dot com for rental homes.

Google "Tuscany Villas".