Dream come true

Will you have a car?

Are you fluent in Italian ?

Yes we will have a car and yes I am fluent.

I just did a search on booking.come for apartments in “Tuscany” with one bedroom, private bath, and air conditioning, rated 8 or higher, available May 22-June 20. It came up with over 1000 hits, ranging in price from $2000-$12,000. Then I picked one at random in the south of Florence and looked at the map. That showed the one property along with all others in the area. Then I kept scrolling south, toward Siena, while the map kept populating with more and more choices ( not all of them available for those particular dates).

You could try that and then focus on the type of place you actually want to be—a suburb of Florence, a village, etc. Some looked to be quite rural, like agriturismo properties, and it sounds like you want to be more “in town”.

Have you searched booking.com or VRBO?

Both have filters that will help you narrow down choices

Thank you everyone, I have looked on Booking.com but because I do not know the area I'm not sure where the best place to stay is. So I'm also wanting recommendations of suburbs/areas that are worth staying at for one month.

I haven't looked at any other site for the same reason.

It's been a while since I was there, but I spent a week in an apartment in Barbarino Val d'Elsa and loved the location. The village itself was an old walled village, and was somewhat centrally located between areas such as Greve and San Gimignano. But, it's a small village, where not many folks were speaking English (good, because I got to practice), and the tourist wave never hit there. I loved going into places like the bakery and chatting with the women there. A little quiet in the evening, but there were some beautiful terrace restaurants that looked out over the countryside, and life was good.