Tuscany

There is no right answer to your question. It's really up to you.
Just know that villas are usually out of town, therefore I presume you will have a rental car.

It depends on how many in your party, what you wish to see and how much money you wish to spend.

I will assume that you won't have a rental car. Many that rent cars get horrendous tickets in the mail after they return from Italy.

You can stay in Florence, I recommend staying in a hotel close to the city center. The Hotel Ballesteri is nice.
Unless you have a large party and need accommodations for several, I recommend this.

Renting a villa would be very expensive and you would probably be away from the city center and therefore need transportation to go into the city.

From Florence, you can take the train to visit cities like Siena, Pisa, and other smaller towns.

It really depends on what you want to do and see in Tuscany, and for how long. If you will be in a Tuscan city, then a hotel may be easier. If you will have a car, stay in the countryside or village, and perhaps want to prepare your own meals, then a private villa may suit you better. Or perhaps an agriturismo. There's no right or wrong, but a rural area or village may necessitate a rental car. Contrary to popular belief, it's perfectly possible to travel by car and not get a traffic ticket. You just need to know the rules of the Italian roads. And each driver will need an international driver permit.

If you're going to tour the countryside in Tuscany, I would suggest you find an agriturismo and stay on a farm. You would need to rent a car to see the hillside towns, however.

The farms in Tuscany are predominantly olive and wine grape farms and 20 acres is about average. Virtually every farm in the area will have apartments and rooms for rent as a secondary source of income.

They can be found on the internet and on Booking.com.

We stayed on an agriturismo between Certaldo and San Gimignano. We did our grocery shopping in Poggibonsi. And we hit a bunch of hilltowns on our daily excursions. Especially liked Volterra--a little to the west.