Villa/Rental in Tuscany Sept 2019


New member
So grateful I found Discover! We are two senior couples who will be in Tuscany for a week in Sept 2019 and would like to rent a villa or house for the week. Lourdes recommends staying somewhere between Siena and Florence, but it's difficult to pinpoint exactly where. Website gives so many choices of towns/cities it's daunting. Can someone reduce our choices down to perhaps 5 to 7 "best view" cities for me to research? We will have a car and it would be fun to have a pool. Our goal is to explore many cities in Tuscany, including Florence, Siena, San Gi, Piza, Cinque Terre, etc. Thank you so much!


Well-known member
My very first recommendation is not to do too much.

Since you talk of only a week then I would suggest you consider the following:

1. 2 days covering Florence
2. 1 day which could cover both Siena and San Gimignano
3. 1 day which could cover Pisa and Lucca
4. 1 day which could cover Arezzo and Cortona

For the days covering Florence you do not need a car whereas for the other locations it is advantageous as it means you do not have to follow any timetables apart from yours!

For the final 2 days I would humbly suggest that you experiment. The joy of Tuscany is to take the unexpected turning discovering the wonderful view not listed on any guide, the small shop selling wonderful produce which you promise to take back to your villa or whatever location but find you have finished it all before you have arrived, the small pieve (church) with a genuine della Robbia almost ignored by everyone.

Unless you have boundless energy avoid le Cinque Terre which are not even in Tuscany.

As a suggestion look for something in the hills of Fiesole where there is easy transport to Florence for those first days and then you can consider a rental.


The Tuscan Expert ;-)
Staff member
If you want the pool and your dates are not yet set in stone, make sure it is in the earlier part of the month as by the end fall generally makes an entrance.... and places close their pools down by the start of October.

As far as places, I suggest the area in general because it is pretty central but leave the details to places you find that you fall in love with -- take a look at to look at lodgings and go from there.
With a car, you'll see the area is actually not that wide or large, and that whether you choose Castellina or Panzano will not make much of a difference. The entire area merits exploring - and you will as you drive here and there.
But the place you choose will matter.

As far as the type of accommodation: keep in mind many villas are divided into apartments and you share any common spaces, such as the pool area, with other guests. Others are used as B&Bs and therefore are rooms, with common areas inside, like living room, with kitchen use generally not included.
Traveling as 2 couples, you might want to either have completely separate apartments or a large apartment with 2 bedrooms and share the common spaces or get 2 rooms in a B&B. Up to you!

Your search can be either by location and then by type, or start with type of lodging you want and then find an area to base yourself in. I find Siena a great base for exploring most of Tuscany, but the countryside between San Gimignano to the west and Gaiole in the east to be very romantic and emblematic of Tuscany so generally suggest staying in the area. If you decide on a type of lodging, I can suggest some specific ones ;-).

I also suggest planning on doing less and going with the flow... CT is not in Tuscany and would be a long drive and long day, if you want to include it. Map it on Google Maps to get a better idea.