San Giovanni Valdarno suits families and groups wanting a pool base halfway between Florence and Arezzo, just outside a Florentine new town. Homes are grouped just outside town, and most list a pool; check each listing. San Giovanni itself is a real town of over 16,000 people, not a hilltop village among vines.
San Giovanni Valdarno was founded by Florence in 1296 as one of its new towns in the Arno valley, and it keeps the plan: a large central piazza and streets lined with shady porticoes, surrounded by hills and mountains. The Palazzo d'Arnolfo, its façade covered in coats of arms, holds the Museum of the New Lands. Masaccio was born here, and Casa Masaccio is where he lived in his youth; the basilica museum has Fra Angelico's Annunciation. With over 16,000 people and a railway station, it is a real town rather than a holiday village. The homes are grouped together just outside it.
Cavriglia's MINE mining museum is an indoor option for a wet day, and the Fineschi rose garden keeps more than 6,000 rose varieties.
Village surrounded by woods, with a water mill dating back to the year 1000 that still grinds wheat, corn and chestnut flour, and a Romanesque stone bridge.
Clay pinnacles up to 100 metres high, mainly around Reggello, said to be the landscape behind the Mona Lisa.
Fly to Florence. The drive from Florence Airport is about 50 km and takes around 45 minutes; by tram and train via Firenze Santa Maria Novella it is about an hour and a half. The homes are outside the centre, so a car makes sense.
Yes, for a morning at least. The Palazzo d'Arnolfo holds the Museum of the New Lands, Casa Masaccio is where the painter lived in his youth, and the museum of the Basilica of Santa Maria delle Grazie has an Annunciation by Fra Angelico from around 1430.
You can. The town has a railway station on the line from Firenze Santa Maria Novella, which makes a car-free day in Florence simple. From the homes outside town, drive to the station.
It can be. Most homes here list a pool and a few take large groups, though most sleep four to six. Check each listing for the pool and the sleeping arrangements.
Stufato alla sangiovannese, a stew that local cooks compete over each year in the Stufato Palio. Tarese, a cured meat taken up by Slow Food, is the other speciality to look for.
Written by the TrustedVillas team. Last reviewed November 2026.
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