Luxury villas for rent in San Gimignano

What the houses here are like

The offering here is stone farmhouses among the vineyards with tower views — the picture you see from the pool is the postcard one — and manor villas in the Val d’Elsa countryside. This being our home turf, it is also where our portfolio runs deepest: from houses for two families to farmhouses for large groups, nearly always with a private pool and generous outdoor space.

Book with the people who manage the houses directly

Tripcare, a luxury villa property-management company in Tuscany, manages every house in this area directly. Tripcare’s operational base is in Poggibonsi, ten minutes from San Gimignano: no area do we cover more closely. Direct management of every villa, in-person check-in, immediate maintenance, and a concierge playing at home — Vernaccia tastings in the cellar, tables at the right restaurants, shortcuts to see the towers without the queue.

Where to stay in San Gimignano

San Gimignano

Fourteen towers survive of the seventy-two of the medieval town, UNESCO-listed since 1990, at 324 metres. Worth knowing before you choose: between ten and six the two squares fill with day groups, and after seven they empty almost completely — sleeping inside the walls is a different experience altogether from visiting them. Market on Thursday morning in the piazzas. Vernaccia, drunk everywhere here, was in 1966 the first Italian wine to be granted DOC status — and it is white, which is not what most people arriving in Tuscany expect.

Certaldo

Two towns in one: Certaldo Basso in the valley, with the station and the shops, and Certaldo Alto above, the medieval brick village cars do not climb into. A funicular joins them — a hundred and thirty metres long at a forty-nine per cent gradient, a one-minute ride, one every quarter of an hour. Boccaccio, born here and buried here in 1375, gives his name to everything. It is the only base in the area with a direct train to both Florence and Siena — about thirty-five minutes by car from central Florence, fifty by rail — which makes it the choice if you would rather not drive every day.

Colle di Val d’Elsa

This one is on two levels too: Colle Alta on the ridge, Colle Bassa in the valley. It is a town that genuinely works — around fifteen per cent of the world’s crystal is made here, and there is a museum devoted to it — and Arnolfo di Cambio, the architect of the Palazzo Vecchio, was born in it. In the evening Colle Alta is quiet in a way San Gimignano never is. Market on Friday morning in piazza Arnolfo. A lift connects the lower town to the upper one, though it has been out of service for long spells: check before relying on it, the road being the alternative.

Poggibonsi

Not a picture-postcard village, and not worth selling as one: much of it was rebuilt after the war. Its value is practical, and it is real — it is the only place here with a proper railway station (Poggibonsi–San Gimignano, on the Empoli–Siena line), it has two exits of its own on the Florence–Siena expressway, and supermarkets, pharmacies and garages are minutes away. On a long stay, or with children, that counts for more than a view. Market on Tuesday morning.