Villas for rent in Poggibonsi

Poggibonsi is the right base if you want San Gimignano, Siena and Chianti in the same week without giving up a supermarket open in the evening. It is not a postcard village: it is the working centre of the Valdelsa, with a station on the Empoli–Siena line, the Nord and Sud exits of the Florence–Siena motorway link and the Medici fortress of Poggio Imperiale, designed by Giuliano da Sangallo in the late fifteenth century, watching the town from above. The villas are not in the centre but in the hill hamlets: Staggia Senese with its castle, the slopes towards San Gimignano and Castellina. San Gimignano is a quarter of an hour away, Siena half an hour, Florence fifty minutes. Tripcare’s office is in via del Masso, so the team that welcomes you sets out from a few minutes away.

The stay

The houses around Poggibonsi are stone farmsteads on the hills towards San Gimignano, with a private pool, olive grove and the towers on the horizon. “Casale Esclusivo Piscina & vista su San Gimignano” sleeps four and suits a couple with children; “Podere Casanuova - Viridis, Peace in San Gimignano”, for six, works for two families travelling together; a larger group takes “Villa con piscina a sfioro nel cuore del Chianti”, ten beds, eleven kilometres away. Check-in is in person, with the team arriving from the office. The concierge arranges tastings in the Sienese Chianti and around San Gimignano, a chef in the villa cooking with produce from the Poggibonsi weekly market, transfers from the station and the airports, and days in Siena and Volterra with a private guide and driver.

Why Poggibonsi

Compared with Castellina or Barberino, Poggibonsi wins on practicality: it is the junction where the railway, the motorway link and the road to Castellina meet, and the services — supermarkets, pharmacy, hardware shop, Campostaggia hospital — stay open all year, something Radda cannot offer. It suits you if you move around a lot: San Gimignano a quarter of an hour away, Siena half an hour, Florence fifty minutes, Volterra within a day. It is the base for families and groups of friends who book a week in high season, and for long weekends in spring and autumn, when the hills towards Staggia are green and the roads are empty.