Best holiday homes in Siena province & villas with soul

Stylish, character rich self catering retreats in Siena and beautiful villas

A steep terracotta staircase, silken morning light through lead paned windows, a private courtyard framed by Siena’s medieval brickwork – this is the atmosphere of charming holiday homes in Siena. Here, architecture carries centuries of civic pride: the curve of Piazza del Campo, the striped marble façade of the Duomo, the poised height of Torre del Mangia. Whether nestled within historic walls or perched among Chianti draped hills, these stylish villas and apartments blend rustic authenticity with refined comfort. Tastefully restored farmhouses offer quiet views of olive groves and vineyards, while town dwellings open directly onto lanes murmuring with local rituals. Each holiday home in our collection has been handpicked for its style, soul, and sense of place.