Villas in Chianti for rent with private pool

What the houses here are like

Chianti’s houses are mostly restored stone farmhouses and manor villas on wine estates: exposed beams, original terracotta floors, olive trees all around and a pool — often infinity-edge, facing the hills. Many sit in isolated positions at the end of a gravel road: total privacy, silence, and a sunset that belongs to you alone. Nearly all our villas here have a private pool and outdoor spaces designed for living outside from June to September.

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 manages every villa in its portfolio directly — no intermediaries, real availability, and a local team based in the heart of the area. Our concierge arranges tastings in Gallo Nero cellars, in-villa chefs, transfers and private guides; and if something breaks at eight in the evening, it is us who turn up, not a call centre.

Where to stay in Chianti

Greve in Chianti

The largest village in Chianti Classico and the most practical base: about 30 km south of Florence, with its triangular piazza, the wine museum and the Saturday market (8:30 to one o’clock). It is the one village well served by the 365 bus from Florence, so it suits anyone who would rather not drive every day — the trade-off is that it is also the most touristy of the three historic villages.

Panzano

A hamlet of Greve overlooking the conca d’oro — the amphitheatre of south-facing vineyards that yields the area’s most structured wines. This is the stop for food lovers: Dario Cecchini, Italy’s best-known butcher, works here and runs three restaurants of his own. Market on Sunday morning in piazza Bucciarelli. The right choice if you are coming above all to eat and drink well.

Radda in Chianti

A medieval hilltop village, regarded as the capital of Chianti Classico and recently restored with its original layout intact. It is the most compact and the quietest of them: a handful of streets, the old walls, and vineyards beginning just outside. For those after the Chianti of the imagination, and unbothered by the bends it takes to get there.

Castellina in Chianti

One of the oldest villages in the area, Etruscan in origin, and the best placed for touring: sitting near the main roads, it gains roughly half an hour on Greve for trips to Siena, San Gimignano and Volterra. The base to choose if Chianti is your starting point rather than your only destination.

Gaiole in Chianti

The eastern side, at the foot of the Monti del Chianti: wilder, more wooded and steeper than the rest, and because it sits in a basin it is also the coolest spot in the denomination — which tells in July and August. The houses here are genuinely isolated: you come for the silence, not for the restaurants.