Gaiole in Chianti Unique Homes

Whispering Cypresses

• 6 guests

• 3 bedrooms

Montevarchi, Arezzo

On the border between Valdarno and Chianti, this hilltop villa in the heart of Tuscany is just a short drive from the town of Montevarchi and within an hour of Arezzo. The rustic interior may feel dated to some, though we think it’s part of the charm.

The Olive Vine

• 6 guests

• 3 bedrooms

Gaiole in Chianti, Siena

Just outside of Gaiole's idyllic town, serving authentic cuisine and Chianti wine, this hillside home offers pastoral vistas. There's an upside-down layout inside, putting the bedrooms below the living space, which opens out onto several terraces and a leafy garden with an infinity pool.

The Chianti Essence

• 8 guests

• 4 bedrooms

Gaiole in Chianti, Siena

Surrounded by vineyards and olive groves, this charming stone villa welcomes families to explore Chianti. Drive to the lively market town of Gaiole and Brolio Castle, or admire the Tuscan countryside of Castellina in Chianti.