Luxury Tuscany Villas with Private Pools

Compare private villas across Chianti, Florence, Siena and Val d'Orcia, from intimate wine-country homes to whole estates for large groups. Every villa in this collection has a pool; selected stays also offer chef service, wedding spaces and on-site support.

Every villa listed here has been visited in person by our team. We do not list properties we wouldn't stay in ourselves, and we negotiate directly with the owner so the rate you pay is the rate they receive — no third-party booking fees layered on top.