Destination

Chianti villa rentals among the vines.

Between Florence and Siena, Chianti remains Tuscany’s most lived-in wine country—gravel drives, family cellars, and estates that still harvest the slopes you see from the terrace.

Chianti Classico is not a single village but a chain of hills stitched by secondary roads: Greve, Radda, Castellina, and the quieter ridges between them. Day-trippers skim the main routes; villa guests settle into the rhythm of market mornings, cellar visits, and long dinners under festoon light.

Our Chianti collection favours houses with genuine vineyard context—courtyards that hold the day’s heat, pools set among olives, and enough bedrooms for families or friends travelling together. Private chef service and concierge arrangements are available when you want the table handled as carefully as the cellar list.

Why stay in Chianti

  • Vines at the door and Florence or Siena within an easy drive
  • Wine estates and farmhouses suited to private chef evenings
  • Hill towns that still keep a local evening pace after the coaches leave
  • Strong choice of 4–12 bedroom houses for families and celebrations

Best suited for: Travellers who want vineyard atmosphere without surrendering city access—wine lovers, multi-generational families, and groups who prefer a private house to a hotel corridor.

Nearby towns & attractions

Greve in Chianti · Radda in Chianti · Castellina in Chianti · Florence · Siena

  • Chianti Classico cellar visits and family tastings
  • Market mornings in Greve and neighbouring hill towns
  • Day trips to Florence’s museums and Siena’s Campo
  • Olive oil mills, gravel ridge walks, and harvest-season roads

Getting there

Most guests arrive via Florence Airport (FLR) or Pisa (PSA), then drive 45–90 minutes depending on the estate. A car is essential for village hopping; we can arrange transfers and drivers for tasting days when you prefer not to navigate the hills yourself.

Frequently asked questions

Are Chianti villa rentals close to Florence?

Many estates sit within an hour of Florence, depending on traffic and exact location. Guests often spend a morning in the city and return to the villa for lunch—an easier rhythm than basing entirely in the centre.

Do your Chianti villas have private pools?

Most houses in this collection include a private pool set among gardens or olives. Confirm amenity details when you enquire—availability and seasonality vary by estate.

Can you arrange wine tastings from the villa?

Yes. Our concierge team books cellar visits with producers who still prefer a quiet introduction to a loud booking engine, timed around your house and harvest calendar.

Private Enquiry

Plan your Chianti stay.

Tell us your dates, party size, and the atmosphere you want—we will suggest the right house.