Tuscany, one castle
and one vineyard at a time
Castles in the Chianti hills, villas ten minutes from Florence, wine estates around Montalcino, farmhouses with a pool in the Val d'Orcia.
The region Americans know best, seen from inside its houses
Most first trips to Italy pass through Tuscany, and most of them stay in hotels that could be anywhere. Our 54 homes here are the other option: a 16th-century hamlet in Chianti still run by the family, a palazzo three hundred metres from Piazza del Campo, a convent in the Sienese hills with a panoramic pool. Florence and Siena are an hour apart; everything else on this page sits between them or just south.
Four homes we would book first
Different budgets, different moods, all with breakfast included and a real owner behind the door.
Check dates across 54 homes in Tuscany
Pick a property or leave it open: we check every home in the area and show you the ones available, with the real price, breakfast included. Nothing is charged until the property confirms.
Ask our assistant
Tell it your dates, who is coming and what you like. It replies with a plan built on our Tuscan homes and can check availability in the same conversation.
- We have 6 nights in late September, a couple, wine and small towns. Where should we base ourselves?
- Which of these homes is easiest without a car?
- Can you check rates at Borgo Vescine for October 10 to 13?
