Arezzo suits visitors who want a working Tuscan city, Piero della Francesca's True Cross frescoes and a monthly antiques fair. Homes are spread across the countryside around the city, and most have a private pool and a garden, so a car matters more than the city's size suggests.
Arezzo is a hill city, not a village. The old centre climbs a slope that takes in four valleys: Valtiberina, Casentino, Valdarno and Valdichiana. Part of the medieval city was destroyed in the Second World War, and what survives is gathered around Piazza Grande, also called Piazza Vasari, with its arcade of the Loggiato Vasariano. The True Cross cycle sits inside the Basilica of San Francesco. Our homes are scattered over a wide area around Arezzo rather than packed into the centre, so read each listing's position before booking. Most are sized for small groups, with a handful for large parties. Evenings mean restaurants and small wine bars serving ribollita or Chianina steak, and the antiques fair takes over Piazza Grande, Piazza San Francesco and the Logge Vasari one weekend a month.
The valley north of Arezzo, where the Arno runs its first stretch.
The valley to the east, with the Alpe della Luna nature reserves in its upper reaches.
A plain to the south made by reclaiming former marshland, with the Chiana canal as its main waterway.
Two hill towns both within a short drive of Arezzo, useful for a second day out.
Florence Airport is the practical choice, about an hour by car (roughly 84 km). The station sits at the edge of the old town with frequent trains to Florence and Rome, but homes here are spread around the countryside, so plan on a car. Leave it in a municipal car park and walk up into the centre.
Arezzo works in any month because its draw is the city itself. The antiques fair runs on the first Sunday of each month and the Saturday before it, and serious buyers start bargaining the evening before, while stock is still on the lorries. The Giostra del Saracino, a knightly tournament of medieval origin, is held in Piazza Grande on the penultimate Saturday of June or the first Sunday of September, so book early for those dates.
It runs on the first Sunday of each month and the Saturday before, mainly around Piazza Grande, Piazza San Francesco and the Logge Vasari. More than 500 exhibitors come, and buying continues until sundown on Sunday.
They are in the Basilica of San Francesco, which preserves his series called the Legend of the True Cross. The cathedral of San Donato also holds a Magdalene by him.
The old town is small enough to cover on foot, but it sits on a steep incline, so expect uphill walking and wear comfortable shoes. Drivers can leave the car in a municipal car park for the day.
Yes, the station is at the edge of the old town with frequent connections to both cities. Trains help for day trips, though homes in the countryside around Arezzo still need a car.
Most do, and most also have a garden. Sizes range from small places for a couple to very large houses for big groups, so filter by sleeps before you compare.
Written by the TrustedVillas team. Last reviewed October 2026.
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