Villas in Asciano
Asciano suits a quiet stay in the Crete Senesi, a medieval hill town with the abbey of Monte Oliveto Maggiore about 10 km to the south. It is a small town, the airports are a long way off, and nearly every home here has a private pool.
- Villas
- 9
About Asciano
Asciano is a hill town of about 7,000 at 200 m, well inside the Crete Senesi, an area named for its grey, clayey soil. The streets keep a medieval layout, around the Romanesque Basilica of Sant'Agata, Piazza del Grano with its 15th-century fountain, and two museums: Palazzo Corboli, for sacred art and archaeology, and the Cassioli Museum of 19th-century Sienese painting. The homes sit close to the town and nearly all have a private pool and a garden, with a fireplace in many. They sleep around five.
Is Asciano right for you?
- Best for
- Slow countryside stays near Siena with a pool
- Not for you if
- You want a lively evening scene, as Asciano is a small medieval hill town.
Near Asciano
Monte Oliveto Maggiore
A Benedictine monastery about 10 km south of Asciano, founded in 1320, with cloister frescoes by Luca Signorelli and Il Sodoma.
Siena
Roughly 30 km from Asciano by rail, the nearest big city.
Getting to Asciano
Florence airport is around an hour and a half by car. By bus the trip from the airport takes about four hours, ending with line 109 from Siena, and the town also has a rail link with Siena. For homes out in the countryside, hire a car.
When to go to Asciano
Autumn is white truffle season, with a market exhibition each year. The Palio dei Ciuchi runs on Sundays in September, Carnival comes in February, and Eroica, a vintage cycling event largely on dirt roads, is held in October.
Villas in Asciano
4-star property
2-Bedroom Home, Asciano
Asciano, Siena and surroundings, Italy
6
2
0
Air ConBBQParking+10 more
4-star property
2-Bedroom Home, Asciano
Asciano, Siena and surroundings, Italy
6
2
0
Air ConBBQParking+10 more
5-star property
flach 'Molinello Cipresso
Asciano, Siena and surroundings, Italy
8
3
0
Air ConBBQParking+9 more
2-Bedroom Home, Asciano
Asciano, Siena and surroundings, Italy
5
2
0
Air ConParkingDishwasher+8 more
1-Bedroom Home, Asciano
Asciano, Siena and surroundings, Italy
3
1
0
Air ConParkingDishwasher+8 more
Asciano villa holidays: questions answered
Does Asciano have a cycling event?
Yes. Eroica, a non-competitive vintage cycling event, is held in October, with riders in vintage clothing largely on dirt roads. It has run since 1997.
Which museums are in Asciano?
Palazzo Corboli has sacred art and archaeology sections, the Cassioli Museum is devoted to 19th-century Sienese painting, and there is a Museo d'Arte Sacra beside the basilica and an archaeological museum.
How far is Monte Oliveto Maggiore from Asciano?
About 10 km to the south. The Benedictine monastery was founded in 1320, and its cloister has frescoes of the life of St Benedict, begun by Luca Signorelli and finished by Il Sodoma in 1505.
When is truffle season around Asciano?
Autumn. The white truffle is the area's signature product, celebrated each year with a White Truffle Market Exhibition, truffle farm visits and tasting menus.
Nearby towns to Asciano
Written by the TrustedVillas team. Last reviewed October 2026.
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