Villas in Montalcino
Montalcino is a hill town in the Val d'Orcia, famous for Brunello wine, and the villas around it suit wine lovers who have a car. Homes are scattered across the countryside and most have a private pool. The catch is that Florence Airport is nearly two hours away by road.
- Villas
- 10
- From, per week
- £798
About Montalcino
Montalcino keeps a medieval layout of steep, straight streets that open onto wide views at the top. A citadel built in 1361 on earlier walls was the Sienese Republic's last defence against Medici expansion, and the Palazzo dei Priori has a tall bell tower on Piazza del Popolo. The town gives its name to Brunello di Montalcino, a Sangiovese wine developed in the mid-1800s. The 13th-century abbey of Sant'Antimo stands near Castelnuovo dell'Abate. The homes are spread over a wide area of countryside, sleeping mostly four to nine, and most have a pool.
Is Montalcino right for you?
- Best for
- Wine lovers wanting a hill-town base in the Val d'Orcia
- Not for you if
- You want a beach, or to manage without a car.
Near Montalcino
Abbey of Sant'Antimo
Thirteenth-century abbey near Castelnuovo dell'Abate, one of the finest examples of French Romanesque in Italy. Buses run there from Montalcino.
San Giovanni d'Asso
Village in the Montalcino area with a red-brick castle and a museum dedicated to the truffle.
Montepulciano
Nearby Tuscan wine town, often described as Montalcino's rival.
Getting to Montalcino
Florence Airport is about 1 hour 50 minutes from Montalcino by car, roughly 110 km. Public transport means several changes via Siena or Buonconvento and takes most of a day. Montalcino is close to Siena, and a hire car is essential for the villas.
When to go to Montalcino
The Sagra del Tordo, with historical costumes and re-enactments, takes place on the last Sunday of October. San Giovanni d'Asso holds truffle events in March, June and November, with the White Truffle Market Fair in November.
Villas in Montalcino
5-star property
Villa Montisi
Montalcino, Siena and surroundings, Italy
6
3
0
Air ConBBQDishwasher+11 more
from£383
per night
5-star property
La Suite del Benessere
Montalcino, Siena and surroundings, Italy
4
1
0
Air ConBBQDishwasher+8 more
from£114
per night
5-star property
3-star property
Monteroni
Montalcino, Siena and surroundings, Italy
4
2
0
DishwasherParkingPool+7 more
from£116
per night
3-star property
Asciano
Montalcino, Siena and surroundings, Italy
6
2
0
DishwasherParkingPool+8 more
from£133
per night
3-star property
Siena
Montalcino, Siena and surroundings, Italy
4
2
0
DishwasherParkingPool+6 more
from£116
per night
3-star property
Pienza
Montalcino, Siena and surroundings, Italy
4
2
0
DishwasherFireplaceParking+7 more
from£123
per night
3-star property
Casa del Sole
Montalcino, Siena and surroundings, Italy
6
3
0
DishwasherMicrowaveParking+4 more
3-star property
Il Cipresso
Montalcino, Siena and surroundings, Italy
9
5
0
BBQDishwasherParking+9 more
from£184
per night
3-star property
Torrenieri
Montalcino, Siena and surroundings, Italy
6
2
0
DishwasherParkingPool+7 more
from£123
per nightMontalcino villa holidays: questions answered
What is Brunello di Montalcino?
A wine from Sangiovese grapes named after the town, developed in the mid-1800s and able to improve over years of ageing. The estates around Montalcino are the reason many visitors come.
Is Montalcino a good base for Siena?
It works well for a day trip, as Montalcino is close to Siena. Florence Airport is much further, about 1 hour 50 minutes by car, which is worth knowing when planning arrival and departure days.
Can you visit Sant'Antimo Abbey from Montalcino?
Yes. The abbey is near Castelnuovo dell'Abate, with a Montalcino to Sant'Antimo exit if you drive, and buses also run from Montalcino. A 27.5 km bike route links the two.
When are the truffle events near Montalcino?
San Giovanni d'Asso, in the Montalcino area, holds truffle events in March, June and November. The White Truffle Market Fair is in November, and the Sagra del Tordo falls on the last Sunday of October.
Nearby towns to Montalcino
Written by the TrustedVillas team. Last reviewed October 2026.
Find Your Perfect Villa in Montalcino
Our villa experts are here to help you find the ideal property for your vacation. Contact us for personalized recommendations.