Villas in Casole d'Elsa
Casole d'Elsa suits couples and families wanting a hill village in the Sienese countryside with a private pool at the house. It sits on the hills of the Valdelsa rather than among the Chianti wine villages, and you will need a car to get anywhere.
- Villas
- 21
- From, per week
- £684
About Casole d'Elsa
Casole d'Elsa is a hilltop village strung along a ridge, with wide views over the Sienese countryside and Etruscan origins. Its oval circuit of walls survives with two 15th-century round towers. The 14th-century fortress, the Rocca, is now the town hall, and the 12th-century Collegiata di Santa Maria Assunta and a small archaeological museum with Etruscan finds are in the centre. The village has been given the Touring Club's Orange Flag. Out in the woods between Casole and Chiusdino, the Selva di Sogno park is dotted with sculptures and murals. Each summer the Palio di Sant'Isidro ends in a horse race between six districts. The homes sit close together in the surrounding country. Nearly all have a private pool and a garden, and a typical one sleeps about three.
Is Casole d'Elsa right for you?
- Best for
- Quiet countryside stays with a pool, close to Siena and Volterra
- Not for you if
- You want evenings out on foot, because the homes are in the country and the village is small.
Near Casole d'Elsa
Siena
Around 40 minutes by road; buses need a change at Colle di Val d'Elsa.
San Gimignano
A UNESCO World Heritage Site, and one of the towns near Casole d'Elsa to visit by car.
Volterra
Another town near Casole d'Elsa, reached by road from the village; a car is the practical way.
Monteriggioni
A third town near Casole d'Elsa, also reached by road from the homes in the countryside.
Getting to Casole d'Elsa
Florence airport is about an hour by road. Public transport is slow: the train from Florence to Poggibonsi and then a bus takes well over three hours, and buses to Siena change at Colle di Val d'Elsa. A hire car is essential for homes in the countryside.
When to go to Casole d'Elsa
Summer brings the Palio di Sant'Isidro, a horse race between six of the village's districts, with a craft market alongside. At Christmas locals stage a large open-air living nativity. Outside those dates the village is small, so check restaurant and museum hours before an off-season stay.
Villas in Casole d'Elsa
4-star property
4-star property
2-Bedroom Home, Casole d'Elsa
Casole d'Elsa, Tuscany Chianti, Italy
5
2
0
Air ConBBQParking+10 more
from£240
per night
4-star property
2-Bedroom Home, Casole d'Elsa
Casole d'Elsa, Tuscany Chianti, Italy
3
2
0
BBQParkingDishwasher+8 more
from£171
per night
2-Bedroom Home, Casole d'Elsa
Casole d'Elsa, Tuscany Chianti, Italy
3
2
0
Air ConBBQParking+9 more
4-star property
2-Bedroom Home, Casole d'Elsa
Casole d'Elsa, Tuscany Chianti, Italy
4
2
0
Air ConBBQParking+9 more
from£201
per night
2-Bedroom Home, Casole d'Elsa
Casole d'Elsa, Tuscany Chianti, Italy
2
2
0
Air ConBBQMicrowave+6 more
from£98
per night
2-Bedroom Home, Casole d'Elsa
Casole d'Elsa, Tuscany Chianti, Italy
3
2
0
Air ConBBQParking+9 more
from£201
per night
4-star property
2-Bedroom Home, Casole d'Elsa
Casole d'Elsa, Tuscany Chianti, Italy
3
2
0
BBQParkingDishwasher+8 more
from£176
per night
5-star property
2-Bedroom Home, Casole d'Elsa
Casole d'Elsa, Tuscany Chianti, Italy
3
2
0
BBQParkingDishwasher+8 more
from£162
per night
2-Bedroom Home, Casole d'Elsa
Casole d'Elsa, Tuscany Chianti, Italy
3
2
0
Air ConBBQParking+9 more
from£201
per night
2-Bedroom Home, Casole d'Elsa
Casole d'Elsa, Tuscany Chianti, Italy
2
2
0
Air ConBBQMicrowave+7 more
from£104
per night
2-Bedroom Home, Casole d'Elsa
Casole d'Elsa, Tuscany Chianti, Italy
3
2
0
Air ConBBQParking+9 more
from£176
per night
4-star property
2-Bedroom Home, Casole d'Elsa
Casole d'Elsa, Tuscany Chianti, Italy
3
2
0
Air ConBBQParking+9 more
from£187
per night
2-Bedroom Home, Casole d'Elsa
Casole d'Elsa, Tuscany Chianti, Italy
3
2
0
Air ConBBQParking+9 more
from£176
per night
5-star property
2-Bedroom Home, Casole d'Elsa
Casole d'Elsa, Tuscany Chianti, Italy
5
2
0
BBQParkingDishwasher+9 more
from£201
per night
1-Bedroom Home, Casole d'Elsa
Casole d'Elsa, Tuscany Chianti, Italy
3
1
0
Air ConBBQParking+9 more
from£153
per night
4-star property
1-Bedroom Home, Casole d'Elsa
Casole d'Elsa, Tuscany Chianti, Italy
3
1
0
Air ConBBQParking+7 more
from£119
per night
3-Bedroom Home, Casole d'Elsa
Casole d'Elsa, Tuscany Chianti, Italy
3
3
0
Air ConBBQParking+9 more
from£153
per night
5-star property
5-star property
5-Bedroom Home, Casole d'Elsa
Casole d'Elsa, Tuscany Chianti, Italy
6
5
0
Air ConBBQParking+9 more
from£405
per nightCasole d'Elsa villa holidays: questions answered
Is Casole d'Elsa in Chianti?
No. Casole d'Elsa is a hill village of the Valdelsa, looking out over the Sienese countryside, and it is not one of the Chianti wine villages.
How far is Casole d'Elsa from Siena?
About 40 minutes by road. The drive is a little over 20 miles. A bus exists but means a change at Colle di Val d'Elsa, and the whole trip takes well over an hour.
Can you get to Casole d'Elsa from Florence airport without a car?
Only with patience. The train goes from Florence to Poggibonsi and a bus finishes the trip, taking around three and a half hours. By road the airport is about an hour away, which is why most guests drive.
What is the Palio di Sant'Isidro in Casole d'Elsa?
A horse race held each summer between six of the village's districts, with a craft market alongside it.
Is Casole d'Elsa a good base for San Gimignano and Volterra?
Yes. San Gimignano and Volterra are both nearby, and Siena is about 40 minutes away. The village itself is small, so you will be driving to each.
Nearby towns to Casole d'Elsa
Written by the TrustedVillas team. Last reviewed October 2026.
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