Villas in Montespertoli
Montespertoli is a wine town about 20 km south-west of Florence, with castles and a wine trail. It suits couples and families wanting a pool and Florence day trips, but the homes are scattered widely, so you drive for everything.
- Villas
- 18
- From, per week
- £547
About Montespertoli
Montespertoli lies roughly midway between Florence, Volterra and Siena, at 257 metres, and the old Via Volterrana runs through the area. The municipality takes in about 30 hamlets, which is why the homes are spread across a wide area rather than gathered in one place. The town has medieval origins and grew around the church of Sant'Andrea. There are two museums, one of sacred art and one of grapes and wine. Castles stand around the municipality, among them Montegufoni, once home to the Acciaioli and later the Sitwell family, and the Sidney Sonnino castle, now a winery. Nearly every home has a pool and a garden. Most are small, sleeping two to four, with a few built for very large groups.
Is Montespertoli right for you?
- Best for
- Florence day trips from a private pool in wine country
- Not for you if
- You want a lively centre on the doorstep, because the homes are spread across a wide area of hamlets.
Near Montespertoli
Florence
About 20 km north-east, with a line 373 bus from Montespertoli that takes around 40 minutes.
Montegufoni Castle
A castle in the municipality, a former home of the Acciaioli and later the Sitwell family.
Poppiano and Botinaccio
Two surviving castles that belonged to the Guicciardini family.
Certaldo
The old Via Volterrana meets the Via Francigena at the top of Certaldo.
Getting to Montespertoli
Florence is about 20 km away: by car it takes around half an hour, and the line 373 bus takes about 40 minutes to Terminal Vittorio Veneto. A car still makes sense, because the homes are spread across the hills and villages. Check flights into Florence.
When to go to Montespertoli
The Chianti Exhibition is the event of the summer and has run for over 60 years, with wine and local food tastings, lectures, meetings and shows. The 11 km wine trail runs past the area's wineries, farms and oil mills. The museums keep their own hours, so check before an off-season visit.
Villas in Montespertoli
5-star property
10-Bedroom Home, Montespertoli
Montespertoli, Tuscany Chianti, Italy
19
10
0
Air ConBBQParking+9 more
from£706
per night
5-Bedroom Home, Montespertoli
Montespertoli, Tuscany Chianti, Italy
14
5
0
Air ConBBQParking+11 more
from£543
per night
3-Bedroom Home, Montespertoli
Montespertoli, Tuscany Chianti, Italy
6
3
0
Air ConBBQParking+8 more
from£168
per night
1-Bedroom Home, Montespertoli
Montespertoli, Tuscany Chianti, Italy
2
1
0
BBQParkingFireplace+6 more
"Ciclamini capponi
Montespertoli, Tuscany Chianti, Italy
3
1
0
Air ConBBQParking+8 more
from£78
per night
flach "Giaggioli capponi
Montespertoli, Tuscany Chianti, Italy
3
2
0
Air ConBBQParking+7 more
from£99
per night
3-Bedroom Home, Montespertoli
Montespertoli, Tuscany Chianti, Italy
5
3
0
Air ConBBQParking+9 more
from£144
per night
"Melograni capponi
Montespertoli, Tuscany Chianti, Italy
4
2
0
Air ConBBQParking+8 more
from£102
per night
4-star property
2-Bedroom Home, Montespertoli
Montespertoli, Tuscany Chianti, Italy
4
2
0
Air ConBBQParking+8 more
2-Bedroom Home, Montespertoli
Montespertoli, Tuscany Chianti, Italy
6
2
0
Air ConBBQParking+8 more
2-Bedroom Home, Montespertoli
Montespertoli, Tuscany Chianti, Italy
4
2
0
Air ConBBQParking+7 more
1-Bedroom Home, Montespertoli
Montespertoli, Tuscany Chianti, Italy
2
1
0
BBQParkingFireplace+8 more
2-Bedroom Home, Montespertoli
Montespertoli, Tuscany Chianti, Italy
4
2
0
Air ConBBQParking+9 more
4-star property
3-Bedroom Home, Montespertoli
Montespertoli, Tuscany Chianti, Italy
5
3
0
Air ConBBQParking+7 more
from£132
per night
2-Bedroom Home, Montespertoli
Montespertoli, Tuscany Chianti, Italy
5
2
0
BBQParkingFireplace+8 more
2-Bedroom Home, Montespertoli
Montespertoli, Tuscany Chianti, Italy
5
2
0
Air ConBBQParking+8 more
Montespertoli villa holidays: questions answered
How far is Montespertoli from Florence?
About 20 km to the south-west. It is roughly half an hour by car, and the line 373 bus from Montespertoli takes about 40 minutes to reach Terminal Vittorio Veneto.
Is Montespertoli a wine area?
Yes. The Montespertoli wine trail runs about 11 km past wineries, farms and oil mills, and the town has a museum of grapes and wine. A Chianti Exhibition has been held every summer for over 60 years.
What castles are near Montespertoli?
Montegufoni, home to the Acciaioli and later the Sitwell family, the Sidney Sonnino castle, now a winery, and the Guicciardini family's surviving castles at Poppiano and Botinaccio.
Is Montespertoli quiet?
Yes. It is a municipality of about 30 hamlets rather than a resort, and the homes are spread widely. Expect quiet evenings, and plan to drive for restaurants and shops.
Is Montespertoli good for a pool holiday?
Yes. Nearly every home here has a private pool and a garden, so it works for families who want to spend days at the house and visit Florence on others.
Nearby towns to Montespertoli
Written by the TrustedVillas team. Last reviewed October 2026.
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