Villas in Monteriggioni
Monteriggioni suits families and friends who want a pool in the countryside near a walled hilltop village 14 km from Siena. Every home here has a private pool and most have a garden. The homes are outside the walls, so you drive in to eat and shop.
- Villas
- 7
- From, per week
- £451
About Monteriggioni
Monteriggioni is a fortified village on a hill, built by the Sienese in the early 13th century to guard their front line against Florence, with towers that watched over the Via Cassia. A ring of wall about 570 metres long, with 14 square towers, encloses the village, whose main square, Piazza Roma, holds the Romanesque-Gothic church of Santa Maria Assunta. You can walk sections of the wall for views over the Chianti and Val d'Elsa countryside. The homes are grouped together in the countryside of the comune, outside the walls. There is free parking at the foot of the hill and paid parking further up. The village has restaurants serving Tuscan food and local wine; for more choice at night, Siena is close.
Is Monteriggioni right for you?
- Best for
- Pool holidays within easy reach of Siena
- Not for you if
- You want to walk out of the door to bars and shops, as the homes sit in the countryside outside the walled village.
Near Monteriggioni
Siena
About 14 km away, the city that built Monteriggioni as a stronghold against Florence, and the obvious day trip.
Abbadia a Isola
A hamlet of Monteriggioni built around the Badia of Santi Salvatore e Cirino, a Romanesque abbey from the mid-12th century.
Castellina Scalo
A few kilometres away, with the nearest railway station on the Empoli to Siena line, handy for a car-free day.
Getting to Monteriggioni
Fly to Florence; the drive to Monteriggioni is just under an hour. By car, follow the Via Cassia (SS2) and leave at the Monteriggioni exit. You need a car: public transport from Florence airport, by train and bus via Poggibonsi, takes close to three hours.
When to go to Monteriggioni
Every July the village holds its medieval festival, Monteriggioni di Torri si Corona, across two consecutive weekends, with craftsmen, knights, dancers and musicians in medieval costume filling the streets. Book early if you want to be there for it; if you would rather walk the walls in peace, pick a different fortnight.
Villas in Monteriggioni
5-star property
Relais La Costa
Monteriggioni, Siena and surroundings, Italy
24
12
0
Air ConBBQDishwasher+13 more
from£2278
per night
2-star property
Fattoria Petraglia - Terrazza
Monteriggioni, Siena and surroundings, Italy
4
2
0
BBQGardenParking+8 more
from£75
per night
2-star property
Fattoria Petraglia
Monteriggioni, Siena and surroundings, Italy
23
9
0
BBQFireplaceGarden+10 more
from£505
per night
2-star property
Fattoria Petraglia - Di Mezzo (MTG202)
Monteriggioni, Siena and surroundings, Italy
5
2
0
BBQFireplaceGarden+10 more
from£76
per night
2-star property
Fattoria Petraglia - Loggiato
Monteriggioni, Siena and surroundings, Italy
5
2
0
BBQGardenMicrowave+9 more
from£79
per night
2-star property
Fattoria Petraglia - Cedro
Monteriggioni, Siena and surroundings, Italy
3
1
0
BBQGardenMicrowave+9 more
from£64
per night
2-star property
Fattoria Petraglia - Padronale
Monteriggioni, Siena and surroundings, Italy
6
2
0
BBQFireplaceGarden+10 more
from£85
per nightMonteriggioni villa holidays: questions answered
How far is Monteriggioni from Siena?
About 14 km. That makes Monteriggioni a practical base for Siena day trips, with countryside and a pool to come back to rather than city streets.
Can you walk on the walls of Monteriggioni?
Yes. You can walk along the walls and look out over the Chianti and Val d'Elsa countryside. A small museum in the village shows replicas of medieval and Renaissance arms and armour.
Is there a train station near Monteriggioni?
The closest is Castellina Scalo, a few kilometres away on the Empoli to Siena line. From Florence you can also take a train to Poggibonsi and a bus on, but it is slow.
Is Monteriggioni good for a big group?
It can be. Every home here has a private pool, and a few sleep eight or more, though most are sized for around four to six. Book early for the larger ones.
Does Dante mention Monteriggioni?
He does, in canto XXXI of the Inferno, part of the Divine Comedy. The line Montereggion di torri si corona gives the July festival its name.
Nearby towns to Monteriggioni
Written by the TrustedVillas team. Last reviewed October 2026.
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