Villas in Montaione
Montaione suits groups wanting a pool in Valdelsa farmland, about 35 km south-west of Florence, with a truffle festival in October. It is in the Metropolitan City of Florence, not in Chianti itself.
- Villas
- 48
- From, per week
- £383
About Montaione
Montaione is a hill town of about 3,600 people at 342 metres, listed among the most beautiful villages of Italy. The centre has three parallel streets that meet where the gate once stood, and most of the old walls and towers were lost to bombing in 1944. San Vivaldo, a wooded sanctuary of terracotta chapels, is nicknamed the Jerusalem of Tuscany. The municipality has sixteen frazioni, including Castelfalfi, Iano and San Vivaldo. Our homes are scattered across the countryside around the town over about six kilometres, all with a pool and nearly all with a garden. Most sleep around six, and some sleep far more. Walking trails are well signposted, and the area is promoted for green tourism.
Is Montaione right for you?
- Best for
- Groups wanting pools, hill walks and Pisa flights
- Not for you if
- You want vineyard-lined Chianti roads, since Montaione lies in Valdelsa, not Chianti.
Near Montaione
San Vivaldo
A wooded sanctuary outside the town, whose sixteenth-century terracotta chapels recreate the topography of Jerusalem.
Castelfalfi
A frazione in the hills around Montaione, with a golf club.
Gambassi Terme
A stage on the Via Francigena, known for thermal waters used in local baths since the nineteenth century.
Certaldo
Where the Via Francigena stage to Gambassi starts, and the host of the Mercantia festival in July.
Getting to Montaione
Pisa Airport is about 52 minutes away by car. Public transport takes nearly three hours, with a train to Empoli and a bus from Castelfiorentino station, so a car is the practical way to reach homes scattered through the farmland.
When to go to Montaione
Late October is the main date: the Tartufesta, Montaione's white truffle festival, runs on the last two Sundays of the month. The upper Carfalo valley, woods and springs suit walking in the milder months, and the pools make summer the obvious time for a family stay.
Villas in Montaione
2-Bedroom Home, Montaione
Montaione, Tuscany Chianti, Italy
6
2
0
Air ConBBQParking+10 more
from£148
per night
flach "Madonnino quercia
Montaione, Tuscany Chianti, Italy
6
2
0
Air ConBBQParking+10 more
from£101
per night
2-Bedroom Home, Montaione
Montaione, Tuscany Chianti, Italy
6
2
0
Air ConBBQParking+10 more
from£139
per night
flach "Madonnino corbezzolo T6
Montaione, Tuscany Chianti, Italy
6
2
0
Air ConBBQParking+10 more
from£204
per night
5-star property
Villa Sassolina
Montaione, Tuscany Chianti, Italy
9
4
0
Air ConBBQParking+10 more
from£303
per night
1-Bedroom Home, Montaione
Montaione, Tuscany Chianti, Italy
4
1
0
Air ConBBQParking+10 more
from£91
per night
3-star property
Le Monache - intero nucleo
Montaione, Tuscany Chianti, Italy
16
8
0
Air ConBBQGarden+7 more
from£257
per night
3-star property
3-star property
3-star property
3-star property
3-star property
Baccelli
Montaione, Tuscany Chianti, Italy
26
13
0
BBQDishwasherFireplace+8 more
from£469
per night
3-star property
3-star property
3-star property
Poggio al Colle
Montaione, Tuscany Chianti, Italy
13
6
0
BBQDishwasherGarden+11 more
from£390
per night
3-star property
Villetta La Ginestra
Montaione, Tuscany Chianti, Italy
6
2
0
BBQParkingDishwasher+8 more
from£82
per night
3-star property
3-star property
4-star property
3-star property
3-star property
3-star property
3-star property
Montaione villa holidays: questions answered
Is Montaione in Chianti?
No. Montaione is in the Empolese Valdelsa area, in the Metropolitan City of Florence, about 35 km south-west of the city. It lies in Valdelsa, so expect rolling hills and woods rather than Chianti vineyards.
When is the Montaione truffle festival?
The Tartufesta is held on the last two Sundays of October. Montaione is recognised as a Truffle City for its white truffles, and the festival also features olive oil, saffron, honey and jams.
What is San Vivaldo near Montaione?
A sanctuary in the woods where Fra Tommaso da Firenze extended the oratory in 1515 with terracotta chapels. The chapels recreate Jerusalem's layout, which gave it the nickname Jerusalem of Tuscany.
How do you get to Montaione from Pisa Airport?
By car it is about 52 minutes. The train and bus route via Empoli and Castelfiorentino takes nearly three hours, so most visitors hire a car for the farmland roads around Montaione.
Is there good walking around Montaione?
Yes. The area has well-marked hiking trails, rolling hills, woods, springs and medieval villages such as Iano and Castelfalfi. The upper Carfalo valley is a protected natural area with canyons.
Nearby towns to Montaione
Written by the TrustedVillas team. Last reviewed October 2026.
Find Your Perfect Villa in Montaione
Our villa experts are here to help you find the ideal property for your vacation. Contact us for personalized recommendations.