Villas in Montescudaio
Montescudaio is a small walled hill village in Tuscany, suited to couples and small groups who want a quiet base with sea views. The sea is something you see from the castle walls rather than walk to, so beach days mean getting in the car.
- Villas
- 19
- From, per week
- £389
About Montescudaio
Montescudaio stands on a hill at 242 metres. It is a compact village of old family palaces and the churches of Santissima Annunziata and Santa Maria Assunta, ringed by castle walls up to 15 metres high that keep their original masonry on the north and south sections. From the Guardiola, the only watchtower left, the view runs across the Cecina plain to the Tyrrhenian Sea, and from the walls you can pick out the islands. The first settlement formed around a Benedictine monastery founded in 1091, and the centre today is Piazza Matteotti. The homes are grouped tightly around the village rather than spread over the countryside. Nearly all have a garden, most sleep two to four, and some have a pool. This is a village rather than a resort, so expect quiet evenings. It calls itself a City of Bread and has its own DOC wine.
Is Montescudaio right for you?
- Best for
- Couples and small groups wanting a hill village base with wine
- Not for you if
- You want to walk to a beach or to a long run of restaurants, because the sea here is a view and a drive away.
Near Montescudaio
Guardistallo
A village on a hill along the Etruscan Coast, first built as a Lombard castle and set among olive trees not far from the sea.
Casale Marittimo
Another small village of the area, set between the sea of the Etruscan Coast and the olive groves.
Via dei Pellegrini
A trail in the surroundings of the village that passes a historic abbey and the Scornabecchi garden with its medieval springs.
Pisa
About 45 km to the north-west, for a day trip beyond the hills.
Getting to Montescudaio
Pisa is about 45 km to the north-west and Florence about 70 km to the north-east, so check flights into either city. A car is the practical choice, because the homes sit in and around a hill village and every beach day means driving down from it.
When to go to Montescudaio
The village wine festival has been held on the first weekend of October since 1968, pouring Montescudaio DOC alongside the area's other wines. That makes early autumn a good time to come. Outside that weekend Montescudaio is small enough that you should check restaurant opening times before an off-season stay. Pick a clear day for the views over the plain from the walls.
Villas in Montescudaio
3-star property
3-star property
Erbe
Montescudaio, Riviera degli Etruschi, Italy
4
2
0
BBQFireplaceParking+6 more
from£84
per night
5-Bedroom Home, Montescudaio
Montescudaio, Riviera degli Etruschi, Italy
18
5
0
BBQParkingDishwasher+10 more
4-star property
3-Bedroom Home, Montescudaio
Montescudaio, Riviera degli Etruschi, Italy
7
3
0
BBQParkingDishwasher+6 more
3-star property
Il Castello
Montescudaio, Riviera degli Etruschi, Italy
4
1
0
Air ConGardenParking+7 more
from£66
per night
3-star property
Al casone
Montescudaio, Riviera degli Etruschi, Italy
5
2
0
Air ConBBQFireplace+8 more
from£85
per night
5-star property
Campo del Rosario
Montescudaio, Riviera degli Etruschi, Italy
5
3
0
BBQParkingDishwasher+9 more
3-star property
3-star property
4-star property
Villino PERO
Montescudaio, Riviera degli Etruschi, Italy
3
1
0
Air ConParkingFridge+3 more
from£56
per night
4-star property
3-star property
3-star property
3-star property
3-star property
3-star property
3-star property
3-star property
Podere Sant'Ignazio
Montescudaio, Riviera degli Etruschi, Italy
6
3
0
Air ConDishwasherMicrowave+9 more
Montescudaio villa holidays: questions answered
Is Montescudaio by the sea?
No, it is a hill village at 242 metres. The sea is visible from the castle walls and the Guardiola tower across the Cecina plain, but reaching a beach means driving down from the hill.
What is Montescudaio known for?
Wine and bread. Montescudaio gained its DOC in 1977 for a red based on sangiovese and a white based on trebbiano, and the village is known for Tuscan bread baked in a wood-burning oven.
Is Montescudaio worth a villa stay compared with Guardistallo or Casale Marittimo?
All three are small villages between the sea and the olive groves. Montescudaio adds castle walls up to 15 metres high, the Guardiola watchtower, a central square and its own DOC wine.
When is the Montescudaio wine festival?
It is held each year on the first weekend of October and has run since 1968. Local DOC wines are poured alongside the area's other wines, from Sangiovese to Cabernet and Merlot.
Is Montescudaio a good base for a quiet holiday?
Yes, it is a small hill village rather than a resort. Evenings are quiet, and most homes here are small, sleeping two to four.
Nearby towns to Montescudaio
Written by the TrustedVillas team. Last reviewed October 2026.
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