Villas in Guardistallo
Guardistallo is an olive-grove hill village near the Tuscan coast, where most homes have a private pool and the sea is a drive away. The homes are spread around the village and its countryside, so check each one's position and plan to hire a car.
- Villas
- 27
- From, per week
- £252
About Guardistallo
Guardistallo stands on a hill at 278 metres among olive trees, and was first documented in 1144 as a Lombard castle. The village is small, with a 180-seat theatre, the Marchionneschi, reopened in 1990 and used for community programmes mostly in summer. A convent of contemplative monks nearby, Valserena, makes creams, soaps and liqueurs. Spring brings an olive oil festival where new oil is tasted on bread, and at Christmas residents fill the historic streets with nativity scenes. Homes lie around the village and across the countryside rather than in the centre, and most have a private pool. Most sleep around four, with a minority sleeping more than eight. Nearby beaches are easy to reach by car.
Is Guardistallo right for you?
- Best for
- Private-pool stays among olive groves, with the sea a drive away
- Not for you if
- You want shops, restaurants and the sea within walking distance.
Near Guardistallo
Montescudaio
Medieval streets and Piazza Matteotti, and the source of the DOC wine that carries its name.
Casale Marittimo
A hill village with castle remains and the Casa Nocera Etruscan necropolis, bordering Guardistallo.
Castagneto Carducci
Home to Carducci's house and a stop on the wine route.
Marina di Cecina
Soft sand and a centuries-old pinewood in the Tomboli di Cecina nature reserve, for a beach day by car.
Getting to Guardistallo
Pisa is the nearest airport, about 29 miles away, and Florence is the other option. The village itself is about 50 km from Pisa and 70 km from Florence. Hire a car: the village is on a hill, homes are spread across the countryside, and the beaches are a drive away.
When to go to Guardistallo
Late spring brings the Crogiantina olive oil festival, and summer is when the theatre mostly stages its community programme. Winter is quiet, with the Christmas nativity scenes in the old streets, and down at Marina di Cecina the coast is quiet in winter as well, away from mass tourism. Check theatre and convent hours before you go.
Villas in Guardistallo
3-star property
4-star property
Il sogno del pittore
Guardistallo, Riviera degli Etruschi, Italy
6
3
0
Air ConBBQDishwasher+9 more
3-star property
4-star property
3-star property
2-star property
2-star property
2-star property
2-star property
2-star property
3-star property
3-star property
3-star property
Saxum
Guardistallo, Riviera degli Etruschi, Italy
5
2
0
Air ConBBQMicrowave+8 more
from£120
per night
3-star property
Aves
Guardistallo, Riviera degli Etruschi, Italy
4
1
0
Air ConBBQDishwasher+9 more
from£76
per night
3-star property
3-star property
Amor
Guardistallo, Riviera degli Etruschi, Italy
4
2
0
Air ConBBQDishwasher+8 more
from£113
per night
3-star property
3-star property
3-star property
Le Colmate
Guardistallo, Riviera degli Etruschi, Italy
3
1
0
BBQFireplaceParking+4 more
from£36
per night
3-star property
Le Colmate
Guardistallo, Riviera degli Etruschi, Italy
6
2
0
BBQParkingPool+5 more
from£50
per night
3-star property
3-star property
Tripyou
Guardistallo, Riviera degli Etruschi, Italy
3
1
0
Air ConDishwasherGarden+6 more
from£57
per night
3-star property
Le Colmate
Guardistallo, Riviera degli Etruschi, Italy
4
2
0
BBQParkingPool+4 more
from£39
per night
4-star property
La Rocchetta
Guardistallo, Riviera degli Etruschi, Italy
8
3
0
DishwasherGardenMicrowave+8 more
Guardistallo villa holidays: questions answered
Is Guardistallo near the beach?
Near enough for day trips, but not on foot. The village is on a hill not far from the sea, and nearby beaches are easy to reach by car, such as Marina di Cecina with its soft sand and old pinewood.
What is the Valserena convent near Guardistallo?
Valserena is home to a contemplative community of monks who make creams, perfumes and soaps, plus liqueurs including nocino, hop bitters and eucalyptus extract.
Is Guardistallo quiet in winter?
Quiet, yes, with around 1,200 residents, though Christmas is its main show: residents and school pupils set up a thousand nativity scenes in the historic centre.
Guardistallo or Casale Marittimo?
Guardistallo sits higher, at 278 metres against 214, with a theatre, olive groves and a convent. Casale Marittimo has the Etruscan necropolis and castle remains. The two villages border each other.
Does Guardistallo have an olive oil festival?
Yes. The Crogiantina festival in spring has oil tasted on bread. Local oil is prized for its scent and goes into the village's recipes and bruschetta.
Nearby towns to Guardistallo
Written by the TrustedVillas team. Last reviewed October 2026.
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