San Gimignano villas, Chianti Classico, Tuscany Holiday rentals - villas & holiday homes to rent in San Gimignano

The medieval hill top city of San Gimignano lies within the famous wine growing region of Chianti Classico within the province of Siena in Tuscany. Surrounded by 13th century walls, San Gimignano is rich in culture, history and when you walk around the cobbled streets, it is as if you are stepping back in time.

Famous for its towers - only 14 remain, it is yet another part of Italy that was declared a “World Heritage Site" by UNESCO. For evening entertainment, there are many excellent restaurants to choose from with alfresco dining - dishes of wild boar and Tuscan ham are specialities. The local wines are Vernaccia Rosso DOC and Vernaccia di San Gimignano DOCG - considered to be one of the finest white wines in Italy.

At a glance...
World Heritage Site
Family friendly
Restaurants 20+
Bars 30+
Car recommended
Nearest beach Marina de Cecina (2 hours)
Nearest airport Florence (66km)
Nearest train station Poggibonsi/San Gimignano

Featured villas in San Gimignano

San Gimignano and the surrounding area has an excellent stock of tourist beds from luxury holiday rentals on the fringe of the medieval city walls, many with private pools, to town centre apartments. Many of the self-catering villas are a short drive from the centre so having a car is advisable and more convenient for sight seeing. Nearby areas, all within a 15 minute drive include Gambassi Terme (6km) and Certaldo (9km).

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Places of interest
Piazza Duomo
The beautiful Piazza della Cisterna
Palazzo Vecchio del Podestà
Torri dei Salvucci, in Piazza del Duomo
Fortress - Rocca di Montestaffoli
Porta delle Fonti - 14th century public fountains
Castelvecchio Nature Reserve Val d'Elsa 2km
12th-century Duomo di San Gimignano
San Gimignano towers at night

Our view

San Gimignano and the surrounding area is perfect for family holidays with so much to see and do for all ages.

And during the summer, San Gimignano gets extremely busy with international tourists who come to marvel at the architecture and wander the cobbled back streets. If you enjoy culture and history and the natural beauty of the rolling Tuscan hills, staying in a rented villa or apartment gives you the freedom to do just that.