Book Luxury Vacation Rentals in San Gimignano

Olive & Grace

• 6 guests

• 4 bedrooms

Certaldo, Florence

Tucked into the vine-covered Tuscan hills, this home promises an idyllic escape from day-to-day life. Sure, the traditional interiors may not be everyone’s cup of tea, but you’ll find everything needed for a comfortable stay here and plenty of room to spread out and relax.

Into the Olive Grove

• 10 guests

• 5 bedrooms

San Filippo a Ponzano, Barberino Tavarnelle

Conveniently located in San Filippo a Ponzano, a rural village on a hill in Chianti, from here you'll be within easy reach of Florence (a forty-five-minute drive away) and Siena (a thirty-minute drive away). Prepare to be blown away by the never-ending landscapes amidst fields of oak woods, vineyards, and olive groves upon arrival.

Chestnut & Stone

• 16 guests

• 8 bedrooms

Gambassi Terme, Florence

In the countryside just outside of the spa town of Gambassi Terme, this delightful villa looks out over the Volterra Hills. It’s peaceful and pretty, surrounded by typical Tuscan vegetation including cypresses, chestnuts, and olive trees.