Rocca degli Olivi

Perched among olive groves above San Gimignano, this pet-friendly bed & breakfast sits in a tranquil rural spot about 1.5 miles (2.5 km) from the town’s UNESCO-listed center. It’s a short drive to Sant'Agostino Church, the Rocca of Montestaffoli and the Vernaccia wine museum.

An ancient detached farmhouse with antiques and traditional Tuscan décor, Rocca degli Olivi has five individually decorated, air-conditioned rooms with private patios. Rooms feature minibars, flat-screen TVs and private bathrooms with showers and bidets, and many offer sweeping views of the medieval town.

Standout features include an attached winery, an outdoor pool with poolside bar, a garden terrace and a cozy coffee shop/café. Tour and ticket assistance is available, and summer breakfasts can be enjoyed on the terrace while taking in the countryside views.

Complimentary wireless internet is available on the property and free self parking is provided onsite.

A complimentary buffet breakfast is served daily (8:00–9:30), indoors or on the terrace in summer. Unwind later at the bar/lounge or the poolside bar and sample local Tuscan wines from the on-site winery.