Villa Conventino is a carefully restored historic property in San Casciano in Val di Pesa, at the northern edge of the Chianti Classico zone, 20 km from Florence. The building carries the history in its thick stone walls, broad terracotta floors, and high-ceilinged rooms that hold cool air even through the warmest Tuscan afternoons. The main villa spans approximately 540 square metres across three floors. A separate barn apartment adds 80 square metres of private space next door. Together, the two buildings sleep up to twelve guests, and the property represents the kind of Chianti villa rental that suits an extended family as well as a group of friends looking for a week of genuine immersion in the Florentine hills.
A Stone Fireplace on Every Floor
The ground floor is built around gathering spaces. Two fully equipped kitchens make large-group catering practical. A dining room connects to the main living room, where a large stone fireplace anchors one end of the space. A double bedroom on this floor has its own en-suite bathroom, which works well for guests who prefer to avoid stairs. A separate shower cabin provides additional bathroom capacity at this level. All bedrooms in the villa are air-conditioned, and the restoration throughout has been careful: the original stonework and terracotta remain intact. The overall atmosphere is more country house than holiday rental.
Upstairs, four double bedrooms each have a private en-suite bathroom. Two rooms are fitted with whirlpool tubs; the other two have walk-in showers. One bedroom converts to twin beds on prior request. All four rooms open onto a large upper lounge with a second grand stone fireplace. It is a proper room with real presence: wide enough for armchairs, comfortable enough for the group to gather in the evenings without returning downstairs.
The basement has a historic wine cellar, stocked and available to guests.
The Barn: A Private Annex
Immediately adjacent to the main villa, the Barn is a separate 80-square-metre apartment with its own entrance, kitchen, bathroom with shower, and a sitting area with a sofa bed on the ground floor. A mezzanine level above has a double bed. A private outdoor porch with a table and chairs gives the Barn its own outdoor space. The configuration works well for guests who want proximity to the main group without sharing the same rooms, perfect for older children, or for guests arriving or departing at a different time.
Views Across the Chianti Hills
The outdoor areas match the villa’s scale. A covered terrace directly off the main villa is furnished for alfresco dining and looks across the surrounding Chianti hills. The infinity pool, with a dedicated whirlpool corner, is open from 1 May to 30 September. A traditional wood-fired oven for bread and pizza sits within the garden, alongside a barbecue grill. A gazebo provides shade for outdoor massage or fitness sessions. A small gym and an outdoor shower are also on the property. Table tennis is available, and cycling and hiking trails run through the surrounding hills.
The estate is fully fenced and accessed through two remote-controlled gates, a layout that works well for families with young children or with pets. Villa Conventino is a Chianti villa rental defined by genuine historic character: an ancient building, carefully maintained, with the outdoor space, the pool, the wine cellar, and the views to give a week in this part of Tuscany real depth.