Il Monastero – Tuscany – Chianti

Main House: Accommodates 10+2 - 5 Bedrooms - 6 Baths - Pool - Wi-Fi - A/C
Guest Cottage: Accommodates 2+2 – 1 Bed – 1 Bath

Il Monastero is, as its name suggests, a wonderful old medieval monastery thoroughly restored for really elegant country living. At 570 square meters (6000 square feet), and with essentially equal bedrooms, Il Monastero is ideal for up to six couples traveling together; for an extended family; or for two or three small families. Furnishings throughout are refined and comfortable.

The exterior of Il Monastero, lovely vacation villa rental in Tuscany Chianti set in beautiful vineyards.You just can’t ask for a better location than this. Two kilometers from the Chianti village of Mercatale Val di Pesa, Il Monastero lies just 20 minutes south of Florence and a few minutes from the Florence-Siena highway, meaning that you have the choice either to meander the sinuous Chianti roadways at a slow pace or of quickly reaching a more distant daytrip destination like Pisa, Lucca, Arezzo, or Assisi. For places like San Gimignano, Castellina, Greve, Radda, and Certaldo, you’re just a few minutes’ drive, even if you choose the meandering alternative.

Views from the property are magnificent and varied: vineyards, olive trees, cypresses, woodland, open fields, and distant farmhouses dot the landscape. An oversize infinity pool with separate Jacuzzi pool completes the picture. Housekeeping is included daily, and cooking is available upon request.

    • Entry hall
    • Spacious and comfortable living room with sofabed
    • Study with sofabed
    • Dining room with table for 12
    • Main kitchen
    • Smaller kitchen
    • Down 5 steps: Bedroom with indivisible matrimonial bed and air-conditioning unit
    • En-suite shower room
    • Guest bathroom, also with shower
    • Second spacious and comfortable living room
    • Master bedroom with indivisible matrimonial bed
    • En-suite bathroom with Jacuzzi (no shower)
    • Bedroom with unifiable twin beds
    • En-suite bathroom with shower over Jacuzzi tub
    • Two bedrooms with indivisible matrimonial beds, each with:
    • En-suite shower room
    • Laundry room
    • Ironing room
    • Wine cellar


    • Open-plan living/dining/kitchenette with sofabed
    • Shower room

    Upstairs to loft overlooking lower level:

    • Matrimonial bedroom
    • Mercatale Val di Pesa – 2km (about 15-20 minutes’ easy walk)
    • Firenze – 30km
    • Monteriggioni – 40km
    • Siena – 60km
    • Roma – 295km
    • Gaiole in chianti – 45km
    • Radda in chianti – 35km
    • Castellina in chianti – 27km
    • Montalcino 95km
    • Arezzo – 85km

    We have tried our best to think up something we don’t like about Il Monastero. The downstairs bedroom could take an air-conditioning unit. The stairs connecting the two main floors are irregular and with rather high risers. You can see: We’re really struggling. Il Monastero is, in our opinion, almost perfect. Views are stunning, the location unbeatable. It isn’t cheap, though divided among two or three families or among several couples, it does make economic sense. You really do feel that you’re in Italy in this property. THIS is Italy.


    • 3 hours’ daily housekeeping
    • Bed and bath linens changed midweek
    • Fireplaces
    • Swimming pool – 7.5 x 15 meters – with Jacuzzi
    • Pool house with changing facilities, shower room, and fitness equipment
    • Wi-Fi
    • Satellite TV (Sky)
    • CD player
    • DVD player
    • Dishwasher
    • Microwave
    • Barbecue
    • Computer and printer
    • Clothes washer and dryer
    • Iron and ironing board
    • Wine cellar
    • Window screens
    • Additional housekeeping
    • Cooking
    • Personal laundry and ironing
    • Initial provisions
    • Transfers
    • Driver
    • Childcare
    • Bike rentals
    • 27 May - 9 Oct

    • 1 Apr - 27 May
      9 Sep - 14 Oct
      16 Dec - 6 Jan

    • Other Periods


    Minimum Stay: 1 week
    Arrival: Saturday, but flexible in low season
    Extras: Tourist tax; Electricity metered; final cleaning €250 villa/€120 guest cottage if used
    Pool open: 7 May - 1 Oct