Rent Luxury Holiday Cottages in Montalcino

Tuscan Cottage

• 2 guests

• 1 bedrooms

Radda in Chianti, Tuscany

This beautifully restored and furnished Tuscan home is the true epitome of an Italian cottage done right. Right in the heart of the Chianti countryside, with the iconically distinctive cypress trees all around, this is the perfect haven for honeymooners looking for a romantic getaway or a solo tripper after a comfortable home close to Florence.

The Olive Dawn

• 4 guests

• 2 bedrooms

Gaiole in Chianti, Siena

Set in a hamlet among vine-covered hills, this home is one of eleven houses, with origins dating back to 1400. There’s a flower and plant-filled private garden and shaded terrace perfect for alfresco meals, while the beautiful large pool is shared – it’s located a short stroll from the home and has incredible views.

I Dream of Chianti

• 10 guests

• 5 bedrooms

Gaiole in Chianti, Siena

This former defence watchtower dating back to the 10th century has been beautifully reimagined into a corker of a family home. Within the palatial grounds, there's a ping-pong table, pool table, table-football set, and a children's playground to keep little ones busy and a private secluded pool and sauna for some adult relaxation time.