Luxury Long Stay Rentals in Siena

Chianti Sunrise

• 4 guests

• 2 bedrooms

Castelnuovo Berardenga, Siena

Nestled in a private estate overlooking the Chianti hills, this cottage sets the tone for a magical Italian stay. There’s a private terrace and outdoor seating for alfresco dining, while the rooms make it easy to switch off and unwind.

Mulberry & Olive

• 6 guests

• 3 bedrooms

Casanuova di Ama, Gaiole in Chianti

Full of charm, we love this home’s history. It’s hard to imagine its olive press past, save for the very obvious reminder in the living area.

Land of Beauty

• 12 guests

• 6 bedrooms

Castelnuovo Berardenga, Siena

Surrounded by olive and cypress trees, this home perfectly embodies the timeless charm of Tuscan living. Dating back to the 15th-century, it began its life as a monastery, transitioned into a farm and now exists as the ideal setting for an immersive Italian escape.