This Tuscan stone hideaway can sleep up to 12 in cozy interiors complete with beamed ceilings, antique furniture, and oil paintings. The property is divided into three wings: the main villa has a dining patio and swimming pool; the Ginestra wing comes with its own entrance and kitchenette; and the Vigna guesthouse faces the property’s vineyard. But it’s the setting that makes this villa stand out. La Sassaia enjoys an ideal location just eight miles from Siena and the start of Chianti wine country, half an hour from the hill town of San Gimignano, and an hour from the museums of Florence. Plus, the villa owner and a concierge are on hand for meal preparation and to offer area expertise.