Some have said that the walled city of Siena, located in the Chianti wine region of Tuscany, is frozen in time, citing its narrow streets, medieval architecture, and ward-centric culture as evidence. The city’s infamous rivalry and power struggle with neighboring Florence kept it from expanding and likely contributed to its untouched ambience.

Twice yearly, that ambience is brought to life by spectators and flag-wavers dressed in medieval garb who gather in celebration of the Palio di Siena (see Second Look, page 80)—a traditional horse race dating back to the Middle Ages that takes place in Siena’s most famous square, Piazza del Campo. During the rest of the year the shell-shaped square, rimmed with restaurants and shops, operates as the heart of the city, which also includes within its walls landmarks such as the Duomo di Siena and the Banca Monte dei Paschi, the oldest bank in the world.

Outside the walls of the city, however, undulating green hills, vineyards, and olive groves abound. It is in this setting that villa-rental company HomesAway offers La Senese, a 16th-century farmhouse restored into an idyllic Tuscan villa featuring a mix of modern and traditional decor. The Toronto-based company—which has more than 100 villas in its portfolio spanning France, Italy, Scotland, Spain, and Croatia—searches for homes that are beautiful and historic extensions of the regions they are in. "We choose authentic, quiet corners of the world to explore—places that combine a serene sense of ‘away’ with proximity to great villages and activities," says Dan Legault, who founded HomesAway in 1990. "Our guests enjoy living in a region as a local, rather than as a visitor, and doing things like going to the local markets for their food."

The narrow road that leads to La Senese, located just minutes from Siena’s city center, takes guests past
centuries-old stone homes and through dense foliage to an opening where the Tuscan countryside begins. From there, guests follow a winding dirt path that leads them to an estate adjacent to plowed fields and grape vineyards, and the local fowl that frequent them. Blue-budded rosemary shrubs line the villa’s entrance, providing a fresh aroma.

Sitting high atop a hill with stunning views of vineyards, never-ending valleys, and the towers of Siena, the two-story, 4,300-square-foot La Senese includes seven bedrooms and can accommodate up to 14 people. There is also a pool with a pergola and lounge chairs, an original brick pizza oven and barbecue area, an outdoor shower, Internet access, and a laundry room—but only one television (located in the cozy den on the second floor), as HomesAway knows the real entertainment is found in the surrounding area.

To maximize their time while in Italy, guests are set up with a travel advisor before they arrive to help them customize their trip and arrange transportation to the villa. The travel advisors then work with HomesAway’s local hosts to ensure all the details are put in place on site. "Our local hosts are at the heart of what makes HomesAway so different from other companies," says Legault. "They are so much more than a concierge: They are intelligent, resourceful peers of our guests with unequalled local insights and connections." The host is available to guests for the duration of their stay and can assist with such tasks as suggesting regional activities, accompanying guests on outings as a translator, and arranging a private chef to come to the home.

Weekly rental of La Senese is priced from $14,000, which includes daily housekeeping services. Also in Tuscany, HomesAway offers Campo dell’Amato (from $12,850 per week), a seven-bedroom villa within walking distance of the thermal baths at the Fonteverde Natural Spa Resort; Villa Porsenna (from $22,500 per week), a hilltop estate in the middle of a quaint medieval town overlooking the Val di Chiana that features an 11th-century tower and a swimming pool; and Il Castello (from $30,900 per week), a collection of four houses, each with interiors by British designer David Mlinaric, and other buildings that form a charming hamlet.

"Great bricks and mortar is just our starting point," says Legault. "There are a lot of spectacular homes in Tuscany, but many of them are in isolated locations. All of the homes in our portfolio are in locations that make the entire experience rich, both inside and outside of the property fence."