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La Dolce Vita: Tuscan Villas for Vacation Rental

Indagare’s travel staff does more than scout out the best hotels—it also has access to some of the most exclusive vacation rental homes worldwide. Here are some the best Tuscan villas for those wishing to immerse themselves in local culture.

Villa Laura, Cortona

Channel your inner movie star at this 17th-century estate (complete with a stone oven for an evening of pizza making), which was the stand-in for Bramasole, the villa that Diane Lane’s character buys, in the 2003 film Under the Tuscan Sun. The three-building complex, located outside the walls of Cortona, can be rented in its entirety or in parts.

  • Bedrooms: Ten (sleeps twenty-seven in all
  • Amenities: Chef, butler, chauffeur
  • Highlights: Vespa rides, hot-air ballooning, cooking lessons, shopping trips to Florence, culture weeks organized around such activities as painting or (in the fall) truffle hunting and olive picking
  • Nearby: Cortona proper (Etruscan ruins), Arezzo (antiques market), Montepulciano (wine)

Castiglion del Bosco, Montalcino

The Indagare-Adored property includes ten former farmhouses. lovingly transformed into plush villas that are ideal for families or friends who want pampering amenities or are celebrating a special occasion.

  • Bedrooms: From two to five bedrooms per villa (sleeping four to twelve people)
  • Amenities: Chef, car, delivery service, babysitting; at some, home cinema, tennis court, pool house
  • Highlights: Barrel tasting of two as-yet-unreleased wines, truffle hunting, picnic lunch, golf, painting class, gelato-making class, archery
  • Nearby: Siena, the Val d’Orcia Natural, Artistic and Cultural Park

Villa Il Palagio, Chianti

For the musically inclined, Sting’s 16th-century Tuscan estate is one of the most desirable accommodations in the region. The sprawling 350-hectare property features perfectly manicured gardens, a farmhouse selling products grown on the property and, of course, a recording studio.

  • Bedrooms: Nine in the main building (sleeps up to fifty)
  • Amenities: Chef, tennis court, organic vineyard, gym
  • Highlights: Grape harvesting, a life-size chessboard, tree house, yoga classes
  • Nearby: The small town of Figline Valdarno

Castello di Reschio, Umbria

Castelli di Reschio’s six villas are perfect for those seeking a hideaway, both secluded and idyllic. The former farmhouses were painstakingly restored over the course of twenty years, given a contemporary decor that blended with their traditional Umbrian style.

  • Bedrooms: From three to seven bedrooms each (sleeping six to fourteen people)
  • Amenities: Chef, chauffeur, riding school, tennis court
  • Highlights: Clay-pigeon shooting, wild-boar hunts, fishing, painting classes, art-history excursions
  • Nearby: Assisi, Arrezzo, Cortona, Gubbio, Perugia and Siena

More Inspiration

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