This gorgeously restored stone villa is perfect for big families or those who want to get away from the crowds. Thanks to its previous life as a 13th-century watchtower and barn, the home is blessed with an enviable hilltop position and undisturbed views across the one-time feudal towns of the Siena province (the region was later dominated by nearby power Florence), all the way to the towers of San Gimignano.
Today, the structure has been lovingly restored by Jane and Steven Collins, the couple behind similarly romantic Temple Guiting Manor in the Cotswolds, and is run by Tuscan locals Enzo and Annagloria Corti, who fill the home with their locally grown and made wines and olive oils, toiletries from fragrance house Angeli di Firenze, as well as impeccably chic furnishings sourced from Milan’s Salone del Mobile. The location is at once secluded (there’s not another dwelling for the best part of two kilometers around), but also a brilliant base point for day trips to Florence (one-hour drive) and Pisa (90-minute drive), as well as neighboring vineyards and wineries that speckle the valleys (the nearest of which, the charmingly rustic I Balzini, provided wine for Succession). Each morning, a chef will whip up a feast for breakfast—fresh pastries, Italian coffee, with platters of fruit and eggs cooked to order—and is also available for private dining as well as cooking courses for local dishes. Rooms are seriously spacious, all en suite, and within its original stone structure with farmhouse features (pretty wooden shutters), as well as one studio next to the pool. Outside, there is a BBQ and stone pizza oven on the terrace, numerous dining areas depending on the best spot for the sun, as well as smaller seating nooks, all designed for enjoying Tuscany’s sun-drenched days. —Charlotte Davey
Sleeps: 16 (across seven en suite bedrooms in the main house, plus one self-contained pool studio)
Price: From $31,519 for seven nights