Castello di Gargonza, Monte San Savino
Count Salviati began restoring the 14th-century Castello di Gargonza, his family's former ancestral home, in the 1970s. The hamlet, where Dante Alighieri was once a guest, is set on a hill between Siena and Arezzo, encircled by sturdy walls with an imposing tower poking up through the pine and cypress trees. Now run by the count's son, it offers houses and apartments that can be rented on a daily or weekly basis, a Tuscan restaurant just outside the walls, and a pool with sweeping views of the Val di Chiana.
Castello di Gargonza, Monte San Savino, Arezzo (00 39 0575 847 021; gargonza.it). Doubles start at €150, including breakfast.
Borgo di Pietrafitta, Castellina in Chianti
This borgo is set in the wine-producing region of Chianti just outside its unofficial capital of Castellina. The village was once a toll stop on the old road between Florence and Siena, but now the estate and adjoining hamlet are home to 12 country chic apartments and a further eight hotel-style rooms set in the main villa. There's also a pool and lots of open spaces to contemplate the views over the surrounding vine-draped landscape.
Borgo di Pietrafitta, Castellina in Chianti (00 39 0577 741390; borgopietrafitta.com). B&B doubles from €125. Apartments from €110 per night.
Il Borro, San Giustino
The Ferragamo name is synonymous with style – thanks to couture cobbler, Salvatore. But as well as shoes, the family has an enviable portfolio of boutique hotels. Set in the rolling Tuscan landscape between Florence and Arezzo is the charming Il Borro, run by Ferruccio Ferragamo. Celebrating its 20th year, the estate has suites, apartments and villas, a café and restaurant, spa and a winery whose vintages you can sip while admiring the gorgeous views.
Il Borro, San Giustino, Valdarno (00 39 0559 77053; ilborro.com). Doubles start at €290, including breakfast.
Castel Monastero, Monastero d'Ombrone
This 11th-century village and former monastery near Siena was given a no-expenses-spared makeover three years ago. It's now a hotel with 76 rooms and suites, two restaurants overseen by Gordon Ramsay, a diminutive church and pretty piazza for alfresco dining. Its spa regularly hosts wellness and health retreats and there are no fewer than three outdoor pools to choose from.
Castel Monastero, Monastero d'Ombrone (00 39 0577 570 570; castelmonastero.com). Doubles start at €415, including breakfast.
The estate sits on a wooded ridge not far from Siena. At its heart is an 800-year-old village whose houses are being restored to rent or buy. For now, guests can stay at Castelfalfi's newly opened 31-room boutique hotel, La Tabaccaia, housed in the estate's former cigar factory. The historic borgo has a traditional trattoria, two golf courses and, as of next month, a restored public pool. Further plans include villas, two more luxury hotels and a spa.
Castelfalfi, Montaione (00 39 0571 891 000; castelfalfi.co.uk). Doubles start at €108, including breakfast.
Monteverdi, Castiglioncella del Trinoro
One of the attractions of a stay here is the chance to mingle with permanent residents. Most visitors congregate around the diminutive square amid the sublime scenery of the Val d'Orcia. Monteverdi is a labour of love for its American owner, who in 2004 began restoring a portion of the village into three luxurious villas and a stylish seven-bedroom hotel, which opened last year. Monteverdi, Castiglioncello del Trinoro (00 39 0577 570 570; monteverdituscany.com). B&B doubles start at €325. Villas from €5,500 per week.