The Best Villas to Rent in Italy
Courtesy The Thinking TravelerMasseria Cisterna Rossa, Puglia
In the heart of Puglia’s Salento region (the very tip of the boot), the Masseria Cisterna Rossa is surrounded by olive groves, fruit trees, and a thriving orto—still, the region’s best coastline (Adriatic in one direction, Ionian the other) and landmarks (the Baroque city Lecce) are all within a ten- to 40-minute drive. The grounds have an exquisite pool and a gardener who moonlights as an accomplished pizzaiolo, working the wood-fired oven as guests choose toppings—like fig, ricotta, thyme, and honey—from a thoughtfully stocked larder and the home’s own garden. —David Prior
Sleeps 10; from $7,888 per week. For rental information, click here.
Courtesy The Thinking TravelerVilla Elia, Puglia
This refurbished masseria feels like the country home of an eccentric and well-traveled bohemian friend, with vaulted ceilings, a mix of antiques, woven rugs, and rustic rattan furniture—even a private cinema (Jude Law spent a vacation here). Surrounded by acres of fruit and olive trees, Villa Elia is just a short drive from the historic beaches of Gallipoli.
Sleeps 17; from $7,581 per week. For rental information, click here.
Photo by Gian Luigi ScarfiottiLa Cerbaia, Tuscany
This farmhouse is on the edge of the (also rentable) grand Cetinale estate, in the same wild woods less than ten miles outside of Siena. Though it’s literally the estate’s former pigsty, today, it is anything but. With its own swimming pool, gardens, and shared tennis court, plus a dining room that seats 16 and a living room with fireplace, pizza oven, and ping-pong table, it’s the perfect spot for a multi-generational vacation (the estate’s grounds are open for exploration if no one has rented the Cetinale’s great house.)
Sleeps 13; from $5,000 per week. Rent directly from Villa Cetinale.
Courtesy Castello di ReschioSpinaltermine at Castello di Reschio, Umbria
Renting a spread like this is as close as you might get to living like Italian nobility in the countryside. Reschio is a huge, rambling estate dotted with olive groves, cypress trees and vineyards, whose main castle dates to the 11th century. It’s owned by the Bolza family, who live in the castello and have spent years restoring several of the stone farmhouses on the grounds in a rustic-modern style of exposed timber beams, a mix of antiques and custom pieces, and yards of creamy linens. Spinaltermine comes with its own heated infinity pool surrounded by olive trees and rosemary beds, and is just down the road from Reschio’s private osteria and horse-riding stables, from where you can ride into the Umbrian hills spotting wild boar, deer, and pheasant in the ancient oak forests.
Sleeps 10; $1,790 per night. Rent via One Fine Stay.
Courtesy La BadiaLa Badia, Tuscany
You can totally imagine cooking an epic meal of tagliatelle con ragu and bistecca à la Fiorentina with a food-obsessed group of friends in La Badia’s classic Tuscan kitchen, with its epically long oak table, white marble sinks, and pergola-shaded outdoor dining area. (Or you can dial up the cook who works the kitchen when the owner, an interior designer living in Milan, is in residence.) The owner has decorated the place colorfully and eclectically with art, rugs, and textiles that reflect the eye of a globetrotter, though the effect is completely Italian. The villa is isolated in the woods of central Tuscany, a 25 minutes’ walk to the village of Sambuca, and up the road from a farm that is fun for kids to visit—it’s also not far from the medieval towns of Chianti and San Gimignano.
Sleeps 12; from $11,300 a week. Book via Red Savannah.
Photo by Eric van den BrulleMandola Picola, Umbria
This villa’s backstory is the Plan B we dream of: An American woman fell in love with the Umbrian countryside, married an Italian, and together, they transformed a large farm estate near Perugia, out of which they now produce three labels of wine and their own bottling of olive oil. You’ll find these hyper-local products and more in the semi-professional kitchen of Mandola Picola, a restored farmhouse whose gorgeously minimalist interiors are done with hand-plastered walls, resin floors, oak beams, and décor in various shades of grey-beige. The stone swimming pool, surrounded by cherry groves, lavender, and fig trees, is a stunner (it’s also got a long shallow end, perfect for kids). The aforementioned couple live a few minutes away and can arrange visits to their winery.
Sleeps 8; from $6,600 a week. Book via Red Savannah.
Photo by Alexandra MorrisLe Due Case, Umbria
This historic home, full of cheerful fabrics and country-style antiques, feels like a rustic Italian fantasia, built around a tower that’s more than 1,000 years old. There’s a lawn for games and a garden of hydrangea and jasmine, while the sizable pool has incredible views over nearby Orvieto, with its famous duomo comprising Luca Signorelli frescoes.
Sleeps 9; from $12,800 per week. Book via Homebase Abroad.
Courtesy Villa CarlaVilla Carla, Positano
The two-story family home of the owners of a luxury hotel in Positano, Villa Carla is all about the Mediterranean views overlooking Punta Reginella, one of the most charming parts of Positano’s coastline. The interiors were recently restored by local artisans using traditional techniques, including a mosaic artist’s handiwork in the vaulted living room; the light-filled spaces are lined with artwork from generations of the family’s travels through Asia. Although you’re just five minutes from Positano's Spiaggia beach, you may not be able to pull yourself out of a chaise on the shaded and wide private terrace, made even more Edenic with a potted bower of lemon trees, ferns, and other greenery.
Sleeps 6; from $10,000 per week. Book via Papavero Villa Rentals.
Photo by Manuel ZublenaVilla di San Giuliano (“Villa Fiona”), Sicily
You can enter the villa by the grand gates, or via the 700-year-old estate’s ramshackle farmhouses. I prefer the latter route, which leads to the villa’s Sicilian kitchen. Here, over the course of a week, I watched our hostess and cook, Princess Emanuela Notarbartolo Di Sciara, command a staff in aprons and black dresses that let slip the odd tattoo, who delivered almond sponge cakes at teatime on monogrammed plates. My sister, a garden designer, lived out her dreams in the forest of agapanthus and orange groves. My husband visited Catania’s fish market, buying all the polpo he could stew. My brother-in-law read for days, while all the cousins larked around in the pool. The balls may bounce wonkily on the tennis court, but then there’s the silver, vintage books, 16th-century art, and marble bathtubs fit for everyone from a marquess to Kate Moss. —Sophy Roberts
Sleeps 20; price available upon on request. Book via Unique Properties and Events.
Courtesy Villa Erba ParkPool House at Villa Erba Park, Lake Como
The charm of this rental has as much to do with its history and proximity to one of Lombardy’s grandest estates as it does with its Hansel-and-Gretel-like exterior, where a wisteria tree appears to have swallowed the cottage whole. It’s one of several small houses for rent on the grounds of the park surrounding the Villas Erba and Gastel, once the home of film director Luchino Visconti, who hosted hosted the likes of Maria Callas and Coco Chanel here. The Viscontis are one of Italy’s most prominent families, who have lived at this former Benedictine convent on the western edge of Lake Como, near Cernobbio, for generations. The neoclassical Villa Gastel, which retains its aristocratic grandeur under the stewardship of Visconti descendant Anna Gastel, is also rentable for events or extended stays. But you can still access the surrounding 25 acres of park or lakefront from the pool house, whose interiors exude the lived-in warmth of a rustic hunting cabin, with huge wooden beams and country-style kitchen. And, true to its name, it has its own pool.
Sleeps 5; $275 a night. Book on Airbnb.