Italian Vilas

From a gently aging home where an actual princess is the cook, to a fairytale-looking cottage encircled with vines, renting a villa is the best way to go in Italy.

Masseria Cisterna Rossa, Puglia

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At the cap of Italy's heel, Masseria Cisterna Rossa is a former farmhouse on a working olive-oil grove. The owner is a gallerist based in Rome, and it shows – perfectly positioned sculptures, oversize artworks and impeccable Italian taste grace the interiors. The main house has four bedrooms, each with an ensuite, and there is an outhouse with a further bedroom for extra guests.
 

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Since it's in Italy, dining is of course the focus of any holiday here: the vast kitchen has every utensil you've ever heard of (as well as some you haven't), cupboard-loads of beautiful ceramics made in Ruffano, the next village along, and there's a cellar on-site stocking a catalogue's worth of primitivo from nearby Manduria. There's also an entire cooking station outside, where as well as a barbecue, you'll find a wood-fired forno. Enlist the multi-tasking services of resident gardener, caretaker and pizzaiolo Luciano and he will whip up a series of pizzas, having got the temperature of the oven up to 500º gradually throughout the day.

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If you don't fancy cooking, a chef can be booked to create a local menu for your party; or if you want to learn skills to take home with you, request a class with Anna Maria Chirone Arno, who delights in sharing the secrets of il gusto del tacco (the taste of the heel). The masseria might encourage hermit-like behaviour, but there is plenty to venture out for should you be able to pull yourself away.

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Lecce, an hour's drive north, is a beautiful Baroque town of golden churches, trinket-filled shops and simple restaurants offering spectacular local food (try Mamma Lupa on Via Acaja). Visit the end of the country at Santa Maria de Leuca and have a romantic waterfront meal on the cliff edge at 24RE (24releuca.it).

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Or rummage the antiques at the monthly Sunday stalls in the port town of Gallipoli, before stopping for lunch alongside local octogenarians in the know at a shack in the fish market, where fresh grilled prawns and sea urchins are served on tarpaulin-covered tables. 

Sleeps 10; from $7,888 per week.

Sleeps 10; from $7,888 per week.

Villa Elia, Puglia

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Home is the only place where you can truly be yourself, where you breathe peace, truth and beauty, where it sounds subside, perfumes soften and sensations intensify. Where nothing can hurt you. It is both refuge and certainty. Time flows through certain places like a river, leaving an indelible imprint on every rock and stone it encounters, fusing past and present together in an exquisite equilibrium.
 

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As you walk through the rooms, you are transported to another world that effortlessly blends a cosmopolitan Milanese sensibility with a tribal elan. There are flavors of Puglia, England, Turkey. Art and artefacts from dark, mysterious and fascinating Africa. The interiors offer up a kaleidoscope of emotions, always and everywhere. Shells, necklaces and boxes, books and collections, fragments of personal history displayed with pride and protected with modesty.
 

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Playful coloured masks, droplets of ruby glass, emerald glass, jute curtains. And so, eventually, we are free to look elsewhere, within our being, to the energy, the almost tangible genius loci, that protective spirit that transforms everything and allows you to view reality through renewed eyes. Like mirrors reflecting your own emotions. Finally, you are home.

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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.

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Sleeps 17; from $7,581 per week

Sleeps 17; from $7,581 per week

La Cerbaia, Tuscany

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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.)

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A farmhouse at the foot of the 'Montagnola Senese' on the Cetinale estate, La Cerbaia is set at the end of a private road between the 'Holy Woods' and the  gardens of the villa. With rooms on several levels, the house is furnished with fabrics in warm colours and pretty pictures throughout. A welcoming kitchen and dining area is also the setting for many a Tuscan meal prepared by the cook. Outside the house is surrounded by gardens and lawn, with several sitting areas, endless corners to sit and read, a vine- covered dining pergola and a further shaded area for sundowners. The pool area is furnished with smart rattan sun loungers.
 

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The space and diversity of its many living areas, both inside and out means that guests will be reluctanct to leave. This idyllic retreat is ideally situated for sightseeing, shopping, eating out or just relaxing in the beautiful Tuscan countryside.The property is only 1km from the nearest bus stop and  just 14 kms from Siena. Other interesting excursions can be made to places such as the little-known beautiful Romanesque cloister at Torri, the working monastery of Monte Oliveto or the ruined Cistercian abbey at San Galgano.

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Sleeps 13; from $5,000 per week.

Sleeps 13; from $5,000 per week.

Castello di Reschio, Umbria

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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.

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With unobstructed views of Umbria’s rolling hillside and access to chefs, drivers, stables, and tennis courts, Castello di Reschio is the epitome of secluded luxury. Count Antonio Bolza and his architecturally inclined family spent decades restoring this 2,700 acre estate to its former glory (the main castle and about 50 farmhouses date all the way back to 1202).

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Though the entire property is not yet complete, the rentable cottages, palazzos, and for-sale villas are meticulously furnished with modern pieces and artful details designed by Italy’s top artisans. As far as amenities go, no detail was spared: The infinity pool overlooks ancient mulberry tree groves and fragrant lavender fields, while each home’s bath quarters are stocked with fresh linens and Ortigia Sicilia apothecary items. The Reschio vineyard is famous for producing tantalizing rosés which, along with expertly-prepared, locally sourced meals, you can sample at the property’s private restaurant, Osteria.

Sleeps 10; $1,790 per night.

Sleeps 10; $1,790 per night.

Mandola Picola, Umbria

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This is a superbly designed luxury Umbrian villa in a very picturesque part of the world, close the the towns of Perugia and Todi and the famous Umbrian wine region of Montefalco. Framing the farmhouse are cherry groves, undulating barley fields and a lovely view over the ancient town of Piedicolle.

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The local village offers tennis and a clutch of useful and intriguing amenities from the pizzeria to the butchers shop. There's a great sense of authenticity in this part of Italy and the chance to explore an unadulterated version of the region, steeped in history and preserved in time. Perugia is one of Italy's most interesting cities - a thriving hub of the region offering many dining and exploring opportunities and many lovely shops.

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There are plenty of areas to see and explore, not least the opportunity to visit some of Southern Tuscany's loveliest areas around the Val d'Orcia, including Montepulciano and San Casciano dei Bagni.

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Sleeps 8; from $6,600 a week.

Sleeps 8; from $6,600 a week.