1. Casa Giardino, Spello, Umbria
The ancient hill town of Spello is very much off the tourist trail, but bustles with locals even in the darkest days of winter. Tucked away down a cobbled street is Casa Giardino, a 14th-century villa owned by decorator Andrea Falkner. Her collection of furniture, art and textiles from her travels combined with strong colour schemes make this one of the most original town houses in Italy. Cobalt-blue double showers contrast with exposed-brick walls and wooden beams. Despite being on the edge of town, the garden overflows with wild roses, jasmine and lavender and has uninterrupted views over the Chiona Valley. The terrace is a heavenly place to sit with an aperitivo as swallows dip and dive into the stone swimming pool and the rose-pink sun sets behind the Umbrian hills. While the residence can sleep six, next door are the equally original La Giraffa cottage and Villa la Volta, which allow for a party of up to 16 guests, making it the perfect base for exploring Tuscany and Umbria with friends and family. Weekly rental from $3900.
2. Masseria Monopoli, Puglia
After a meticulous restoration, Masseria Monopoli is one of the most luxurious villas in southern Italy. Built to protect the original owners from marauding pirates, the thick stone walls now provide a cool retreat from the baking Puglian sun. Celebrated decorator Alexander Waterworth has created soothing, contemporary spaces, which include eight spacious ensuite bedrooms, using local materials and taking inspiration from the spectacular surrounding countryside. Privacy is guaranteed - the farmhouse is surrounded by more than 30 hectares of land. Amid the olive groves (the oil they produce is superb), children will revel in collecting fresh eggs for breakfast, while the adults can pluck limes and mint for homegrown cocktails mixed by butler Alessandro. Lounge by the vast lake-style swimming pool or the smaller pool on the rooftop. In the evenings, housekeeper Stefania creates Pugliese feasts using zucchini and eggplant from the kitchen garden with homemade orecchiette. After dinner, classic Italian films are projected onto the wall of the pool house, with crickets providing an additional soundtrack. And if you need some personal space, escape for a sleepover in the vintage Airstream caravan parked in a field of wildflowers and ancient olive groves. Weekly rental from $16,900.
3. Appartamento Trastevere, Rome
In the heart of picturesque Trastevere, this bijou apartment is owned by one of Rome's best-known artists, Sandro Chia. Suitably bohemian in style for an area of Rome that has long been associated with the most creative characters in the city, the apartment is spread over two floors, making it the ideal base for a family or two couples to explore the Eternal City. It's easy to imagine Gregory Peck and Audrey Hepburn sharing cappuccini on the little terrace surrounded by pots of orange trees, terracotta-tiled roofs and washing lines. The cleverly designed rooms are light and airy and filled with contemporary furniture and artworks. Mingle with the great and good of Rome, with invitations to gallery openings and exclusive special events, courtesy of the owners. Weekly rental from $2580.
4. La Scelta di Goethe, Rome
On the top two floors of a palazzo and hidden behind an unassuming door on the central Via del Corso, this Roman residence is the real deal when it comes to five-star service and luxury in a private home. Once the Roman pied-à-terre of the great German writer Goethe, it now consists of two chic suites, the Trinità dei Monti and the Villa Medici. The Trinità dei Monti is lined with art books and a working marble fireplace, and leads onto terraces with wraparound views of the city, taking in the Spanish Steps and the Villa Medici palace. After enjoying the outdoor hot tub, tucked behind a trellis of jasmine and rosemary, breakfast on pastries from the oldest deli in Rome. Both bathrooms are stocked with every possible product from the Santa Maria Novella bodycare range, and the super-king beds ensure the sweetest of sleeps, cocooned from the noise of the city streets below by silk curtains woven in Florence. Weekly rental Villa Medici $16,500, Trinità dei Monti $22,680.
5. Villa la Quieta, Lake Como
Standing on the western shore of Lake Como in Tremezzina, this Baroque villa looks across the lake to the town of Bellagio. Surrounded by mountains, it's one of the most exclusive villas on the lake and certainly one of the most prestigious places to stay. Arrive on a wooden Riva boat at the private lake entrance before walking through ornate wrought-iron gates into the parterre gardens. Built at the beginning of the 16th-century, it is owned to this day by the aristocratic Serbelloni family and remains their private home. In the 18th century, the dukes of Serbelloni commissioned renowned craftsmen and painters to work on the interior and this is reflected in the superb frescoes, antiques and artworks. The villa was recently given an extensive makeover, and the six suites provide every possible comfort, with the ambience of a truly historical residence. Weekly rental from $38,900.
6. Torre Sponda, Positano
If you shook together all the fun, colour and brilliance of Naples into one home, out would pop Torre Sponda - a pocket-sized medieval watchtower, clinging like an eagle's nest to the cliffs just outside Positano. For once it's not just about the views, which admittedly are jaw-dropping, but the crazily brilliant way the owner has created something unique. With its circular bedroom and wrought-iron four-poster bed, the Torre room is undeniably romantic and the vast roof terrace, reached via a stone walkway, is a perfect spot for having a limoncello as the sun goes down over Capri. Part of a larger private estate, it has terraced gardens and orchards that lead to a secluded sandy bay with gin-clear water, a world away from the cramped beaches of Positano. Weekly rental from $2580.
7. Podere Palazzo, Tuscany
Straight out of Bertolucci's Stealing Beauty, Podere Palazzo sits on a hill overlooking mile upon mile of Tuscan countryside. Fields of waving corn are juxtaposed with ancient oak woods unchanged since the Renaissance. The villa is a classic Tuscan farmhouse, but the open-plan interior is contemporary and fresh, with clean lines and strong colours. Traditional terracotta floors, open fireplaces and wooden beams made from local chestnut trees serve as a strong contrast to Philippe Starck fittings and a minimalist designer kitchen. Despite its isolation, the hamlet of Trevinano is a few minutes away by car and home to the Michelin-starred La Parolina restaurant as well as a low-key trattoria offering wood-fired mozzarella and tomato pizze. Weekly rental from $5900.
8. Villa Aci Castello, Sicily
This villa recalls the imagery of Giuseppe Tomasi di Lampedusa's masterpiece, The Leopard. Overlooking the coast of Catania, Villa Aci Castello is the ideal base to explore the complex and fascinating eastern coastline of Sicily. The residence sits regally amid palm trees and lush gardens, with the Mediterranean twinkling in the distance. Interiors are old-fashioned and filled with treasures. The walls are lined with a collection of art, and family photos in silver frames adorn the grand piano and coffee tables. For entertainment, there is a billiard room, tennis court and swimming pool and if more beds are required, there are two cottages on the grounds that bring the total number of guests to 32. Prices available on request (see below).
9. Masseria Prosperi, Puglia
Masseria Prosperi is part of a working farm, tucked away off a dirt track just outside Otranto in southern Puglia. The owners, a hip young local couple, have dedicated themselves to a brilliant restoration, which makes a refreshing change from the sickly sweet trullos further north. The farmhouse sleeps 12 and is perfect for young families, with the resident flock of chickens and goats as company. Donkeys and horses graze among olive groves and owner Antonio prepares feasts using produce from the kitchen garden. The bedrooms are original and clever. Carnival lights, typical of the region, feature in one room, while another has a full glass wall overlooking the surrounding countryside. Puglia remains sunny well into October and the large outdoor pool, plus another indoors and nearby beaches, make the farmhouse ideal for a lazy late-summer holiday. Weekly rental from $13,000.
10. Palazzo Arsenale, Venice
Palazzo Arsenale is the latest creation by decorator Ilaria Miani, whose villas in Tuscany are some of the most sought-after rental properties in Italy. In a district rarely frequented by tourists at the very far end of the island, it's just the place to immerse yourself in Venetian life. The house sleeps up to 16 and was made for parties and fun. Enjoy dancing in the boathouse with its private water entrance, followed by cicchetti on the roof terrace and a Spritz at the bar with its exposed brick walls and crittall windows. Weekly rental from $15,000.