The peace of a private property, the five-star allure of a top hotel, a memorable live-like-a-local experience – it’s difficult to beat a villa holiday. And the appeal only grows when The Thinking Traveller, which is celebrating its 20th anniversary this year, is involved. As the name-to-know in Mediterranean villa rental, the company charts some of the chicest, most intriguing rental properties in the world, all of which are available exclusively through its books. This carefully curated collection of properties is enhanced by a seemingly unrivalled inside track on their locations and on-the-ground team, who are part problem-solvers, part talking guidebooks, part anything-is-possible concierges. It’s little wonder it has come out on top as favourite Villa Rental Company in Condé Nast Traveller’s Readers’ Choice Awards for six years running. So here, we’ve partnered with The Thinking Traveller to round up its most blockbuster villas to rent, for every kind of trip.
BEST FOR DESIGN FIENDS
Enyalos, Tinos
The soul-stirring location on a dramatic headland between the beaches of Agios Petros and Kalivia is striking, but the design of this contemporary Cycladic villa will linger just as vividly in memories of a stay here. Everything revolves around the glistening Aegean, with an emerald-toned infinity pool that stretches out towards waves framed by languid shaded terraces. Inside the villa, a muted colour palette creates a serene atmosphere, with skylights and subtly integrated lighting illuminating a scene that blends matt-black cabinetry, dark hardwood flooring and minimalist touches that nod gently to the surrounding landscape. Accommodation is split between the main house and a guesthouse slightly higher on the hill, where a discreet façade of local stone conceals a temple of modern chic, from polished grey floors to alternating raw concrete and whitewashed, wood-beamed ceilings. Enyalos sleeps 10.
BEST FOR FOODIES
Rocca delle Tre Contrade, Sicily
A painstakingly restored 19th-century aristocratic estate, Rocca delle Tre Contrade is a place in which interior elegance and a focus on food unite to heavenly effect. Soaring handsomely atop its very own hill on Sicily’s east coast, this striking property offers hypnotic vistas of the Ionian Sea and Mount Etna, which can be taken in from the beautiful bedrooms, generously proportioned communal spaces and grounds – with panoramic terraces, an infinity pool and a tennis court. Organic citrus orchards and vegetable gardens mean the kitchen is always well stocked, while the equally abundant wine cellar allows guests to try Sicily’s finest vintages. A dedicated in-house chef conjures up unforgettable feasts every day, so it’s no wonder guests tend to abandon their plans for excursions and cancel restaurant bookings made for the week. Rocca delle Tre Contrade sleeps 24.
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BEST FOR KEEPING ACTIVE
I Bruzzi, Corsica
You might miss I Bruzzi, camouflaged as it is by gardens of fragrant, low-lying maquis. But while its façade of naturally silvered wooden cladding might whisper discretion and modesty, the interior of this villa is a scene of bold, inspiring contemporary design. Clean lines, free-flowing spaces and an atmosphere of informal sophistication make this the perfect property for those looking for a carefree holiday. And staying fit is equally effortless here, with sandy beaches a stroll away and the scenic coastal hiking trails of Bruzzi on the doorstep. Returning to your magnificent sea-view pool terrace and private internal courtyard makes all the exertion worth it. I Bruzzi sleeps 10.
BEST FOR GROWN-UP GATHERINGS
Santhia, Paros
Ravishing and refined, every inch of this beachfront villa on the island of Paros seems set up for a grown-up escape, whether it’s enjoying precious child-free time or a big intergenerational get-together. The pure white exterior sets the tone for the Mediterranean fantasy that can be lived out here, with generous outdoor space that’s occupied by a sprawling sweep of terrace, cleverly divided into shady and sun-kissed spots. Beyond the crystal-clear infinity pool, a path weaves through gardens full of aromatic shrubs and flowers and down to a private sea gate, just a few steps from the beach below (the idyllic sandy bay of Chrisi Akti). Within the whitewashed walls of the villa, simplicity reigns, with a palette of pale wood and white furnishings that comfortably accommodate large groups – if you spend any time inside, that is. Santhia sleeps 12.
BEST FOR A BIG CELEBRATION
Don Arcangelo all’Olmo, Sicily
Staying at this huge, fully staffed country house, set between dramatic hilltop Taormina and the faded baroque splendour of Catania on Sicily’s east coast, is a lot like having your own private five-star hotel – one owned by proper Italian aristocracy, the Marquess Paternò Castello di San Giuliano, that is. Overlooking the startlingly blue Ionian Sea in the shadow of Mount Etna, the estate is a study in effortless good taste, with relaxed yet refined interiors that mix heirloom antiques and finds from the owner’s travels. The two-acre gardens, meanwhile, are the dream setting for a party – whether a wedding, birthday or anniversary – filled with jasmine and banana, carob and fig trees, and bougainvillaea blooming in every colour. Don Arcangelo all’Olmo sleeps 24.
BEST FOR WATER BABIES
Thani, Syros
This sprawling 60-acre estate runs for 1.2 miles along the west coast of Syros, and makes every use of its privileged seaside location. In addition to its splendid 20-metre heatable infinity pool, there are paths that lead down through the grounds to the property’s two beaches, both of which are lapped by translucent waters and equipped with water-sports gear. One also has a private jetty, so anyone renting a boat for the week can enjoy the great luxury of docking it nearby. Between the pair of bays is a private headland, the perfect spot for an aperitif (prepared by the property’s private chef) while watching the burnished sun set into the sea. Back on dry land, panoramic sea views and honeyed Cycladic stone root the villa beautifully in its context and create an airy, relaxing atmosphere. Thani sleeps 16.
BEST FOR OUTDOOR LIVING
Madreterra, Lefkada
In the insanely azure Ionian Sea, under-the-radar Lefkada draws Greek Island insiders for its unspoilt beaches, timeless villages and wild interiors. On its north-west coast, this newly built villa combines traditional touches with ultra-contemporary design. But the real show-stopper here is the outside space. Surrounded by pine forests, the house’s wraparound terraces are dotted with shady spots, hammocks and hanging rattan chairs, as well as a huge dining area and full outdoor kitchen. The pool has a clever beach-effect shallow end, making it perfect for little ones, and peaceful Avali beach is just a short walk below. Madreterra sleeps 12.
BEST FOR MULTI-GENERATIONAL FAMILIES
Trulli Andrea, Puglia
With their distinctive limestone conical roofs, restored trulli are by far the most charming and deeply traditional Puglian stays.. Here in Italy’s far south, Trulli Andrea consists of not one but two immaculately reimagined sets of these cute-hatted houses, each with soothing, modern whitewashed interiors. Outside, two pools make this spot ideal for big broods (dedicate one for shrieking and splashing and the other for lazy laps) and there’s a wood-burning pizza oven for alfresco suppers to please all ages – draft in the on-call pizza chef to stop little fingers from meddling in your toppings. Trulli Andrea sleeps 12.
BEST FOR NATURE LOVERS
Mirkella, Hydra
To stay at Mirkella is to follow in the footsteps of kings, prime ministers and no end of other illustrious guests. It’s not hard to see the appeal of this place, perched high on a rocky promontory 130ft above the irresistible glow of the Aegean and cocooned in a fragrant wood of pine trees. Otherworldly seclusion and complete privacy are par for the course, and with views so captivating and a welcome so comfortable on offer, guests rarely step outside the confines of their new home from home. That said, nature lovers will almost certainly be tempted by the mule tracks that lead out from the property into the evocative, virtually uninhabited hinterland of this enchanting car-free island. Or to the path that winds down to glorious Molos beach, where a jetty provides an easy point of departure for explorations of Hydra’s coastline and trips to the main town. Mirkella sleeps 12.
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Book your stay for 2023 here