One of the glorious things about reading a magazine like House & Garden is the way you can imagine yourself living all kinds of different lives, depending on the house you happen to be looking at. It may well be the case that these lives are, alas, out of reach in reality – moving to an Italian castle might not be the most practical option just at the moment – but the possibility of trying them on for a while is extremely appealing. Fortunately, these days it is increasingly feasible to find impeccably stylish and architecturally striking houses to rent for holidays – the kinds of properties that would and do appear on our pages – and for special destinations in the loveliest corners of the Mediterranean, The Thinking Traveller is the name to know.
This company’s villas are deeply desirable places to stay, each handpicked by The Thinking Traveller’s experts for their unique stories, style credentials and great locations – and are available exclusively through them. Among its impressive portfolio of residences in Greece, Italy and Corsica is a house to suit every traveller and every occasion – from relaxed family get-togethers to memorable celebrations. The team regularly visits its properties and offers an invaluable matchmaking service, ensuring that its clients will end up staying in their perfect space. If your taste runs to contemporary elegance, The Thinking Traveller offers some exceptional modern houses, while those with a yearning for romance and history will find exquisitely restored period buildings in charming locations.
Some of our favourites include the exquisitely lovely Rocca delle Tre Contrade in Sicily, a once-ruined house on the east coast of the island, built by an aristocratic family in the 19th century and lovingly restored by its current owners after years of neglect. Having filled the magnificent vaulted rooms of the villa with a blend of elegant contemporary pieces and well-chosen antiques, the owners have now made it available for others to enjoy through The Thinking Traveller, though it remains very much a characterful home. Elsewhere in Italy you will find equally fascinating historic houses, such as the 18th-century Casina Cinquepozzi in Puglia, set among 40 acres of farmland, orchards and olive groves, or the former monastery Villa Talamo on the rugged Tuscan coast, where you can slip through a garden gate to head down to the sparkling waters of the Tyrrhenian Sea.
Across this body of water, Domaine Saint Jean in Corsica offers a more contemporary take on the villa holiday, its wood-clad exterior blending into the luxuriant greenery around it, while the terrace and infinity pool seem to dissolve into the sea, which stretches out to the horizon. Equally smart and refined is the expansive nine-bedroom Koralli villa looking out over the blue waters of the Aegean Sea at fashionable Porto Heli, with its manicured gardens, private jetty, and easy access to the low-key glamour of nearby islands Hydra and Spetses.
And The Thinking Traveller’s finely honed services do not end with merely finding you your dream villa for the perfect holiday – its team of experts on the ground in that region can curate your stay to the extent that makes sense for you. Perhaps you would like to gain an authentic insight into the local area, in which case they can arrange experiences such as vineyard tours, cooking classes, boat charters or helicopter rides. If there is a celebration in store during your trip, they can take care of the party planning with bands, opera singers and private chefs. Most of the villas can of course be full service if you wish, with cooks and housekeeping teams on hand, but those looking to simply relax and unwind in privacy will be equally happy. Such spectacular houses, it goes without saying, get booked up quickly, so now is the time to get in for 2026.
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