Extraordinary villas with soul

View our villas

Unique villa experiences that unlock the secrets of the Mediterranean

Extraordinary villas with soul

We only work with the finest villas, all available exclusively at The Thinking Traveller

Bespoke matchmaker service

Our experts know each villa personally, so they can help you find your perfect place

Unrivalled local knowledge

We‘re locals with a passion for sharing the places we love and know like no one else

The Thinking Traveller blends a passion for extraordinary villas, unrivalled local knowledge, and thoughtful service. That’s why readers of Condé Nast Traveller have voted us Best Villa Rental Company in the World nine times.

Search all villas

Villas in Tuscany

View Tuscany villas

Villas in Puglia

View Puglian villas

Soulful Sicily

Villas in Sicily

Large family villas

family villas

With a gate to the sea

Villas on the sea

Search all villas

Our destinations

Greece

Sicily

Puglia

Corsica

Tuscany

Search all villa

We're Villa Matchmakers

Because our local experts have personally visited each of our destinations, we know exactly what makes them special. Tell us what your ultimate villa holiday looks like, and allow us take care of the rest

Schedule a call Enquire

Introducing Tuscany

Our new destination for 2025, where Renaissance towns and rolling hills meet an undiscovered coastline. Discover our exclusive villa collection in the idyllic Italian region.

Explore Tuscany

Experiences

A private boat to a secret beach, dinner prepared by a renowned chef, that festival on the hill - the knowledge of our local experts creates experiences that become memories.

Tasting notes

Nowhere in the world is winemaking so historically and culturally intrinsic to life as in the heart of the Mediterranean, and our Dionysian experiences are designed to help you explore and enjoy these oenological traditions to the full.

Gastronomic inspiration

Immersing yourself in the gastronomic life of the locals is a cultural experience that’s not to be missed in our destinations. From in-villa cooks and street food tours, to private cookery lessons - discover our gastronomic experiences here.

Take to the water

No holiday in our destinations would be complete without spending a day or two on the water, cruising in style on a private skippered charter, renting a boat for a couple of days, or enjoying a spot of windsurfing, kayaking or scuba diving.

Stay curious

Unravelling the history of the Mediterranean is easy with our expert guides, whose in-depth knowledge will bring to life the vast heritage of our destinations. Explore fascinating guided archaeological, city and walking tours here.

Thrilling adventures

Few adventures are as thrilling as island helicopter flights, guided treks high into rugged mountains, or bike ride along stunning stretches of coastline. Discover our top adventures in the Mediterranean.

Discover Experiences

Discover

Discover

Sicily

Sicily is the largest and the most diverse island in the Mediterranean. With its intriguing history, enviable climate, stunning beaches, active volcanoes, idyllic archipelagos, mouthwatering cuisine, and excellent wine, it has just about everything you could possibly wish for, and it’s no coincidence that so many of our clients return year after year, always finding something new to explore.