From forges to farmhouses and olive presses to palazzos, To Tuscany has over 715 handpicked properties on their books – and they’ve added new ones for 2019.

Twenty years ago, Sean Caulfield founded To Tuscany in order to connect holiday makers with villa owners in the region he’d made his home.

Today, his aim remains unchanged. He says: “Our quest is clear – to provide you with an excellent service and a wide choice of high-quality villas and apartments in stunning settings.”

To Tuscany’s website promises that they offer the best private rental villas in the region at the best possible prices; expert knowledge of the area and its attractions; an efficient and friendly service; and a secure online booking system.

They visit every one of the villas on offer, ensuring high standards and luxurious touches. They know how important their clients’ feedback is – and they value candid reviews.

An excellent perk is that all To Tuscany customers have access to a free concierge service, through which activities from truffle hunting and hot-air ballooning to wine tasting and cookery courses can easily be booked.

Here, we take a look at To Tuscany’s top five new villas for 2019.


Visit Siena from the comfort of the blissfully appointed Villa Bibbianello. With its five bedrooms, gorgeous gardens and divine swimming pool, this is Tuscan elegance at its finest.


Admire the glorious view from the glass summerhouse, soak up the rays in the pretty pool, tour the cities of Pisa or Lucca – or relax in the enchanting mezzanine library. This romantic property is all things to all men.


The views over Tuscany from this elegant country house are truly magnificent. Luckily, there are plenty of communal, outdoor areas – including beside the stunning infinity pool and the broad, stone veranda – from which to enjoy them.


Lose yourself in the peaceful surroundings of Podere Filazzi, where good things come in small sizes. Sleeping just four, this charming rustic house is all about exposed beams, tiled floors and simple, soothing comfort.


Supreme luxury is to be found here at Fienila San Carlo, with its lush green surroundings, two-tiered swimming pool and vaulted dining room. If you can tear yourself away from its clutches, the nearby town of Greve has lovely shops, restaurants and wineries on offer.

January 2019