I founded To Tuscany in 1998 to connect clients and villa owners in the beautiful part of Italy that I call home.Our quest is clear – to provide you with excellent service and a wide choice of high-quality villas and apartments in stunning settings. We have properties for couples, families and groups of friends, each of which has been personally inspected to meet our exacting standards. And our Price Match Guarantee means that you will not find the same villa at a lower cost anywhere else. Our properties and our friendly and efficient service have won us awards and repeat custom.

We hope you'll become one of our guests, too.​


Pick your perfect villa
Imagine your dream villa in Tuscany. Is it a cosy stone farmhouse surrounded by vineyards? An elegant manor house close to the art galleries of Florence? A dramatic clifftop tower overlooking the deep blue Mediterranean? Take a look at our website and you will find these and more among our wide range of beautiful Tuscan villas and apartments.

You will also discover that almost all our properties come with a pool – just the place to cool off in the heat of the Tuscan summer sun. Choose a spacious apartment with access to a shared pool for a great way for young ones to make new holiday friends. Or for the ultimate indulgence, opt for a secluded villa with a private pool that you, your friends and family can enjoy all to yourselves.

Other touches of luxury at our villas in Tuscany include private gardens, furnished balconies and terraces, often with sublime views; massage rooms, saunas and outdoor hot tubs; tennis courts and games rooms; barbecues and pizza ovens. There are plenty of home comforts, too, including Wi-Fi and satellite TV, board games and books – you can even bring the dog to many of our villas and apartments. Plus, you can be sure of a complete rest if you sign up for our chef, nanny, laundry and maid services, all of which have been personally selected by us.

At To Tuscany, we hand-pick every villa and apartment, putting each one through a rigorous inspection to ensure they meet our high standards. All our properties are spotlessly clean and comfortably furnished, with well-equipped kitchens, and supplied with all the quality bed linen and towels you will need. Whichever property you choose for your villa holiday in Tuscany, it will surpass your expectations and you will be able to relax the moment you open the front door.

Where will you stay?
Our villas and apartments are set in the most beautiful areas of Tuscany, including Arezzo, Florence, Chianti, Grosseto, Livorno, Lucca, Pisa, Pistoia and Siena. And don’t forget, we also have some stunning villas in Umbria, close to Orvieto and Perugia.

Each town, village and hamlet has its own unique character and attractions. If you’re unfamiliar with the area and would like some guidance about the right place for the holiday you’ve been dreaming of, call Dympna Docherty on +44 121 286 7782, and she’ll be happy to help.

Now book your villa holiday in Tuscany
Once you’ve chosen your villa in Tuscany, check the ‘real-time’ availability and make a reservation online. You can be confident that you won’t find your choice cheaper anywhere else thanks to our Price Match Guarantee, and our quick and secure online booking service will ensure your peace of mind.

Why book with To Tuscany?
To Tuscany was founded in 1998 by Sean Caulfield to provide hand-picked family villa rentals for holidays and vacations in the beautiful Chianti region and surrounding areas of Tuscany. Two decades on, we have extended our offering to appeal to couples and groups of friends as well as families, with an expanding collection of more than 700 of the best villa rentals in Tuscany, for 2 to 27 guests. We are renowned for our friendly and efficient service. Our expert team has personal knowledge of the region and our properties, and our website offers in-depth pages for every villa, including floor plans, multiple images, and detailed information about the property’s facilities and local amenities and attractions.

What are you waiting for? Book your villa holiday today with To Tuscany. Click here to search for your perfect villa.

To Tuscany has personally chosen a wide range of Holiday villa rentals in Tuscany and Umbria. To give you maximum choice we have included self catering villas, apartments, cottages, farmhouses and castles in our list of great offerings. You can check the availability of our villas in Tuscany in 'real time' and make a reservation online with confidence, using our secure booking process.

You won’t find better Tuscany villas at a lower price with anyone as passionate as we are about the region so just click here for our price promise. Everyone on our staff has personal knowledge and local experience to help you choose your perfect Tuscany villa rental.

To Tuscany was founded in 1998 by a group who specialised in family holidays in the beautiful Chianti region and surrounding locations in Tuscany. Villas with shared pools formed the core of their portfolio, handpicked to provide the ideal family accommodation.

More than 10 years later we offer a collection of our favourite villa rentals in Tuscany with shared pools and private pools, each of which have private gardens or terraces and which are found in ancient hamlets. Our Tuscan villa rental properties include wine estates, farm houses, cottages and hay barns: all of which have been restored to the highest standards.

Our Tuscany villas can be found all over the region and into Umbria. The Chianti villa rentals remain the most popular of our properties. If you are interested, contact us today!  There are always new villa rentals in Tuscany to explore.