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Villa Categories

  • Family Villas

    Our family villas are known to be very popular with clients who are looking for some time with their families. Each villa has been selected for it’s family friendly furnishings & safety features.

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  • Chianti Villas

    A selection of the best villas in the Chianti Classico region of Tuscany, this collection shows a list of privately owned accommodation available to rent including villas, apartments & farmhouses within the Chianti.

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  • Villas with Private Pools

    Explore our collection of villas with their own private pool, immersed in Tuscany’s famous landscapes and specially selected by our local experts.

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  • Pure luxury villas

    Experience the ultimate in comfort and indulgence with our exquisite collection of luxury villas.

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  • Romantic Retreats for Two

    Escape into a private idyllic sanctuary. These villas are specially designed for two people who want nothing more than to spend quality time together as a couple.

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  • Most popular villas

    Our most popular villas are ‘hot property’, because they get snapped up very quickly. These are the top 100 most requested To Tuscany villas with the highest amount of bookings, so it’s no wonder that they sell out fast.

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What makes us special

Over 20 years ago, our founder Sean and his wife Sabina moved to Tuscany where they created their first villa rental in a restored Chianti winery and provided guests with unique, genuine and authentic experiences. Today guests can enjoy the same local knowledge and personal service Sean and Sabina offered in more than 500 of our superb rental villas.

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All of our villas come with a pool, to offer the perfect relief from the Tuscan summer heat or a blissful backdrop to enjoy a glass of local wine. The type of your pool depends upon the type of holiday you’re looking for. We have Tuscany villas with private and shared pools, for both sociable family holidays and romantic poolside get-a-ways.

Facilities at your To Tuscany Villa

In addition to your choice of pool set ups, our villas in Tuscany are available with a variety of luxury features to make your holiday live up to that perfect picture. We have villas with barbecues, open fire places, saunas, outdoor hot tubs and tennis courts to provide a fertile ground for your holiday stories.

Every To Tuscany villa comes fully stocked with all the kitchenware, bedding and towels you will need, so everything is ready for you to arrive and start enjoying your Tuscan holiday from the moment you open the door. If you want to feel really at home you can even bring your dog to the majority of our villas, and home favourites like satellite TV and Wi-Fi are available. All of our villas are hand-picked by us and comfortably furnished, so you can be confident all of your needs have been expertly catered for.

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 to stay in Tuscany?
Our villas and apartments are located in the most beautiful areas of Tuscany including Pistoia & Montecatini TermeSiena & ChiantiVal d'OrciaArezzo & CortonaLucca & ViareggioPisa & ValderaFlorence & Chianti and Grosseto & Maremma. And don’t forget we also have some stunning Umbria villas in 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, contact us and we’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 2000 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 600 of the best villa rentals in Tuscany, for 2 to 24 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.

Now booking for 2022!

Have first to choice of our unique Tuscan farmhouses restored to perfection, or be the first to book a hilltop resort offering views across cypress-clad hills. You can plan now to discover the unique lifestyle, unparalled Renaissance history and the impossible beauty of Tuscany in 2022.

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If you are making big plans to get together with family and friends in 2022, the picture perfect hills of Tuscany and Umbria is the perfect place.

    Book for 2022 with 25% deposit
    No booking fees, no hidden extras with peace of mind guaranteed
    The Tuscany experts are on hand to help
    Unique by-spoke To Tuscany Experiences

We are the Tuscany specialists and we want to share our passion and extensive local knowledge of Tuscany and its hidden gems. All of our villas are designed to offer a relaxing stay in stylish surrounds merged with irresistible Italian charm. Let and us help you make your trip to Tuscany an unforgettable experience!

Search for your perfect villa

  • Villa Specialists available Monday to Saturday
    UK 9.00am - 5:30pm GMT
    US 4.00am - 12:30pm EST

    1-800-454-5922 Toll Free

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