Luxury Holiday Villas in Tuscany

Our insider guide to choosing the right holiday location in Tuscany

Tuscany is divided into diverse provinces, each bringing its own unique touch to your Italian holiday. Finding the perfect luxury villa depends on the type of holiday you are looking to experience.

Chianti and Florence: The best for wine and culture

If you want a luxury Italian holiday filled with world-class art and wine tastings, look for a property in the Chianti hills or near Florence. Staying in towns like San Gimignano or Greve in Chianti puts you amongst rolling vineyards, while still being a short drive or train ride from the architectural masterpieces of the Renaissance capital.

Siena and Montepulciano: The best for classic Tuscan landscapes

More in the mood for postcard-perfect views? Then visiting Siena or Montepulciano is a great option for your luxury holiday to Tuscany. With its winding roads lined with cypress trees, this region is home to some historic villages, soothing thermal baths and incredible local food markets.

Lucca and Pisa: Best for the coast and history

If you’re looking for a balance of historical sightseeing with days by the sea, Lucca and Pisa in Western Tuscany are where you will want to head. The walled city of Lucca offers flat terrain that’s perfect for family bike rides, while still keeping you within driving distance of the less explored, pristine golden beaches while on your luxury holiday to Tuscany.

Arezzo and Eastern Tuscany: Best for secluded medieval sightseeing

Full of medieval history and Renaissance art, the eastern province of Arezzo offers a beautifully authentic and slightly quieter Tuscan experience. Choosing a luxury holiday villa in this region puts you right in the middle of fortified medieval valleys, olive groves, and historic hilltop gems like Cortona and Sansepolcro. The capital city of Arezzo itself is a paradise for culture lovers, famous for its magnificent Piazza Grande, stunning frescoes by Piero della Francesca, and its monthly antique market.

Essential amenities for your luxury holiday in Tuscany

Whether you are looking for specific property sizes, location-specific villas, or a layout that suits the whole family, here are some of our most popular amenities alongside a few standout properties that showcase them perfectly:

Luxury villas with pools

The vast majority of our luxury estates feature private swimming pools, allowing you to cool off under the Mediterranean sun. To extend your swimming season into the cooler shoulder months of April, May and October, we also have a few properties with heated pools, such as Villa Palagio, a stunning estate in Florence, and the ultra-luxurious Villa Vecchio in the heart of Chianti.

Luxury villas within walking distance of restaurants

Perfect for those who want to experience the local lifestyle without relying on a car for every evening meal or morning espresso trip. Properties like Benedetta in Chianti or Villa Tina offer breathtaking 360-degree countryside views while still being an easy stroll from the local village.

Pet-friendly luxury villas

We believe the entire family should enjoy the holiday, including your four-legged friends. Many of our luxury Tuscan villas have enclosed gardens and grounds. Properties like Villa Bibbona offer absolute privacy, security, and tranquillity within their sizable gated parklands, making them perfect for cats or dogs.

Luxury villas for large groups

Whether you are planning a big family reunion or an intimate destination wedding, properties like The Sunflower House comfortably sleep up to 22 guests across 10 spacious bedrooms, while the sprawling layout of Villa Vetrichina provides more than enough communal dining spaces alongside private corners for peace and quiet.

Things to do in Tuscany

Tuscany ticks all the boxes; from foodies and outdoor enthusiasts to culture vultures and families with children, there is something for everyone.

We’ve already mentioned the incredible food and wine available in regions such as Chianti or Florence. For those looking for a bit of nature or physical activity, staying in rural Tuscany in one of our luxury villas will allow you to enjoy the hikes and cycle rides, not to mention the water sports along its coast.

Florence is full of art and architecture, and children will love the many activities on offer too. From zoos, water parks and aquarium visits to meeting Tuscany’s most famous puppet, Pinocchio, there is plenty to keep little ones entertained.

And whilst Tuscany may be one of Italy’s most popular holiday destinations, there are still plenty of gems to discover off the main tourist trail too. We have a full Tuscany travel guide if you need more information.

Frequently asked Questions

What is Tuscany known for?

Home to some of the world’s most famous cities – Florence, Pisa and Siena – Tuscany is synonymous with the art and architecture that each is home to. However, it’s also known for the rolling hills, vineyards, olive groves and picturesque Medieval villages that abound in its countryside. Tuscany is less known for its coastline but it can also boast some pretty impressive beaches too. The good news is that we have Tuscany villas for rent to make the most of all Tuscany has to offer.

Is Tuscany an expensive holiday destination?

Tuscany doesn’t have to be an expensive holiday option and the region can certainly cater for all budgets. If you are watching the purse strings, then there are some great ways to save money on your Tuscany villa stay. Travel during the shoulder season (April through to June or in September and October) and you will find Tuscany villas for rent are much cheaper. We also recommend you stay outside the major cities and instead opt to base yourself in the countryside. Eat with the locals rather than in the tourist trap restaurants is another great tip. And remember, whilst some of the larger Tuscany villas can, at first sight seem expensive, when you break it down per person, they can actually offer great value for money.

What airport do I fly to for Tuscany?

Tuscany has two main airports – Pisa (Galileo Galilei International Airport) and Florence (also known as the Amerigo Vespucci Airport or Peretola). However, you could also fly into an airport in a neighbouring region when staying in one of our Tuscany villas. Bologna airport in Emilia Romagna, for example, is just a 90 minute drive from Florence. Or Rome in neighbouring Lazio is less than a 90 minute drive from southern Tuscany. And in Umbria, Perugia airport is less than an hours drive from the Tuscan border.

What month is best for visiting Tuscany?

There is no bad month to visit Tuscany – it’s just that each month offers something different. However, our favourite months to stay in one of our Tuscany villas are May, June and September. This is when tourist numbers are less but the weather should still be gloriously sunny with lovely temperatures, perfect for both sunbathing and exploring. If you’re restricted by school holidays, the peak Summer months of July and August are still lovely, especially if you like the heat. But expect it to be at its busiest then. If you want to visit without the crowds, then consider visiting Tuscany in the Easter, or the May or October half terms.