Luxury Villas in Tuscany

Tuscany is the epitome of a dreamy Italian escape. The picturesque rolling hills of the countryside, world-class art from the Renaissance and medieval periods, flavoursome seasonal food and endearing hilltop villages make for a delightful Tuscan holiday. 

Our collection of villas in Tuscany allow you to truly soak up the rural beauty of the region, with our destination experts handpicking them for their proximity to local activities: wine-tasting, rambling, cycling and golfing to name a few. 

Why visit?

  • Florence is perfect for art-lovers, where you can find pieces by Michelangelo, Botticelli and Da Vinci.
  • You can’t visit Tuscany without paying a visit to at least one of the local vineyards and sampling some of their delicious vinos – they’re one of the most famous regions in the world for wine, after all. 

Read the Tuscany Travel Guide

Why stay with us?

Style and character are everything at Oliver’s Travels, and our collection of handpicked villas in Tuscany have this in spades.

We have destination experts who know the ins and outs of all our regions, picking villas that aren’t only unique, but also in the best locations. What's more, our villas are 100% family-friendly, and have the ‘wow’ factor.

Our helpful concierge team are on-hand to make your stay extra special. Whether you want a fully-stocked fridge, a local in-house chef to cook your meals, housekeeping or any other extra service – consider them your holiday genie, who will happily grant your wishes.

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Villas in Tuscany: Our Top Picks

Why visit

Visitors have fallen in love with Tuscany throughout history. The Romans prized the fertile earth, pilgrims walked across it, great artists and poets enshrined its beauty in their work and, more recently, the international jet set has discovered its gentle, rolling hills and stunning coastline

In Tuscany, locals and visitors alike spend a considerable amount of time thinking about food (and wine!). A supremely fertile region, Tuscany has always been famous for its produce and boasts some of the country’s most iconic exports. The Chianti wine region is now an international powerhouse, while excellent olive oil is milled throughout Tuscany. Truffles are a Tuscan mountain delicacy and bistecca alla Fiorentina (chargrilled steak) is a must-try.

Italian Countryside

From the Apuan Alps, down to the foothills and the undulating landscape of the region’s heartlands, all the way to the coast, Tuscany has an enormous amount to offer anyone who enjoys the great outdoors. Whether it’s hiking, cycling, sailing, scuba-diving, horse riding, or kayaking, the area’s diverse natural heritage means the environment is well-suited to a wide range of activities.

Apuan Alps

Apuan Alps

Discover Our Tuscany Luxury Villas

With properties dotted across the region, we have plenty of holiday villas in Tuscany to choose from. Whilst most are concentrated within the region between Siena and Florence, we also have villas to rent as far north as Forte dei Marme and as south as Orbetello. For those that want to head off the Italian mainland, we even rent a property in the Tuscan Archipelago

If you want more information, check the Tuscany Travel Guide in our blog.

What Oliver loves

Few places on earth can match the natural beauty of Tuscany’s rolling hills in spring. Combine the landscape with a large glass of local Chianti and you’re in heaven.

Best time to go

  • Tuscany is a year-round destination and you’ll find something different in every season. From snow-covered hill villages in the winter to the crystal-clear waters of the Med in summer, it’s always a good time to visit Tuscany. 
  • Summer is both the warmest and most popular time to travel to the region. Temperatures regularly top 30°C, prices rise, and attractions are more crowded. 
  • This makes spring and autumn the best times to visit if you prefer cooler days, manageable queues, and better value for your money.

Top tips

  • UNESCO sites: Tuscany boasts seven UNESCO sites – Florence, Siena’s medieval centre, the Leaning Tower, San Gimignano, Pienza, Val d’Orcia, and the 12 Medicean Villas.
  • Must see: Dante’s ‘Divine Comedy’ proved so popular throughout Italy that it resulted in the Tuscan dialect being adopted as the country’s ‘standard tongue.’

Where to go

From the arts of Florence to the hills of Montepulciano, you'll never be short of gorgeous places to stay on your Tuscan villa holiday. Have a look at our quick guide below to see where tickles your tastebuds...

Florence, Puglia, Italy

Known as the ‘Cradle of the Renaissance’ Florence is an alluring destination full of world-class art and architectural masterpieces. And with the whole of the city centre being a UNESCO World Heritage Site, you know you’re in for a treat.

Pisa, Tuscany, Italy

An easy day trip to or from Florence, these charming little spots are great to explore - from the famous leaning tower of Pisa to the incredibly well-preserved medieval walls surrounding Lucca.

Montepulciano, Tuscany Italy

A medieval hilltop town in southern Tuscany, Montepulciano boasts incredible architecture, grand Renaissance palaces, stunning views over the surrounding valleys, and of course the famous Nebile wine. Wander the charming historic squares before finding one of the wine cellars underneath the palazzos to taste a glass or two. 

San Gimignano, Tuscany Italy

With a skyline like no other, San Gimignano is well-known for its medieval architecture – 14 towers rise above the hills to create this unique horizon. Wander the pathways, soak up the history, listen to classical musicians playing in the streets, and cool down with some gelato at the world-famous Gelateria di Piazza. 

Siena, Tuscany

Vibrant streets lined with boutique shops, quaint cafes and decadent pastry shops; Siena is a beautiful spot in central Tuscany. Step back in time as you stroll amongst the Gothic architecture, through the museums and inside the awe-inspiring cathedral.

Family friendly

If you’re travelling with kids, you’ll be happy to know that Tuscany provides a wide range of activities for all the family. While many of our villas in Tuscany have a pool and should keep the kids happy for hours on end, you don’t have to venture far to find a region bursting with exciting possibilities.

Bring Learning to Life

From the interactive museums and galleries of Florence to the living history of Lucca’s city walls, Tuscany is a place in which it’s impossible not to learn a little. Having played an important role in Italian, European and world history, Tuscany is the perfect place to get your kids interacting with Renaissance art and Roman history on a first-hand basis. 

Lucca Italy

Piazza anfiteatro in Lucca, Italy

Get Outside and Enjoy the Province

Not many places offer the incredible range of activities that visitors enjoy in Tuscany. The region is a cyclist’s paradise, and trails, routes, and famous climbs can be found near the majority of our holiday villas. In the rural interior, there’s plenty of opportunities to go hiking, mountaineering, and exploring or to get your hands dirty and try helping out on a farm. Horse riding is also a popular option for children of all ages.

Tuscan Beaches

The resorts and nature parks that make up a significant portion of the Tuscan coast are the ideal place to try your hand at any one of a number of water-sports. Whether your teens want to give scuba-diving a shot or the whole family fancies kayaking down a gently-flowing river, there’s plenty of opportunities to dive on in and get yourself wet.

Why it's perfect for families

  • For babies: Tuscany is an ideal destination for toddlers and babies. The weather is never usually too hot, the food is fantastic, and the lifestyle is laidback. The Livorno Aquarium is a popular attraction for younger kids. Check out our baby-friendly villas.
  • For kids: Thrill the kids with a 4x4 tour of the marble quarries near Carrara. The Cava di Marmo tours take you up and down the steep gravel slopes before dropping you off to visit a real marble cave. See our list of child-friendly villas.
  • For teens: The Parco Regionale della Maremma is an outdoor enthusiast’s dream holiday destination. Cycle, hike, horse ride and kayak your way around 20km of pristine coastline – perfect for those older kids who want a little more freedom.Discover our list of teen-friendly villas.

Top Tips

  • Head to the beach and the Etruscan Coast for some relaxing down-time. The coast combines town-based beaches and super-secluded spots, so there’s something for everyone.
  • Enjoy Tuscany’s famous rolling hills and get involved with day-to-day rural life. Olive picking, pig-feeding and horse riding are all on the cards when you head to the countryside.

Beaches in Tuscany

Tuscany’s beaches are almost as diverse as the landscapes of its renowned interior. To the north, the coast brushes up against the Apuan Alps, allowing you to enjoy a hike in the morning and sandy stretches of coast in the afternoon.

Further south, Versilia is famed as a hotspot for the Italian social elite and for its lively nightlife. This stretch of coast is more developed than many other parts, so makes for a good destination for those who are happy to sacrifice quieter beaches for better access to facilities, bars, and restaurants.

The Pisan Coast offers unspoiled beaches and long stretches of sand, with impressive dunes, quaint fishing villages, and leisure facilities. With fantastic conditions for sailing and windsurfing, it’s perfect for active families.

Continuing south, the Etruscan Coast is largely defined by smaller coves and beautiful beach towns, while the Piombino Coast features white, sandy beaches backed by pine forests that manage to avoid overcrowding in even the busiest of months.

The Maremma and Silver are both spectacular stretches of coast, much of which is protected by pine forests and wilderness areas that add to their secluded, romantic feel. 

Oliver's Hidden Gem

The Principina a Mare is a secret delight that’s situated in the Grosseto region. Backed by dense pine forest, there’s a tonne of things to keep you busy here, including kayaking, cycling and horse riding. 

Grosseto region Italy


Forte dei Marmi, Puglia

A popular choice amongst the Italian glitterati, as well as international jet-setters, this stretch of coast includes several beaches, all of which back on to the famous esplanade. The town is well-known for its vibrant nightlife.

Marina di Alberese, Tuscany

If you want to escape the crowds and see a wilder side of the Tuscan coast, Marina di Alberese is a very good choice. Accessible via an 8km bike path, the beach’s relative isolation means it remains in pristine condition. 

Cala Violina, Tuscany

Though it requires a little bit of a walk to reach, Cala Violina is a stunning crescent bay that combines pristine, clear waters and white sands in the way only the Mediterranean can. The beach is located near Scarlino.

Tombolo della Feniglia, Puglia

Situated next to the Laguna di Orbetello, it’s home to hundreds of species of migratory bird. The beach itself is long, sandy, unspoilt, and far less crowded than many of those further north.

Cala di Forno, Tuscany

Isolated in the middle of the striking Parco Uccellina, Cala di Forno is a little slice of paradise at the heart of a wild, rocky, and craggy stretch of coast. Bring your own picnic as facilities are scarce.

Isola Giglio, Tuscany

If you’re heading off the mainland to explore one of the islands of Tuscan Archipelago, we recommend Isola Giglio for its incredible beaches. Picturesque coves, great scuba-diving and snorkelling make it one of our favourite islands.

Things to do

Tuscany packs a lot into a relatively small geographical area, without ever feeling too busy or overcrowded. Whether you’re a beach bum, an adventure sports enthusiast, a culture nut, or someone who appreciates all three, the region makes for a fantastic holiday destination.

Home to breath-taking architecture, world-class museums and galleries, and bustling marketplaces, Florence is a wonderfully romantic city that the whole family can enjoy.

If you’re a bit of a foodie and enjoy a glass or two of wine, there’s a good chance that you’ll never want to leave Tuscany. With the Chianti region at its heart, a delightful mix of fresh seafood from the coast and mountain specialities up high, there’s no better way to spend your time than enjoying tasting tours with local producers.

Top activities in Tuscany 

  • Visit the world-famous Leaning Tower of Pisa -  Get a classic holiday snap of you holding up the tower. The city also features a remarkable cathedral and the impressive Camposanto – making it an excellent day trip for those who appreciate their history and architecture.

Pisa tower, Tuscany

Pisa Tower

  • Tour the Chianti wine region -  Ideally situated between Florence and Siena and surrounding many of our holiday villas in Tuscany, the Chianti region has a stellar reputation and produces some of the finest wines in the country. 
  • Enjoy endless art in the Uffizi in Florence - One of the world’s foremost collections of paintings, the Uffizi is so large it’ll take at least a full day to see it all.
  • Combine hot water springs and excellent wine with a trip to the Val d’Orcia region - You’ll find springs in Bagno Vignoni, Bagni San Filippo, and Vivo d’Orcia, and there’s beautiful wine wherever you go.

Val d’Orcia, Tuscany

Val d’Orcia

  • Rent a bike and cycle one of the world’s foremost road racing regions -  Alternatively, head off-road to follow the route taken by the Strade Bianche, a future classic that takes place on Tuscany’s striking white gravel roads.
  • Embrace Tuscany’s mouth-watering culinary history - Learn a thing or two with a cooking class at the Good Tastes of Tuscany - ideal for solo travellers, pairs, families, and large groups, the class will help you get to grips with some of the region’s most important dishes.

Oliver's Hidden Gem

While Tuscany is rightly famed for its wine, there are several other local delicacies you have to try, too. No one does olive oil like the Italians, so book yourself on a tasting tour with Arianna & Friends.

If truffles are more your thing, Tuscany is the place to be. Go Truffle hunting with the Truffle Hunter


Towns and villages

Tuscany is the epitome of a dreamy Italian escape. The picturesque rolling hills of the countryside, world-class art from the Renaissance and medieval periods, flavoursome seasonal food and endearing hilltop villages make for a delightful Tuscan holiday. 

Our collection of villas in Tuscany allow you to truly soak up the rural beauty of the region, with our destination experts handpicking them for their proximity to local activities: wine-tasting, walking, hiking and golfing to name a few. 

If you want to be close to the main towns, discover these villas close to villages

Oliver’s Hidden Gem

If one town could sum up the beauty, history, and splendour of Tuscany’s iconic towns and villages, we’d say it was Pitigliano. Set atop an intimidating stone cliff, the cobblestone streets wind their way up past intriguing synagogues to the town’s beating heart, Piazza Garibaldi.

Barga, Tuscany

Tucked beneath the mountains and scattered amongst chestnut forests, Barga has a lively and close-knit community feel. The town features the smallest library in Tuscany – a traditional British red phone box that was gifted to the town by an Edinburgh-based fish and chip shop owner. 

San Gimignano, Puglia

Famed for its 15 towers, the slate and stone cottages of San Gimignano have inspired poets, artists, and visitors for generations. Located within easy reach of many of our central villas in Tuscany, it’s also pretty much equidistant from Florence and Sienna, making it an ideal visit for anyone travelling between the two.

Cortona, Tuscany

With its winding alleyways, colourful flower displays, and unbeatable views of the surrounding plains, this medieval town is the perfect place to visit if you want a taste of Tuscany’s hilltop retreats. Make sure you catch one of the many town markets and enjoy the area’s amazing local cuisine – especially the wine and panino co i' lampredotto (beef-tripe slow-cooked in vegetable broth, served in a soft bread roll).

Montepulciano, Tuscany

Wine connoisseurs will want to take a trip to Montepulciano, which shares its name with one of the country’s most popular red grapes. While the surrounding area is covered in vineyards, the town itself offers a fascinating insight into the region’s history. The central Piazza Grande is a must-see and a glittering jewel atop a beautiful crown of a town.

Lucca, Tuscany

Though smaller than Tuscany’s second city, Siena, Lucca makes up for its diminutive size with bucket-loads of charm. Visitors can walk around the city’s 16th-century walls, relax on the tree-topped Guinigi Tower, or people-watch in the lively Piazza dell’Anfiteatro. Those visiting Tuscany on a family holiday will enjoy the playgrounds and picnic areas just outside the city walls. 

Florence, Tuscany

With its world-class art collections, unparalleled architectural beauty, and vibrant café and restaurant scene, you could spend weeks exploring the wonders of Florence. Whether you want to check out the San Lorenzo Market, visit the Duomo, or just wander the streets, you’ll have a cracking time.

Getting Around

Once you’ve decided where to stay, you can start planning your arrival. Tuscany has great connections throughout Italy and internationally, so you’ve got plenty of choice.


Tuscany is served by two international airports, Amerigo Vespucci Airport in Florence and Galileo Galilei International Airport in Pisa. Pisa is the larger of the two airports and also receives a larger number of budget flights from European airports. Both airports offer good access to our villas in Tuscany. It’s worth noting that Amerigo Vespucci Airport is also often referred to as Peretola Airport. 

Car rental

If you want to get the most from your Tuscany family holiday, it’s likely you’ll need to rent a car. While public transport is an option, it makes moving around the spectacular Tuscan hills and up and down the coast a lot more time-consuming and challenging. Rentals can be arranged for pick-up at your arrival airport or from one of the region’s major cities.


Train travel in Tuscany is affordable and relatively convenient. While you won’t be able to visit many towns and villages as easily as you would with a car, the railway service remains a realistic option for anyone who’s travelling on a budget or who won’t be venturing too far, too often.


Without a rental car, buses are often the only means of reaching some of the smaller Tuscan villages that are scattered across the countryside and up in the hills. Timetables can be difficult to read, and holidays and weekends often affect scheduled services, so be sure to plan your journey in advance.


Taxis are always a good option in the urban centres but are more difficult to find in the countryside. If you’re looking to grab a ride after a meal out in a small town, make sure that you book in advance


Whether you’re the next Bradley Wiggins or just looking to roll your way across the undulating landscape, Tuscany is a fantastic place to cycle. Families can rent bikes for the duration of their stay, while cycle tourists can tackle parts of the Gran Tour Maremma and Grand Tour della Val di Merse if they fancy a challenge.

Top tips

  • Public transport services are likely to operate heavily altered schedules on Sundays. In many rural areas, it may not operate at all. This makes careful planning essential.

  • Many of the region’s most beautiful coastal spots are only accessible if you rent a car. Unlike most other Italian regions, the Puglian coast is still relatively undeveloped, so there’s plenty of secret spots for you to discover.
  • While travel between the region’s cities and major towns is facilitated by modern highways, many rural areas are serviced by small country lanes and the occasional gravel track. This means it’s good practice to always factor in a little extra travel time when travelling to the countryside.

From the blog...