Villa rentals near Cortona
Cortona is a quintessential Tuscan town; surrounded by medieval walls, it is nestled into a towering hillside high above the Valdichiana. A cultural centre of this valley in southern Tuscany, it is best known for its Etruscan heritage, ceramics, artworks by Fra Angelico, and unrivalled panoramic views across the plains of Arezzo and Orvieto.
Cortona is the perfect base for exploring the main attractions of Tuscany and Umbria in equal measure, from historic cities to heartwarming hilltop towns. It is in this region that you will find some of the prettiest countryside most emblematic of Tuscany, from vibrant sunflowers fields to timeless cypress groves.
Our villas near Cortona range from elegant 17th-century estates to lovingly restored stone farmhouses. Sleeping 6 to 16 people, all of our luxury villas are air-conditioned, ideal for a warm Tuscan and Umbrian summer.
At Tuscany Now & More we take pride in our service. We have 30 years’ experience matching every guest to the right villa. Someone from our small team visits or stays in every Cortona villa we list and knows the area. This is why we keep our portfolio small — and probably why the world’s leading luxury travel magazine says we’re one of Italy’s top five villa rental companies.
Every Tuscany Now & More villa has a private swimming pool, free use of our concierge service, for pre-trip arrangements and an emergency number available 24/7 while you are in-destination. Your concierge can arrange a private chef, daily maid service, or shopping delivered to your villa, and memorable experiences like Tuscan cookery classes in your holiday rental’s kitchen.
To see what real travellers think of our service, and the experience of staying in a Tuscany Now & More luxury villa, read our verified reviews.
About Cortona
Cortona is best known as the film setting for “Under the Tuscan Sun”, based on the best-selling novel by Frances Mayes. This romantic-comedy may have transformed the small city into a popular tourist destination, but it has not altered its tranquil character or true Italian charm. Cortona is defined by its steep winding streets, medieval and renaissance architecture, picturesque squares, bustling weekend markets and of course, those all-important views. The town’s spectacular panoramas across the Chianna Valley and Lake Trasimeno have to be seen to be believed.
At the heart of Cortona is the Via Nazionale, known to the locals as the Ruga Piana, since it is the only flat street in the town. The city is enclosed by stone walls with Etruscan foundations and is home to one of Italy’s most important provincial museums for ancient archaeology and history. Situated near the border between Umbria and southern Tuscany, Cortona is within an hour’s drive of the cities of Siena, Arezzo and Perugia, making it the ideal base for exploring these two central Italian regions.
What to do in Cortona
The Piazza della Repubblica is the main square in Cortona, which is lined with restaurants and shops. It is here that you will find the impressive Palazzo Comunale, with its petite belltower and wide staircase leading up to the building's main entrance.
The Museo dell’Accademia Etrusca e della Città (MAEC), housed in the Palazzo Casali, is one of Cortona’s main attractions and one of Italy’s most important museums for Etruscan artefacts. Many of the items on display come from the Etruscan tombs around Camucia and Sodo, which are well worth visiting after a tour of the museum. Amongst the most valuable pieces on display, is an ornate bronze chandelier and the Tabula Cortonensis, a bronze tablet inscribed with one of the longest known Etruscan texts.
The Museo Diocesano is another important museum in Cortona, which can be found opposite the Duomo. It houses several spectacular artworks including the “Annunciation of Cortona”, also known as the Cortona Altarpiece, by the renaissance artist Fra Angelico. The birthplace of the Sienese painter, Sasseta, and Cortonese artists, Pietro of Cortona and Luca Signorelli, this is an unmissable collection.
It may be quite the climb, but the crumbling Fortezza Medicea Girifalco (“Girifalco Fortress”), at Cortona’s highest point, offers some of the best views across the Valdichiana and Umbrian countryside.
You will also find the Basilica di Santa Margherita here. There are countless churches to discover in Cortona, but few compare to this, with a neo-gothic facade as richly decorated as the interior. Margherita di Cortona, or Saint Margaret, once lived in the Basilica and is often credited with its rebuilding in the 13th-century.
For more ideas on what to do in Cortona, read our Cortona travel guide.
Food & Drink in Cortona
Every Saturday a farmer’s market is held in the Piazza Signorelli in Cortona, where you will find everything from fresh bread and seasonal vegetables to locally produced cheese, olive oil and salami.
Florence might be the Tuscan capital of the Bistecca alla Fiorentina, but this beef comes from a white Chianina breed of cattle native to the valley. So while countless authentic Tuscan dishes are served in Cortona’s many restaurants, the Chianina steak is top of the menu. Cortona’s public gardens are transformed into a food festival in mid-August, celebrating this tender T-bone steak, as well as Tuscany’s famous porcini mushrooms.
Wherever you end up staying in Tuscany, great wineries will never be far from reach. This hilltop town gives its name to the Cortona DOC wine region, producing traditional local grapes like Sangiovese, as well as Cabernet, Merlot and Syrah variants. Cortona is also just a few kilometres from the prestigious wine regions of Montepulciano and Montalcino.
Travellers with a passion for wine should consult our award-winning concierges, who can arrange a wine tour of some of the finest local vineyards or a sommelier-led tasting in your villa. Our villas in vineyards offer an even more personal experience with the vines, bringing Tuscany’s best wines directly to your doorstep.
Shopping in Cortona
Cortona has a long history of ceramics productions and is well-known for its hand-painted pottery, ranging from full dinner services to colourfully glazed vases and plates. Look out for the green and gold Cortonese sunflower in the town’s many ceramic workshops.
On the fourth Sunday of each month, Cortona hosts an antique market in Piazza Signorelli. If you are likely to miss this while on holiday, an antique fair is also held in the nearby city of Arezzo on the first Sunday, and preceding Saturday, of each month.
For more brand-conscious shoppers, the nearby Valdichiana Outlet Village and The Mall Outlet are two of the best fashion outlets in Tuscany for well-known labels at discounted prices.
