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. 

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Showing: 8 villas

Sleeping: 16 - Bedrooms: 8 - Bathrooms: 8

  • Cook Included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Elegant 17th-century villa with a private pool surrounded by a stunning park which includes an amphitheatre. Air-conditioned bedrooms with en suite bathrooms. Breakfast service and maid service included.

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€ 6,680
€ 10,484
$ 9,057
$ 14,214
£ 6,424
£ 10,082

Sleeping: 16 - Bedrooms: 8 - Bathrooms: 8

  • Cook Included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Wedding option for up to 50 guests (up to 90 with an extra fee) in an elegant 17th century villa with a private pool & stunning park which includes an amphitheatre. Air-conditioned bedrooms with en suite bathrooms. Breakfast service and maid service included.

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€ 8,350
€ 13,104
$ 11,321
$ 17,767
£ 8,030
£ 12,602

Sleeping: 8 - Bedrooms: 4 - Bathrooms: 8

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool
  • Hot Tub

Charming stone farmhouse & guest house with a large pool. Air-conditioned bedrooms in the main house, shaded living areas, sauna, billiards table, gym. Private location and peaceful garden with well-kept lawns and impeccable views.

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€ 3,933
€ 5,795
$ 5,332
$ 7,857
£ 3,782
£ 5,573

Sleeping: 14 - Bedrooms: 7 - Bathrooms: 8

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool
  • Hot Tub

Charming stone farmhouse & guest house with a large pool. Air-conditioned bedrooms in the main house, shaded living areas, sauna, billiards table, gym. Private location and peaceful garden with well-kept lawns and impeccable views.

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€ 4,916
€ 7,244
$ 6,665
$ 9,822
£ 4,727
£ 6,967

Sleeping: 6 - Bedrooms: 3 - Bathrooms: 3

  • Fully Air-conditioned villa
  • Internet Connection
  • Private Pool

Fully air-con luxury stone farmhouse with a private pool, just minutes from Cortona. Stunning views, sophisticated kitchen, ensuite bathrooms . Lush garden and three dining areas and a lounge.

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€ 3,846
€ 6,883
$ 5,214
$ 9,332
£ 3,699
£ 6,619

Sleeping: 8 - Bedrooms: 4 - Bathrooms: 4

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Beautifully renovated farmhouse near Cortona with air-conditioned bedrooms and a private swimming pool. Bright interiors with by original wood beams. Modern kitchen & bathrooms. Large pergola for al fresco meals with dazzling views.

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€ 2,856
€ 5,259
$ 3,872
$ 7,130
£ 2,747
£ 5,057

Sleeping: 10 - Bedrooms: 5 - Bathrooms: 5

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Beautifully renovated farmhouse near Cortona with air-conditioned bedrooms and a private swimming pool. Bright interiors with by original wood beams. Modern kitchen & bathrooms. Large pergola for al fresco meals with dazzling views.

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€ 3,321
€ 6,115
$ 4,503
$ 8,290
£ 3,194
£ 5,880

Sleeping: 10 - Bedrooms: 5 - Bathrooms: 6

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Luxury hilltop stone farmhouse & guesthouse with private swimming pool, 28km from Cortona. Interior has original terracotta floors & beamed ceilings, with light-filled A/C bedrooms & en-suite bathrooms. Manicured lawns with panoramic, al fresco dining & living areas.

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€ 3,606
€ 5,715
$ 4,889
$ 7,748
£ 3,468
£ 5,496

Sleeping: 6 - Bedrooms: 3 - Bathrooms: 3

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Luxury stone farmhouse with private pool, air-con bedrooms & very modern bathrooms in travertine. Exceptional views and close to Cortona. Fantastic modern kitchen and sophisticated outdoor furniture.

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€ 3,150
€ 4,878
$ 4,271
$ 6,613
£ 3,030
£ 4,691

Sleeping: 8 - Bedrooms: 5 - Bathrooms: 4

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Luxury stone farmhouse with private pool, air-con bedrooms & very modern bathrooms in travertine. Exceptional views and close to Cortona. Fantastic modern kitchen and sophisticated outdoor furniture.

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€ 3,317
€ 5,345
$ 4,497
$ 7,247
£ 3,190
£ 5,140

Sleeping: 6 - Bedrooms: 4 - Bathrooms: 4

  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

A picture-perfect Umbrian farmhouse with a private pool & air conditioned bedrooms amid olive groves. Many sitting areas one of which air-conditioned and a huge well equipped kitchen.

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€ 1,917
€ 3,746
$ 2,599
$ 5,078
£ 1,844
£ 3,602

Sleeping: 10 - Bedrooms: 5 - Bathrooms: 5

  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

A picture-perfect Umbrian farmhouse with a private pool & air conditioned bedrooms amid olive groves. Many sitting areas one of which air-conditioned and a huge well equipped kitchen.

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€ 2,206
€ 4,135
$ 2,991
$ 5,606
£ 2,122
£ 3,977

Sleeping: 10 - Bedrooms: 5 - Bathrooms: 5

  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Gorgeous stone farmhouse with a private pool on a hill top. Beautifully updated main kitchen, air-conditined bedrooms with en-suite bathrooms, three living rooms, huge garden with two summer kitchens, wheelchair access.

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€ 1,993
€ 3,795
$ 2,702
$ 5,146
£ 1,916
£ 3,650

Why stay near Cortona 

Every traveller is different, so there is no such thing as the “best” villa near Cortona; only the best Cortona holiday rental for you. When you contact Tuscany Now & More, you will talk to someone who has stayed at the villas which interest you. It’s our golden rule — and why we stick to a focused, specialist portfolio of around 135 handpicked villas.

Whether you are a returning visitor to Tuscany looking to broaden your horizons into neighbouring Umbria, or this is your first time in Italy, Cortona is the ideal base for exploring both of these central regions. 

Try a day trip to the Tuscan city of Siena with its central piazza, Il Campo, the Palazzo Pubblico and impressive marble Duomo. Arezzo, also within 40 minutes of Cortona, is home to countless museums, Etruscan walls, a Medici fortress and the famous  “Legend of the True Cross” fresco cycle by Piero della Francesca. The city’s central square, the Piazza Grande is just as magnificent as it’s feature in Roberto Benigni’s “La Vita è Bella” (1997). 

Cross the border into Umbria and you will find the medieval towns of Perugia and Città di Castello with their grand Palazzi, cobbled streets and views over the mountainous landscape. If you are prepared to venture slightly further afield, the towns of Todi and Orvieto are also well within reach.

It’s a well-known fact that Umbria, the ‘Green Heart’ of Italy, is one of the best regions for hiking and cycling, making it a great destination for outdoor lovers. Lago Trasimeno is the fourth largest lake in Italy and is within 13km of Cortona — a great day out for watersports or a relaxing afternoon sunbathing on a sandy beach at Castiglione del Lago. 

When to visit Cortona 

Spring temperatures are pleasant throughout most of Tuscany and Umbria, including Cortona. Average daytime temperatures reach a high of 17℃ (62℉) and lows of 8℃ (46℉) overnight by May. Spring is one of the best times to visit Cortona if you want to avoid the popular summer season while enjoying warm and relatively dry weather. 

Summer is high season across Italy and daytime temperatures around Cortona rise to an average high of 30℃ (86℉), with lows of 14℃ (57℉) overnight. 

This is the season for sunbathing by your own private pool or on a sandy beach on the shores of Lake Trasimeno. Venture into Cortona’s historic centre by evening when temperatures drop and you can enjoy the buzzing atmosphere of the town's main piazzas. 

There are plenty of food festivals and events happening in Tuscany and Umbria during this time, including the Palio di Siena horse race in July and August. Cortona hosts its own historical reenactment each June; the Archidado Joust transforms the town with medieval decoration and people dressed in fine costumes as ladies, knights and soldiers. 

Despite the cooler temperatures, Autumn and Winter are still great times to visit Cortona, particularly if you are interested in exploring the many cities in Tuscany and Umbria at your own pace. The sun shines most days during the fall with an average daytime high of 18℃ (64℉) and overnight lows of 8℃ (46℉).

For more month-by-month advice on travelling to these central Italian regions, read our guides to the Best Time to Visit Tuscany and the Best Time to Visit Umbria

About Our Handpicked Villas near Cortona 

All of our villas at Tuscany Now & More are locally owned and staffed, and we take pride in being able to offer each of our guests a unique experience tailored to their needs. If you are interested in learning more about what makes us different, you can read the Tuscany Now & More story.

Concierge service

Everyone renting a villa near Cortona with Tuscany Now & More gets free, unlimited access to our renowned concierge service. If you want shopping stocked in your fridge on arrival, or a private chef to cook dinner for a special occasion, just ask. Making your holiday lettings extra-special is part of our service. While you are in Italy, our 24-hour ground staff are available by phone or WhatsApp.

Checking in & out

You should check-in at your Cortona holiday rental between 4pm and 7pm. We can accommodate different arrival times — just communicate this in advance to our office staff. Upon arrival, the villa owner or caretaker will inspect the property with you and demonstrate appliances, equipment and utilities.

Check-out is 10am on the last day of your holiday rental. The villa owner or caretaker will arrive at 9am to settle outstanding payments, if you have any. If you want to depart earlier, please let us know in advance.     

Cleaning

Both the luxury villa and your private swimming pool will be cleaned prior to your arrival. Some holiday villas have additional cleaning and pool/garden maintenance scheduled during the week. Maid service included with vacation rentals involves cleaning and tidying but does not cover making beds, kitchen cleaning, laundry or ironing. Extra services can be organised via our dedicated travel concierge team.     

Bed linen & towels

Our Cortona holiday rentals include bed linens, bathroom and swimming pool towels for all guests. These are provided weekly. Extra services and changes can be organised via our concierges.

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