
Excellence Luxury Villas · Cortona
Farmhouses, estates and villas with pools below an Etruscan hill town, looking out over the Val di Chiana
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Cortona sits on a steep hillside around 500 metres up, and from its walls you look straight across the Val di Chiana to the glint of Lake Trasimeno. It was an Etruscan city long before Rome, and the town still climbs in narrow stone lanes from Piazza della Repubblica up to the sanctuary of Santa Margherita and the old fortress above. Most British readers know it first from Frances Mayes and Under the Tuscan Sun. It turns out to be rather better than the book.
Our Cortona collection runs to 60+ properties, from restored stone farmhouses with olive groves and long views to grand historic estates for large family gatherings, and spacious apartments within shared country estates, nearly all with a pool.
Here is where to stay around Cortona, what to see and when to come.
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Villa numbers and guide prices are updated daily from our live collection.
Casa Sant’Egidio Cortona: Elegant 6-Bedroom Luxury Apartment with Pool – Cortona6 bedrooms
Villa Montecchio Cortona: Luxurious 11-Bedroom Villa with Pool in Scenic Tuscany11 bedrooms
Palazzo Lago Cortona: Spacious 7-Bedroom Apartment with Infinity Pool – Cortona7 bedrooms
Casa Girasole Cortona: Elegant 5-Bedroom Apartment with Pool – Tuscany Countryside5 bedroomsThe slopes just below Cortona for walking up to dinner, Camucia and the Val di Chiana for easy access and flat cycling, and the quieter hills around Farneta and Sant'Egidio for space and views, with Montepulciano and Arezzo close by.

Cortona is a walking town, and only a fair amount of it is flat. Via Nazionale, which locals call the Ruga Piana, runs level between the two main squares. Almost everything else goes uphill.
The Museo dell'Accademia Etrusca, known as MAEC, sits in Palazzo Casali and holds the Etruscan bronze lamp and the Tabula Cortonensis, a bronze tablet inscribed in Etruscan. Across the square, the small Diocesan Museum has Fra Angelico's Annunciation, which is worth the trip by itself. Below the walls, the Renaissance church of Santa Maria delle Grazie al Calcinaio and the Etruscan burial mounds known as the Meloni make a good morning's wander.
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Where you stay depends on what you want from the evenings. Villas on the hillside close to the walls put the town's restaurants within a short, if steep, stroll. Down on the valley floor, around Camucia, life is easier: shops, a railway station and flat lanes for cycling through the Val di Chiana.
For more room and quiet, the hamlets to the south and east have restored farmhouses and old estates among vines and sunflowers. Farneta has a Romanesque abbey, and the higher wooded slopes towards Sant'Egidio are cooler in high summer, with views that go on a very long way.
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Cortona sits right on the border with Umbria, which helps a great deal when it comes to day trips. Lake Trasimeno is a short drive away for a swim, a boat out to Isola Maggiore and lunch by the water. Montepulciano, with its Vino Nobile cellars, is around half an hour in the other direction. Arezzo is about as close, and its church of San Francesco holds Piero della Francesca's fresco cycle of the Legend of the True Cross.
Siena, Perugia and Assisi all make a comfortable day out, and you will still be home for a swim before supper.
Explore Montepulciano
The white Chianina cattle of the Val di Chiana produce the beef for a true bistecca alla fiorentina, and Cortona celebrates it every August at the Sagra della Bistecca, held in the Parterre gardens in the days up to Ferragosto. The local wine to try is Syrah, which the Cortona DOC has made something of a speciality.
From May into June the Giostra dell'Archidado fills the town with costume, flag throwers and a crossbow tournament. May, June and September are the loveliest months, and July and August are hot but lively. Our concierge can book wine tastings, cookery lessons, a private chef and restaurant tables.
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Villa Levante Sodo Cortona: Elegant 3-Bedroom Villa with Pool & Spa – Cortona3 bedrooms · sleeps 6From £8,141 a week
Porta Berarda | 5-Bedroom Villa with Private Pool in Arezzo Cortona5 bedrooms · sleeps 10From £7,818 a week
Palazzo Chiana Cortona: Luxury 5-Bedroom Apartment with Pool & Countryside Views – Tuscany5 bedrooms · sleeps 10From £7,805 a week
Le Celle Italy4 bedrooms · sleeps 8From £7,622 a week
Fattoria Falterona Cortona: Elegant 3-Bedroom Apartment with Pool – Cortona3 bedrooms · sleeps 6From £7,609 a week
Casa Ginepro Cortona: Charming 3-Bedroom Apartment with Private Pool – Cortona3 bedrooms · sleeps 8From £7,553 a week
Villa Thania | 5-Bedroom Villa with Private Pool in Arezzo Cortona5 bedrooms · sleeps 10From £7,072 a week
Villa Amelinda | 6-Bedroom Villa with Private Pool in Arezzo Cortona6 bedrooms · sleeps 12From £7,072 a weekCortona's villas range from farmhouses a stroll from the town walls to remote estates high in the hills, and we know which ones suit walkers, which suit drivers and which give you the views over Trasimeno. With 60+ properties in Cortona, we can usually find the house that suits you rather than the one that happens to be free. Search by size, pool, location and price, or tell us what you have in mind and we will put together a shortlist.
You book with us directly, with no booking fees. Questions about access, parking, pool heating or how far it really is to the nearest beach go to people who can find out the answer.
Wine tastings in Montepulciano and the Cortona hills, cookery lessons, a private chef, Sagra della Bistecca and restaurant bookings, guided visits to the Etruscan sites, car hire and transfers from Perugia or Florence. Our concierge team arranges all of it, leaving you free to decide which terrace to sit on.
Couples, families with small children, three generations together or a crowd of friends celebrating a birthday: we match the house to the group, down to the number of bathrooms and whether the pool is fenced.
Choose the hillside just below the walls if you want to walk into town for dinner. Camucia and the valley floor are easier for shops, trains and cycling. Farneta and the slopes towards Sant'Egidio give you more space, peace and views.
May, June and September bring warm days and the countryside at its best. The Giostra dell'Archidado runs from May into June, and the Sagra della Bistecca is in mid-August, when the town is busiest and hottest.
Yes. Frances Mayes wrote her 1996 memoir about restoring Bramasole, a house on the hillside just outside the town, and the 2003 film was partly shot in Cortona's streets and squares.
Yes. Our concierge can arrange a private chef for a single dinner or your whole stay, along with cookery lessons, guided visits, transfers and restaurant reservations.
Across our 60+ villas in Cortona, weekly rates typically range from £3,500 to £7,100, with the most affordable from around £2,100 a week and the largest estates well above. Prices depend on the size of the property, its location and the season, with July and August the most expensive. These are guide prices based on current listings; each property page shows its own rates for your dates.
Perugia airport is around 45 minutes by car, and Florence around an hour and a half. Pisa and Rome take longer. Regional trains stop at Camucia-Cortona and Terontola-Cortona, and our concierge can arrange car hire and private transfers.
Yes. Our Cortona collection includes properties with up to 14 bedrooms. Tell us the size of your party and the occasion, and we will send a shortlist that suits it.
60+ villas and farmhouses around Cortona, booked direct with our concierge on hand
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