Excellence Luxury Villas · Val di Chiana
Luxury Villa Rentals in The Val di Chiana
Stone villas and old farmhouses between Cortona and Montepulciano, above a valley Leonardo once mapped
As featured in
A drained marsh, a ring of hill towns and the best steak in Italy
Five centuries ago the floor of the Val di Chiana was a long, marshy lake full of malaria. Leonardo da Vinci drew it around 1502, probably for a drainage scheme, and that map now sits in the Royal Collection at Windsor. The marsh was drained over the centuries that followed. What you see today is a broad, fertile valley of wheat, sunflowers and vines, with Etruscan and medieval hill towns looking down on it from both sides.
Our collection here runs to 39 villas, most of them with pools. You'll find restored stone farmhouses and old fattorie on working estates, villas on the slopes below Cortona and around Lucignano, and large country houses with up to 12 bedrooms for families travelling together.
Below you'll find where to stay, what to see and when the valley is at its best.
The Val di Chiana at a glance
- Villas
- 39 with pools, with up to 12 bedrooms
- Guide prices
- Typically £3,700 to £7,900 a week, from around £3,000
- Best bases
- Cortona, Montepulciano, Lucignano and the countryside around Foiano della Chiana
- Best time
- May, June, September and October; August for the town festivals
- Getting there
- Perugia airport around an hour away, Florence around 75 to 90 minutes by road
Browse all 39 villas in the Val di Chiana
Villa numbers and guide prices are updated daily from our live collection.
Villa Cipressi Cortona: Luxury 9-Bedroom Villa with Swimming Pool – Val di Chiana9 bedrooms
Villa Amaranto Farneta Val di Chiana: Luxury 7-Bedroom Villa with Heated Pool & Wellness Suite – Val di Chiana7 bedrooms
Palazzo Cipresso Cortona: Spacious 6-Bedroom Apartment with Infinity Pool – Val di Chiana6 bedrooms
Palazzo Gargonza Monte San Savino: Spacious 12-Bedroom Luxury Apartment with Pool & Tennis Court – Tuscany12 bedroomsWhere to stay in the Val di Chiana
Cortona for Etruscan history and the liveliest town life, Montepulciano for Vino Nobile and the Siena side of the valley, and Lucignano and Foiano for quieter countryside on the valley floor.
Steep streets and Etruscan walls
Cortona climbs a hillside on the eastern edge of the valley. It began as an Etruscan town, and stretches of the old walls survive. The MAEC museum displays finds from the tombs in the plain below. In the Museo Diocesano is Fra Angelico's Annunciation, one of the loveliest paintings in Tuscany.
Many British readers know the town from Frances Mayes's Under the Tuscan Sun, and it does attract visitors in summer. In the evening, though, the Piazza della Repubblica goes back to the locals. Our villas on the slopes below Cortona look out over the valley and are a short drive from dinner in town.
Browse villas near Cortona
Wine cellars and a barrel race
On the western rim of the valley stands Montepulciano, a Renaissance hill town with cellars cut deep into the rock beneath its palazzi, where Vino Nobile has aged for centuries. On the last Sunday of August the town's districts race heavy wine barrels uphill to the cathedral square in the Bravio delle Botti.
Chiusi, further south, has painted Etruscan tombs. Sarteano is a quiet base with its own castle. The Val d'Orcia, a UNESCO World Heritage Site, is close enough for a day among the cypresses of Pienza and Montalcino.
Browse villas near Montepulciano
An oval town, a carnival and an English mercenary
Lucignano is built in concentric ovals around its hilltop. Its civic museum holds the Tree of Love, a gilded medieval reliquary with coral blossoms. Nearby Foiano della Chiana holds the oldest carnival in Italy, recorded since 1539, with papier-mâché floats paraded on Sundays in late winter.
Above Castiglion Fiorentino stands the castle of Montecchio Vesponi, which Florence gave to Sir John Hawkwood, the English mercenary captain. Lake Trasimeno, across the border in Umbria, is an easy drive for a lakeside lunch.
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Chianina beef, pici and a long autumn
The valley gives its name to the Chianina, a huge, pale breed of cattle and the traditional source of bistecca alla fiorentina. Cortona celebrates it with a steak festival in mid-August. Expect hand-rolled pici with garlic and tomato, local pecorino, and a glass of Vino Nobile.
Late spring and early autumn are the best seasons, warm without the heat of high summer. The olive harvest comes in November, when the new oil is bright green and peppery. Our concierge can arrange cellar visits in Montepulciano, cooking classes, tables in Cortona and transfers.
Ask our conciergeFeatured villas in the Val di Chiana
Fattoria Pievese Cortona: Spacious 10-Bedroom Apartment with Pool – Tuscany Countryside10 bedrooms · sleeps 18From £7,203 a week
Villa Chianina Cortona: Luxury 6-Bedroom Villa with Pool in Val di Chiana – Tuscany6 bedrooms · sleeps 12From £7,000 a week
Villa San Biagio: 12-Bedroom Apartment with Pool in Val di Chiana – Tuscany12 bedrooms · sleeps 25From £6,741 a week
Fattoria Poggio Cortona: Luxury 6-Bedroom Apartment with Sauna & Pool – Val di Chiana6 bedrooms · sleeps 12From £6,678 a week
Fattoria Quercia Lucignano: Luxurious 11-Bedroom Apartment with Pool in Tuscany – Val di Chiana11 bedrooms · sleeps 21From £6,594 a week
Villa Collina Savino: Spacious 7-Bedroom Villa with Pool & Countryside Views – Tuscany7 bedrooms · sleeps 14From £6,335 a week
Fattoria Poggio Valdichiana: Luxury 7-Bedroom Villa with Pool & Gardens – Tuscany7 bedrooms · sleeps 14From £6,090 a week
Cascina Pievaccia Montepulciano: 9-Bedroom House with Swimming Pool – Tuscany9 bedrooms · sleeps 20From £5,803 a weekWhy book your Val di Chiana villa with Excellence Luxury Villas
The right house, not the nearest one
The Val di Chiana spans two provinces and both sides of a wide valley, and we know which villas are a short drive from Cortona or Montepulciano and which are deep in the countryside. With 39 properties in the Val di Chiana, 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.
Book direct
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.
A concierge who knows the territory
Wine tastings in Montepulciano's cellars, cooking classes, restaurant tables in Cortona, day trips to the Val d'Orcia and Lake Trasimeno, car hire and transfers from Florence or Perugia. Our concierge team arranges all of it, leaving you free to decide which terrace to sit on.
A house for every kind of party
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.
Frequently Asked Questions
Where is the best place to stay in the Val di Chiana?
Cortona suits those who want restaurants, museums and an evening passeggiata close by. Montepulciano is the base for wine lovers and for day trips into the Val d'Orcia. The countryside around Lucignano and Foiano della Chiana is quieter and puts you in the middle of the valley, close to both.
When is the best time to visit the Val di Chiana?
May, June, September and October bring warm days and fewer visitors. August is hot but full of festivals, including the Bravio delle Botti in Montepulciano. Foiano's carnival takes place on Sundays in late winter.
What is Chianina beef?
Chianina is an ancient breed of white cattle named after the valley, and one of the largest breeds in the world. It is the traditional beef for bistecca alla fiorentina, a thick T-bone grilled over wood and served rare. Our concierge can recommend the best places to try it.
Can you arrange a private chef at a villa in the Val di Chiana?
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.
How much does a luxury villa in the Val di Chiana cost?
Across our 39 villas in the Val di Chiana, weekly rates typically range from £3,700 to £7,900, with the most affordable from around £3,000 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.
How do I get to the Val di Chiana?
Perugia airport is around an hour from most of the valley, and Florence around 75 to 90 minutes by road. Rome Fiumicino is around two and a half hours. Trains on the line between Florence and Rome stop at Camucia-Cortona, Terontola and Chiusi, and the A1 motorway runs through the valley.
Are there villas in the Val di Chiana for large groups?
Yes. Our Val di Chiana collection includes properties with up to 12 bedrooms. Tell us the size of your party and the occasion, and we will send a shortlist that suits it.
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Find your villa in the Val di Chiana
39 villas across the Val di Chiana, with a concierge who knows the valley well