# Cortona Villa & Vacation Rentals 2027 | Tuscany | Doorways

> Villas around Cortona, the hill town of Under the Tuscan Sun, including Villa Laura, the real Bramasole. Hand-inspected, with full travel advisor service.

Source: https://villavacations.com/destinations/cortona/

![Cortona villas — hand-selected luxury rentals](https://villavacations.com/wp-content/uploads/2026/06/laura-02-estate-establishing.jpg)

Under the Tuscan Sun

# Cortona Villa Rentals

A hilltown above the plains, stone streets warm underfoot, and a piazza that feels like a secret kept.

Cortona sits high above the Val di Chiana on the southeast edge of [Tuscany](https://villavacations.com/destinations/tuscany/) — the hilltown that Frances Mayes made famous and that quietly outlasted the moment. Stone streets, Etruscan walls, a piazza that fills up at six o'clock and empties by ten.

Stay in a villa here and you trade the crowds of [Tuscany](https://villavacations.com/destinations/tuscany/)'s bigger names for olive groves, wide views over the plain, and a town small enough that the butcher knows you by Tuesday.

Looking west across the region? See our [Siena villa rentals](https://villavacations.com/destinations/siena/) in the hills around the city.

Villas

Hand-selected stays in Cortona

[Browse Villas →](https://villavacations.com/villas/?region=Cortona)

Best Villas

## Best villas in *Cortona*

![Villa Tullia](https://villavacations.com/wp-content/uploads/2026/06/Villa-Tullia-hero-1024x683.webp)

Cortona

### Villa Tullia

6 Beds·5 Baths·12 Guests

From €5,005 / week

![Villa Ivana](https://villavacations.com/wp-content/uploads/2026/06/Villa-Ivana-hero-1024x1024.webp)

Cortona

### Villa Ivana

9 Beds·12 Baths·18 Guests

From €9,450 / week

![Villa Laura](https://villavacations.com/wp-content/uploads/2026/06/laura-02-estate-establishing-1024x683.jpg)

Cortona

### Villa Laura

10 Beds·10.5 Baths·20 Guests

From €25,000 / week

[View All Villas in Cortona](https://villavacations.com/villas/?region=Cortona)

Private experiences

## Book a private *experience*

Expert-led private tours with Context Travel, priced per group, so the cost per person drops the more of you there are. Book direct, with no markup.

![Introduction to Siena Tour with the Duomo](https://villavacations.com/wp-content/uploads/2026/06/eod-context-siena-introduction-to-siena.jpg)

From

$108

per person

Half day · private

### Introduction to Siena Tour with the Duomo

A walk through medieval Siena with an art historian — the Duomo, the Campo, the Palazzo Pubblico, the contradas. Why this city stopped in the 14th century and was preserved by stopping.

Private, priced per group: $478 for 2, about $108 per person for 12.

Book this experience

![Chianti Excursion with Wine Tasting from Florence](https://villavacations.com/wp-content/uploads/2026/06/eod-context-florence-chianti-excursion-wine-tasting.jpg)

From

$1,696

per group

Half day · private · tastings included

### Chianti Excursion with Wine Tasting from Florence

Private tour: Chianti Excursion with Wine Tasting from Florence. Led by Context Travel's local expert in Florence.

Book this experience

![Full-Day Tuscany Day Trip from Siena with Wine Tasting](https://villavacations.com/wp-content/uploads/2026/06/eod-context-siena-day-in-val-d.jpg)

From

$582

per person

Full day · private · tastings included

### Full-Day Tuscany Day Trip from Siena with Wine Tasting

Pienza, Montepulciano, the cypress road outside San Quirico, the abbey at Monte Oliveto Maggiore. The full Crete Senesi day with a local driver and a historian.

Private, priced per group: $2,572 for 2, about $582 per person for 6.

Book this experience

![Full-Day Tuscany Day Trip from Florence with Wine Tasting](https://villavacations.com/wp-content/uploads/2026/06/eod-context-florence-tuscany-day-trip-florence.jpg)

From

$2,718

per group

Full day · private · tastings included

### Full-Day Tuscany Day Trip from Florence with Wine Tasting

Private tour: Full-Day Tuscany Day Trip from Florence with Wine Tasting. Led by Context Travel's local expert in Florence.

Book this experience

From

$85

per person

Half day · private

### Siena Palio Tour

The story of the Palio, the horse race that has run twice a year since 1656, told by a member of one of the city's seventeen contradas. The best way to understand why this race matters.

Private, priced per group: $467 for 2, about $85 per person for 12.

Book this experience

From

$1,557

per group

Half day · private · tastings included

### Half-Day Tuscany Carmignano Wine Tasting Tour from Florence

Private tour: Half-Day Tuscany Carmignano Wine Tasting Tour from Florence. Led by Context Travel's local expert in Florence.

Book this experience

[See all Siena experiences 5 private tours](https://villavacations.com/experiences/siena/)

[See all Florence experiences 24 private tours](https://villavacations.com/experiences/florence/)

Disclosure: experiences are delivered by [Context Travel](https://www.contexttravel.com/?ref=Doorways_Villa_Vacations). Bookings made through these links may earn Doorways a referral commission, at no additional cost to you. Doorways does not mark up Context Travel pricing.

Experiences

## Activities & *experiences*

### Sunset on the Palazzo Comunale steps

The piazza fills slowly between six and seven. A glass of wine from the café, a half-hour of people-watching, and the warmest light of the day on the bell tower above.

### Cortona Syrah tasting at a family estate

A morning at a small producer below the town — most of them still under-the-radar despite making excellent Cortona DOC Syrah. Cellar tour, four wines, lunch.

### Cooking class with a Cortonese nonna

Hand-rolled pici, fresh ricotta gnudi, a Chianina ragù, and the tiramisu that everyone fights over. Half a day, ending with the meal.

### A morning at the Etruscan museum

The Museo dell'Accademia Etrusca holds the Tabula Cortonensis — one of the longest Etruscan inscriptions ever found. Smaller than the great museums and far more personal.

### Lake Trasimeno boat day

Twenty minutes by car. A private boat across to Isola Maggiore for a long lunch of fresh perch and a swim in clear water.

### The Saturday market in Camucia

Down on the plain, just below Cortona. Cheeses, salumi, vegetables, and the cookware everyone in Tuscany seems to own. The shopping morning of the trip.

Travel Advisor

## Let our specialists *plan your trip*

From the right villa to private chefs, boat charters, and bespoke experiences, we take care of every detail.

[Email a travel advisor](https://villavacations.com/contact-us/)

[Call 1 (800) 409-4346](tel:+18004094346)

Beyond the Villa

## Day *trips*

### Montepulciano & Pienza

Forty-five minutes south into the Val d'Orcia. A Nobile di Montepulciano tasting in the morning, pecorino in Pienza for lunch, the most photographed valley in Italy in between.

### Assisi

Fifty minutes east, across the border into Umbria. The Basilica of San Francesco with its Giotto frescoes, the medieval town in pink Subasio stone, dinner in the Eremo delle Carceri woods.

### Perugia

One hour east. The medieval centro storico, the Galleria Nazionale dell'Umbria, the underground Etruscan well, and Perugia's chocolate.

### Arezzo

Forty-five minutes north. The Piero della Francesca fresco cycle in San Francesco, the antiques market on the first Sunday of each month, and dinner in a 14th-century courtyard.

### Siena

Ninety minutes northwest. The Campo, the Duomo, and a trattoria lunch in the Crete Senesi just south.

### Rome

Ninety minutes by car, two hours by train from Camucia–Cortona. A long day or an overnight — the Vatican Museums before opening, lunch in Trastevere, sleep on the train back.

Climate

## Average *monthly highs*

| January | February | March | April | May | June | July | August | September | October | November | December |
| --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- |
| 50°F | 52°F | 58°F | 64°F | 72°F | 80°F | 85°F | 85°F | 78°F | 66°F | 56°F | 51°F |

Source: long-term monthly averages for the region. Sea temperatures stay comfortable for swimming May through October.

Where it is

## Cortona on the *map*

3 villas in Cortona. Tap a pin to see the villa; locations are approximate. [See all our villas on the map](https://villavacations.com/villa-map/).

Travelers Ask

## Frequently asked *questions*

Cortona is a quieter, slower [Tuscany](https://villavacations.com/destinations/tuscany/). The town itself is medieval and walkable — Piazza della Repubblica, the Palazzo Comunale steps where everyone sits at sunset, the Museo dell'Accademia Etrusca with its Etruscan bronzes, the Diocesan Museum with two Fra Angelicos and a Signorelli.

The countryside is olive groves and small wineries, on the gentle hills that roll down to Lake Trasimeno and the Val di Chiana plain. The Strada del Vino runs through here. You'll drink a lot of Cortona DOC Syrah, which most people have never heard of and most people should.

The food is Chianina beef from the valley below, hand-rolled pici with garlic and tomato, fresh ricotta from local farms, and aged pecorino. Restaurants in town stay genuinely local: Osteria del Teatro, La Bucaccia, Il Cacciatore. A short drive away in Montepulciano and Pienza you have Brunello country and pecorino country at the same time.

Cortona is the right base for travellers who want Tuscany without Tuscany's queue — and who want to be able to reach Rome, Florence, Siena, Assisi, and Umbria all in under two hours.

May, June, and September are our favourite months in Cortona — long warm days, the surrounding vineyards either in flower or in fruit, and the town busy enough to feel alive but never crowded. July and August are hot (mid-80s°F) and August coincides with Italian holidays. Late September into mid-October is the vendemmia and one of the most beautiful times in the area.

Cortona has a typical inland [Tuscan](https://villavacations.com/destinations/tuscany/) climate — hot dry summers and cool wet winters. Monthly highs range from around 50°F in January to 85°F in July and August. Pool weather is reliably mid-May to late September. Spring and autumn are mild and the most pleasant times to walk the hills.

Chianina beef from the valley below (bistecca alla fiorentina at its source), hand-rolled pici with garlic, ricotta gnudi, fresh pecorino, panzanella in summer, wild-boar ragù in autumn, and Cortona DOC Syrah throughout. Don't miss Osteria del Teatro, La Bucaccia, Il Cacciatore, and Locanda del Molino just below the town.

Cooking classes, vineyard tastings at small Syrah producers, Etruscan museum mornings, Lake Trasimeno boat days, antique-market mornings (Camucia on Saturdays), and slow afternoons on the piazza. We can arrange any of it.

Montepulciano and Pienza (45 min south), Assisi (50 min east), Perugia (1 hr east), Arezzo (45 min north), Siena (90 min), Florence (90 min), and Rome (2 hr by train from Camucia–Cortona).

Yes. The town itself is walkable but everything around it — wineries, day trips, restaurants in the surrounding countryside — needs a car. We arrange private drivers for full-day tours.

Yes — better than Florence or Siena if you're staying a week and want a small-town pace. Cortona sits at the meeting point of Tuscany and Umbria, so you can reach Florence, Siena, Assisi, Perugia, Lake Trasimeno, and the Val d'Orcia all in under two hours.

[See our full Italian Villa Rentals FAQ →](https://villavacations.com/italian-villa-rentals-faq/)

Cortona — Reading

## From the *journal*

ON SCREEN

### Where Was Under the Tuscan Sun Filmed? Cortona and the Story of Villa Laura

DAY TRIP IDEAS

### Day Trip Ideas from Cortona

ON SCREEN

### Villa Laura Featured by Soft Surroundings

Explore

## Other *destinations*

Each region is hand-picked, walked, and slept in by us first. See which one is calling.

### Amalfi *Coast*

Costiera Amalfitana

### *Chianti*

Classic Tuscany

### *Florence*

Renaissance Tuscany

### Lake *Como*

Lakeside Elegance

[See all destinations](https://villavacations.com/destinations/)

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Doorways Villa Vacations, Italian villa specialists since 1994. Book through a travel advisor: https://villavacations.com/contact-us/