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Villas in Cortona, Tuscany

Escape to Tuscany's hidden gem: discover luxurious villas, rich history, and breathtaking views in Cortona, Italy.

Villas in Cortona

Beautiful private villa for 18 people with ABeautiful private villa for 18 people with A/C, WIFI, hot tub, private pool, TV, patio and parking/C, WIFI, hot tub, private pool, TV, patio and parking
£1001  night
18
9
10
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Belvilla by OYO Diana
5.0/5
£262  night
12
6
8
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Tuscany holiday rental
£833  night
16
9
11
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Casale Fonteluccia - Two Bedroom Villa, Sleeps 4
£393  night
4
2
2
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Casa Laura - Holiday Rental in Montecchio, Tuscany
5.0/5
£136  night
4
2
2
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10 people villa with stunning views of Trasimeno lake, Cortona and Umbria area
£403  night
10
5
3
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COPPA DI SOPRA - Beautiful villa with superb view
5.0/5
£150  night
6
6
6
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Fiordaliso
4.3/5
£71  night
4
1
1
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Casa White - Holiday Home with private pool and big garden near Castiglion Fiorentino, in Tuscany
5.0/5
£622  night
12
5
3
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VILLA SERENA x6 Beautiful villa surrounded by nature, with swimming pool just 1 km from Cortona
£640  night
6
1
3
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Beautiful private villa for 10 people with WIFI, ABeautiful private villa for 10 people with WIFI, A/C, private pool, TV and parking, close to Cor.../C, private pool, TV and parking, close to Cor...
£852  night
10
5
6
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Beautiful private villa for 4 people with ABeautiful private villa for 4 people with A/C, private pool, WIFI, TV and parking, close to Cort.../C, private pool, WIFI, TV and parking, close to Cort...
4.8/5
£120  night
4
1
1
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405372
£696  night
16
8
5
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Stone farmhouse with private swimming pool, hilly, panoramic and quiet position, surrounded by silve
4.0/5
£115  night
5
2
2
Details View Offers
Private Villa with WIFI, private pool, APrivate Villa with WIFI, private pool, A/C, TV, patio, panoramic view, parking, close to Cortona/C, TV, patio, panoramic view, parking, close to Cortona
5.0/5
£808  night
21
11
10
Details View Offers
Villa Ada is a 5-star Luxury Holiday Villa Available for Weekly Rentals on the Border of Tuscany and Umbria That has Received top Rated Guests Reviews
£1719  night
14
7
7
Details View Offers
Le Volpaie 6+1, Emma Villas
5.0/5
£618  night
7
4
2
Details View Offers
Agri-Tourism Le Capanne, Castiglion Fiorentino-Oli
4.3/5
£121  night
4
2
1
Details View Offers
Villa Gioia near Cortona, Private Pool,Bband,bbq,stunning views.
4.8/5
£343  night
8
3
3
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Villa Colle degli Ulivi with pool in Tuscany
£395  night
14
7
6
Details View Offers

Why a holiday villa in Cortona

Cortona, Tuscany is a hidden gem waiting to be discovered by those seeking a unique and unforgettable villa holiday experience. Nestled on a hilltop overlooking the rolling hills of the Chiana Valley, this charming medieval town offers breathtaking views, rich history, and authentic Italian charm that will leave you enchanted.

Imagine yourself strolling through Cortona's narrow cobblestone streets, admiring the ancient Etruscan ruins, Renaissance palaces, and quaint piazzas. Enjoy a leisurely lunch at one of the many local trattorias, savoring traditional Tuscan cuisine and wine. In the evening, watch the sunset over the countryside from your villa's private garden or pool, before heading out to explore Cortona's vibrant cultural scene.

Cortona is also an ideal base for exploring Tuscany's famous hilltop towns, vineyards, and olive groves. Visit nearby San Gimignano with its medieval towers, Siena with its stunning piazza, or Arezzo with its charming old town. Take a wine-tasting tour or go cycling through the picturesque countryside. With our curated selection of villas in Cortona, you'll find the perfect retreat to relax and unwind after a day of exploring this beautiful region.

From modern villas with private pools and stunning views to restored ancient farmhouses with rustic charm, our collection offers something for every taste and budget. Many of our villas come equipped with all the mod cons, including Wi-Fi, air conditioning, and fully-equipped kitchens. Others offer more traditional Tuscan experiences, such as wood-fired cooking and antique furnishings.

Whether you're looking for a romantic getaway, a family vacation, or a group of friends' reunion, Cortona has something to offer everyone. With its rich history, stunning landscapes, and warm Italian hospitality, this charming town is the perfect destination for your next villa holiday in Tuscany.

When to rent a villa in Cortona

Cortona, Tuscany enjoys a Mediterranean climate, with warm summers and mild winters. The ideal time to visit for a villa holiday is during the spring (April to June) and autumn (September to November), when the weather is pleasant, with average highs around 22°C (72°F). These shoulder seasons offer a more relaxed atmosphere, with smaller crowds and lower prices compared to the peak summer months. The scenery is particularly stunning in these periods, with wildflowers blooming in the countryside and vines ripening on the local vineyards.

If you're looking for a villa holiday experience with warm weather and long days, consider visiting Cortona during July and August, when temperatures often reach the mid-20s (77°F). However, keep in mind that this is peak tourist season, and popular areas may be busier. On the other hand, if you prefer milder weather without the crowds, winter (December to February) can be a great time to visit Cortona, with average highs around 12°C (54°F). Many villas offer discounts during the low season, making it an excellent value for money. If you're planning to enjoy outdoor activities like hiking or biking, spring and autumn are the best times to experience Cortona's beautiful landscape in all its glory.

Where to go in Cortona

Cortona's historic center is a must-visit destination for any villa holiday in this charming town. This medieval gem is packed with narrow cobblestone streets, quaint piazzas, and ancient Etruscan ruins waiting to be explored. Stroll through the streets and admire the stunning architecture, visit the 16th-century Palazzo Comunale, or simply sit back and enjoy a coffee in one of the many charming cafes. For those seeking a more relaxed pace, the hills surrounding Cortona offer peaceful walking trails with breathtaking views over the Chiana Valley.

However, if you're looking for a villa holiday experience that combines relaxation with activity, consider staying in one of the quieter areas on the outskirts of town. San Gimignano-style hilltop villages like Sambuca and Celle sul Rigo offer stunning views, peaceful walks, and easy access to Cortona's amenities. Alternatively, opt for a villa located near Lake Trasimeno, which offers water sports, boat rentals, and breathtaking sunsets. For those seeking a beach experience, head to the nearby Lake Chiusi or explore the coastal towns of Castiglione della Pescaia and Grosseto, both about an hour's drive from Cortona.

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Family friendly villas
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Private pool villas
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Villas near golf course
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Villas in Cortona

Beautiful private villa for 18 people with ABeautiful private villa for 18 people with A/C, WIFI, hot tub, private pool, TV, patio and parking/C, WIFI, hot tub, private pool, TV, patio and parking
£1001  night
18
9
10
Details View Offers
Belvilla by OYO Diana
5.0/5
£262  night
12
6
8
Details View Offers
Tuscany holiday rental
£833  night
16
9
11
Details View Offers
Casale Fonteluccia - Two Bedroom Villa, Sleeps 4
£393  night
4
2
2
Details View Offers
Casa Laura - Holiday Rental in Montecchio, Tuscany
5.0/5
£136  night
4
2
2
Details View Offers
10 people villa with stunning views of Trasimeno lake, Cortona and Umbria area
£403  night
10
5
3
Details View Offers
COPPA DI SOPRA - Beautiful villa with superb view
5.0/5
£150  night
6
6
6
Details View Offers
Fiordaliso
4.3/5
£71  night
4
1
1
Details View Offers
Casa White - Holiday Home with private pool and big garden near Castiglion Fiorentino, in Tuscany
5.0/5
£622  night
12
5
3
Details View Offers
VILLA SERENA x6 Beautiful villa surrounded by nature, with swimming pool just 1 km from Cortona
£640  night
6
1
3
Details View Offers
Beautiful private villa for 10 people with WIFI, ABeautiful private villa for 10 people with WIFI, A/C, private pool, TV and parking, close to Cor.../C, private pool, TV and parking, close to Cor...
£852  night
10
5
6
Details View Offers
Beautiful private villa for 4 people with ABeautiful private villa for 4 people with A/C, private pool, WIFI, TV and parking, close to Cort.../C, private pool, WIFI, TV and parking, close to Cort...
4.8/5
£120  night
4
1
1
Details View Offers
405372
£696  night
16
8
5
Details View Offers
Stone farmhouse with private swimming pool, hilly, panoramic and quiet position, surrounded by silve
4.0/5
£115  night
5
2
2
Details View Offers
Private Villa with WIFI, private pool, APrivate Villa with WIFI, private pool, A/C, TV, patio, panoramic view, parking, close to Cortona/C, TV, patio, panoramic view, parking, close to Cortona
5.0/5
£808  night
21
11
10
Details View Offers
Villa Ada is a 5-star Luxury Holiday Villa Available for Weekly Rentals on the Border of Tuscany and Umbria That has Received top Rated Guests Reviews
£1719  night
14
7
7
Details View Offers
Le Volpaie 6+1, Emma Villas
5.0/5
£618  night
7
4
2
Details View Offers
Agri-Tourism Le Capanne, Castiglion Fiorentino-Oli
4.3/5
£121  night
4
2
1
Details View Offers
Villa Gioia near Cortona, Private Pool,Bband,bbq,stunning views.
4.8/5
£343  night
8
3
3
Details View Offers
Villa Colle degli Ulivi with pool in Tuscany
£395  night
14
7
6
Details View Offers