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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

Villa Pozzonovo is an old stone farmhouse within walking distance of the centre of Castiglion Fioren
5.0/5
£237  night
8
3
3
Details View Offers
Wonderful private villa for 12 guests with AWonderful private villa for 12 guests with A/C, WIFI, TV, pets allowed and parking/C, WIFI, TV, pets allowed and parking
£388  night
12
6
5
Details View Offers
Belvilla by OYO Seccatoio
4.0/5
£179  night
6
3
2
Details View Offers
Villa Senaia tuscan charm country house
5.0/5
£489  night
8
4
3
Details View Offers
tuscan charming cottage
5.0/5
£489  night
8
4
3
Details View Offers
Villa in Cortona with 3 bedrooms sleeps 8
£330  night
8
3
3
Details View Offers
Villa Farneta Comfortable holiday residence
£3031  night
17
8
7
Details View Offers
Belvilla by OYO Villa San Pietro
5.0/5
£534  night
14
7
10
Details View Offers
Villa Fornace Comfortable holiday residence
£2139  night
29
14
13
Details View Offers
Casa Liliana In Cortona, Tuscany
£503  night
10
5
5
Details View Offers
Beautiful apartment in villa for 6 guests with WIFI, pool, TV, patio and parking
£112  night
6
3
2
Details View Offers
Villa Casale Federica Large Private Pool, WiFi
4.9/5
£299  night
14
7
3
Details View Offers
Villa Lugnano, villa with private pool perfect for families or groups
£515  night
18
7
4
Details View Offers
Beautiful Tuscan Country-House and Grounds (get in touch for events & weddings)
£303  night
15
7
5
Details View Offers
Villa San Vicenzo By MMega
£347  night
12
5
5
Details View Offers
Beautiful private villa with WIFI, private pool, ABeautiful private villa with WIFI, private pool, A/C, TV, veranda and parking, close to Cortona/C, TV, veranda and parking, close to Cortona
5.0/5
£198  night
10
4
3
Details View Offers
Marvelous Villa Offering Enchanting Panorama View
£985  night
22
9
9
Details View Offers
Villa la Ghiandaia By MMega
£396  night
6
3
3
Details View Offers
Nice apartment in villa for 2 people with WIFI, ANice apartment in villa for 2 people with WIFI, A/C, TV, pets allowed and parking/C, TV, pets allowed and parking
£98  night
2
1
1
Details View Offers
Villa Giare - Holiday Rental in Valdichiana, Tuscany
5.0/5
£1071  night
24
12
13
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.

Picture of two young girls swimming in a pool with their floatation rings
Family friendly villas
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Image of a woman swimming in a pool at a holiday home
Private pool villas
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Villas near golf course
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Villas in Cortona

Villa Pozzonovo is an old stone farmhouse within walking distance of the centre of Castiglion Fioren
5.0/5
£237  night
8
3
3
Details View Offers
Wonderful private villa for 12 guests with AWonderful private villa for 12 guests with A/C, WIFI, TV, pets allowed and parking/C, WIFI, TV, pets allowed and parking
£388  night
12
6
5
Details View Offers
Belvilla by OYO Seccatoio
4.0/5
£179  night
6
3
2
Details View Offers
Villa Senaia tuscan charm country house
5.0/5
£489  night
8
4
3
Details View Offers
tuscan charming cottage
5.0/5
£489  night
8
4
3
Details View Offers
Villa in Cortona with 3 bedrooms sleeps 8
£330  night
8
3
3
Details View Offers
Villa Farneta Comfortable holiday residence
£3031  night
17
8
7
Details View Offers
Belvilla by OYO Villa San Pietro
5.0/5
£534  night
14
7
10
Details View Offers
Villa Fornace Comfortable holiday residence
£2139  night
29
14
13
Details View Offers
Casa Liliana In Cortona, Tuscany
£503  night
10
5
5
Details View Offers
Beautiful apartment in villa for 6 guests with WIFI, pool, TV, patio and parking
£112  night
6
3
2
Details View Offers
Villa Casale Federica Large Private Pool, WiFi
4.9/5
£299  night
14
7
3
Details View Offers
Villa Lugnano, villa with private pool perfect for families or groups
£515  night
18
7
4
Details View Offers
Beautiful Tuscan Country-House and Grounds (get in touch for events & weddings)
£303  night
15
7
5
Details View Offers
Villa San Vicenzo By MMega
£347  night
12
5
5
Details View Offers
Beautiful private villa with WIFI, private pool, ABeautiful private villa with WIFI, private pool, A/C, TV, veranda and parking, close to Cortona/C, TV, veranda and parking, close to Cortona
5.0/5
£198  night
10
4
3
Details View Offers
Marvelous Villa Offering Enchanting Panorama View
£985  night
22
9
9
Details View Offers
Villa la Ghiandaia By MMega
£396  night
6
3
3
Details View Offers
Nice apartment in villa for 2 people with WIFI, ANice apartment in villa for 2 people with WIFI, A/C, TV, pets allowed and parking/C, TV, pets allowed and parking
£98  night
2
1
1
Details View Offers
Villa Giare - Holiday Rental in Valdichiana, Tuscany
5.0/5
£1071  night
24
12
13
Details View Offers