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Cortona villas
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97 Villa rentals in Cortona

Holiday Homes with a Pool in Cortona, Italy

Plunge into a cool, private pool after working up a massive sweat on the trails at mountain houses in Cortona, Italy.

450 M² House ∙ 10 Bedrooms ∙ 14 Guests - Cortona
No reviews

450 M² House ∙ 10 Bedrooms ∙ 14 Guests

house, Cortona
This large Tuscan villa is situated in a tranquil hamlet a short 5km drive from Cortona's historic centre, offering easy access to Siena (under 100km) and Lake Trasimeno (15km).
The 450 square metre property boasts 10 bedrooms, 11 bathrooms, and a private swimming pool, comfortably accommodating up to 16 guests, and features a 'Sala della Pastaia' dining room and a pietra serena staircase.
Villa Cortonese - Fifteen Bedroom Villa, Sleeps 34 - Cortona
No reviews

Villa Cortonese - Fifteen Bedroom Villa, Sleeps 34

house, Cortona
This historic 17th-century Tuscan villa is located on the hillsides of Cortona, 28 kilometres from Arezzo, within easy reach of Siena, Perugia, Assisi, and Florence.
This 550 square metre manor offers 15 bedrooms, accommodation for 34 guests, a swimming pool, air conditioning, and is set within an 8-hectare park with opportunities for equestrian excursions and pitch & putt golf.
Holiday Home Il Cherubino By Interhome - Cortona
No reviews

Holiday Home Il Cherubino By Interhome

house, Cortona
This Cortona vacation home is located 29 km from Piazza Grande and 38.6 km from Montepulciano Terme, making it an ideal base for exploring the beautiful Tuscan countryside. It has received excellent user ratings, indicating a high level of satisfaction from previous guests.
The property spans 328 square metres and comfortably accommodates up to 13 guests, with seven bedrooms and six bathrooms. Guests can enjoy a private pool, a fully equipped kitchen, air conditioning, a garden, and free parking.
Casa La Fonte By Posarellivillas - Cortona
9.9 68 reviews

Casa La Fonte By Posarellivillas

house, Cortona
La Fonte by PosarelliVillas is located just outside Cortona's centre, a short drive from Piazza Grande and the thermal baths of Montepulciano Terme, offering a peaceful escape with stunning views. The property has received excellent ratings for location, cleanliness, and user experience.
This 160 square metre, 3-bedroom villa comfortably accommodates up to 6 guests. The property features a private pool and patio, a fully equipped kitchen, air conditioning, Wi-Fi, and a garden, allowing guests to enjoy both indoor and outdoor relaxation.

Best Cortona villas and holiday homes with a kitchen

Dependance 2 Pax - Cortona
9.1 48 reviews

Dependance 2 Pax

house, Cortona
Dependance 2 pax is situated just a short drive from Cortona's historic centre, offering easy access to attractions like Piazza Grande, San Severo Church, and Montepulciano Terme, while enjoying a peaceful location away from the hustle and bustle. The accommodation has received very good ratings for its cleanliness and user experience, and an excellent rating for its location.
This charming property features a private terrace and balcony, perfect for enjoying stunning views and fresh air. You'll also find a fully equipped kitchen, air conditioning, free private parking, and a garden with a swimming pool and tennis court, making it ideal for a relaxing and enjoyable stay.
Villa In Cortona With Pool - Cortona
8.9 154 reviews

Villa In Cortona With Pool

house, Cortona
Villa Nigra is situated in Cortona, just 30km from Piazza Grande and 37km from Montepulciano Terme, making it an ideal base for exploring the charming Tuscan countryside. The property has received very good ratings for cleanliness and user experience, with an excellent location rating.
This holiday home offers a private swimming pool, a fitness centre, and air conditioning for a comfortable stay. Guests can enjoy a fully equipped kitchen, an outdoor terrace with barbecue facilities, free Wi-Fi, a peaceful garden, a sauna, a spa, and parking.
Villa In Il Castagno With 4 Bedrooms Sleeps 8 - Cortona
10 1 review

Villa In Il Castagno With 4 Bedrooms Sleeps 8

house, Cortona
Villa Eleonora is a recently renovated country house, located 5 kilometres from Cortona, offering unparalleled panoramic views of the Tuscan countryside from a private, elevated setting.
This 170 square metre villa accommodates up to 8 guests across 3 bedrooms, featuring 5 bathrooms, air conditioning, Wi-Fi, a private swimming pool set within 2 hectares of olive groves, and a garden with a barbecue and wood-burning oven.
Cottage Contadina - Cortona
9.0 40 reviews

Cottage Contadina

house, Cortona
This rustic cottage, sleeping four, is situated 6km from Cortona's centre, 30km from Lake Trasimeno, and enjoys a secluded woodland setting at 800m above sea level, offering easy access to Arezzo (32km), Florence (100km), Siena (80km), and Perugia (40km).
The 75 square metre property boasts a private garden, swimming pool, terrace, and amenities including a washing machine, barbecue, and outdoor shower; a cot and highchair are available for families, and one dog is welcome.

Frequently asked questions about villa rentals in Cortona

  • What are the must-see attractions in and around Cortone?

    Cortona is a beautiful medieval town with many attractions. The Etruscan Museum is a must-see, as is the Palazzo Comunale with its stunning frescoes. For beautiful views, climb to the top of the Fortezza di Cortona, a 13th-century fortress. If you're looking for a day trip, the nearby Trasimeno Lake is a popular destination for swimming, boating, and exploring.
  • What are the best villa rentals in Cortona?

  • What types of wildlife can travelers expect to see in the area of Cortone?

    The area around Cortona is home to a variety of wildlife. You might spot birds of prey like buzzards and kestrels soaring in the sky. In the surrounding countryside, you may encounter wild boar, foxes, and hares. If you're lucky, you might even see a rare Italian wolf.
  • What are the best villa rentals with a pool in Cortona?

  • What is the best time to visit Cortone?

    Cortona is a beautiful town year-round, but the best time to visit is during spring (April-May) or autumn (September-October). The weather is pleasant, and the crowds are smaller. Summer can be hot and crowded, while winter can be chilly and rainy.
  • What are the best villa rentals with a jacuzzi in Cortona?

  • When is it easiest to book a villa rental in Cortone?

    The easiest time to book a villa rental in Cortona is during the shoulder seasons (spring and autumn). Prices are usually lower, and there is less competition for rentals. If you're looking for a villa during the peak season (summer), book well in advance, especially if you want a specific property.
  • What are the best villa rentals for families and kids in Cortona?

  • What are the top hiking trails near Cortone?

    There are many great hiking trails near Cortona. The Sentiero della Bonaccia is a popular choice, offering stunning views of the Valdichiana valley. Another great option is the Sentiero del Lago Trasimeno, which follows the shores of Lake Trasimeno. For a more challenging hike, try the Sentiero del Monte Cetona.
  • What are the best pet friendly villa rentals in Cortona?

    The best pet friendly villa rentals in Cortona are Wonderful Casa Idilio Cortona, Charming House In Cortona - Tuscany and La Casa Di Letizia.

  • What are the advantages of renting a house or a villa in Cortone

    Renting a villa in Cortona offers a more private and spacious accommodation option compared to a hotel. You have your own kitchen and living space, allowing you to cook your own meals and relax in comfort. It's also a great option for families or groups of friends traveling together.
  • What are the best villa rentals with parking in Cortona?

  • Are there popular destinations near Cortone?

    Yes, there are many popular destinations near Cortona. Lake Trasimeno is a short drive away and offers water sports, boat trips, and charming towns like Castiglione del Lago. Arezzo is a beautiful medieval city with a rich history and art scene. The Tuscan countryside is also easily accessible, with vineyards, olive groves, and charming villages to explore.

Popular destinations

Holiday Homes with a Fireplace in Cortona, Italy

Find mountain houses with a fireplace in Cortona, Italy for cosy alpine evenings.

Holiday Home Cottage Contadina By Interhome - Cortona
9.5 2 reviews

Holiday Home Cottage Contadina By Interhome

house, Cortona
Holiday Home Cottage Contadina, located in Cegliolo, offers a peaceful countryside escape near Cortona, approximately 30km from Piazza Grande and 39km from Montepulciano Terme.
This 75 square metre cottage features one bedroom, one bathroom, a fully equipped kitchen, a private terrace and garden, a swimming pool, and parking; perfect for couples or small families.
Corte Della Luna - Cortona
9.5 34 reviews

Corte Della Luna

house, Cortona
Corte della Luna is a detached villa located in Cortona, 27 kilometres from Piazza Grande and 39 kilometres from Montepulciano Terme.
This family-friendly villa offers four bedrooms, a private swimming pool, extensive gardens, air conditioning, WiFi, and private parking.
Casa Le Celle - Cortona
9.0 6 reviews

Casa Le Celle

house, Cortona
Casa Le Celle is a detached holiday home located near Cortona, approximately 34 kilometres from Perugia and 27 kilometres from Arezzo.
This 140 square metre property offers four bedrooms, a private swimming pool, a garden, a terrace, free Wi-Fi and free parking, making it a comfortable and convenient choice for families or groups of up to eight people.
Borgo Syrah - Cortona
8.7 28 reviews

Borgo Syrah

house, Cortona
Borgo Syrah, near Cortona, offers self-catering villas with private entrances, situated 37 kilometres from Piazza Grande and 31 kilometres from Montepulciano Terme.
Each villa provides air conditioning, a private garden, swimming pool access, free Wi-Fi, parking, and features well-equipped kitchens including dishwashers and fridges; pets are welcome.

Houses with a Hot Tub in Cortona, Italy

Soak under a canopy of pine trees in a steaming outdoor hot tub at mountain houses with a hot tub in Cortona, Italy.

250 M² Villa ∙ 5 Bedrooms ∙ 12 Guests - Cortona
No reviews

250 M² Villa ∙ 5 Bedrooms ∙ 12 Guests

house, Cortona
This villa is situated in a district of Cortona, offering straightforward access to local landmarks and attractions.
This spacious villa, covering 250 square meters, accommodates up to 12 guests with 5 bedrooms, multiple kitchens, living areas, indoor and outdoor dining, a garden with a swimming pool, hot tub, and barbecue facilities, all equipped with air conditioning and WiFi.
Casa Primo Stylish-townhouse W/ Patio & Jetted Tub - Cortona
10 73 reviews

Casa Primo Stylish-townhouse W/ Patio & Jetted Tub

house, Cortona
Casa Primo, a two-bedroom holiday home in Cortona's historic centre, offers easy walking access to shops, restaurants, and major landmarks.
This excellently-rated property sleeps four guests and boasts a private garden, Jacuzzi, air conditioning, and a fully equipped kitchen including a dishwasher, all within a short distance of artisan workshops and art galleries.
Villa Casupoli - Cortona
10 1 review

Villa Casupoli

house, Castiglion Fiorentino
Villa Casupoli, a secluded property 24 kilometres from Castiglion Fiorentino's Piazza Grande, offers tranquil accommodation with easy access to the town.
This 160 square metre villa boasts three bedrooms, five bathrooms, and can comfortably sleep eleven guests, featuring a private pool, hot tub, and terrace with barbecue facilities.
Borgo Dolci Colline Resort - Cortona
8.7 3 reviews

Borgo Dolci Colline Resort

farm, Castiglion Fiorentino
Borgo Dolci Colline Resort is located in Castiglion Fiorentino, approximately 21 kilometres from Piazza Grande and 43 kilometres from Montepulciano Terme, with Magione Motorspeedway 45 kilometres away.
This farm stay offers units with kitchen facilities, air conditioning, a swimming pool with garden views, and a sauna, with free private parking and bed linen and towels provided, and guests can enjoy nearby cycling activities and is 48 kilometres from Parco Sculpture Del Chianti.

See Guest-Favourite High-End Houses in Cortona, Italy

Experience rugged nature with elite five-star comforts and sweeping peak views at luxury mountain houses in Cortona, Italy.

Casa Bordoli - Cortona
9.7 13 reviews

Casa Bordoli

house, Cortona

Find the Best Family Holiday Homes in Cortona, Italy

Give the kids a classic wilderness adventure with a massive timber home and outdoor space at family mountain houses in Cortona, Italy.

Agriturismo Fattoria Podere Peciano - Cortona
9.6 70 reviews

Agriturismo Fattoria Podere Peciano

farm, Cortona
The Small Castle - Cortona
9.6 27 reviews

The Small Castle

house, Cortona
Margherita Holiday Home - Cortona
9.4 65 reviews

Margherita Holiday Home

farm, Cortona
Monastero San Silvestro - Cortona
9.1 674 reviews

Monastero San Silvestro

farm, Cortona
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