cortona val di chiana villas with pool rentals

Holiday villas with pool in Tuscany, Umbria, Apulia, Amalfi Coast...
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Last update: May 01, 2025

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Colle Fiorito 9

Area: Tuscany: Cortona and Val di Chiana
Number of people: 9
Number of bedrooms: 4
Number of bathrooms: 3
Weekly prices: from 2.170,00 € to 3.598,00 €

Colle Fiorito is a lovely villa which comes from the restructuration of an old country house situated in a beautiful and panoramic position.

Il Condottino

4 reviews
Area: Tuscany: Cortona and Val di Chiana
Number of people: 11
Number of bedrooms: 4
Number of bathrooms: 3

Il Condottino is a beautiful rural home placed on the hills covered with olives groves between Castiglion Fiorentino and Cortona, in a very panoramic position and very close to the magnificent medieval castle of Montecchio Vesponi.

Il Palazzo della Fratta

Area: Tuscany: Cortona and Val di Chiana
Number of people: 20
Number of bedrooms: 9
Number of bathrooms: 11
Weekly prices: from 2.730,00 € to 4.130,00 €

Villa Il Palazzo is a beautiful villa with pool located at walking distance from the village of Fratta and 7 km from Cortona. Wi-Fi access, satellite TV, air conditioning. Ideal for groups of 20 people and family reunions.

Il Vecchio Casale del Pozzo

Area: Tuscany: Cortona and Val di Chiana
Number of people: 24
Number of bedrooms: 12
Number of bathrooms: 6
Weekly prices: from 3.815,00 € to 5.600,00 €
IL VECCHIO CASALE DEL POZZO is an ancient villa in the Valdichiana valley of Tuscany , very near to the major cities of art: Siena , Florence , Perugia, Cortona and Assisi . The villa is surrounded by a park of olive-trees ......
La Casina del Biondo

10 reviews
Area: Tuscany: Cortona and Val di Chiana
Number of people: 4
Number of bedrooms: 2
Number of bathrooms: 2
Weekly prices: from 890,00 € to 1.390,00 €

Casina del Biondo is a small stone house, recently renovated, which lies on the hills of the small village of Monte S Savino; the cottage is perfect for a romantic vacation for two or for a small family.

La Madonnina

1 review
Area: Tuscany: Cortona and Val di Chiana
Number of people: 8
Number of bedrooms: 4
Number of bathrooms: 3
Weekly prices: from 3.200,00 € to 4.500,00 €

Surrounded by lush olive groves and majestic Cypress trees, La Madonnina is a recently restored property nestling on a hillside with truly breathtaking views over the Val di Chiana.

La Malva

Area: Tuscany: Cortona and Val di Chiana
Number of people: 10
Number of bedrooms: 4
Number of bathrooms: 3
Weekly prices: from 1.435,00 € to 2.870,00 €

Villa with private pool for 10 people, 4 bedrooms and 3 bathrooms. In a quiet and panoramic position, near Arezzo. The village of Civitella in Valdichiana is about 3 km away.

Olmo

Area: Tuscany: Cortona and Val di Chiana
Number of people: 6
Number of bedrooms: 4
Number of bathrooms: 3
Weekly prices: from 1.064,00 € to 1.820,00 €

Olmo is a typical country house placed on a hill and surrounded by the silvery foliage of olive trees, which create an beautiful and peaceful atmosphere. Situated between Arezzo and Castiglion Fiorentino it offers uncountable opportunities for tourism.

Podere Ciggiano

4 reviews
Area: Tuscany: Cortona and Val di Chiana
Number of people: 8
Number of bedrooms: 3
Number of bathrooms: 2
Weekly prices: from 1.078,00 € to 2.240,00 €

 Podere Ciggiano is a lovely stone farmhouse set in a beautiful and panoramic position near the small village of Ciggiano in the Province of Arezzo. The house dates back to the end of the 700's and has been restructured respecting the tuscan tradition.

Podere Marilena

1 review
Area: Tuscany: Cortona and Val di Chiana
Number of people: 6
Number of bedrooms: 2
Number of bathrooms: 2
Weekly prices: from 840,00 € to 1.281,00 €

The lovely Podere Marilena is an ancient, stone farmhouse recently restored and situated very close to the small village of Cantalena. The old village is about 15 km away from Cortona and Castiglion Fiorentino, two famous medieval towns.

SUNNYHILL

2 reviews
Area: Tuscany: Cortona and Val di Chiana
Number of people: 6
Number of bedrooms: 3
Number of bathrooms: 3
Weekly prices: from 1.540,00 € to 2.520,00 €

SUNNYHILL is located in the area called Valdichiana valley, near Monte San Savino, on top of a soft rolling hill, an ideal location for relaxing holidays and trips dedicated to discovering the art treasures of Tuscany and Umbria.

Tenuta La Selva 14

Area: Tuscany: Cortona and Val di Chiana
Number of people: 14
Number of bedrooms: 7
Number of bathrooms: 6
Weekly prices: from 3.900,00 € to 5.900,00 €

Podere il Borgo di Lucignano is a beautiful property located between the provinces of Arezzo and Siena overlooking the charming village of Lucignano. It is the ideal place for relaxing holidays with your family and with groups of friends, where you can relax and enjoy the countryside and visit the beauties of Tuscany.

Tenuta la Selva 18 Il Borgo di Lucignano

9 reviews
Area: Tuscany: Cortona and Val di Chiana
Number of people: 18
Number of bedrooms: 9
Number of bathrooms: 8
Weekly prices: from 5.000,00 € to 7.200,00 €

Podere il Borgo di Lucignano is a beautiful property located between the provinces of Arezzo and Siena overlooking the charming village of Lucignano.
It is the ideal place for relaxing holidays with your family and with groups of friends, where you can relax and enjoy the countryside but also and above all to come and visit the beauties of Tuscany.

Tenuta La Selva 22 Il Borgo di Lucignano 22

Area: Tuscany: Cortona and Val di Chiana
Number of people: 22
Number of bedrooms: 11
Number of bathrooms: 8
Weekly prices: from 6.500,00 € to 8.800,00 €

This wonderful property, perfectly suited to large groups of friends or families who wish to share their holiday home while retaining some independence, offers everything one could ask for on a Tuscan holiday.

Villa Allegra

Area: Tuscany: Cortona and Val di Chiana
Number of people: 4
Number of bedrooms: 2
Number of bathrooms: 1
Weekly prices: from 1.470,00 € to 2.870,00 €

Ancient stone farmhouse with private pool, situated in a quiet and secluded position, a few km from the village of Monte San Savino. Ideal for the holidays of a family with children or for two couples of friends.

Villa Cappuccetto

Area: Tuscany: Cortona and Val di Chiana
Number of people: 14
Number of bedrooms: 6
Number of bathrooms: 6
Weekly prices: from 2.380,00 € to 3.990,00 €
Villa Cappuccetto is a wonderful villa situated only 1 km outside the medieval village of Castiglion Fiorentino, reachable with a short walk, endowed with shops, cafés and restaurants.
Villa Cleo

Area: Tuscany: Cortona and Val di Chiana
Number of people: 12
Number of bedrooms: 6
Number of bathrooms: 4
Weekly prices: from 2.060,00 € to 3.060,00 €

FLEXIBLE ARRIVAL AND DEPARTURE DAY

VILLA CLEO is a charming, recently renovated Tuscan farmhouse in a splendid panoramic position, on the outskirts of the village of Ciggiano, in the middle of the typical Tuscan landscape. This landscape with its endless fields of wheat and sunflowers harmonizes with the ancient villages on the hills and the villas and farmhouses surrounded by vineyards and olive groves, which produce excellent wine and extra virgin olive oil.

Villa Crispino

Area: Tuscany: Cortona and Val di Chiana
Number of people: 9
Number of bedrooms: 4
Number of bathrooms: 4
Weekly prices: from 2.661,00 € to 4.092,00 €

Villa Crispino is a beautiful villa with pool ready to receive you for a elegant vacation in Tuscany. At every occasion this beautiful villa will give its guests a memorable experience under the sign of luxury.

Villa del Giotto

Area: Tuscany: Cortona and Val di Chiana
Number of people: 10
Number of bedrooms: 4
Number of bathrooms: 5

Stone villa accessible by wheelchair, situated in a hilly position 2 km from the village of Castiglion Fiorentino. Private swimming pool with hydromassage corner and tennis court for the enjoyment of adults and children.

Villa Fringuello

Area: Tuscany: Cortona and Val di Chiana
Number of people: 6
Number of bedrooms: 3
Number of bathrooms: 3

Old stone villa of peasant origins, perfect for holidays with friends or family. Three bedrooms, ample space and private pool. Situated not far from the village of Castiglion Fiorentino, at the gateway to the Val di Chio.

Italy Dream Villas by Toskana Holiday GmbH
Toskana Holiday GmbH, Tannenbergstr. 15b, D – 23617 Stockelsdorf (Lübeck)
HRB 1773 Bad Schwartau - UStID: DE214233350 Tel. 0451/479 98 05 - Fax. 0451/479 98 17
Customer Service Tuscany - Monika Wunderlich - Monte San Savino.
0049-(0)151 61 55 73 58 - 0039-348-811 90 33