cortona val di chiana villas with pool rentals

Holiday villas with pool in Tuscany, Umbria, Apulia, Amalfi Coast...
Code or Name:

Last update: May 02, 2025

  Order by
AAA stagione 2025 Eurocasa 1

Area: Tuscany: Cortona and Val di Chiana
Number of people: 0
Number of bedrooms: 0
Number of bathrooms: 0
Al Castello

Area: Tuscany: Cortona and Val di Chiana
Number of people: 10
Number of bedrooms: 6
Number of bathrooms: 4
Weekly prices: from 1.800,00 € to 4.400,00 €

Al Castello stands close to the small village of Rigutino near Arezzo, inside the Natural Park of Lignano.  The property has an extension of ​​3 hectares and is made up of an old farmhouse surrounded by over 35,000 sqm of an enclosed property

Al Podere del Monte

9 reviews
Area: Tuscany: Cortona and Val di Chiana
Number of people: 11
Number of bedrooms: 6
Number of bathrooms: 3
Weekly prices: from 2.100,00 € to 3.700,00 €

AL PODERE DEL MONTE with heated Jacuzzi in panorama position

Al Podere del Monte with private pool and whirlpool is uniquely situated on the edge of the medieval hamlet Monte San Savino, in a peaceful panoramic position with views of 180° of the surrounding countryside.

Amarena

1 review
Area: Tuscany: Cortona and Val di Chiana
Number of people: 5
Number of bedrooms: 2
Number of bathrooms: 1
Weekly prices: from 826,00 € to 1.624,00 €

Amarena  is an old, stone farmhouse, wisely restored and situated on an extremely panoramic position, 751 m on the sea level, being part of the very small hamlet of Cantalena Alta.

Borghetto Bevignano

Area: Tuscany: Cortona and Val di Chiana
Number of people: 16
Number of bedrooms: 7
Number of bathrooms: 7
Weekly prices: from 2.310,00 € to 3.500,00 €

Ancient monastery between the provinces of Arezzo and Siena in a panoramic position a few km from the village of Monte San Savino. 15 sleeps, large swimming pool and private tennis court.  

Borghetto Caprile

Area: Tuscany: Cortona and Val di Chiana
Number of people: 11
Number of bedrooms: 5
Number of bathrooms: 5
Weekly prices: from 1.260,00 € to 2.639,00 €

Ancient stone hamlet in an extremely panoramic position overlooking the wooded Val di Chio. Private swimming pool and fenced green space with furnished terrace. The village of Castiglion Fiorentino, with shops and restaurants, is 6 km away.

Borgo Il Santo 12+2

Area: Tuscany: Cortona and Val di Chiana
Number of people: 14
Number of bedrooms: 6
Number of bathrooms: 5
Weekly prices: from 10.010,00 € to 12.070,00 €
Agriturismo with swimming pool, “Borgo Il Santo”, was a small Tuscan farming homestead constructed around the 1850. It is situated in a panoramic position on the Tuscan hillside of Santo Stefano.
Borgo Maggiolino

Area: Tuscany: Cortona and Val di Chiana
Number of people: 28
Number of bedrooms: 13
Number of bathrooms: 13
Borgo Maggiolino is a small borough, hamlet, on the east side of Val di Chio in the Tuscan countryside just a few steps away from Cortona and Umbria.
Borgo Vecchio

1 review
Area: Tuscany: Cortona and Val di Chiana
Number of people: 16
Number of bedrooms: 7
Number of bathrooms: 6
Weekly prices: from 1.470,00 € to 3.800,00 €
Borgo Vecchio is a beautiful farmhouse on the high hills separating the wide green Valdichiana from the high Tevere valley which opens up before your eyes like a vast amphitheater. This villa situated on the border between Tuscany and Umbria
Casa Cinzia

Area: Tuscany: Cortona and Val di Chiana
Number of people: 6
Number of bedrooms: 3
Number of bathrooms: 2
Weekly prices: from 1.012,00 € to 2.284,00 €

Casa Cinzia is a welcoming vacation rental with private swimming pool in the countryside of Pietraia, in the beautiful region of Tuscany.

Casa Giolo

1 review
Area: Tuscany: Cortona and Val di Chiana
Number of people: 14
Number of bedrooms: 6
Number of bathrooms: 6
Weekly prices: from 1.890,00 € to 4.620,00 €

Casa Giolo is an enchanting holiday farmhouse ideal for those of you who want to spend an unforgettable holiday in the warm and relaxing atmosphere of the old farmhouses that still preserve their original architectural features. 

Casa Klementine

Area: Tuscany: Cortona and Val di Chiana
Number of people: 12
Number of bedrooms: 5
Number of bathrooms: 4
Weekly prices: from 1.540,00 € to 2.275,00 €
Casa Klementine is a newly built house situated in the small village of Santa Maria just outside the quaint village of Lucignano.
Casa Melino

8 reviews
Area: Tuscany: Cortona and Val di Chiana
Number of people: 13
Number of bedrooms: 6
Number of bathrooms: 6
Weekly prices: from 2.890,00 € to 4.590,00 €

NEW ALL INCLUSIVE RATES 
Casa Melino is a lovely holiday house set in a beautiful and panoramic position near the small village of Ciggiano in the Province of Arezzo. Monte San Savino is only 5 km away from the villa and it is one of the most important villages of the Valdichiana

Casa Rosina

Area: Tuscany: Cortona and Val di Chiana
Number of people: 12
Number of bedrooms: 5
Number of bathrooms: 4
Weekly prices: from 1.540,00 € to 2.275,00 €
Casa Rosina is surrounded by the country side near Lucignano, a beautiful little town dated back to the middle age, characterized by an elliptic-shape circle of walls. Casa Rosina is a part of a farmhouse which is composed by three floors and small annex.
Casale Annalisa

Area: Tuscany: Cortona and Val di Chiana
Number of people: 18
Number of bedrooms: 9
Number of bathrooms: 8
Weekly prices: from 4.300,00 € to 6.850,00 €

CIN: IT051017 B5XM9 FN4CD

Casale Annalisa, an elegant farmhouse renovated in 2017, is located just a few kilometres from the beautiful Etruscan town of Cortona, in the fertile Chiana Valley which for the ancient Romans was the barn of the eternal city.

Casale Annalisa is a beautiful and comfortable villa suitable for those who want to spend their holidays in an environment that combines the comforts of a modern home with the ancient beauty of the surrounding landscape.

Casale Annalisa 14

Area: Tuscany: Cortona and Val di Chiana
Number of people: 14
Number of bedrooms: 7
Number of bathrooms: 6
Weekly prices: from 4.100,00 € to 6.850,00 €

Casale Annalisa, an elegant farmhouse renovated in 2017, is located just a few kilometres from the beautiful Etruscan town of Cortona, in the fertile Chiana Valley which for the ancient Romans was the barn of the eternal city.

Casale Annalisa is a beautiful and comfortable villa suitable for those who want to spend their holidays in an environment that combines the comforts of a modern home with the ancient beauty of the surrounding landscape.

Casale Brolio

Area: Tuscany: Cortona and Val di Chiana
Number of people: 10
Number of bedrooms: 4
Number of bathrooms: 3
Weekly prices: from 1.295,00 € to 2.065,00 €

Ancient farmhouse amidst olive groves and vineyards a few km from the village of Castiglion Fiorentino. Large private pool and wide outdoor space. Suitable for families or groups of friends who love the rural environment and wish to visit Tuscany.

Casale Mattino

Area: Tuscany: Cortona and Val di Chiana
Number of people: 12
Number of bedrooms: 4
Number of bathrooms: 5
Weekly prices: from 3.380,00 € to 4.070,00 €
Casale mattino is a private villa situated 550 meters above sea level and nestled in an isolated Tuscan hillside surrounded by olive groves and oak trees. It is located 8 km from the town of Castiglion Fiorentino.
Casetta degli Ulivi

Area: Tuscany: Cortona and Val di Chiana
Number of people: 3
Number of bedrooms: 1
Number of bathrooms: 1
Weekly prices: from 735,00 € to 875,00 €

Characteristic small stone house ideal for couples for a romantic holiday. Air conditioning, Wi-Fi available, garden with equipped pergola and small pool. A welcome basket for breakfast is provided free of charge

Casina Cuore

Area: Tuscany: Cortona and Val di Chiana
Number of people: 3
Number of bedrooms: 1
Number of bathrooms: 1
Weekly prices: from 588,00 € to 924,00 €

Casina Cuore is only a few minutes driving from Cortona, town rich in Etruscan reminiscences, works of art of inestimable value and beauty, noble palaces and characteristic lanes. Also the Trasimeno Lake is easily reachable.

Italy Dream Villas by Toskana Holiday GmbH
Toskana Holiday GmbH, Tannenbergstr. 15b, D 23617 Stockelsdorf (Lbeck)
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