tuscany: cortona and val di chiana - italy dream villas

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

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Villa Glory

Area: Tuscany: Cortona and Val di Chiana
Number of people: 8
Number of bedrooms: 4
Number of bathrooms: 3
Weekly prices: from 1.000,00 € to 3.392,00 €

By renting this villa in Tuscany you will enjoy your holiday in a unique and prestigious property, also offering to your guests a charming vacation. At every time in the year this villa will ensure unforgettable and unique memories.

Villa Granducato di Toscana

Area: Tuscany: Cortona and Val di Chiana
Number of people: 33
Number of bedrooms: 17
Number of bathrooms: 13
Weekly prices: from 8.750,00 € to 11.970,00 €

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Villa Granducato di Toscana is perfect for reunions with your friends or your family and to celebrate events amidst the Tuscan countryside in a perfect combination of sport and relax. 

Villa Granducato di Toscana
is a luxury estate with private pool, tennis court and golf.
An ideal destination for a family / friends reunion or a celebration event that can comfortably accommodate 33 persons. Panoramic position close by Arezzo and Monte San Savino.

Villa Il Guardiano

Area: Tuscany: Cortona and Val di Chiana
Number of people: 10
Number of bedrooms: 4
Number of bathrooms: 4
Weekly prices: from 3.380,00 € to 4.070,00 €
Villa Il Guardiano is nestled in the Tuscan hillside covered by an olive grove at 350 meters above sea level in a panoramic position showcasing the town of Castiglion Fiorentino which is only 2 km away.
Villa Ortensia

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 Ortensia is a typical Tuscan stone villa, renovated while preserving the farmers houses characteristics: open large fireplaces, wooden beams and terracotta floors. The style furniture, the ancient pottery and the local antiques give the villa a warm and welcoming atmosphere.

Villa Ovidio

5 reviews
Area: Tuscany: Cortona and Val di Chiana
Number of people: 12
Number of bedrooms: 6
Number of bathrooms: 6
Weekly prices: from 3.345,00 € to 5.830,00 €
Villa Ovidio is a wonderful villa with stunning views on a unique beautiful Tuscan landscape. Perched on top of a hill, in a scenic and secluded position, it offers modern facilities such as a very well equipped kitchen, Jacuzzi, sauna, airconditioning
Villa PUCCI

2 reviews
Area: Tuscany: Cortona and Val di Chiana
Number of people: 12
Number of bedrooms: 6
Number of bathrooms: 6

The property is located in the small town of Monte San Savino in a hilly and panoramic position about 1 km from a small village, Alberoro, with every basic service. The location is strategic and ideal to reach the most important communication routes and the main towns of Tuscany and Umbria.

Villetta Cortona

Area: Tuscany: Cortona and Val di Chiana
Number of people: 6
Number of bedrooms: 3
Number of bathrooms: 2
Weekly prices: from 1.166,00 € to 3.074,00 €
Villetta Cortona is one of the most charming villas in Tuscany, lovely stone farmhouse situated in a panoramic and peaceful location offering splendid views over the Chiana Valley and over the ancient church S. Maria delle Grazie al Calcinaio.
Casa Melino 9

1 review
Area: Tuscany: Cortona and Val di Chiana
Number of people: 9
Number of bedrooms: 5
Number of bathrooms: 5
Weekly prices: from 2.090,00 € to 3.790,00 €

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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. This property has been transformed into a comfortable holiday villa with private pool

Dimora Michelangelo

Area: Tuscany: Cortona and Val di Chiana
Number of people: 18
Number of bedrooms: 9
Number of bathrooms: 10
Weekly prices: from 5.800,00 € to 9.100,00 €

Dimora Michelangelo is situated in the centre of Valdichiana, between Arezzo and Cortona at the top of a hill that dominates a scene of pleasant tuscan countryside with green fields and ancient villages. The relais is a typical old country residence, renovated..

Villa di Mezzo

Area: Tuscany: Cortona and Val di Chiana
Number of people: 10
Number of bedrooms: 6
Number of bathrooms: 5
Weekly prices: from 2.950,00 € to 3.750,00 €

Villa di Mezzo is a beautiful and ancient stone farmhouse recently renovated located just 10 km from the renowned town of Cortona. The fully fenced property with an automatic gate has a private swimming pool and a large garden with a panoramic view of the Valdichiana.

Casina Pina

1 review
Area: Tuscany: Cortona and Val di Chiana
Number of people: 4
Number of bedrooms: 1
Number of bathrooms: 1
Weekly prices: from 910,00 € to 1.456,00 €
Casina Pina is a cozy holiday house with pool, ideal for 2 people, situated in the heart of the Val di Chio, just a few kilometres far from the beautiful medieval village of Castiglion Fiorentino.
IL Roseto di Cortona 12

Area: Tuscany: Cortona and Val di Chiana
Number of people: 12
Number of bedrooms: 6
Number of bathrooms: 5
Weekly prices: from 2.750,00 € to 4.950,00 €
Il Roseto di Cortona is a beautiful stone villa with private pool and hydro-massage tub. The fully fenced and well kept garden with part of a wood plenty of roses and geraniums together with the high level furnishings will guarantee relax and comfort.
Casa Farneta

Area: Tuscany: Cortona and Val di Chiana
Number of people: 12
Number of bedrooms: 6
Number of bathrooms: 4
Weekly prices: from 1.800,00 € to 3.490,00 €

CASA FARNETA is a beautiful farmhouse recently restored and located only 2 km from the roman Abbazia di Farneta, a historic abbey located only 15 km from Cortona. 

The villa is the ideal location for a Tuscan holiday, enabling guests to explore one of the most beautiful region of the country, close to the most important art cities such as Florence, Pisa, Siena, Lucca and San Gimignano. 

San Savino

1 review
Area: Tuscany: Cortona and Val di Chiana
Number of people: 10
Number of bedrooms: 4
Number of bathrooms: 3
Weekly prices: from 1.715,00 € to 3.080,00 €

San Savino is a pretty old stone farmhouse with private pool, located in the hills surrounding the town of Monte San Savino. The property is completed with a beautiful and fenced garden equipped with outdoor furniture.

Casa Tuori

Area: Tuscany: Cortona and Val di Chiana
Number of people: 9
Number of bedrooms: 4
Number of bathrooms: 2
Weekly prices: from 1.155,00 € to 2.345,00 €
Casa Tuori is situated in a strategic area of Tuscany and set in a extremely panoramic position on the high hills between Val d'Ambra and the Valdichiana. The furniture is refined and comfortable. The farm produces excellent extra-virgin organic olive oil
La Montanella

Area: Tuscany: Cortona and Val di Chiana
Number of people: 4
Number of bedrooms: 2
Number of bathrooms: 1
Weekly prices: from 728,00 € to 1.344,00 €
La Montanella is a typical farmhouse which has been recently renovated but still maintaining its original architectural features. It is situated a few kilometres from Castiglion Fiorentino and Cortona.
Villa Foscola

Area: Tuscany: Cortona and Val di Chiana
Number of people: 8
Number of bedrooms: 3
Number of bathrooms: 3
Weekly prices: from 1.351,00 € to 2.590,00 €

Villa Foscola is a beautiful house situated on the slopes of one of the hills which face the Senese Valdichiana, which has been carefully restored. It takes advantage of a panoramic and quiet position, very close to Lucignano, village in Southern Tuscany.

Casa Lara

Area: Tuscany: Cortona and Val di Chiana
Number of people: 2
Number of bedrooms: 1
Number of bathrooms: 1
Weekly prices: from 500,00 € to 700,00 €
Casa Lara is a cozy studio with separate entrance and common use of the pool, located in a wing of the beautiful villa inhabited by the owners. It is the ideal destination for a couple looking for relax and the proximity of the top destinations of Tuscany
Casale Ivano

Area: Tuscany: Cortona and Val di Chiana
Number of people: 10
Number of bedrooms: 4
Number of bathrooms: 4
Weekly prices: from 1.029,00 € to 2.590,00 €
Casale Ivano is a beautiful villa and cottage on the edge of the tiny hamlet of Palazzuolo, with old pine trees that shade the beautiful garden which has lovely views all around.
La Vecchia Aia

Area: Tuscany: Cortona and Val di Chiana
Number of people: 18
Number of bedrooms: 9
Number of bathrooms: 6
Weekly prices: from 1.365,00 € to 3.920,00 €
La Vecchia Aia is an old stone farmhouse located a few kilometers from Cortona. It is an ideal location for a large group of friends or with children as it is equipped with 2 pools, tennis court, fishing lake,table tennis, table football, childrens' games
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