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Holiday villas with pool in Tuscany, Umbria, Apulia, Amalfi Coast...
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Last update: Jun 16, 2025

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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.

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.

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 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.

Villa La Fonte

3 reviews
Area: Tuscany: Cortona and Val di Chiana
Number of people: 8
Number of bedrooms: 3
Number of bathrooms: 3
Weekly prices: from 1.155,00 € to 2.695,00 €

Villa La Fonte is a beautiful old farmhouse set in a lovely position on the hills around the old medieval town of Castiglion Fiorentino that also has Roman origins. Dominated by its ancient tower the town today is full of shops and services.

Il Roseto di Cortona 8

Area: Tuscany: Cortona and Val di Chiana
Number of people: 8
Number of bedrooms: 4
Number of bathrooms: 4
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.
Poggio Savino

Area: Tuscany: Cortona and Val di Chiana
Number of people: 8
Number of bedrooms: 4
Number of bathrooms: 2
Weekly prices: from 1.715,00 € to 3.080,00 €
Poggio Savino is set in a lovely position just outside Monte San Savino (about 500 m), in the province of Arezzo. The house is equipped with tennis court and swimming pool.
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.

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.

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

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 Chianina

Area: Tuscany: Cortona and Val di Chiana
Number of people: 9
Number of bedrooms: 4
Number of bathrooms: 4
Weekly prices: from 980,00 € to 1.750,00 €
La Chianina is and old farmhouse situated in the Valdichiana Valley with private pool and comfortable furnishing to offer hospitality to whomever wish to spend a relaxing holiday in the charming Tuscan countryside.
La Primavera

Area: Tuscany: Cortona and Val di Chiana
Number of people: 9
Number of bedrooms: 4
Number of bathrooms: 2

Rustic house with a beautiful view set on the border between Tuscany and Umbria.
Fully fenced garden and swimming pool, ideal for holidays with your 4-legged friends.
About 5 km away lies the characteristic village of Mercatale.

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

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.

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.

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 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 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.

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