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Holiday villas with pool in Tuscany, Umbria, Apulia, Amalfi Coast...
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Last update: Feb 27, 2026

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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 Luigino 18

Area: Tuscany: Pisa and Lucca
Number of people: 18
Number of bedrooms: 9
Number of bathrooms: 11
Weekly prices: from 4.300,00 € to 7.400,00 €
Luigino is immersed in the Alta Valdera, in between Pisa and Volterra, in an estate of about 500 heactres.The property dates back to the beginning of the early 11th century and has seen the change of hand from Monastery (Benedettini followed by Camaldones
Podere Rosmarino

Area: Coast Tuscany: Etruscan Coast
Number of people: 18
Number of bedrooms: 9
Number of bathrooms: 10
Weekly prices: from 5.100,00 € to 7.350,00 €

Podere Rosmarino is a prestigious villa with swimming pool located on the ridge of a hill in the heart of the Etruscan land just a few kilometers from the sea and famous places like Bolgheri, Castagneto Carducci, Volterra and S. Gimignano.

This beautiful villa with pool is ideal for multiple families and large groups.

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.

Villa Capolina

Area: Tuscany: Arezzo and Casentino
Number of people: 18
Number of bedrooms: 9
Number of bathrooms: 5
Weekly prices: from 2.613,00 € to 5.695,00 €
Villa Capolina is a beautiful villa situated in the surroundings of Arezzo in an ancient village dating back to the 12th century.
Villa Merlino

Area: Tuscany: Firenze, Chianti and Valdarno
Number of people: 18
Number of bedrooms: 9
Number of bathrooms: 9
Weekly prices: from 8.480,00 € to 13.250,00 €

This lovely property for 18 persons and private pool is composed of a farmhouse and two barns, restored into a luxurious villa with two annexes:  Villa Merlino is the right choice to offer a prestigious vacation to your family or friends.

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..

Bello Orizzonte

Area: Tuscany: Siena and Val d'Orcia
Number of people: 18
Number of bedrooms: 8
Number of bathrooms: 9
Weekly prices: from 2.489,00 € to 4.970,00 €

Bello Orizzonte is an 8 bedrooms villa dating back to the 19th Century with private pool. It is the ideal starting point to visit to the most important places of Tuscany and Umbria and perfect for large groups up to 18 people.
Villa with private pool and Wi-Fi access, very panoramic location, near the village of Sinalunga. Large outdoor area with terrace with views.

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
Casale  Lucca

Area: Tuscany: Pisa and Lucca
Number of people: 20
Number of bedrooms: 8
Number of bathrooms: 8
Weekly prices: from 5.985,00 € to 8.290,00 €

Casale Lucca is an ancient villa, dating back to the 1800s and recently restored by the owners. This old villa was beautifully, elegantly restored and furnished with all the modern comforts.

Casale del Pero

Area: Tuscany: Arezzo and Casentino
Number of people: 20
Number of bedrooms: 10
Number of bathrooms: 8
Weekly prices: from 3.500,00 € to 5.250,00 €

Casale del Pero and its two small cottages which date back to 1851, are placed on a panoramic position, perched on a high hill, surrounded by olive groves and green forests of oaks and holm oaks.

Casale I Gigli

Area: Latium: Lakes
Number of people: 20
Number of bedrooms: 10
Number of bathrooms: 8
Weekly prices: from 3.450,00 € to 5.160,00 €

Casale I Gigli is a wonderful spacious villa spread over three floors near Lake Bolsena on the border of the regions of Latium, Umbria and Tuscany. This villa offers breathtaking panoramic views due to its hilltop position and is only 2km away from the popular town of Montefiascone and from the lake

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 Central Italy

Casale Luigino 20

Area: Tuscany: Pisa and Lucca
Number of people: 20
Number of bedrooms: 10
Number of bathrooms: 12
Weekly prices: from 4.940,00 € to 8.510,00 €

Casale Luigino is immersed in the Alta Valdera, in between Pisa and Volterra, in an estate of about 500 heactres. San Luigi, is part of a notable farm founded at the beginning of 1940’s, which is renowned for a wonderful production of a great San Giovese wine and a tasty oil.

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 4.060,00 €

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 Podere San Giustino

1 review
Area: Tuscany: Firenze, Chianti and Valdarno
Number of people: 20
Number of bedrooms: 9
Number of bathrooms: 6
Weekly prices: from 2.485,00 € to 3.920,00 €

The beauty of natural surroundings, the hot summer sun and the peace and quietness of the countryside will help you to set your mind free from everyday worries of modern life, recharging body and spirit with new positive energy.

Podere La Collina

Area: Tuscany: Siena and Val d'Orcia
Number of people: 20
Number of bedrooms: 10
Number of bathrooms: 9
Weekly prices: from 7.915,00 € to 11.533,00 €

Podere La Collina is a beautiful property, situated in a wonderful panoramic position, located on two levels with a third party indicated that the tower located near the lovely medieval town of Cetona, about an hour from cities such as Florence, Siena,..

Villa Beata

Area: Tuscany: Siena and Val d'Orcia
Number of people: 20
Number of bedrooms: 10
Number of bathrooms: 7
Weekly prices: from 7.237,00 € to 10.374,00 €

Villa Beata is a beautiful house situated in a panoramic position in the tuscan countryside, only a few miles from the charming medieval town of Cetona. The villa offers a very relaxing holiday, and, thanks to its geographical location, is the ideal departure point for visiting important artistic and cultural centers of area such as Montepulciano, Pienza, Montalcino, Cortona, Orvieto and Città della Pieve

Villa Heidi 20

Area: Tuscany: Pisa and Lucca
Number of people: 20
Number of bedrooms: 10
Number of bathrooms: 9
Weekly prices: from 7.800,00 € to 10.900,00 €

Villa Heidi 20 is a typical 18th Century Manor villa with its own small formal park and chapel, at the centre of an estate with farmhouses where the farmers looking after the winery used to live.

Villa Marlon

Area: Veneto
Number of people: 20
Number of bedrooms: 10
Number of bathrooms: 8
Weekly prices: from 14.990,00 € to 17.990,00 €

This imposing property was built in the 15th Century and since then it has remained the property of the Conti Brandolini d'Adda. Villa Marlon is located in Cison di Valmarino, a charming village in the foothills of the Dolomites.

Podere Lavanda

Area: Coast Tuscany: Etruscan Coast
Number of people: 20
Number of bedrooms: 10
Number of bathrooms: 10
Weekly prices: from 4.900,00 € to 7.350,00 €

Podere Lavanda is a prestigious villa with swimming pool located on the ridge of a hill in the heart of the Etruscan coast, just a few kilometres away from the sea as well as many famous towns such as Bolgheri, Castagneto Carducci, Volterra and San Gimignano.  
This beautiful villa with pool is ideal for multiple families and large groups.

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