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Siena Villas Pool, Villas with pool in Siena countryside

Properties by Type » Discovering Tuscany » A Holiday in Villa » Villas with pool by Area » Siena

Villas with pool in Siena countryside

Siena fascinates its visitors with its almost untouched historical centre, full of narrow streets leading to Piazza del Campo, where the famous " Palio " takes place twice a year.

Siena’s suggestive countryside is scattered with small historical towns, such as San Gimignano , Monteriggioni , Montalcino , Pienza , Montepulciano and Colle Val d’Elsa .

If you are planning to spend your holidays in Siena , in this page and in our website you will find a wide selection of villas with swimming pool in Siena.

For your holidays in Tuscany, choose the accommodation that fits your needs among the villas in Siena countryside we have selected for you.

Our most requested holiday homes:
Villa Borgo San Gimignano Villa Borgo San Gimignano

Villa situated in an ancient 8th-century burg already existing in Charlemagne`s times near San Gimignano (Siena), in Valdelsa. Sleeps 28, wide garden, swimming pool, sauna, Internet connection, air conditioning, hydromassage. Golf club, riding stable and tennis courts nearby.

7 days: min: 7300 € - max: 17400 €
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Villa Massimiliano Villa Massimiliano

Exclusive luxury villa with swimming pool near San Gimignano, in Valdelsa, between Florence and Siena. 10 sleeping accommodations, satellite TV, air conditioning, barbecue, Internet connection.

7 days: min: 4000 € - max: 5650 €
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Villa Fortezza Montalcino Villa Fortezza Montalcino

Beautiful villa in Montalcino (Siena), in Valdorcia, facing the fortress. Sleeps 6, Internet connection, air conditioning, swimming pool, hydromassage. Possibility of booking private wine-tasting lessons with a sommelier in the ancient fortress. Thermal baths nearby.

7 days: min: 4690 € - max: 5140 €
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Villa Santa Lucia Villa Santa Lucia

Elegant villa (in the past an aristocratic residence) in Valdelsa, in Monteriggioni (Siena). Sleeps 14, park, swimming pool, air conditioning, Internet connection, panoramic terrace. Possibilty of organising dinners at the property.

7 days: min: 3640 € - max: 6440 €
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Villa Cleopatra Villa Cleopatra

Luxurious independent villa in scenery location in the Chianti region, near San Gimignano (Siena). Sleeps 8, swimming pool, solarium area, air conditioning, sauna, hydromassage. Possibility of organising lunches, dinners, wine tastings and cooking lessons at the villa.

7 days: min: 4740 € - max: 7420 €
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Villa Casale Cortona Villa Casale Cortona

Luxury villa in Cortona (Arezzo), in Valdichiana. 12 sleeping accommodations, swimming pool, wide garden, satellite TV, Internet connection.

7 days: min: 3360 € - max: 4360 €
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Villa Paolina Villa Paolina

Ancient historic luxury villa in Valdichiana, in Montepulciano (Siena). Sleeps 16, wide garden, swimming pool, Internet connection, barbecue. Tennis courts, thermal baths, riding stable and golf club nearby.

7 days: min: 4740 € - max: 4740 €

Reviews 1
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Villa Sarteano Villa Sarteano

Elegant luxury villa situated in a historic site in the province of Siena, in Valdichiana. In the past an Etruscan site and then a medieval citadel, it affords magnificent views of the Tuscan countryside. Sleeps 14, wide park, swimming pool, sauna, Internet connection, air conditioning. Tennis club and thermal baths within a few kilometres.

7 days: min: 8835 € - max: 11315 €
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Villa Navigatore Villa Navigatore

Elegant villa in panoramic location in the heart of Chianti Classico, just a few kilometres from Gaiole in Chianti (Siena). Sleeps 8, heatable swimming pool, Finnish sauna, air conditioning, Internet connection. Possibility of organising wine tasting events, cooking lessons and wellbeing itineraries. Utmost peace and privacy.

7 days: min: 3240 € - max: 4860 €
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Villa Pietro Villa Pietro

Beautiful 19-century villa in Valdichiana, a few kilometres from Cortona (Arezzo). Sleeps 9, swimming pool, Internet connection, air conditioning. Utmost privacy.

7 days: min: 700 € - max: 2770 €
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Villa Pettirosso Villa Pettirosso

Elegant villa near Sarteano (Siena), in Valdichiana. Sleeps 9, garden, swimming pool, Internet connection. A few kilometres from Val d'Orcia and the thermal baths of Chianciano Terme and San Casciano dei Bagni. The villa is part of vast estate including an 11th-century abbey.

7 days: min: 715 € - max: 3165 €

Reviews 2
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Villa Botticelli Villa Botticelli

Tuscan villa with pool near Radda in Chianti in the countryside of Chianti between Siena and Florence. Sleeps 10, Internet connection.

7 days: min: 1750 € - max: 2800 €

Reviews 6
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Villa Montalcino Villa Montalcino

Holiday villa for rent on the hills around Montalcino, in Val d`Orcia (Siena). 11/13 sleeping accommodations, swimming pool.

7 days: min: 1940 € - max: 2315 €
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Villa Simona Villa Simona

Villa for vacation rentals in Siena countryside. 4+2 sleeping accommodations, swimming pool.

7 days: min: 1016 € - max: 1544 €

Reviews 2
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Villa Bucolica Villa Bucolica

Villa with exclusive swimming pool in Valdichiana near Cortona (Arezzo). 10/11 sleeping accommodations, Internet connection.

7 days: min: 1200 € - max: 2400 €

Reviews 1
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Villa Casole Villa Casole

Villa with swimming pool in Casole d`Elsa (Siena), in Valdelsa countryside. 8 sleeping accommodations.

7 days: min: 1760 € - max: 2785 €
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Villa Mauro Villa Mauro

Villa in panoramic position on the hills near Terontola, in proximity to Cortona (Arezzo), in Valdichiana. 10+2 sleeping accommodations, swimming pool, garden, wood-burning oven, small gym, Internet connection.

7 days: min: 1335 € - max: 3335 €
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Villa Montepulciano Villa Montepulciano

Villa with swimming pool near Montepulciano in the countryside of the Valdichiana between Siena and Arezzo. Sleeps8/10, air conditioning.

7 days: min: 1600 € - max: 2800 €

Reviews 1
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Villa Arbia Villa Arbia

Villa with private swimming pool near Monteroni d `Arbia and Buonconvento, in the Crete Senesi, in the countryside of Siena. Sleeps 13, furnished garden, Internet connection, air conditioning, wood-burning oven. Possibility of organising dinners at the property and horseback rides. Thermal baths in the neighbourhood.

7 days: min: 3300 € - max: 5960 €
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Villa Manola Villa Manola

Elegant luxury villa with private swimming pool situated in Val d`Orcia, near Pienza (Siena). 10 sleeping accommodations, satellite TV, welcome basket.

7 days: min: 3840 € - max: 5190 €
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Villa Valdichiana Villa Valdichiana

Villa near Montepulciano (Siena) with magnificent view on the Valdichiana. Sleeps 10, private garden and swimming pool, air conditioning, Internet connection.

7 days: min: 2200 € - max: 4115 €
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Villa Montecchio Villa Montecchio

Villa ex-medieval sighting tower in Montecchio di Cortona, in Valdichiana, near Arezzo. 9 sleeping accommodations, wide garden, swimming pool, Finnish sauna, Internet connection, air conditioning.

7 days: min: 1125 € - max: 1750 €

Reviews 2
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Villa Convento Villa Convento

Villa with swimming pool in the Crete senesi, near the small village called Monteroni d`Arbia (Siena). 20 sleeping accommodations, satellite TV, Internet connection, wide garden.

7 days: min: 5460 € - max: 8160 €
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Villa Stefano Villa Stefano

Ancient 13th-century villa in Monteroni d`Arbia, in the Crete Senesi, near Siena. 14/15 sleeping accommodations, panoramic garden, swimming pool, Internet connection, barbecue. Tennis courts, golf club and thermal baths in the neighbourhood.

7 days: min: 2490 € - max: 3615 €
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Villa Sinalunga Villa Sinalunga

Villa near the small village of Sinalunga (Siena), in Valdichiana, between Montepulciano and Pienza. 14 sleeping accommodations, swimming pool, barbecue, satellite TV, wonderful panorama.

7 days: min: 2630 € - max: 5125 €
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Villa Bettolle Villa Bettolle

Elegant 18th-century villa in Valdichiana, near Cortona and Chianciano Terme , in the province of Arezzo. 10/12 sleeping accommodations, swimming pool, Internet, barbecue, hydromassage, satellite TV, bicycles. Riding stable and tennis club in the neighbourhood.

7 days: min: 1355 € - max: 2810 €
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Villa Focette Villa Focette

Villa with swimming pool for rent near Sarteano (Siena), in Valdichiana. Sleeps 14, beautiful private garden, satellite TV. Thermal baths within a few kilometres. Ideal lodging for relaxing holidays in the peaceful Tuscan countryside.

7 days: min: 1915 € - max: 5585 €
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Villa Amiata Villa Amiata

Villa with outhouse for rent on the hillside of Mount Cetona, near San Casciano dei Bagni and a few dozen kilometres from Chianciano Terme (Siena), in Valdichiana. Sleeps 11, swimming pool, Internet connection, air conditioning, table-tennis table. Thermal baths within a few kilometres.

7 days: min: 2605 € - max: 5105 €
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Villa Sorgente Villa Sorgente

Beautiful 15th-century villa in the Crete Senesi region, near Monteroni d'Arbia (Siena). Sleeps 11, swimming pool, Internet connection, panoramic terrace with breathtaking views over the surrounding hills.

7 days: min: 2235 € - max: 2820 €
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Villa Scannagallo Villa Scannagallo

Ancient villa in Valdichiana, close to Cortona (Arezzo). 18+4 sleeping accommodations, swimming pool, Internet.

7 days: min: 2650 € - max: 5300 €
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Villa Cascina Villa Cascina

Elegant ancient villa in the Val di Chiana, near Cortona (Arezzo). 6+2 sleeping accommodations, swimming pool, air conditioning, outdoor hydromassage, Internet connection, children's toys.

7 days: min: 1330 € - max: 3990 €

Reviews 1
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Villa Bolsena Villa Bolsena

Villa close to Lake Bolsena, San Casciano dei Bagni (Siena) and Pitigliano (Grosseto). 10 sleeping accommodations. Natural park and thermal centres in the vicinity, possibility of doing water sports, swimming pool.

7 days: min: 1700 € - max: 2000 €

Reviews 1
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Villa Andrea Villa Andrea

Elegant villa in panoramic position in Siena. 5 sleeping accommodations, private swimming pool, tennis court, wide park, air conditioning and Internet connection. The celebrated Piazza del Campo is within easy reach.

7 days: min: 1390 € - max: 2790 €
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Villa Bocena Villa Bocena

Holiday villa in Valdichiana, close to Cortona, in the province of Arezzo . 7 sleeping accommodations, swimming pool, private garden, barbecue.

7 days: min: 1345 € - max: 2490 €
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Villa Campo Villa Campo

Former farmhouse converted into a villa with swimming pool in Valdichiana, near Montepulciano (Siena). Sleeps 14, wide garden, barbecue equipment. Thermal baths nearby.

7 days: min: 2500 € - max: 3700 €

Reviews 1
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Villa Angelo Villa Angelo

Villa with swimming pool near Cortona (Arezzo), in Valdichiana. 8 sleeping accommodations, garden, hydromassage, outdoor toys, air conditioning.

7 days: min: 1200 € - max: 2250 €

Reviews 3
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Villa Val d`Orcia Villa Val d`Orcia

Villa with pool immersed in the gorgeous landscape of Val d`Orcia, in Castiglione d`Orcia (Siena). Sleeps 12+3, Internet connection, barbecue, outdoor toys for children. Wonderful panorama. Thermal baths within a few kilometres.

7 days: min: 2285 € - max: 4205 €

Reviews 1
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Villa Piana Verde Villa Piana Verde

Villa sleeping 5 in Valdichiana countryside, near Montepulciano (Siena). Garden, swimming pool, Internet connection, air conditioning, hydromassage, children`s playground. Tennis club, golf club, riding stable and spa resorts in the neighbourhood.

7 days: min: 900 € - max: 1100 €

Reviews 1
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Villa Simonetta Villa Simonetta

Villa with pool in Valdichiana, near Cortona (Arezzo). Sleeps 6, garden, Internet connection, air conditioning, barbecue. Tennis club, golf club and riding stable nearby.

7 days: min: 985 € - max: 1680 €
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Villa Marinella Villa Marinella

Villa with pool in Valdelsa, in Colle Val d`Elsa (Siena). Sleeps 15, garden, swimming pool with whirlpool area, Internet connection, small gym, children`s playground. Tennis club, golf club and riding stable nearby.

7 days: min: 1950 € - max: 2700 €

Reviews 4
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Villa Radi Villa Radi

Villa (former farmhouse) in Monteroni d`Arbia (Siena), in the Crete Senesi region. Sleeps 8, wide garden, swimming pool, Internet connection, air conditioning, barbecue, hydromassage. Wonderful 360-degree view of Siena and the Crete Senesi region. Golf club, tennis club, riding stable and spa resorts within a few kilometres.

7 days: min: 1850 € - max: 3600 €

Reviews 1
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Villa Fabiane Villa Fabiane

Villa with swimming pool in Monte San Savino in Valdichiana between Arezzo and Siena. Panoramic location and swimming pool. 10+2 beds.

7 days: min: 1500 € - max: 3500 €

Reviews 1
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Villa Cattaneo Villa Cattaneo

Beautiful villa on the hills of Chianti Classico, between Siena and Florence, near Castellina in Chianti. Sleeps 12, panoramic swimming pool, barbecue, Internet connection, air conditioning. Gorgeous views of the surrounding countryside. Possibility of purchasing the olive oil and wine produced in the farm.

7 days: min: 2725 € - max: 5115 €
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Villa Madonna Villa Madonna

Beautiful villa with swimming pool in a peaceful and panoramic position on the hills of Val d'Orcia, near San Casciano dei Bagni (Siena), at the border between Tuscany, Lazio and Umbria. Sleeps 8, Internet connection, barbecue. Thermal baths within a few kilometres.

7 days: min: 1015 € - max: 3680 €

Reviews 1
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Villa Panorama Villa Panorama

Villa with private swimming pool in the region of Montagnola Senese, near Sovicille (Siena), in a peaceful and panoramic position. Sleeps 8, air conditioning, wide garden, barbecue equipment. Just a few kilometres from Siena and the towns of the Chianti district.

7 days: min: 1845 € - max: 3075 €
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Villa Pieve Villa Pieve

Villa in panoramic position on the hills of Valdichiana, near Chianciano Terme (Siena). Sleeps 10, garden, swimming pool, Internet connection. Important thermal towns nearby.

7 days: min: 3385 € - max: 4305 €
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Villa Maretta Two Villa Maretta Two

Nice small villa on the hills that surround Cortona (Arezzo), in Valdichiana. Sleeps 4, fenced swimming pool, air conditioning, children's toys, barbecue. Lake Trasimeno within a few kilometres.

7 days: min: 570 € - max: 2095 €
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Villa Carmen Villa Carmen

Small and charming villa with swimming pool in Valdichiana, near Cortona (Arezzo). Sleeps 7, garden, barbecue, Internet connection.

7 days: min: 1200 € - max: 2100 €
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Villa Lago Villa Lago

Nice recently built villa a few kilometres from Cortona (Arezzo) and Lake Trasimeno. Sleeps 6, swimming pool, wide garden with solarium area, barbecue, Internet connection. Beautiful view of the lake and the surrounding countryside. Possibility of windsurfing, sailing and fishing.

7 days: min: 950 € - max: 3146 €
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Villa Tuoro Villa Tuoro

Villa in a very peaceful area of the Tuscan countryside, near Montepulciano (Siena), in Valdichiana, just a few kilometres from Lake Trasimeno. Sleeps 6+2, swimming pool, Internet connection, hydromassage, children`s playground.

7 days: min: 1500 € - max: 2000 €
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Villa Buonconvento Villa Buonconvento

Villa with wonderful view of Montalcino (Siena), in Val d`Orcia. Sleeps 7, swimming pool, air conditioning, Internet connection.

7 days: min: 2075 € - max: 3415 €
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Villa Camucia Villa Camucia

Elegant villa in panoramic location just a few kilometres from Cortona (Arezzo), in Valdichiana. Sleeps 8, swimming pool, wood-burning oven, table-tennis table, Internet connection, air conditioning.

7 days: min: 1735 € - max: 3085 €
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Villa Gallo Villa Gallo

Independent villa near Castellina in Chianti (Siena), in the heart of the Chianti Classico area. Sleeps 6, swimming pool, air conditioning, Internet connection. Possibility of organising wine tasting events and dinners.

7 days: min: 750 € - max: 1700 €
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Villa Zanobi Villa Zanobi

Independent house in an old hamlet in the Chianti Classico area, near the village of Gaiole in Chianti (Siena). Sleeps 8, swimming pool, wood-burning oven, children's playground with slide and swing, air conditioning.

7 days: min: 1530 € - max: 2555 €
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Villa Lorenzetti Villa Lorenzetti

Beautiful villa in scenic location on the verdant hills of Val d'Orcia (Siena), near Campiglia d'Orcia. Sleeps 8, swimming pool, Internet connection, barbecue, hydromassage. Thermal baths nearby.

7 days: min: 2980 € - max: 4765 €
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Villa Viola Villa Viola

Charming independent villa on the hills around the Etruscan town of Cortona (Arezzo), in Valdichiana. Sleeps 4, swimming pool, barbecue, Internet connection, hydromassage, steam bath. Possibility of organising traditional Tuscan dinners.

7 days: min: 915 € - max: 1675 €
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Villa Viola 2 Villa Viola 2

Cosy small stone villa part of a farm situated on the hills around Cortona (Arezzo). Sleeps 7, swimming pool, Internet connection, children's playground, table-tennis table.

7 days: min: 450 € - max: 2295 €
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Villa Barozzi Villa Barozzi

Beautiful independent villa in Siena countryside, near Montepulciano, in Valdichiana. Sleeps 6, swimming pool, hydromassage, Internet connection. Thermal baths within a few kilometres.

7 days: min: 1065 € - max: 2180 €
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Villa Fonti Villa Fonti

Very affordable villa near San Casciano dei Bagni, on the border between Tuscany and Umbria. Sleeps 9, swimming pool, Internet connection, barbecue. Ideal lodging for holidays in close contact with nature. Riding stable, tennis club and thermal baths within a few kilometres. Possibility of organising cooking lessons.

7 days: min: 1125 € - max: 1375 €
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Villa Giotto Villa Giotto

Large villa for rent on the hills of Val d'Orcia, near Sarteano (Siena). Sleeps 16, wide garden, swimming pool, Internet connection, barbecue. Beautiful views of the surrounding countryside. Thermal resorts within a few kilometres.

7 days: min: 1000 € - max: 4590 €

Reviews 1
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Villa Acqua Villa Acqua

Charming villa in the province of Siena, near Sarteano, in Val d'Orcia. Sleeps 14, wide garden, swimming pool, Internet connection, barbecue. Thermal resorts within a few dozen kilometres. Utmost privacy.

7 days: min: 790 € - max: 3835 €
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Villa Mario Villa Mario

Cosy villa in the countryside between Florence and Empoli, near Vinci, in Lower Valdarno. Sleeps 5, swimming pool, barbecue, Internet connection, hydromassage. Florence historic centre, Pisa, Lucca, Siena and Pistoia within easy driving distance.

7 days: min: 2130 € - max: 2980 €
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Villa Maretta Villa Maretta

Nice small villa on the hills that surround the town of Cortona (Arezzo), in Valdichiana. Sleeps 6, swimming pool, children's toys, barbecue, air conditioning. Great views. A few kilometres from Lake Trasimeno.

7 days: min: 555 € - max: 2360 €

Reviews 1
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Villa Diana Villa Diana

Villa for weddings and ceremonies in Tuscany, in Siena countryside, in Monticiano. Sleeps 18, wide garden, swimming pool, Internet connection. Golf club and thermal resorts within a few kilometres.

7 days: min: 7685 € - max: 8095 €
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Villa Fonte Villa Fonte

Beautiful villa in the countryside of Siena, just a few kilometres from Chianciano Terme thermal baths and the villages of Val d'Orcia. Sleeps 16, swimming pool, Internet connection, barbecue.

7 days: min: 870 € - max: 4355 €
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Farmhouse Elsa Farmhouse Elsa

Luxurious villa (ex farmhouse) in Valdelsa, near the historical village of Casole d`Elsa, in the province of Siena. Sleeps 11/12. Swimming pool, satellite TV, hydromassage, barbecue, Internet connection. Possibility of organising tastings, visits to nearby wineries, cooking lessons and horseback rides.

7 days: min: 1105 € - max: 3130 €
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Villa Silla Villa Silla

Apartment in villa on the hills around Cortona (Arezzo). Sleeps 7, swimming pool, fenced garden, air conditioning. Tennis club and golf club within a few kilometres of the property.

7 days: min: 450 € - max: 1100 €
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