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.
Sienas suggestive countryside is scattered with small historical towns, such as San Gimignano , Monteriggioni , Montalcino , Pienza , Montepulciano and Colle Val dElsa .
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.
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.
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.
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.
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.
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.
Luxury villa in Cortona (Arezzo), in Valdichiana. 12 sleeping accommodations, swimming pool, wide garden, satellite TV, Internet connection.
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.
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.
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.
Beautiful 19-century villa in Valdichiana, a few kilometres from Cortona (Arezzo). Sleeps 9, swimming pool, Internet connection, air conditioning. Utmost privacy.
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.
Tuscan villa with pool near Radda in Chianti in the countryside of Chianti between Siena and Florence. Sleeps 10, Internet connection.
Holiday villa for rent on the hills around Montalcino, in Val d`Orcia (Siena). 11/13 sleeping accommodations, swimming pool.
Villa for vacation rentals in Siena countryside. 4+2 sleeping accommodations, swimming pool.
Villa with exclusive swimming pool in Valdichiana near Cortona (Arezzo). 10/11 sleeping accommodations, Internet connection.
Villa with swimming pool in Casole d`Elsa (Siena), in Valdelsa countryside. 8 sleeping accommodations.
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.
Villa with swimming pool near Montepulciano in the countryside of the Valdichiana between Siena and Arezzo. Sleeps8/10, air conditioning.
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.
Elegant luxury villa with private swimming pool situated in Val d`Orcia, near Pienza (Siena). 10 sleeping accommodations, satellite TV, welcome basket.
Villa near Montepulciano (Siena) with magnificent view on the Valdichiana. Sleeps 10, private garden and swimming pool, air conditioning, Internet connection.
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.
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.
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.
Villa near the small village of Sinalunga (Siena), in Valdichiana, between Montepulciano and Pienza. 14 sleeping accommodations, swimming pool, barbecue, satellite TV, wonderful panorama.
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.
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.
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.
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.
Ancient villa in Valdichiana, close to Cortona (Arezzo). 18+4 sleeping accommodations, swimming pool, Internet.
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.
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.
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.
Holiday villa in Valdichiana, close to Cortona, in the province of Arezzo . 7 sleeping accommodations, swimming pool, private garden, barbecue.
Former farmhouse converted into a villa with swimming pool in Valdichiana, near Montepulciano (Siena). Sleeps 14, wide garden, barbecue equipment. Thermal baths nearby.
Villa with swimming pool near Cortona (Arezzo), in Valdichiana. 8 sleeping accommodations, garden, hydromassage, outdoor toys, air conditioning.
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.
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.
Villa with pool in Valdichiana, near Cortona (Arezzo). Sleeps 6, garden, Internet connection, air conditioning, barbecue. Tennis club, golf club and riding stable nearby.
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.
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.
Villa with swimming pool in Monte San Savino in Valdichiana between Arezzo and Siena. Panoramic location and swimming pool. 10+2 beds.
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.
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.
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.
Villa in panoramic position on the hills of Valdichiana, near Chianciano Terme (Siena). Sleeps 10, garden, swimming pool, Internet connection. Important thermal towns nearby.
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.
Small and charming villa with swimming pool in Valdichiana, near Cortona (Arezzo). Sleeps 7, garden, barbecue, Internet connection.
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.
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.
Villa with wonderful view of Montalcino (Siena), in Val d`Orcia. Sleeps 7, swimming pool, air conditioning, Internet connection.
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.
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.
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.
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.
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.
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.
Beautiful independent villa in Siena countryside, near Montepulciano, in Valdichiana. Sleeps 6, swimming pool, hydromassage, Internet connection. Thermal baths within a few kilometres.
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.
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.
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.
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.
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.
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.
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.
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.
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.