Villas with swimming pool in Siena - Villas with swimming pool for vacation rentals in Siena
Villas with swimming pool for vacation rentals in Siena

Siena should be visited in any season because the beauty and charm of this city are endless. In summer, however, the best choice is one of our villas with pool in Siena to take a dip in the cool water whenever you want. On this page our villas for rent with swimming pool in Siena with pictures and descriptions. You will also find in this section of the menu our villas with swimming pool in San Gimignano and our villas with swimming pool in Montepulciano .

toscana-siena-palio
Siena is a beautiful city that stands on three hills between the river Arbia and Elsa. Get ready to walk uphill and downhill in the medieval streets of this fascinating city. The highest hill is where the Cathedral of Siena was built and today it unveils itself to its visitors after a long climb along 'Via di Citta'. The facade of the Cathedral and the works inside are well worth the effort of the climb! Going down again you can enjoy an ice cream in Piazza del Campo and admire the Torre del Mangia. Siena has no nearby airports, but it is well connected to Florence by bus and train. The station of Siena is slightly off center, while buses coming from Florence allow you to get directly in the center. By car you can visit other areas and nearby villages, known throughout the world for their scenic beauty. Think of Chianti, Val d'Orcia and the Crete Senesi...

The city offers numerous concerts thanks to the Accademia Chigiana and numerous plays at the major theaters. Inside the Fortress of Siena are often organized food events that will allow you to taste the typical products and the famous wines of this area. The event that characterizes the city, however, is definitely the 'Palio' that on July 2nd and August 16th involves the 17 'contrada' (neighborhoods) in which the city is divided since the Middle Ages. The viewer rushes to Piazza del Campo and has to wait for several hours in the sun for the thrill of the race: 10 runners that with three laps around the square change every time predictions on the winner and the other nine districts, considered all losers. The atmosphere is unique, full of tension that then explodes and manifests itself in all its power in the celebrations into the night of the winning contrada. It will continue throughout the year. Definitely an event not to be missed!

Choose one of the villas with pool in Siena that we offer below and get ready for a vacation in the city of the Palio!

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 €
Villa (formerly a farmhouse) in Val d`Orcia , in Pienza ( Siena ). Sleeps 8+2, swimming pool, Internet connection, hydromassage, children`s toys. Spas, tennis courts and riding stable within a few kilometres.
7 days: min: 1390 € - max: 2400 €
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 €
Luxurious villa in Empoli countryside, between Volterra and San Gimignano, in the centre of Tuscany, in an equidistant position between Siena, Florence and Pisa. 8/10 sleeping accommodations, swimming pool, garden, children`s playground, Internet connection.
7 days: min: 1850 € - max: 3050 €
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 €
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 €
Villa for vacation rentals in Siena countryside. 4+2 sleeping accommodations, swimming pool.
7 days: min: 1016 € - max: 1544 €
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 €
Ancient church transformed into an elegant villa with 6 sleeping accommodations. The villa is situated in Valdelsa, close to San Gimignano (Siena). Swimming pool, air conditionig.
7 days: min: 1000 € - max: 2300 €
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 €
Elegant villa (ex-farmhouse restored with elegance and charme) between Pienza and Montepulciano in Val d`Orcia . A few kilometres away, there are the famous towns of Arezzo and Siena. Surrounded by the typical Tuscan landscape, with total privacy and peace. Internet WI-FI Connection. 8+2 beds.
7 days: min: 2500 € - max: 4140 €
Luxury villa with breathtaking view over Siena. 10+2 sleeping accommodations, swimming pool, satellite TV.
7 days: min: 3190 € - max: 4665 €
Beautifully renovated house (formerly a barn) dating from the early 20th century near Poggibonsi and San Gimignano (Siena), in Valdelsa. Sleeps 4+1, swimming pool, barbecue, Internet connection, air conditioning, whirlpool facilities.
7 days: min: 1215 € - max: 2025 €
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 €
Elegant villa (ex 19th-century farmhouse) near Volterra and San Gimignano in Val di Cecina, between Pisa and Livorno. Panoramic position. Garden and swimming pool. Dependance with kitchen and barbecue. Air conditioning, Internet WI-FI Connection. 8+3 beds.
7 days: min: 3690 € - max: 6750 €
Holiday villa for rent a few kilometres from San Gimignano, in Valdesa counryside, between Florence and Siena. 8 sleeping accommodations, swimming pool, Internet connection. Air conditioning in the bedrooms of the villa.
7 days: min: 1733 € - max: 3335 €
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 €
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 €
Villa in Lucignano, in Valdichiana, at the border between the provinces of Siena and Arezzo. 12 sleeping accommodations, swimming pool, air conditioning, Internet connection.
7 days: min: 1500 € - max: 3000 €
Holiday villa in Montespertoli, in Florentine Chianti, between Florence and Siena. 8/11 sleeping accommodations, fully enclosed garden, hydromassage. Trekking routes in the surroundings.
7 days: min: 1590 € - max: 2585 €
Elegant luxury villa in Barberino Val d`Elsa (Florence), in the Chianti Classico region. Sleeps 10, swimming pool, air conditioning, Internet connection. Riding stable in the neighbourhood.
7 days: min: 3500 € - max: 6900 €
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 €
Villa with swimming pool in Casole d`Elsa (Siena), in Valdelsa countryside. 8 sleeping accommodations.
7 days: min: 1760 € - max: 2785 €
Chiusi villa rental in Valdichiana near Siena. The villa is a calm and comfortable complex for a holiday getting in strait contact with nature. Swimming pool. 9 sleeping accommodations.
7 days: min: 1125 € - max: 2900 €
Villa in Radicondoli, in Valdelsa countryside, near Siena. 10+2 sleeping accommodations, swimming pool, barbecue, satellite TV, Internet connection.
7 days: min: 1990 € - max: 3150 €
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 €
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 €
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 €
Farmhouse in the Tuscan countryside between Chianciano Terme and Orvieto close to Siena. 10+2 sleeping accommodations. Private swimming pool, satellite TV, parking. Animals admitted.
7 days: min: 1355 € - max: 2765 €
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 €
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 €
Villa in Colle Val d`Elsa ( Siena ), in Valdelsa. Sleeps 12+2, swimming pool, garden, barbecue equipment, toys for children, Internet connection. Just a few kilometres from San Gimignano.
7 days: min: 1850 € - max: 2590 €
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 €
Villa in Chianti, near Monteriggioni (Siena). The villa is divided into three apartments and sleeps 11+3. Swimming pool, Internet connection, air conditioning. Tennis courts, riding stable and golf club within a few kilometres.
7 days: min: 2900 € - max: 5600 €
Elegant luxury villa (originally a farmhouse) with panoramic view over San Gimignano . The villa is in San Gimignano , in Valdelsa, near the Chianti district, between Florence and Siena . Sleeps 12+2, swimming pool, Internet connection, air conditioning, hydromassage, gym, toys for children. Riding stable, tennis club and golf club nearby.
7 days: min: 5400 € - max: 7800 €
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 €
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 €
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 €
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 €
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 €
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 €
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 €