Villa for vacation rental in Siena

toscana-siena
Choosing a villa in Siena for your vacations in Tuscany is a choice that you won’t regret. This town offers everything: history, art, culture, entertainment, breathtaking views and delicious dishes and wines famous worldwide. Renting a villa in Siena will guarantee you privacy and independence. You can plan your days without following hotel schedules, invite friends over for dinner and prepare for them tasty dishes using the good ingredients the Sienes territory is known for while feeling exactly like at your own home.

If you love art and history, the historic centre of Siena will amazed you. Walking down the main street, you can see the Monte dei Paschi di Siena, the oldest bank in the world (1472) and reach the Cathedral that houses works by Michelangelo, Donatello, Bernini, Pinturicchio and Pisano. After a visit to the Duomo, it is time for an icecream under the Mangia Tower in Piazza del Campo, one of the most impressive medieval squares in Europe.

The town is strongly linked to its history and traditions and the atmosphere changes completly during the days of the Palio (July, 2nd and August, 16th). If you love folkloristic events, July and August are the best months to rent a villa in Siena and to see with your own eyes how Middle Ages times come to life during the historic parade that precedes the horse race of the 10 contradas (neighborhoods) in which Siena is divided.

Autumn is the perfect season to visit Siena if you love the countryside and wine. Vineyards and olive groves on the hills of Siena show their wonderful frutis and it is a period of the harvest. We suggest you to choose this period to rent a villa in Siena to completely enjoy the beauty of territories such as Chianti, Val d’Orcia, Valdichiana and Crete Senesi.

Winter with its cultural events and spring with its colors are also good periods to spend a vacation in villa in Siena. In fact, this special town is able to amaze and give you unforgettable memories in every period of the year. Just choose the villa in Siena that best suits your needs and preferences among the prestigious villas we have selected for you.


Farmhouse in the Crete Senesi, in San Giovanni d`Asso (Siena). Swimming pool, 8 sleeping accommodations, garden, satellite TV.
7 days: min: 1020 € - max: 1150 €
360-02
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 €
418-00
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 (formerly a farmhouse) in Rapolano Terme (Siena), in the Crete Senesi. Sleeps 9+2, panoramic position, swimming pool, Internet connection. Tennis courts, riding stable and thermal establishments within a few kilometres.
7 days: min: 1875 € - max: 2815 €
369-02
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 €
58-00
Holiday villa for rent on the hills around Montalcino, in Val d`Orcia (Siena). 9/11 sleeping accommodations, swimming pool.
7 days: min: 1400 € - max: 1990 €
62-00
Tuscany 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 €
488-00
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 €
132-00
Villa for vacation rentals in Siena countryside. 4+2 sleeping accommodations, swimming pool.
7 days: min: 1016 € - max: 1544 €
Villa (former farmhouse) in Monteroni d`Arbia (Siena), in the Crete Senesi region. Sleeps 8, wide garden, swimming pool, Internet connection, air conditioning and barbecue. 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: 3300 €
493-00
Peaceful farmhouse immersed in the countryside of Val d`Orcia (UNESCO World Heritage site), near Bagni San Filippo (Siena) and its thermal baths. Sleeps 18+7, swimming pool, Internet connection. Riding stable and tennis club nearby.
7 days: min: 2875 € - max: 7655 €
305-00
Villa with swimming pool near Montepulciano in the countryside of the Valdichiana between Siena and Arezzo. Sleeps8/10, air conditioning.
7 days: min: 1500 € - max: 2700 €
309-00
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 €
351-00
Villa with pool immersed in the gorgeous landscape of Val d`Orcia, in Castiglione d`Orcia (Siena). Sleeps 15/21, Internet connection, barbecue, outdoor toys for children. Wonderful panorama. Thermal baths within a few kilometres.
7 days: min: 1850 € - max: 4205 €
414-00
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 €
122-50
Luxury villa with breathtaking view over Siena. 10+2 sleeping accommodations, swimming pool, satellite TV.
7 days: min: 3190 € - max: 4665 €
257-00
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 €
355-00
Elegant villa (ex-farmhouse) on the hills that surround Pienza (Siena), with a wonderful view over the pure landscape of Val d`Orcia. Sleeps 8+2, swimming pool, Internet connection, air conditioning. Spa resorts within a few kilometres.
7 days: min: 2200 € - max: 4415 €
368-02
Ancient luxury villa in Valdelsa, in Colle Val d`Elsa (Siena). Sleeps 14, wide garden, swimming pool, solarium area, Internet connection. Tennis courts and golf club within a few kilometres. Wonderful view over the Tuscan countryside.
7 days: min: 4700 € - max: 7000 €
436-00
Ancient tower of a historic 11th-century castle near Siena, in the Chianti district. Sleeps 5+2, garden, swimming pool, Internet connection, air conditioning. Tennis courts and riding stable nearby.
7 days: min: 1277 € - max: 2128 €
449-00
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 €
553-00
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: 1595 € - max: 3140 €
33-00
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 €
85-00
Farmhouse near Pienza, in the Val d`Orcia (Siena). Garden and private swimming pool. Sleeps 4, Internet connection.
7 days: min: 1245 € - max: 1750 €
105-02
Small luxury villa in Valdelsa , in Monteriggioni , 5 kilometres from Siena. 6 sleeping accommodations, swimming pool, barbecue, satellite TV. Wonderful panorama and view on the castles surrounding the villa.
7 days: min: 1350 € - max: 2330 €
452-00
Ancient castle in Valdichiana, between Chianciano Terme and Montepulciano (Siena). Sleeps 12+2, wide park, two swimming pools, Internet connection, barbecue equipment. Excellent location for celebrating weddings and special events in an elegant and refined atmosphere. Just a few kilometres from Chianciano Terme thermal baths. Golf club, riding stable and tennis club nearby.
7 days: min: 4500 € - max: 5375 €
498-00
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 €
536-00
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: 435 € - max: 1735 €
541-00
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.
7 days: min: 1530 € - max: 2555 €
521-00
Traditional Tuscan farmhouse in the heart of Chianti Classico, a few kilometres from Siena. Sleeps 16, swimming pool, wide garden, air conditioning, Internet connection. Possibility of organising wine tasting events and buying the produce of the farm.
7 days: min: 1155 € - max: 5935 €
201-50
Villa with swimming pool in Casole d`Elsa (Siena), in Valdelsa countryside. 8 sleeping accommodations.
7 days: min: 1760 € - max: 2785 €
306-00
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 €
140-00
Farmhouse rental in Pienza in Val d`Orcia close to Siena. Sleeps 8. Swimming pool, table-tennis table.
7 days: min: 1600 € - max: 2265 €
09-01
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 €
73-00
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: 2695 € - max: 4955 €
346-00
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: 4200 € - max: 5600 €
111-00
Farmhouse with swimming pool in Montaione, in Florence countryside. Sleeps 10, private swimming pool, satellite TV, Internet connection.
7 days: min: 1215 € - max: 2090 €
322-00
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: 2340 € - max: 3500 €
84-00
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: 4000 € - max: 5405 €
81-00
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 €
87-00
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 €
25-00
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: 6250 € - max: 8840 €
48-02
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 €
400-00
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 €
222-00
Farmhouse in Montisi, close to Sinalunga (Siena), in Valdichiana. 6/7 sleeping accommodations, swimming pool, barbecue equipment, satellite TV, Internet connection. Wonderful view of the surrounding countryside. Golf club, tennis club, riding stable and SPA in the neighbourhood. Pets welcome.
7 days: min: 1330 € - max: 2975 €
64-00
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 €
260-00
Farmhouse in the Chianti region, near Siena. Sleeps 9, swimming pool, Internet connection. Panoramic position with views of Siena, the hills of Chianti and the Crete Senesi region.
7 days: min: 1625 € - max: 2625 €
247-00
Old farmhouse for rent for holidays in Valdichiana, close to Montepulciano, in the province of Siena. Sleeps 6, swimming pool. Wonderful panorama.
7 days: min: 750 € - max: 1500 €
468-00
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 €
275-00
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: 1920 € - max: 2665 €
320-00
Holiday farmhouse in the heart of the Chianti Classico district, near Siena. 4/6 sleeping accommodations, garden, swimming pool, Internet connection.
7 days: min: 1240 € - max: 1735 €
352-00
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 €
395-00
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 €
405-00
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 €
429-00
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: 5070 € - max: 5575 €
446-00
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: 980 € - max: 3475 €
450-00
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 €
455-00
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 €
552-00
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 €
463-00
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 €
516-00
Welcoming country house on the hills of Chianti, near Certaldo (Florence) and San Gimignano (Siena). Sleeps 6, swimming pool, Internet connection.
7 days: min: 1205 € - max: 2105 €
539-00
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 €
547-00
Beautiful stone farmhouse in panoramic position in a peaceful area near Sarteano (Siena). Sleeps 7, swimming pool, air conditioning. Possibility of organising dinners with traditional Tuscan dishes. Thermal baths nearby.
7 days: min: 1550 € - max: 2905 €