If for your next holiday in Tuscany you want to stay in a holiday home among the hills of Siena that has all the comforts and privacy you may need, choose one of our villas in Montepulciano in Val di Chiana. On this page we offer you our best villas for rent in Montepulciano, a beautiful medieval village between the Val di Chiana and Val d'Orcia.

The Vino Nobile di Montepulciano is a typical wine of the area. From the town walls, in fact, you can admire a breathtaking landscape of hills covered with vineyards. There are many wine cellars in Montepulciano where you can make wine tastings and taste also other local products.
Castle Montepulciano
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.
Villa Limoni
Aristocratic 19th-century luxury villa in Cortona, in Valdichiana, near Arezzo. 4/6/10 sleeping accommodations, swimming pool, wide garden, satellite TV, air conditioning, small animals admitted.
Villa Casale Cortona
Luxury villa in Cortona (Arezzo), in Valdichiana. 12 sleeping accommodations, swimming pool, wide garden, satellite TV, Internet connection.
Villa Cellini
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.
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.
Villa Fontana
Ancient, luxuriously renovated farmhouse south of Cortona (Arezzo), near Lake Trasimeno. Sleeps 14+5, swimming pool, Internet connection, air conditioning, steam room, hydromassage. Tennis club and riding stable nearby.
Villa Pietro
Beautiful 19-century villa in Valdichiana, a few kilometres from Cortona (Arezzo). Sleeps 9, swimming pool, Internet connection, air conditioning. Utmost privacy.
Villa Cris
Independent house near Cortona (Arezzo), in Valdichiana. Sleeps 7, swimming pool, fully fenced property, Internet connection and barbecue. Wonderful views of the town of Cortona.
Villa Bucolica
Villa with exclusive swimming pool in Valdichiana near Cortona (Arezzo). 10/11 sleeping accommodations, Internet connection.
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.
Villa Montepulciano
Villa with swimming pool near Montepulciano in the countryside of the Valdichiana between Siena and Arezzo. Sleeps8/10, air conditioning.
Villa Manola
Elegant luxury villa with private swimming pool situated in Val d`Orcia, near Pienza (Siena). 10 sleeping accommodations, satellite TV, welcome basket.
Villa Valdichiana
Villa near Montepulciano (Siena) with magnificent view on the Valdichiana. Sleeps 10, private garden and swimming pool, air conditioning, Internet connection.
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.
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.
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.
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.
Villa Scannagallo
Ancient villa in Valdichiana, close to Cortona (Arezzo). 18+4 sleeping accommodations, swimming pool, Internet.
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.
Villa Bocena
Holiday villa in Valdichiana, close to Cortona, in the province of Arezzo . 7 sleeping accommodations, swimming pool, private garden, barbecue.
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.
Villa Angelo
Villa with swimming pool near Cortona (Arezzo), in Valdichiana. 8 sleeping accommodations, garden, hydromassage, outdoor toys, air conditioning.
Villa Orcia
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.
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.
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.
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.
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.
Villa Carmen
Small and charming villa with swimming pool in Valdichiana, near Cortona (Arezzo). Sleeps 7, garden, barbecue, Internet connection.
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.
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.
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.
Villa Zefiro
Comfortable independent house situated in a farm on the hills around Cortona (Arezzo), in Valdichiana. Sleeps 7, swimming pool, Internet connection. Beautiful view over the surrounding landscape.
Villa Acquaviva
Beautiful country house at the border between Tuscany and Umbria, just a few kilometres from Montepulciano (Siena) and Lake Trasimeno. Sleeps 10, swimming pool, wood-burning oven, Internet connection, air conditioning, table-tennis table. Thermal baths within a few kilometres.
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.
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.
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.
Villa Scala
Ancient country house in Castiglion Fiorentino (Arezzo), in Valdichiana. Sleeps 13, swimming pool, Internet connection, table-tennis table, wood-burning oven. Golf club, riding stable, outlet village and Lake Trasimeno within a few kilometres.
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.
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.
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.
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.
Farmhouse Villa La Rosa
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.
Farmhouse Garden
Old farmhouse for rent for holidays in Valdichiana, close to Montepulciano, in the province of Siena. Sleeps 6, swimming pool. Wonderful panorama.
Farmhouse Cortona
Ancient farmhouse close to Cortona (Arezzo), in the Valdichiana region. 10+4 sleeping accommodations, air conditioning, hydromassage, swimming pool, Internet
Farmhouse Greppia
Farmhouse in panoramic position near Cortona (Arezzo), in Valdichiana. 8/10 sleeping accommodations, garden, swimming pool with hydromassage, air conditioning.
Farmhouse Marcos
Farmhouse in Valdichiana, near Cortona (Arezzo). Sleeps 5, swimming pool, garden, barbecue, Internet connection. Riding stables and tennis courts in proximity.
Farmhouse Lory
Farmhouse with swimming pool for rent in Cortona (Arezzo), in Valdichiana. Sleeps 8+7, Internet connection, organic vegetable garden, hydromassage, children's playground, table-tennis table, table-football table, barbecue. Riding stable, golf club and tennis courts within a few kilometres.
Villa Giuseppe
Renovated stone farmhouse for rent in Valdichiana, a few kilometres from Cortona (Arezzo). Sleeps 7, swimming pool, wide garden, Internet connection. Cooking lessons and wine tasting events organised upon request.
Farmhouse Ginepro
Beautiful stone farmhouse standing in panoramic position close to Cortona (Arezzo) with a splendid view over Valdichiana. Sleeps 5+1, swimming pool, hydromassage, Internet connection, air conditioning.
Farmhouse Montefeltro
Beautiful 19th-century farmhouse in Valdichiana, between Cortona (Arezzo) and Lake Trasimeno. Sleeps 3+4, wide garden, swimming pool, barbecue. Riding stable nearby. Ideal solution for holidays in close contact with nature in the peaceful countryside between Tuscany and Umbria.
Farmhouse Radiante
Beautiful 19th-century farmhouse within close distance of Cortona (Arezzo), in Valdichiana. Sleeps 8, swimming pool with solarium area, air conditioning, hydromassage. Wonderful panoramic vistas.
Farmhouse Igor
Ancient, elegantly renovated Tuscan farmhouse near Cortona (Arezzo). Sleeps 10, swimming pool, Internet connection, air conditioning, wood-burning oven, children's toys.
Villa Capodanno
Independent farmhouse in Sienese Valdichiana, a few kilometres from Chianciano Terme and Val d'Orcia. Sleeps 16, swimming pool, barbecue, Internet connection. Immersed in the green Tuscan countryside for holidays in the utmost privacy.
Villa Legno
Farmhouse for rent near Sarteano and a few kilometres from Chianciano Terme (Siena) thermal baths, in Sienese Valdichiana. Sleeps 12, swimming pool, Internet connection, barbecue. Wonderful views.
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.
Arezzo Apartments
Luxury apartments with swimming pool and air conditioning in Cortona , in Valdichiana , in Arezzo countryside. From 2 to 4 sleeping accommodations.
Borgo Montepulciano
Elegant apartments in farmhouse in Montepulciano, in Valdichiana, near Siena. In total it sleeps 20+11. Apartments from 2 to 6 sleeping accommodations. Swimming pool, barbecue, satellite TV, air conditioning. Tennis courts, golf course and riding stable nearby.