Tuscany Holiday Rentals
DeuEngEspFraHollItaPol
  • Home
  • Booking procedure
  • Contact us
  • Last Minute & Special Offers

Villas in Montepulciano, Villas for rent in Montepulciano in Val di Chiana

Properties by Type » Villas by Geographical Area » Val di Chiana » Montepulciano

Villas for rent in Montepulciano in Val di Chiana

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 historic center of Montepulciano is extremely impressive, with narrow uphill streets , among medieval buildings, lead to the town's main square with the seventeenth-century Renaissance Cathedral, the Town Hall built in the fourteenth century by Michelozzo and the Pozzo dei Grifi e dei Leoni.

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.

Do not miss the opportunity to visit the Church of San Biagio at the foot of the town of Montepulciano. The church dates back to the sixteenth century and is the work of Antonio da Sangallo il Vecchio. The extraordinary beauty of this church will leave you speechless.
 
For your next holiday in Tuscany, choose one of our Villas in Montepulciano in Val di Chiana.

Our most requested holiday homes:
Castle Montepulciano 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.

7 days: min: 4500 € - max: 5375 €
More details
Villa Limoni 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.

7 days: min: 600 € - max: 3400 €

Reviews 4
More details
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 €
More details
Villa Cellini 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.

7 days: min: 2500 € - max: 4140 €

Reviews 2
More details
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
More details
Villa Fontana 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.

7 days: min: 5200 € - max: 7500 €
More details
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 €
More details
Villa Cris 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.

7 days: min: 1170 € - max: 2555 €
More details
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
More details
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 €
More details
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
More details
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 €
More details
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 €
More details
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
More details
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 €
More details
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 €
More details
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 €
More details
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 €
More details
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
More details
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 €
More details
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
More details
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
More details
Villa Orcia 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.

7 days: min: 2200 € - max: 4420 €

Reviews 1
More details
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
More details
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 €
More details
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 €
More details
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 €
More details
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 €
More details
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 €
More details
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 €
More details
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 €
More details
Villa Zefiro 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.

7 days: min: 560 € - max: 2295 €
More details
Villa Acquaviva 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.

7 days: min: 2080 € - max: 3105 €
More details
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 €
More details
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 €
More details
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 €
More details
Villa Scala 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.

7 days: min: 1435 € - max: 2515 €
More details
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
More details
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 €
More details
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
More details
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 €
More details
Farmhouse Villa La Rosa 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.

7 days: min: 1355 € - max: 2765 €

Reviews 1
More details
Farmhouse Garden Farmhouse Garden

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 €
More details
Farmhouse Cortona Farmhouse Cortona

Ancient farmhouse close to Cortona (Arezzo), in the Valdichiana region. 10+4 sleeping accommodations, air conditioning, hydromassage, swimming pool, Internet

7 days: min: 2500 € - max: 3500 €

Reviews 1
More details
Farmhouse Greppia Farmhouse Greppia

Farmhouse in panoramic position near Cortona (Arezzo), in Valdichiana. 8/10 sleeping accommodations, garden, swimming pool with hydromassage, air conditioning.

7 days: min: 1500 € - max: 2700 €
More details
Farmhouse Marcos Farmhouse Marcos

Farmhouse in Valdichiana, near Cortona (Arezzo). Sleeps 5, swimming pool, garden, barbecue, Internet connection. Riding stables and tennis courts in proximity.

7 days: min: 850 € - max: 1400 €

Reviews 3
More details
Farmhouse Lory 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.

7 days: min: 1200 € - max: 2300 €
More details
Villa Giuseppe 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.

7 days: min: 1460 € - max: 2430 €
More details
Farmhouse Ginepro 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.

7 days: min: 555 € - max: 2595 €
More details
Farmhouse Montefeltro 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.

7 days: min: 600 € - max: 1000 €
More details
Farmhouse Radiante 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.

7 days: min: 1470 € - max: 2570 €
More details
Farmhouse Igor Farmhouse Igor

Ancient, elegantly renovated Tuscan farmhouse near Cortona (Arezzo). Sleeps 10, swimming pool, Internet connection, air conditioning, wood-burning oven, children's toys.

7 days: min: 1800 € - max: 3225 €
More details
Villa Capodanno 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.

7 days: min: 715 € - max: 3835 €

Reviews 1
More details
Villa Legno 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.

7 days: min: 790 € - max: 3730 €
More details
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 €
More details
Arezzo Apartments Arezzo Apartments

Luxury apartments with swimming pool and air conditioning in Cortona , in Valdichiana , in Arezzo countryside. From 2 to 4 sleeping accommodations.

7 days: min: 490 € - max: 1120 €

Reviews 1
More details
Borgo Montepulciano 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.

7 days: min: 590 € - max: 1035 €

Reviews 1
More details

SEARCH VILLAS

Are you an agency?

Offer for agencies and tour operators…

 

Click here

Discover Tuscany

Learn more about Tuscany and its beauties…

 

Click here
Properties by Type
⟩ Castles
⟩ Luxury Villas
⟩ Villas with pool
⟩ Wedding Villas
⟩ Farmhouses
⟩ Apartments in Villa
⟩ Apartments
Villas by City
⟩ Arezzo
⟩ Florence
⟩ Lucca
⟩ Pisa
⟩ Pistoia
⟩ Siena
Villas by Geographical Area
⟩ Casentino
⟩ Chianti
⟩ Crete Senesi
⟩ Garfagnana
⟩ Maremma
⟩ Mugello
⟩ Val di Cecina
⟩ Val di Chiana
Cortona
Castiglion Fiorentino
Civitella in Val di Chiana
Monte San Savino
Marciano della Chiana
Lucignano
Foiano della Chiana
Sinalunga
Montepulciano
Chianciano Terme
Chiusi
San Casciano dei Bagni
⟩ Val d`Orcia
⟩ Valdelsa
⟩ Valdinievole
⟩ Valtiberina
⟩ Versilia
⟩ Villas at the sea in Tuscany

Holiday Homes Tuscany srl - Via San Piero - Rignano sull'Arno - Florence (ITALY) - P.IVA 05612680487