Villas in Val di Chiana - Villas in Valdichiana for vacation rentals
Villas in Valdichiana for vacation rentals

If you want to take a vacation in Tuscany, rely on our agency. We have selected for you the best villas in the entire territory of Tuscany. In this page you will find our proposals for villas in Val di Chiana.


The Val di Chiana is a beautiful valley located between the provinces of Arezzo and Siena in Tuscany and those of Terni and Perugia in Umbria. As one of the most fertile regions of Italy, in this area we not only find the remains of the Etruscan civilization, spas, small towns rich in history and art, splendid hilly landscapes but also excellent typical products, well known and appreciated all over the world.

The Tuscan territory owes part of its beauty to the Etruscan civilization, that between the seventh and fifth centuries BC came to this area and began a major agricultural production. Today, we suggest you to visit the town of Cortona, Chiusi, Arezzo and Brolio with their Etruscan remains.

In the past, as today, lovers of thermal waters find in the Val di Chiana their ideal place. Chianciano Terme, San Casciano dei Bagni, Montepulciano are famous for its ancient tradition as spas and among the illustrious visitors lovers of these springs, we find Horace, Pirandello, Fellini, Chagall.

The characteristic villages full of works of art and architecture of the prestigious Val di Chiana are about five kilometers from each other, fascinating without interruption their visitors.

If you are planning your vacation in Tuscany, renting one of our villas in Val di Chiana will be the best choice if you want to live with your family in a unique setting, privacy and comfort. You can stay for long periods without spending much, organize your days exploring the vast territory of the Val di Chiana without having to respect times that hotels usually require and maybe invite friends to dinner without problems, cooking for them delicious dishes with the genuine ingredients of the area.

The Chianina meat (kind of meat for the Florentine steak), the Vino Nobile di Montepulciano, extra-virgin olive oil and honey are just some of the excellent products of the Val di Chiana.

Continue reading this page and choose one of our villas in Val di Chiana for your next vacation in Tuscany.

Small farmhouse in Valdichiana, near Foiano della Chiana (Arezzo). Sleeps 4+1, garden, swimming pool, Internet connection, wood-burning oven, barbecue. Tennis club, riding stable and golf club nearby.
7 days: min: 535 € - max: 1265 €
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 €
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 €
Villa with swimming pool in Valdichiana, near Monte San Savino (Arezzo). Sleeps 10, garden, barbecue, air conditioning, Internet connection. Tennis club and riding stable within a few kilometres.
7 days: min: 1065 € - max: 2535 €
Small and suggestive farmhouse near Lucignano, in Valdichiana (Arezzo). Swimming pool garden, Internet connection. 5+1 sleeping accommodations.
7 days: min: 500 € - max: 900 €
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 €
Former, recently renovated mill a few kilometres from Cortona (Arezzo), in Valdichiana. Sleeps 4, swimming pool, Internet connection.
7 days: min: 970 € - max: 1385 €
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 €
Aristocratic 19th-century luxury villa in Cortona, in Valdichiana, near Arezzo. 6/8 sleeping accommodations, swimming pool, wide garden, satellite TV, air conditioning, small animals admitted.
7 days: min: 640 € - max: 3240 €
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 €
Villa with exclusive swimming pool in Valdichiana near Cortona (Arezzo). 10/11 sleeping accommodations, Internet connection.
7 days: min: 1200 € - max: 2400 €
Villa in Cortona, in Valdichiana, near Arezzo. Farmhouse with swimming pool, 8 sleeping accommodations, wide garden, Internet connection.
7 days: min: 1815 € - max: 3250 €
Villa with swimming pool near Cortona (Arezzo), in Valdichiana. 8 sleeping accommodations, garden, hydromassage, outdoor toys, air conditioning.
7 days: min: 1200 € - max: 2250 €
Ancient farmhouse renovated and transformed into a villa in a farm with vineyards on the hills around Arezzo. Sleeps 10+2, swimming pool, wide garden, Internet connection. Riding stable and tennis club in the neighbourhood. Wonderful view over Arezzo.
7 days: min: 2990 € - max: 4390 €
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 €
Farmhouse in Marciano della Chiana, in Valdichiana, near Arezzo. 8/10 sleeping accommodations, wide garden, swimming pool, Internet connection, organic vegetable garden, cooking lessons. Wonderful panorama.
7 days: min: 1986 € - max: 2383 €
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: 530 € - max: 2035 €
Welcoming farmhouse near Castiglion Fiorentino (Arezzo), in Valdichiana. Sleeps 5, swimming pool, Internet connection, wood-burning oven. Tennis club, riding stable and golf club within a few kilometres.
7 days: min: 900 € - max: 1395 €
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 €
Ancient villa in Valdichiana, close to Cortona (Arezzo). 18+4 sleeping accommodations, swimming pool, Internet.
7 days: min: 2500 € - max: 4980 €
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 €
Villa with private swimming pool in Upper Valdarno, between Arezzo and Florence, near Pergine Valdarno. Sleeps 8, garden, wood-burning oven.
7 days: min: 1500 € - max: 2200 €
Farmhouse with swimming pool just a few kilometres from Arezzo historic centre, in Valdichiana. Sleeps 8+3, barbecue, wood-burning oven, hydromassage, Internet connection, air conditioning. Tennis club and riding stable nearby.
7 days: min: 1375 € - max: 3515 €
Ancient villa in Lucignano (Arezzo), in Valdichiana. Sleeps 18+4, wide garden, swimming pool, Internet connection, hydromassage. Spas, tennis club, riding stable and golf club nearby.
7 days: min: 3250 € - max: 6190 €
Villa with swimming pool in Civitella in Val di Chiana (Arezzo), in Valdichiana. Sleeps 8+2, wide garden, Internet connection, barbecue equipment. Tennis club and outlet village within a few kilometres.
7 days: min: 1735 € - max: 3335 €
Panoramic villa in Valdichiana, in Castiglion Fiorentino (Arezzo). Sleeps 9+3, garden, swimming pool, air conditioning, Internet connection, children`s play ground, barbecue, wood-burning oven. Tennis courts, riding stable and golf club within a few kilometres.
7 days: min: 1735 € - max: 2665 €
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: 750 € - max: 2595 €
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.
7 days: min: 1735 € - max: 3085 €
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 €
Villa in Valdichiana, near Arezzo. 10/12 sleeping accommodations, swimming pool, garden, barbecue.
7 days: min: 1425 € - max: 2970 €
Villa with swimming pool between Sansepolcro and Monterchi, in Valtiberina (Arezzo). 8+4 sleeping accommodations, tennis court.
7 days: min: 1850 € - max: 2200 €
Villa with wonderful panoramic view over Valdichiana near the small town of Lucignano (Arezzo). Sleeps 12, swimming pool, Internet connection, barbecue. Tennis courts, riding stable, golf club and thermal establishments within a few kilometres.
7 days: min: 3150 € - max: 4500 €
Villa with swimming pool in Valdichiana near Lucignano (Arezzo). 10 sleeping accommodations, barbecue, wide garden.
7 days: min: 2790 € - max: 4090 €
Villa in Valdichiana, just a few hundred metres from the small town of Lucignano ( Arezzo ). Sleeps 8, swimming pool, barbecue, Internet connection. Tennis courts, golf club, riding stable and thermal establishments within a few kilometres.
7 days: min: 1980 € - max: 2900 €
Luxury villa in Cortona (Arezzo), in Valdichiana. 12 sleeping accommodations, swimming pool, wide garden, satellite TV, Internet connection.
7 days: min: 3360 € - max: 4340 €
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 €
Elegant villa near Cortona (Arezzo), in Valdichiana. 10 sleeping accommodations, swimming pool, satellite TV, barbecue, Internet, hydromassage, small gym. Tennis and golf club and riding stable in the neighbourhood.
7 days: min: 1495 € - max: 2890 €
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 €
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 €
Beautiful independent villa in Valdichiana, between Arezzo and Cortona. Sleeps 9, garden, swimming pool, Internet connection. Panoramic terrace with charming view over the surrounding countryside. Possibility of organising dinners and Tuscan cooking lessons.
7 days: min: 2070 € - max: 3180 €
Independent house with swimming pool in Monte San Savino, in Valdichiana (Arezzo). 6+2 sleeping accommodations. Swimming pool, panoramic position, hydromassage.
7 days: min: 1000 € - max: 1800 €
Elegant villa for holidays in Arezzo, in Valdichiana. 10 sleeping accommodations, swimming pool, air conditioning, Internet connection, satellite TV, breathtaking view of Arezzo.
7 days: min: 3380 € - max: 5630 €
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 €
Eighteenth-century villa in Civitella, in Valdichiana, in the province of Arezzo. 8/9 sleeping accommodations, wide garden, Internet connection. Breathtaking views over the surrounding countryside.
7 days: min: 2090 € - max: 3215 €
Holiday villa in Valdichiana countryside, in Cortona (Arezzo). 6 sleeping accommodations, swimming pool, Internet connection, air conditioning.
7 days: min: 1750 € - max: 2850 €
Holiday villa in Valdichiana, close to Cortona, in the province of Arezzo . 7 sleeping accommodations, swimming pool, private garden, barbecue.
7 days: min: 1400 € - max: 2705 €
Holiday villa near Cortona (Arezzo), in the Valdichiana. 6/10 sleeping accommodations, swimming pool, garden, air conditioning. Jogging, walking and mountain-bike routes in the neighbourhood.
7 days: min: 1650 € - max: 3300 €
Farmhouse in Valdichiana, near Cortona (Arezzo). 10 sleeping accommodations, garden, swimming pool, Internet connection, air conditioning, barbecue.
7 days: min: 2550 € - max: 4350 €
Villa with swimming pool in Monte San Savino in Valdichiana between Arezzo and Siena. Panoramic location and swimming pool. 10+2 beds.
7 days: min: 1500 € - max: 3500 €
Tuscan luxury villa between Arezzo and Cortona, in Valdichiana. Sleeps 18+6, outdoor swimming pool, wide park, indoor swimming pool with hydromassage and sauna, air conditioning, Internet connection. Tennis courts, riding stable and golf club nearby.
7 days: min: 4000 € - max: 8390 €
Old farmhouse in Lucignano (Arezzo), in Valdichiana. Sleeps 12+6, wide park, swimming pool, Internet connection, air conditioning, wood-burning oven, barbecue, swing and roundabout for children. Riding stable, golf club, tennis club and thermal baths nearby.
7 days: min: 3500 € - max: 4500 €
Small and charming villa with swimming pool in Valdichiana, near Cortona (Arezzo). Sleeps 7, garden, barbecue, Internet connection.
7 days: min: 1200 € - max: 2100 €
Farmhouse dating back to the late 19th century situated in panoramic position on the hills of Valdichiana, in Foiano della Chiana (Arezzo). Sleeps 9, swimming pool, Internet connection, air conditioning, children`s playground.
7 days: min: 1435 € - max: 2460 €
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 €
Nice recently built villa a few kilometres from Cortona (Arezzo) and Lake Trasimeno. Sleeps 6+1, swimming pool, wide garden with solarium area, barbecue. Beautiful view of the lake and the surrounding countryside. Possibility of windsurfing, sailing and fishing.
7 days: min: 1010 € - max: 2765 €
Beautiful farmhouse a few kilometres from Castiglion Fiorentino and Cortona (Arezzo). Sleeps 8, swimming pool, Internet connection, barbecue. Wonderful view of Valdichiana countryside.
7 days: min: 1595 € - max: 3460 €
Beautiful villa atop a hill overlooking Arezzo and Valdichiana. Sleeps 8, swimming pool, whirlpool area, Internet connection, air conditioning. Possibility of organising wine, olive oil, spirits and balsamic vinegar tasting events.
7 days: min: 2765 € - max: 3830 €
Beautiful modern villa on the hills of Valdichiana, at a short distance from Arezzo historic centre. Sleeps 8, swimming pool, Internet connection, hydromassage, wood-burning oven. Possibility of organising dinners and cooking lessons.
7 days: min: 1595 € - max: 2660 €
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 €
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 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 €
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 €
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 €
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 €
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 €
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 €
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 €
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 €