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Villas in Cortona, Villas for rent in Cortona in Val di Chiana for a holiday like being in the movies

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

Villas for rent in Cortona in Val di Chiana for a holiday like being in the movies

When you saw the movie 'Under the Tuscan Sun' did you decide it was time to pack up and leave? For your next holiday in Tuscany choose the town where most of the scenes in the film were shot, and also you like the protagonist, stay in one of the many villas in Cortona in Val di Chiana. Do not worry: the villas for rent in Cortona that we offer are all newly renovated and elegantly furnished . Yours is really  going to be a relaxing holiday!

The town was chosen by the director of 'Under the Tuscan Sun'  for its beauty and charm. This town is set on the Tuscan hills between Siena and Arezzo and will not disappoint your expectations.

Visit the historic center of Cortona: admire Piazza della Repubblica and Piazza Signorelli, the Town Hall built in 1236 and the wonderful Renaissance Cathedral in Piazza del Duomo. Inside the museum of the Cathedral of Cortona find an unmissable fifteenth century work by Fra Angelico. Inside the Museum of the Etruscan Academy there are countless historical artifacts and works that we recommend you see. The historic center of the town is so suggestive that walking through the narrow medieval streets surrounded by stone buildings will make you experience the sensation of being in another era.

And if you really want to go back in time do not miss the famous Giostra dell'Archidado on the first Sunday of June each year: you will find people in medieval costumes, flag bearers, parades and decorated historical buildings and streets. The festival commemorates the marriage that took place in 1397 between two important nobles of Cortona and Siena.

For a holiday like a movie star, choose one of our Villas in Cortona in Val di Chiana.

Our most requested holiday homes:
Villa Buccellati Villa Buccellati

Elegant villa with wide garden and wonderful views situated in the countryside around Arezzo. Sleeps 10, swimming pool, Internet connection, air conditioning, wood-burning oven, barbecue. Tennis club and riding stable within a few kilometres.

7 days: min: 3200 € - max: 5100 €
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Villa Torre Medioevale Villa Torre Medioevale

Ancient medieval tower transformed into a luxury villa in Monterchi, in Valtiberina, in Arezzo countryside. 6/8/10 sleeping accommodations, swimming pool.

7 days: min: 1490 € - max: 3850 €
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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
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Villa Lorena Villa Lorena

Former farmhouse dating from the late 19th century in Arezzo countryside. Sleeps 12, panoramic swimming pool, Internet connection, air conditioning, wood burning oven. Tennis club and riding stable nearby.

7 days: min: 3700 € - max: 5600 €

Reviews 1
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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 €
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Villa Castiglione Villa Castiglione

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: 6920 € - max: 8575 €
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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
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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 €
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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 €
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Villa Sanzio Villa Sanzio

Beautiful independent villa in Umbria, near the border with Tuscany and the town of Cortona (Arezzo). Sleeps 11, swimming pool, fenced garden, Internet connection, barbecue. Possibility of organising lunches and dinners at the property. Golf club within a few kilometres.

7 days: min: 790 € - max: 4170 €
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Villa Cassa Villa Cassa

Beautiful villa on the hills around Arezzo, near Capolona, at the border between Casentino and Valdichiana. Sleeps 9, swimming pool, internal and external hydromassage, gym, steam bath, Internet connection, wood-burning oven, table-tennis and pool tables. Gorgeous panoramic views.

7 days: min: 715 € - max: 2825 €
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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 €
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Villa Brunetto Villa Brunetto

Welcoming small villa near Foiano della Chiana, a few kilometres from Arezzo, in Valdichiana. Sleeps 4+1, swimming pool, bicycles, garden swing, barbecue, fully fenced property. Golf club, riding stable, tennis club and outlet village nearby.

7 days: min: 535 € - max: 1335 €
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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
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Villa Corso Villa Corso

Holiday villa for rent in Monterchi, in Valtiberina (Arezzo). 14+1 sleeping accommodations, panoramic swimming pool, yoga classes for free, wifi internet connection.

7 days: min: 1125 € - max: 2500 €

Reviews 2
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Villa del Poggio Villa del Poggio

Villa with swimming pool atop a hill in the Tuscan countryside with spectacul view of the ancient city of Arezzo. 6/8/10 sleeping accommodations, wide fenced park.

7 days: min: 1255 € - max: 3060 €
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Villa Cortona Villa Cortona

Villa in Cortona, in Valdichiana, near Arezzo. Farmhouse with swimming pool, 8 sleeping accommodations, wide garden, Internet connection.

7 days: min: 1815 € - max: 3250 €

Reviews 1
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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 €
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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 €
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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
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Villa Lucia Villa Lucia

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 €
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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 €
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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 €
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Villa Jacopo Villa Jacopo

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 €
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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 €
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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
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Villa Creti Villa Creti

Holiday villa in Valdichiana countryside, in Cortona (Arezzo). 6 sleeping accommodations, swimming pool, Internet connection, air conditioning.

7 days: min: 1750 € - max: 2850 €
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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 €
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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
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Villa Belvedere Villa Belvedere

Villa in Valtiberina, near Arezzo. Sleeps 12/14, wide garden, swimming pool, Internet connection, cooking lessons. The villa is just a few kilometres from Anghiari and Arezzo. Wonderful panorama.

7 days: min: 2600 € - max: 4100 €

Reviews 1
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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 €
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Villa Arcangelo Villa Arcangelo

Beautiful villa in Valdichiana countryside, between Arezzo and Cortona. Sleeps 14, swimming pool, wide garden, barbecue, Internet connection, air conditioning.

7 days: min: 1275 € - max: 3830 €
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Villa Castiglion Fiorentino Villa Castiglion Fiorentino

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 €
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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 €
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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 €
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Villa Tuscia Villa Tuscia

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 €
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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 €
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Villa Staggiano Villa Staggiano

Ancient elegantly renovated farmhouse dating from the 17th century transformed into a beautiful villa with swimming pool situated in the Tuscan countryside, a few kilometres from Arezzo. Sleeps 10+2, Internet connection, air conditioning, barbecue. Riding stable and tennis club nearby.

7 days: min: 1865 € - max: 3865 €
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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 €
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Villa Mulinetto Villa Mulinetto

Former, recently renovated mill a few kilometres from Cortona (Arezzo), in Valdichiana. Sleeps 4, swimming pool, Internet connection.

7 days: min: 970 € - max: 1385 €

Reviews 2
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Villa Piccolomini Villa Piccolomini

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 €
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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 €
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Villa Igor Villa Igor

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 €
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Villa Lorenzo Villa Lorenzo

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 €
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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 €
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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 €
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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 €
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Villa Viti Villa Viti

Beautiful villa in the picturesque Tuscan countryside around Castiglion Fiorentino, near Cortona, in Valdichiana. Sleeps 14+1, swimming pool, Internet connection, hydromassage, private tennis court, table-tennis table, wood-burning oven. Golf club within a few kilometres.

7 days: min: 1890 € - max: 3700 €
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Villa Feritoie Villa Feritoie

Villa in scenery location in Castiglion Fiorentino, between Arezzo and Cortona, in Valdichiana. Sleeps 9+2, swimming pool, private tennis court, Internet connection. Golf club within a few kilometres.

7 days: min: 1190 € - max: 2380 €
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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
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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 €
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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
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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 €
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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
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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 €
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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 €
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Villa Rosetta Villa Rosetta

Farmhouse in a panoramic area of Valdichiana, near Cortona (Arezzo). Sleeps 12, swimming pool, fenced garden, Internet connection. Cooking lessons and wine tastings organised upon request.

7 days: min: 960 € - max: 2205 €
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Farmhouse Capanna Farmhouse Capanna

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 €

Reviews 4
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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 €
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Farmhouse Croce Farmhouse Croce

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: 3190 € - max: 5055 €
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Farmhouse Aretino Farmhouse Aretino

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 €
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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 €
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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 €
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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 €
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Farmhouse Fiore Farmhouse Fiore

Holiday farmhouse in Castiglion Fiorentino (Arezzo) countryside, in Valdichiana. Sleeps 8, swimming pool, Internet connection, barbecue. Ideal accommodation for holidays in close contact with nature.

7 days: min: 1490 € - max: 2980 €
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Farmhouse Stocchi Farmhouse Stocchi

Farmhouse in Valdichiana, near Cortona (Arezzo). 10 sleeping accommodations, garden, swimming pool, Internet connection, air conditioning, barbecue.

7 days: min: 2550 € - max: 4350 €
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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 €
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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
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Farm Holiday Valiano Farm Holiday Valiano

Farm holiday apartments with swimming pool in Cortona, in Valdichiana, near Arezzo. Apartments from 2 to 8 sleeping accommodations.

7 days: min: 420 € - max: 1350 €
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