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Villas in Castiglion Fiorentino, Villas for rent in Castiglion Fiorentino in Val di Chiana

Properties by Type » Villas by Geographical Area » Val di Chiana » Castiglion Fiorentino

Villas for rent in Castiglion Fiorentino in Val di Chiana

Our agency is specialized in the rent of holiday homes in Tuscany. On this page we are pleased to offer you our best  villas in Castiglion Fiorentino in Val di Chiana. By choosing one of the villas in Castiglion Fiorentino that we propose to you, you will be able to stay in a place surrounded by greenery, in total privacy and freedom between Arezzo and Lake Trasimeno.

Castiglion Fiorentino is an incredibly charming medieval town on the hills of the Val di Chiana. The historical center appears to its visitors with the Torre del Cassero that dominates the town.  The Logge del Vasari date back to 1513 and the 15th-century Town Hall. In town you will also find the Archaeological Museum. Even if it is not particularly large, it hosts interesting works and archaeological remains. 

But what most fascinates anyone visiting the territory is the high numbers of castles on the surrounding hills. Don't miss the opportunity to explore the entire hilly area of Castiglion Fiorentino looking for ancient castles. Castle Montecchio Vesponi, Castle Mammi and Castle Montanina are just a few castles built between 1000 and 1200 that you may see during your vacation.

And, at last, the churches in Castiglion Fiorentino are extremely rich in history and charm. Both in the historical center and on the hills you will find numerous churches that will leave you speechless: the Church of San Francesco, the Church of Sant'Agostino, the Church of Sant'Angelo al Cassero and the splendid Sanctuary of the Madonna del Bagno. 

For a holiday among castles, medieval villages and evocative churches, choose one of our Villas in Castiglion Fiorentino 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 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 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 Parto Villa Parto

Beautiful independent villa at the border between Tuscany and Umbria, near Monterchi (Arezzo), in Valtiberina. Sleeps 12, swimming pool, Internet connection, air conditioning, wine tasting. Possibility of organising dinners at the property.

7 days: min: 2660 € - max: 5840 €
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Villa Colle Villa Colle

Luxurious villa with swimming pool for rent near Monterchi (Arezzo), in Valtiberina. Sleeps 8, Internet connection, air conditioning, wide garden, barbecue. Wonderful views of the surrounding hills. Guided tour of Valtiberina, guided tours of local wineries with wine tasting experiences.

7 days: min: 2180 € - max: 4035 €
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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 Renai Villa Renai

Holiday villa for rent in Castelfiorentino (Florence), in Empoli countryside. 10+2 sleeping accommodations, swimming pool, accessible to disabled people.

7 days: min: 1625 € - max: 2625 €
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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 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 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 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 Vigneto Villa Vigneto

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 €

Reviews 1
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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 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 Elisabeth Farmhouse Elisabeth

Farmhouse in Marciano della Chiana, in Valdichiana, near Arezzo. 8/10 sleeping accommodations, wide garden, swimming pool, Internet connection, cooking lessons. Wonderful panorama.

7 days: min: 1986 € - max: 2383 €

Reviews 2
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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 Arezzo Farmhouse Arezzo

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: 4125 €

Reviews 1
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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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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 Righi Farmhouse Righi

Farmhouse for rent near Monterchi (Arezzo), in the countryside at the border between Tuscany and Umbria. Sleeps 14, swimming pool, barbecue. Wonderful views of the medieval town of Monterchi.

7 days: min: 1055 € - max: 2875 €
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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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