Holiday villas for rent in Valdichiana


Town of Etruscan origins, medieval villages, spas, castles, excellent local produce, art and beautiful hills will characterize your holiday in Tuscany if you decide to rent one of our villas in Val di Chiana. On this page, our agency specialized in villas for rent is pleased to present a wide selection of Villas in Val di Chiana with pictures and prices.


The Val di Chiana is a large fertile and hilly territory divided between the provinces of Siena and Arezzo and bordering Terni and Perugia in Umbria. The Val di Chiana is particularly known for the medieval villages rich in works of art and archaeological sites, as well as wine and food products of high quality. The famous Chianina beef, used for Florentine steak, takes its name from here.

By choosing to rent one of the villas in Cortona offered by our agency you will have comfort and tranquility close to a medieval village that over the years has won tourists, artists and filmmakers from all over the world. Choosing, instead, one of our villas in Montepulciano you can enjoy a good bottle of Nobile di Montepulciano in the garden of your private villa or poolside. One of the villas in San Casciano dei Bagni will be the ideal choice for spa lovers ... and if you want to add to the hot springs shopping you just have to choose between the villas in Chianciano Terme that we offer on these pages.

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Farmhouse Capanna Farmhouse Capanna

Pretty farmhouse sleeping 4+1 in the countryside south of Arezzo, in Valdichiana. Garden, swimming pool, barbecue, wood-burning oven, Internet connection. Golf club, riding stable and tennis club within a few kilometres.

7 days: min: 535 € - max: 1265 €
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Villa Piana Verde Villa Piana Verde

Villa with pool near Montepulciano (Siena), in Valdichiana. Sleeps 5, garden, air conditioning, hydromassage, Internet connection, outdoor toys for children. Spas, golf club, tennis club and riding stable within a few kilometres.

7 days: min: 900 € - max: 1100 €
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Farmhouse Marcos Farmhouse Marcos

Farmhouse for holidays in Cortona, in Valdichiana, in the province of Arezzo. Sleeps, garden, swimming pool, barbecue, Internet connection. A few kilometres from the farmhouse there are a riding stable and some tennis courts.

7 days: min: 850 € - max: 1400 €
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Villa Alberoro Villa Alberoro

Beautiful villa sleeping 10 situated in panoramic position in Valdichiana, near Monte San Savino (Arezzo). Wide garden, swimming pool, Internet connection, air conditioning, barbecue. Riding stable and tennis club within a few kilometres.

7 days: min: 1065 € - max: 2535 €
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Farmhouse Lucignano Farmhouse Lucignano

Holiday farmhouse in Valdichiana, in Lucignano, in the province of Arezzo. 5/6 sleeping accommodations, swimming pool, satellite TV, Internet connection, wonderful panorama.

7 days: min: 500 € - max: 900 €
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Farmhouse Lory Farmhouse Lory

Farmhouse sleeping 8+7 in Cortona (Arezzo), in Valdichiana. Wide garden, swimming pool with whirlpool corner, organic vegetable garden, barbecue, Internet connection, children's playground. Tennis club, golf club and riding stable nearby.

7 days: min: 1200 € - max: 2300 €
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Villa Tuoro Villa Tuoro

Small villa sleeping 6+2 in Valdichiana, just a few kilometres from Montepulciano (Siena) and Lake Trasimeno. Fully fenced garden, swimming pool, children`s playground, Internet connection, hydromassage. Tennis club and riding stable within a few kilometres.

7 days: min: 1500 € - max: 2000 €
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Villa Mulinetto Villa Mulinetto

Villa sleeping 4 near Cortona (Arezzo), in Valdichiana. Fenced garden, swimming pool, Internet connection.

7 days: min: 970 € - max: 1385 €
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Villa Cascina Villa Cascina

Ancient villa in the neighbourhood of Cortona, in the province of Arezzo, in the Valdichiana. 6+2 sleeping accommodations, swimming pool, outdoor hydromassage, air conditioning, barbecue, children's toys, Internet connection.

7 days: min: 1330 € - max: 3990 €
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Villa Limoni Villa Limoni

Luxury villa for vacation rental near Cortona (Arezzo) in Tuscany . Villa with 4/6/10 beds, beautiful garden, exclusive swimming pool.

7 days: min: 600 € - max: 3400 €
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Villa Bucolica Villa Bucolica

Villa for rent with private swimming pool in the Tuscan countryside near Cortona (Arezzo). Accommodation for 10/11 people, garden, Internet connection and parking.

7 days: min: 1200 € - max: 2400 €
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Villa Montepulciano Villa Montepulciano

Villa in a panoramic position on a typical Florentine hill near Chianciano Terme and Montepulciano. Villa with accommodation for 8/10 people, swimming pool, air conditioning.

7 days: min: 1600 € - max: 2800 €
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Villa Cortona Villa Cortona

Former farmhouse transformed in a holiday villa in Valdichiana, in Castiglion Fiorentino, near Cortona (Arezzo). Sleeps 8, garden, swimming pool, Internet connection.

7 days: min: 1815 € - max: 3250 €
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Villa Angelo Villa Angelo

Holiday villa in proximity to Cortona (Arezzo), in Valdichiana. 8 sleeping accommodations, swimming pool, air conditioning, hydromassage, outdoor toys for kids.

7 days: min: 1200 € - max: 2250 €
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Villa Vigneto Villa Vigneto

Villa sleeping 10/12 near Arezzo, in Valdichiana. Garden, swimming pool, Internet connection, view over Arezzo. Tennis courts and riding stable nearby.

7 days: min: 2990 € - max: 4390 €
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Villa Simonetta Villa Simonetta

Small holiday villa sleeping 6 in Valdichiana, near Cortona (Arezzo) and the Abbey of Farneta. Garden, swimming pool, air conditioning, Internet connection. Riding stable, tennis club, and golf club within a few kilometres.

7 days: min: 985 € - max: 1680 €
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Villa Zefiro Villa Zefiro

Villa sleeping 7 in Valdichiana, near Cortona (Arezzo). Garden, swimming pool, Internet connection, barbecue. Magnificent panorama.

7 days: min: 560 € - max: 2295 €
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Farmhouse Elisabeth Farmhouse Elisabeth

Holiday farmhouse in Valdichiana, in Marciano della Chiana, in the province of Arezzo. Sleeping 8/10 people, swimming pool, garden, Internet connection, cooking lessons.

7 days: min: 1986 € - max: 2383 €
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Villa Mauro Villa Mauro

Holiday villa near Cortona, in Terontola (Arezzo), in Valdichiana. 10/12 sleeping accommodations, swimming pool, garden, Internet connection, small gym.

7 days: min: 1335 € - max: 3335 €
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Villa Scannagallo Villa Scannagallo

Holiday villa close to Cortona (Arezzo), in the Valdichiana. 18/22 sleeping accommodations, swimming pool, satellite TV, Internet connection, wide park. Rooms accessible to disabled people.

7 days: min: 2650 € - max: 5300 €
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Villa Montecchio Villa Montecchio

Medieval sighting tower converted into a holiday villa in Montecchio di Cortona (Arezzo), in Valdichiana. Sleeps 9, swimming pool, garden, air conditioning, Internet connection, Finnish sauna.

7 days: min: 1125 € - max: 1750 €
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Villa Valdarno Villa Valdarno

Villa sleeping 8 in Pergine Valdarno (Arezzo), in Upper Valdarno. Garden, swimming pool, wood-burning oven.

7 days: min: 1500 € - max: 2200 €
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Villa Fioremma Villa Fioremma

Elegant holiday villa sleeping 18+4 in Valdichiana, close to the ancient town of Lucignano (Arezzo). Wide park, swimming pool, hydromassage, Internet connection. Riding stable, tennis courts, spas and golf club within a few kilometres.

7 days: min: 3250 € - max: 6190 €
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Villa Marciano Villa Marciano

Villa sleeping 8+2 in Valdichiana, in Civitella in Val di Chiana, in the province of Arezzo. Wide garden, swimming pool, Internet connection. Outlet village and tennis club nearby.

7 days: min: 1735 € - max: 3335 €
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Villa Castiglion Fiorentino Villa Castiglion Fiorentino

Former farmhouse sleeping 9+3 guests in panoramic position in Valdichiana, in Castiglion Fiorentino (Arezzo). Swimming pool, barbecue, wood-burning oven, children`s playground, air conditioning, Internet connection. Riding stable, tennis courts and golf club nearby.

7 days: min: 1735 € - max: 2665 €
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Villa Camucia Villa Camucia

Beautiful villa sleeping 8 in Valdichiana, near Cortona (Arezzo). Swimming pool, Internet connection, table-tennis table, wood-burning oven, air conditiong.

7 days: min: 1735 € - max: 3085 €
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Villa Viola Villa Viola

Charming villa sleeping 4 on the hills of Valdichiana, near Cortona (Arezzo). Wide garden, swimming pool, hydromassage, steam bath, Internet connection. Dinners with Tuscan dishes are organised upon request.

7 days: min: 915 € - max: 1675 €
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Castle Montepulciano Castle Montepulciano

Castle sleeping 12+2 just a few kilometres from Chianciano Terme (Siena) and its thermal baths, in Valdichiana. Wide garden, park with exotic trees, two swimming pools, Internet connection. Possibility of celebrating weddings and special occasions. Tennis courts, riding stable and golf club in proximity to the estate.

7 days: min: 4500 € - max: 5375 €
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Farmhouse Arezzo Farmhouse Arezzo

Holiday farmhouse sleeping 8+3 people in Valdichiana, close to Arezzo. Wide garden, swimming pool with whirlpool area, barbecue, wood-burning oven, air conditioning, Internet connection. Riding stable and tennis courts within a few kilometres.

7 days: min: 1375 € - max: 4125 €
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Farmhouse Aretino Farmhouse Aretino

Small and cosy farmhouse sleeping 5 in Valdichiana, near Castiglion Fiorentino (Arezzo). Swimming pool, wood-burning oven, Internet connection. Tennis club, riding stable and golf club within a few kilometres.

7 days: min: 900 € - max: 1395 €
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Farmhouse Ginepro Farmhouse Ginepro

Farmhouse sleeping 5+1 in Valdichiana, near Cortona (Arezzo). Swimming pool, Internet connection, hydromassage, air conditioning. Wonderful view over the surrounding countryside.

7 days: min: 555 € - max: 2595 €
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Villa Ventura Villa Ventura

Villa for rent near Arezzo in Tuscany. Villa with accommodation for 8/12 people, garden, swimming pool, tennis courts.

7 days: min: 1850 € - max: 2200 €
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Villa Chiusi Villa Chiusi

Villa with swimming pool for holidays in the middle of a naturalistic oasis. Swimming pool, accommodation for 9 people.

7 days: min: 1125 € - max: 2900 €
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Villa La Rosa Villa La Rosa

Farmhouse immersed in the tranquil Valdichiana forests, between Tuscany and Umbria. 10+2 beds. Parking, private swimming pool, panoramic position. Animals admitted.

7 days: min: 1355 € - max: 2765 €
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Villa Valdichiana Villa Valdichiana

Villa with swimming pool in the countryside around Siena, in the neighbourhood of Montepulciano. 10 beds, private parking, satellite TV, air conditioning, Internet connection.

7 days: min: 2200 € - max: 4115 €
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Villa Lucignano Villa Lucignano

Villa in Valdichiana, close to Lucignano (Arezzo). 10 beds, private swimming pool, wide garden, barbecue, satellite TV.

7 days: min: 2790 € - max: 4090 €
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Villa Lilly Villa Lilly

Villa sleeping 8 in Lucignano (Arezzo), in Valdichiana. Garden, swimming pool, barbecue, Internet connection. Thermal establishments, golf club, riding stable and tennis club nearby.

7 days: min: 1980 € - max: 2900 €
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Villa Sinalunga Villa Sinalunga

Elegant villa with swimming pool in Sinalunga (Siena), between Montepulciano and Pienza, in Valdichiana. 14 sleeping accommodations, wide garden, barbecue, bowls pitch, satellite TV, wood-burning oven.

7 days: min: 2630 € - max: 5125 €
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Villa Bettolle Villa Bettolle

Villa with swimming pool for holidays in Valdichiana, near Cortona (Arezzo). 10/12 sleeping accommodations, hydromassage, gym, satellite TV, Internet, barbecue, table tennis. Riding stable and tennis club in the neighbourhood.

7 days: min: 1355 € - max: 2810 €
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Villa Poggiolo Villa Poggiolo

Holiday villa near Arezzo, in Valdichiana. 10/12 sleeping accommodations, swimming pool, garden.

7 days: min: 1425 € - max: 2970 €
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Villa Irene Villa Irene

Villa with swimming pool for holidays in Valdichiana, at the border between the provinces of Arezzo and Siena, in Lucignano. 12 sleeping accommodations, air conditioning, Internet connection. Rooms accessible to disabled people.

7 days: min: 1500 € - max: 3000 €
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Villa Monte S Savino Villa Monte S Savino

Typical Tuscan cottage close to Monte San Savino, in the province of Arezzo, in the Valdichiana region. 6/8 sleeping accommodations, swimming pool, barbecue, hydromassage. Wonderful panoramic view.

7 days: min: 1000 € - max: 1800 €
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Villa Piccolomini Villa Piccolomini

Villa sleeping 9 in Valdichiana, near Monte San Savino (Arezzo). Fully fenced garden, swimming pool, panoramic terrace, Internet connection. Tuscan cooking lessons and dinners at the villa are organised upon request.

7 days: min: 2070 € - max: 3180 €
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Villa Creti Villa Creti

Charming holiday villa in the heart of Valdichiana, near Cortona (Arezzo). 6 sleeping accommodations, swimming pool, air conditioning, Internet connection. Golf and tennis club, riding stables and outlet village in the vicinity.

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

Nice holiday villa in Valdichiana, close to Cortona (Arezzo). 7 sleeping accommodations, swimming pool, barbecue.

7 days: min: 1345 € - max: 2490 €
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Villa Lucia Villa Lucia

Villa in Valdichiana, in Cortona, in the province of Arezzo. 6/10 sleeping accommodations, garden, swimming pool, air conditioning. Mountain-bike and walking routes in the surroundings.

7 days: min: 1650 € - max: 3300 €
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Villa Fabiane Villa Fabiane

Villa in Monte San Savino in Valdichiana between Siena and Arezzo . Panoramic position. Quiet and isolated. Swimming pool, garden, parking area. 10+2 beds.

7 days: min: 1500 € - max: 3500 €
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Villa Petraia Villa Petraia

Villa sleeping 12 in Lucignano (Arezzo), in Valdichiana. Swimming pool, barbecue, Internet connection, breathtaking view over the valley below. Thermal establishments, golf club, riding stable and tennis club nearby.

7 days: min: 1290 € - max: 3940 €
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Villa Campo Villa Campo

Villa sleeping 14 in the countryside around Montepulciano (Siena), in Valdichiana. Wide garden, swimming pool, barbecue. Thermal baths, tennis club and riding stable within a few kilometres.

7 days: min: 2500 € - max: 3700 €
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Villa Pieve Villa Pieve

Villa with swimming pool close to Chianciano Terme (Siena), in Valdichiana. Sleeps 10, wide garden, Internet connection, wonderful panorama. Just a few kilometres from the thermal baths of Chianciano Terme and San Casciano dei Bagni.

7 days: min: 3385 € - max: 4305 €
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Villa Carmen Villa Carmen

Small villa sleeping 7 in the province of Arezzo, near Cortona, in Valdichiana. Garden, swimming pool, Internet connection.

7 days: min: 1200 € - max: 2100 €
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Villa Lago Villa Lago

Villa sleeping 6 a few kilometres from Montepulciano (Siena). Garden, swimming pool, solarium area, masonry barbecue, Internet connection. Possibility of sailing, windsurfing and fishing in nearby Lake Trasimeno.

7 days: min: 950 € - max: 3146 €
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Villa Tuscia Villa Tuscia

Nineteenth-century farmhouse sleeping 9 near Foiano della Chiana (Arezzo), in Valdichiana. Swimming pool, children`s playground, air conditioning, Internet connection, beautiful panoramic view.

7 days: min: 1435 € - max: 2460 €
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Villa Igor Villa Igor

Villa sleeping 8 on a hill in Valdichiana with views of Arezzo. Wide garden, swimming pool, whirlpool area, air conditioning, Internet connection. Olive oil, wine, balsamic vinegar and spirits tasting events organised upon request.

7 days: min: 2765 € - max: 3830 €
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Villa Lorenzo Villa Lorenzo

Elegant villa sleeping 8 a few kilometres from Arezzo, in Valdichiana. Fully fenced park, swimming pool, wood-burning oven, Internet connection. Possibility of organising cooking lessons and dinners at the property.

7 days: min: 1595 € - max: 2660 €
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Villa Viola 2 Villa Viola 2

Small holiday villa sleeping 7 in Valdichiana, a few kilometres from Cortona (Arezzo). Swimming pool, children's playground, table-tennis table, Internet connection.

7 days: min: 450 € - max: 2295 €
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Villa Medici Villa Medici

Beautiful stone villa sleeping 10 for holidays in Valdichiana, near Monte San Savino (Arezzo). Wide garden, swimming pool, wood-burning oven, barbecue, Internet connection. Tuscan cooking lessons are organised upon request.

7 days: min: 2385 € - max: 3655 €
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Casale Cortona Casale Cortona

Elegant luxury villa with wide garden and swimming pool near Cortona, in Valdichiana, south of Arezzo. 12 beds, barbecue, satellite TV, Internet connection.

7 days: min: 3360 € - max: 4360 €
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Villa Jacopo Villa Jacopo

Luxury villa for holidays in Valdichiana, near Cortona, in the province of Arezzo. 10 sleeping accommodations, swimming pool, gym, hydromassage, Internet, satellite TV, table-tennis table, barbecue. Tennis club and golf club nearby.

7 days: min: 1495 € - max: 2890 €
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Villa Arezzo Villa Arezzo

Wonderful luxury villa close to Arezzo, for holidays in Valdichiana. 10 sleeping accommodations, swimming pool, satellite TV, Internet connection, air conditioning. Animals admitted.

7 days: min: 3380 € - max: 5630 €
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Villa Castiglione Villa Castiglione

Elegant villa sleeping 18+6 near Castiglion Fiorentino (Arezzo), in Valdichiana. Wide park, two swimming pools, sauna, hydromassage, barbecue, air conditioning, Internet connection. Golf club, riding stable and tennis club within a few kilometres.

7 days: min: 6920 € - max: 8575 €
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Villa Paolina Villa Paolina

Luxurios historic villa sleeping 16 in Sienese Valdichiana, in Montepulciano. Wide garden, barbecue, swimming pool, Internet connection. Wonderful view. Thermal baths, tennis club, riding stable and golf club nearby.

7 days: min: 4740 € - max: 4740 €
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Villa Sarteano Villa Sarteano

Luxurious villa sleeping 14 in Valdichiana, in Siena countryside. Swimming pool, wide park, air conditioning, Internet connection, sauna. Wonderful view. Thermal baths and tennis club nearby.

7 days: min: 8835 € - max: 11315 €
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Villa Cipressi Villa Cipressi

Fourteenth-century villa sleeping 10+2 in Valdichiana, near Capolona (Arezzo). Swimming pool, wide garden, Internet connection.

7 days: min: 775 € - max: 2770 €
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Villa Fontana Villa Fontana

Luxurious villa sleeping 14+5 just a few kilometres from Cortona (Arezzo), in Valdichiana. Wide garden, swimming pool, barbecue, steam room, hydromassage, air conditioning, Internet connection. Riding stable and tennis club nearby.

7 days: min: 5200 € - max: 7500 €
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Farmhouse Montisi Farmhouse Montisi

Holiday farmhouse for rent in Valdichiana, near Montisi, in the province of Siena. 6/7 sleeping accommodations, swimming pool, satellite TV, Internet connection, barbecue. Golf club, tennis club, riding stables and thermal establishments nearby. Pets allowed.

7 days: min: 1275 € - max: 2855 €
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Farmhouse Greppia Farmhouse Greppia

Holiday farmhouse in Valdichiana, near Cortona, in the province of Arezzo. 8/10 sleeping accommodations, swimming pool with hydromassage, garden, air conditioning. Wonderful panorama.

7 days: min: 1500 € - max: 2700 €
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Farmhouse Garden Farmhouse Garden

Ancient farmhouse dating back to the 17th century between Sinalunga and Montepulciano (Siena), in the Valdichiana. Sleeps 6, wide garden. Wonderful view of the Tuscan countryside.

7 days: min: 750 € - max: 1500 €
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Farmhouse Cortona Farmhouse Cortona

Ancient farmhouse close to Cortona, in the province of Arezzo, in the Valdichiana region. 10/14 sleeping accommodations, swimming pool, air conditioning, hydromassage.

7 days: min: 2500 € - max: 3500 €
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Farmhouse Stocchi Farmhouse Stocchi

Ancient holiday cottage in proximity to Arezzo, in Valdichiana. 10 sleeping accommodations, swimming pool, garden, air conditioning, Internet connection.

7 days: min: 2550 € - max: 4350 €
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Farmhouse Radiante Farmhouse Radiante

Ancient farmhouse sleeping 8 for rent near Cortona (Arezzo), in Valdichiana. Wide garden with swimming pool and solarium area, hydromassage, air conditioning. Wonderful views.

7 days: min: 1470 € - max: 2570 €
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Farmhouse Valdichiana Farmhouse Valdichiana

Farmhouse sleeping 12+6 in Valdichiana, near Lucignano (Arezzo). Swimming pool, wide park, children`s toys, Internet connection, air conditioning, wood-burning oven. Tennis club, riding stable, golf club and thermal baths within a few kilometres.

7 days: min: 3500 € - max: 4500 €
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Farmhouse Croce Farmhouse Croce

Farmhouse sleeping 10 with wonderful views over the Valdichiana situated between Castiglion Fiorentino and Cortona, in the province of Arezzo. Swimming pool, barbecue, Internet connection.

7 days: min: 3190 € - max: 5055 €
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