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Holiday Houses Siena, House rentals for holidays in Siena

Properties by Type » Apartments in Villa » Holiday houses by area » Siena

House rentals for holidays in Siena

Are you planning to spend your holidays in Siena ? In this page and in our website you will find a wide selection of holiday houses in Siena and in the historical towns scattered in its countryside, such as San Gimignano , Monteriggioni , Montalcino , Pienza ...
Renowned all over the world for its Cathedral, the " Torre del Mangia " and Piazza del Campo, where twice a year the famous Palio takes place, Siena is situated in an area of the Tuscan countryside bounded on the north by the Chianti hills, Monteriggioni and San Gimignano , on the east by the Valdichiana and Arezzo , on the south by the Crete senesi , Montalcino and Montepulciano and on the west by the Colline Metallifere .
Thousands of tourists visit Siena every year, fascinated by its landscapes, its monuments and works of art, its folkloric events, its Medieval historical centre, its wines and cuisine and by its countryside, scattered with historical towns, such as San Gimignano , Monteriggioni , Montalcino , Pienza , Montepulciano and Colle Val d`Elsa .

For pleasant holidays in Siena, look for the accommodation that fits your needs among those we have selected for you

Our most requested holiday homes:
Villa Scanno Villa Scanno

Elegant 17th-century farmhouse in the heart of Val d'Orcia, near San Quirico d'Orcia (Siena). Sleeps 12, swimming pool, Internet connection, barbecue, possibility of organising cooking lessons. Wonderful views on the surrounding countryside.

7 days: min: 3830 € - max: 6330 €
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Farmhouse San Gimignano Farmhouse San Gimignano

Elegant luxury villa (originally a farmhouse) with panoramic view over San Gimignano . The villa is in San Gimignano , in Valdelsa, near the Chianti district, between Florence and Siena . Sleeps 12+2, swimming pool, Internet connection, air conditioning, hydromassage, gym, toys for children. Riding stable, tennis club and golf club nearby.

7 days: min: 5400 € - max: 7800 €

Reviews 1
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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
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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 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 Botticelli Villa Botticelli

Tuscan villa with pool near Radda in Chianti in the countryside of Chianti between Siena and Florence. Sleeps 10, Internet connection.

7 days: min: 1750 € - max: 2800 €

Reviews 6
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Villa Montalcino Villa Montalcino

Holiday villa for rent on the hills around Montalcino, in Val d`Orcia (Siena). 11/13 sleeping accommodations, swimming pool.

7 days: min: 1940 € - max: 2315 €
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Villa Simona Villa Simona

Villa for vacation rentals in Siena countryside. 4+2 sleeping accommodations, swimming pool.

7 days: min: 1016 € - max: 1544 €

Reviews 2
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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 Arcobaleno Villa Arcobaleno

Large country house in scenery location on the hills of the Chianti Classico region, a few kilometres from Castellina in Chianti (Siena). Sleeps 16, swimming pool, barbecue, Internet connection. Possibility of organising Tuscan dinners at the property.

7 days: min: 785 € - max: 3735 €

Reviews 1
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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 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 €
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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
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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
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Villa Radi Villa Radi

Villa (former farmhouse) in Monteroni d`Arbia (Siena), in the Crete Senesi region. Sleeps 8, wide garden, swimming pool, Internet connection, air conditioning, barbecue, hydromassage. Wonderful 360-degree view of Siena and the Crete Senesi region. Golf club, tennis club, riding stable and spa resorts within a few kilometres.

7 days: min: 1850 € - max: 3600 €

Reviews 1
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Villa Vanessa Villa Vanessa

Villa (formerly a farmhouse) in Val d`Orcia , in Pienza ( Siena ). Sleeps 8+2, swimming pool, Internet connection, hydromassage, children`s toys. Spas, tennis courts and riding stable within a few kilometres.

7 days: min: 1390 € - max: 2400 €

Reviews 3
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Villa Poggibonsi Villa Poggibonsi

Beautifully renovated house (formerly a barn) dating from the early 20th century near Poggibonsi and San Gimignano (Siena), in Valdelsa. Sleeps 4+1, swimming pool, barbecue, Internet connection, air conditioning, whirlpool facilities.

7 days: min: 1215 € - max: 2025 €

Reviews 1
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Villa Stefania Villa Stefania

Welcoming country house on the hills of Chianti, near Certaldo (Florence) and San Gimignano (Siena). Sleeps 6, swimming pool, Internet connection.

7 days: min: 1240 € - max: 2280 €

Reviews 1
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Villa Amerigo Villa Amerigo

Traditional Tuscan farmhouse in the heart of Chianti Classico, a few kilometres from Siena. Sleeps 16, swimming pool, wide garden, air conditioning, Internet connection. Possibility of organising wine tasting events and buying the produce of the farm.

7 days: min: 1990 € - max: 5465 €
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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 Zanobi Villa Zanobi

Independent house in an old hamlet in the Chianti Classico area, near the village of Gaiole in Chianti (Siena). Sleeps 8, swimming pool, wood-burning oven, children's playground with slide and swing, air conditioning.

7 days: min: 1530 € - max: 2555 €
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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 €
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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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Farmhouse Pienza Farmhouse Pienza

Farmhouse rental in Pienza in Val d`Orcia close to Siena. Sleeps 8. Swimming pool, table-tennis table.

7 days: min: 1600 € - max: 2265 €
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Farmhouse Tavarnelle Farmhouse Tavarnelle

Farmhouse in Tavarnelle in Val di Pesa, in the Chianti region, between Florence and Siena. Sleeps 8/11, garden, swimming pool, Internet connection, barbecue. Riding stables and tennis courts nearby.

7 days: min: 1700 € - max: 3780 €
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Villa Ponte Villa Ponte

Holiday farmhouse for rent in the Tuscan countryside near Sarteano (Siena), in Valdichiana. Sleeps 14, swimming pool, satellite TV,  Internet connection, wonderful views over the surrounding gentle rolling hills.

7 days: min: 790 € - max: 3710 €
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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
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Farmhouse Val d`Orcia Farmhouse Val d`Orcia

Farmhouse near Pienza, in the Val d`Orcia (Siena). Garden and private swimming pool. Sleeps 4, Internet connection.

7 days: min: 1195 € - max: 1680 €
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Farmhouse Paris Farmhouse Paris

Farmhouse in the Crete Senesi, in San Giovanni d`Asso (Siena). Swimming pool, 8 sleeping accommodations, garden, satellite TV.

7 days: min: 1020 € - max: 1150 €

Reviews 6
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Farmhouse Elsa Farmhouse Elsa

Luxurious villa (ex farmhouse) in Valdelsa, near the historical village of Casole d`Elsa, in the province of Siena. Sleeps 11/12. Swimming pool, satellite TV, hydromassage, barbecue, Internet connection. Possibility of organising tastings, visits to nearby wineries, cooking lessons and horseback rides.

7 days: min: 1105 € - max: 3130 €
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Farmhouse Radicofani Farmhouse Radicofani

Independent farmhouse on the hills surrounding the small village of Radicofani, in Val d`Orcia, near Siena. Swimming pool, 11/13 sleeping accommodations.

7 days: min: 1470 € - max: 2670 €
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Farmhouse Montisi Farmhouse Montisi

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: 1275 € - max: 2855 €
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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 Siena Farmhouse Siena

Farmhouse in the Chianti region, near Siena. Sleeps 9, swimming pool, Internet connection. Panoramic position with views of Siena, the hills of Chianti and the Crete Senesi region.

7 days: min: 1625 € - max: 2625 €
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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 Rapolano Farmhouse Rapolano

Villa (formerly a farmhouse) in Rapolano Terme (Siena), in the Crete Senesi. Sleeps 9+2, panoramic position, swimming pool, Internet connection. Tennis courts, riding stable and thermal establishments within a few kilometres.

7 days: min: 1690 € - max: 3125 €

Reviews 3
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Farmhouse Cetona Farmhouse Cetona

Beautiful stone farmhouse in panoramic position in a peaceful area near Sarteano (Siena). Sleeps 7, swimming pool, air conditioning. Possibility of organising dinners with traditional Tuscan dishes. Thermal baths nearby.

7 days: min: 1755 € - max: 3150 €
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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 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 Flora Farmhouse Flora

Farmhouse between Florence, Siena and Arezzo, and about 15 minutes from Radda in Chianti. Sleeps 8+2, fireplace, Jacuzzi, olive grove, Wi-Fi Internet connection, large swimming pool exclusively reserved to guests, hamlet with all services within short walkable distance.

7 days: min: 1230 € - max: 2460 €

Reviews 3
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Farmhouse San Filippo Farmhouse San Filippo

Peaceful farmhouse immersed in the countryside of Val d`Orcia (UNESCO World Heritage site), near Bagni San Filippo (Siena) and its thermal baths. Sleeps 18+7, swimming pool, Internet connection. Riding stable and tennis club nearby.

7 days: min: 2875 € - max: 7655 €

Reviews 1
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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 Romea Farmhouse Romea

Ancient and beautiful farmhouse between Florence and Siena, near San Gimignano and Colle Val d'Elsa. Sleeps 20, swimming pool, Internet connection, barbecue. Tennis club, riding stable and golf club nearby.

7 days: min: 2125 € - max: 3125 €
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Farmhouse Stigliano Farmhouse Stigliano

Beautiful farmhouse in scenic and peaceful location near the medieval town of Stigliano (Siena), in the Crete Senesi region. Sleeps 9, swimming pool, Internet connection, barbecue. Possibility of organising Nordic-walking tours.

7 days: min: 1200 € - max: 2330 €
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Farmhouse Carlo Farmhouse Carlo

Farmhouse in scenery location on the hills of Chianti Classico, between Florence and Siena, in Greve in Chianti. Sleeps 9, swimming pool, wide garden, barbecue. Just a few kilometres from Florence centre. Possibility of organising Italian cooking lessons.

7 days: min: 1065 € - max: 3190 €
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Farmhouse Sesta Farmhouse Sesta

Farmhouse dating back to the early 20th century situated in the countryside around Arezzo, a few kilometres from the Chianti region. Sleeps 8, wide fully fenced park, swimming pool, Internet connection.

7 days: min: 635 € - max: 2365 €

Reviews 1
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Farmhouse Brunello Farmhouse Brunello

Charming farmhouse in proximity to Montalcino (Siena), in Val d'Orcia. Sleeps 8, swimming pool, Internet connection. Wonderful panoramic views. Thermal baths within a few kilometres.

7 days: min: 1595 € - max: 3030 €
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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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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
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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 €
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Farmhouse Gina Farmhouse Gina

Holiday farmhouse in the heart of the Chianti Classico district, near Siena. 4/6 sleeping accommodations, garden, swimming pool, Internet connection.

7 days: min: 1240 € - max: 1735 €
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House Radicondoli House Radicondoli

Holiday house in the centre of the small and suggestive village of Radicondoli (Siena) in Maremma, atop a hill south of Siena. Swimming pool, air conditioning, panoramic terrace. 9+3 sleeping accommodations. Tennis courts in the vicinity, possibility of horse riding.

7 days: min: 804 € - max: 2680 €
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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
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House Maremma House Maremma

House divided into two apartments sleeping 10+2 people near Torniella, a medieval village in the Maremma region, between Siena and Grosseto. Internet connection, swimming pool. The coast is about 40 kilometres from the house.

7 days: min: 1330 € - max: 2525 €
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