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42 Results   |  

from £441 / night

£3085 - £3383 / week

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Excellent 5/5 

24 Photos

Province of Siena / Castellina In Chianti

Villa / 7 Bedrooms / sleeps 14

Excellent 5/5 

5 Nights min stay

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from £441 / night

£3085 - £3383 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
Sleeps 14 with possibility to add adjacent apartments up to total of 33. A beautiful 15th-century villa in the heart of the Chianti countryside, with 360° uninterrupted views of olives, vines and forests, with amazing sunset views over San Gimignano and the Apennines  …see more

from £86 / night

£596 - £1008 / week

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Very Good 4/5 

20 Photos

Province of Siena / Castellina In Chianti

House / 4 Bedrooms / sleeps 5

Very Good 4/5 

1 night min stay

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from £86 / night

£596 - £1008 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
CASALTA di PESA: Beautiful stone Tuscan hamlet in the splendid Chianti Classico vineyards. This property still shows the blazon of the astronomer Galileo Galilei who stayed in this hamlet many years and drew inspiration from the beauties of the surrounding landscape. Casalta di Pesa is an Holiday Home surrounded by vineyards, just outside Castellina in Chianti  …see more

from £48 / night

£330 - £479 / week

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16 Photos

Castellina In Chianti / Cagnano di Sotto

Apartment / 2 Bedrooms / sleeps 4

7 Nights min stay

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from £48 / night

£330 - £479 / week

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Key info:

  • Nearest beach 85 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
TUSCAN STYLE STONE MADE APARTMENT WITH TERRACE OUTDOOR EATING SPACE AND POOL TO SHARE WITH TWO BEDROOMS THAT CAN ACCOMMODATE 4 ADULTS, THIS HOUSE IS SURROUND BY GREEN. HEART OF CHIANTI , PEACEFUL RELAXING AREA, PERFECTLY LOCATED TO TOUR AROUND  …see more

Featured properties

from £144 / night

£1004 - £1179 / week

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Excellent 5/5 

24 Photos

Province of Siena / Castellina In Chianti

Villa / 3 Bedrooms / sleeps 7

Excellent 5/5 

7 Nights min stay

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from £144 / night

£1004 - £1179 / week

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Key info:

  • Nearest beach 85 km
  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
The Cypresses Villa is a real amazing place, peaceful, green, sunny, a great place for families and also for a small group of friends.There is a large list of sites to visit around, it is a perfect spot in between Sienna and Florence, an ideal postcard of Tuscany.  …see more

from £475 / night

£3320 - £5302 / week

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22 Photos

Province of Siena / Castellina In Chianti

Villa / 6 Bedrooms / sleeps 10

7 Nights min stay

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from £475 / night

£3320 - £5302 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Enchanting typical Villa located in the very heart of Chianti between Siena and Firenze.  …see more

from £83 / night

£580 - £720 / week

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27 Photos

Province of Siena / Castellina In Chianti

Apartment / 2 Bedrooms / sleeps 7

7 Nights min stay

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from £83 / night

£580 - £720 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Long-term Renters Welcome children welcome non smoking only pets not allowed wheelchair inaccessible  …see more

from £64 / night

£442 - £1545 / week

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24 Photos

Province of Siena / Castellina In Chianti

Farmhouse / 2 Bedrooms / sleeps 6

3 Nights min stay

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from £64 / night

£442 - £1545 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Pets welcome
www.ilcellese.it  …see more

from £131 / night

£912 - £1203 / week

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14 Photos

Province of Siena / Castellina In Chianti

Apartment / 2 Bedrooms / sleeps 5

5 Nights min stay

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from £131 / night

£912 - £1203 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
Le Stalle is a lovely 2-bedroom apartment situated on the ground floor of Podere Patrignone, a 15th century farmhouse in the heart of Chianti, surrounded on all sides by olives, vines, hills and forest. It has a kitchen, dining area, outside porch and use of the pool.  …see more

from £122 / night

£850 - £1004 / week

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24 Photos

Province of Siena / Castellina In Chianti

Apartment / 3 Bedrooms / sleeps 6

3 Nights min stay

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from £122 / night

£850 - £1004 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Four rooms, 90 sqm, fully equipped kitchen and living room, 3 double bedrooms (one with high window). Inside, each bedroom has TV and bathroom with shower (total 3 baths).  …see more

from £81 / night

£567 - £608 / week

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24 Photos

Province of Siena / Castellina In Chianti

Apartment / 2 Bedrooms / sleeps 8

3 Nights min stay

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from £81 / night

£567 - £608 / week

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Key info:

  • Nearest beach 90 km
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Large, elegant, comfortable apartment in incomparable surroundings. Peaceful and relaxing with spectacular scenery. 3 km from Castellina in Chianti with its medieval town centre, shops, bars, restaurants. 22 km from Siena., 37km from Florence. No neighbours or noise. Perfect to come home to after the day's excursions. A glass of wine in the garden, dinner under the stars.  …see more

from £160 / night

£1118 - £1339 / week

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7 Photos

Province of Siena / Castellina In Chianti

Apartment / 2 Bedrooms / sleeps 4

3 Nights min stay

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from £160 / night

£1118 - £1339 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Beautiful and typical apartment for 4/6 people located inside a wine farm up to a Chianti hill, close to Siena. The resort has also a restaurant that propose tuscan receipts, an enchanting swimming pool overlooking the valley  …see more

from £100 / night

£699 - £898 / week

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9 Photos

Province of Siena / Castellina In Chianti

Apartment / 1 Bedroom / sleeps 2

1 night min stay

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from £100 / night

£699 - £898 / week

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Key info:

  • Swimming pool
  • Suitable for children over 5
  • No pets allowed
Beautiful and typical apartment for 2/4 people located inside a wine farm up to a Chianti hill, close to Siena. The resort has also a restaurant that propose tuscan receipts, an enchanting swimming pool overlooking the valley  …see more

from £64 / night

£442 - £1103 / week

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13 Photos

Province of Siena / Castellina In Chianti

Farmhouse / 2 Bedrooms / sleeps 6

3 Nights min stay

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from £64 / night

£442 - £1103 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
CHIANTI , TOSCANA , AGRITURISMO , WINE , COOKING CLASS , LANDSCAPE , VIEW , SWIMMING POOL  …see more

from £78 / night

£541 - £644 / week

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18 Photos

Province of Siena / Castellina In Chianti

Apartment / 1 Bedroom / sleeps 4

3 Nights min stay

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from £78 / night

£541 - £644 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Double room, living room with truckle bed, kitchen, bathroom with shower. Ground floor. 60 sqm  …see more

from £52 / night

£361 - £438 / week

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18 Photos

Province of Siena / Castellina In Chianti

Apartment / 1 Bedroom / sleeps 2

3 Nights min stay

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from £52 / night

£361 - £438 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Two Rooms, 40 sqm, a kitchen and tv, a double bedroom, a bathroom with shower. The apartments are at the first floor. On the ground floor externally there are tables, chairs and umbrellas for common use.  …see more

from £52 / night

£361 - £438 / week

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15 Photos

Province of Siena / Castellina In Chianti

Apartment / 1 Bedroom / sleeps 2

3 Nights min stay

Add to shortlist

from £52 / night

£361 - £438 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Double room, kitchen, bathroom with shower. First floor.40 sqm  …see more

from £78 / night

£541 - £644 / week

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17 Photos

Province of Siena / Castellina In Chianti

Apartment / 2 Bedrooms / sleeps 4

3 Nights min stay

Add to shortlist

from £78 / night

£541 - £644 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Three rooms, 60 square meters, with kitchen and TV, 2 double bedrooms (one with high window), a bathroom with shower. The apartment is at the first floor. enfant bed  …see more

from £52 / night

£361 - £438 / week

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23 Photos

Province of Siena / Castellina In Chianti

Apartment / 1 Bedroom / sleeps 2

3 Nights min stay

Add to shortlist

from £52 / night

£361 - £438 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Two Rooms, 40 sqm, a kitchen and tv, a double bedroom, a bathroom with shower. The apartments are at the first floor. On the ground floor externally there are tables, chairs and umbrellas for common use.  …see more

from £142 / night

£993 - £1242 / week

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10 Photos

Province of Siena / Castellina In Chianti

Apartment / 5 Bedrooms / sleeps 5

1 night min stay

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from £142 / night

£993 - £1242 / week

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Key info:

  • Suitable for children over 5
  • Some pets are welcome - please contact the owner
'Cispiano' is part of our Estate Il Palagione which offers a total of 10 Houses and apartments.  …see more

from £69 / night

£478 - £699 / week

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23 Photos

Province of Siena / Castellina In Chianti

B&B / 21 Bedrooms / sleeps 46

2 Nights min stay

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from £69 / night

£478 - £699 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
Villa hotel Castellina Chianti Siena giardino parco piscina tennis camere vista ristorante bar terrazza camino parcheggio wi-fi degustazioni vino cucina tartufi italiano biciclette escursioni cavallo animali accettati. Matrimoni cerimonie eventi. Albergo storico del Chianti  …see more

from £368 / night

£2574 / week

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16 Photos

Province of Siena / Castellina In Chianti

Condo / 9 Bedrooms / sleeps 16

Short stays welcome

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from £368 / night

£2574 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Pets welcome
  • Private garden
Arrivo: Sabato pomeriggio dalle 5 p.m. alle 8 p.m., Partenza: Sabato mattina entro le ore 10 a.m. * Esiste la possibilità di unire i due appartamenti * In dotazione: Tv Satellitare, riscaldamento autonomo, biancheria e cucina completamente attrezzata. * Aria condizi  …see more

Pricing unknown

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18 Photos

Province of Siena / Castellina In Chianti

Farmhouse / 1 Bedroom / sleeps 3

Min stay varies

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Pricing unknown

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
CHIANTI , SWIMMING POOL , VIEW , COOKING CLASS, AGRITURISMO , NATURE , RELAX , LANDSCAPE , WINE  …see more

Pricing unknown

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14 Photos

Province of Siena / Castellina In Chianti

Farmhouse / 1 Bedroom / sleeps 4

Min stay varies

Add to shortlist

Pricing unknown

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
WINE , CHIANTI CLASSICO , CHIANTI , COOKING CLASS , VIEWS , LANDSCAPE  …see more

Pricing unknown

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23 Photos

Province of Siena / Castellina In Chianti

Farmhouse / 2 Bedrooms / sleeps 5

Min stay varies

Add to shortlist

Pricing unknown

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
CHIANTI , WINE , COOKING CLASS , AGRITURISMO , LANDSCAPE , VIEW  …see more

Pricing unknown

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14 Photos

Province of Siena / Castellina In Chianti

Farmhouse / 2 Bedrooms / sleeps 7

Min stay varies

Add to shortlist

Pricing unknown

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
WINE , CHIANTI , DOCG, VIEW , LANDSCAPE , AGRITURISMO  …see more

from £45 / night

£309 / week

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10 Photos

Province of Siena / Castellina In Chianti

Apartment / 2 Bedrooms / sleeps 5

1 night min stay

Add to shortlist

from £45 / night

£309 / week

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Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Chianti, Castellina, Siena, Toscana, Firenze, Natura, Vino, Arte, Cultura  …see more

from £78 / night

£541 - £644 / week

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18 Photos

Province of Siena / Castellina In Chianti

Apartment / 2 Bedrooms / sleeps 4

3 Nights min stay

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from £78 / night

£541 - £644 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Three rooms, 55 sqm, consisting of small kitchen and TV, 2 double bedrooms, a bathroom with shower. The apartment is at the first floor.  …see more

from £279 / night

£1949 - £3523 / week

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Excellent 5/5 

22 Photos

Province of Siena / Castellina In Chianti

Villa / 5 Bedrooms / sleeps 9

Excellent 5/5 

7 Nights min stay

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from £279 / night

£1949 - £3523 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Casale Cipressi is an exclusive Tuscan country house 2.7km from Castellina in Chianti furnished to a high standard and consists of two floors. Stone built with traditional terracotta tiled floors and chestnut wooden beams gracing the old style ceilings.  …see more

from £202 / night

£1412 - £2353 / week

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Excellent 5/5 

24 Photos

Province of Siena / Castellina In Chianti

Villa / 4 Bedrooms / sleeps 8

Excellent 5/5 

7 Nights min stay

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from £202 / night

£1412 - £2353 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa Casanovina is situated only a few kilometres from the town of Castellina in Chianti. The villa is set in a great location on a hillside overlooking the surrounding Chianti countryside. There are four bedrooms in total - two in the main house and two in the annexe.  …see more

from £419 / night

£2927 - £5140 / week

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Excellent 5/5 

20 Photos

Province of Siena / Castellina In Chianti

Farmhouse / 6 Bedrooms / sleeps 12

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £419 / night

£2927 - £5140 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Conveniently located in the heart of Chianti close to Siena. Practical layout. Fantastic views. Helpful owners available for assistance.  …see more

from £172 / night

£1200 - £1950 / week

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Excellent 5/5 

20 Photos

Province of Siena / Castellina In Chianti

Farmhouse / 3 Bedrooms / sleeps 6

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £172 / night

£1200 - £1950 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Chianti - well situated farmhouse with beautiful views  …see more

from £258 / night

£1802 - £2795 / week

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Excellent 5/5 

12 Photos

Province of Siena / Castellina In Chianti

Villa / 5 Bedrooms / sleeps 10

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £258 / night

£1802 - £2795 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Beautiful independent restored villa (400 sqm) sleeping 10 with private pool, astro turf tennis court, gardens. Located in panoramic position on a Chianti Hillside only 5km from Castellini in Chianti. The property is surrounded by a well-maintained large garden.  …see more

from £117 / night

£814 - £1370 / week

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16 Photos

Province of Siena / Castellina In Chianti

Castle / 2 Bedrooms / sleeps 4

3 Nights min stay

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from £117 / night

£814 - £1370 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Relais chianti, luxury apartment chianti, hamlet chianti, medieval village, infinity swimming pool ,outdoor dining area , barbecue grill.  …see more

from £172 / night

£1200 - £1600 / week

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20 Photos

Province of Siena / Castellina In Chianti

House / 3 Bedrooms / sleeps 6

7 Nights min stay

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from £172 / night

£1200 - £1600 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa Arnica A is a characteristic and welcoming ancient tuscan country house surrounded by vineyards and olive groves. It sleeps six people. From Villa Arnica A you will enjoy a charming view of the Chianti hills  …see more

from £258 / night

£1804 - £3223 / week

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16 Photos

Province of Siena / Castellina In Chianti

Villa / 4 Bedrooms / sleeps 8

2 Nights min stay

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from £258 / night

£1804 - £3223 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
This beautiful, detached stone farmhouse, situated near Castellina in Chianti, was restored in 1995. Surrounded by ample private grounds, it sits in a panoramic position and is reached by its own driveway  …see more

from £489 / night

£3420 / week

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24 Photos

Province of Siena / Castellina In Chianti

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

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from £489 / night

£3420 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Just 4 km from Castellina in Chianti Villa Rosa boasts unique views over the Chianti countryside from its romantic terrace and from whole of the villa. The classically furnished interior complete the picture.  …see more

from £296 / night

£2070 - £3881 / week

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24 Photos

Province of Siena / Castellina In Chianti

Villa / 5 Bedrooms / sleeps 12

7 Nights min stay

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from £296 / night

£2070 - £3881 / week

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Key info:

  • Nearest beach 85 km
  • Swimming pool
  • Great for children of all ages
  • No pets allowed
This extraordinary villa welcomes up to 12 people in its ample common areas and bedrooms, and it has a wonderful garden and swimming pool. It is ideal for large families or groups of friends.  …see more

from £129 / night

£900 - £1300 / week

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20 Photos

Province of Siena / Castellina In Chianti

House / 2 Bedrooms / sleeps 4

7 Nights min stay

Add to shortlist

from £129 / night

£900 - £1300 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa Arnica B is a graceful cottage surrounded by vineyards and olive groves. It sleeps four people. From Villa Arnica B you will enjoy a thrilling view of the Chianti hills and of the vineyards. Villa Arnica B is 100 square meters (1076 square feet)  …see more

Pricing unknown

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24 Photos

Province of Siena / Castellina In Chianti

Villa / 8 Bedrooms / sleeps 16

Min stay varies

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Pricing unknown

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
elegant house sleeps 16 people, so it is ideal for a large group of friends to enjoy an unforgettable trip to Chianti. The villa offers a swimming pool and an internet Connection.  …see more

from £241 / night

£1686 - £2525 / week

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24 Photos

Province of Siena / Castellina In Chianti

Villa / 5 Bedrooms / sleeps 10

3 Nights min stay

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from £241 / night

£1686 - £2525 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
This grand house, with 5 bedrooms and 5 bathrooms can host 10 people, so it is ideal for large families. Located in Tuscany Italy, this house offers a swimming Pool, an internet Connection .  …see more

from £427 / night

£2987 - £4706 / week

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16 Photos

Province of Siena / Castellina In Chianti

Villa / 6 Bedrooms / sleeps 11

2 Nights min stay

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from £427 / night

£2987 - £4706 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Food and wine-lovers wanting a memorable holiday in Tuscany shouldn't look any further than Villa Fermini. This beautiful farmhouse lies at the centre of an agricultural estate that produces excellent Chianti Classico wines and extra virgin olive oil.  …see more

from £334 / night

£2337 - £3186 / week

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24 Photos

Province of Siena / Castellina In Chianti

Villa / 8 Bedrooms / sleeps 16

7 Nights min stay

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from £334 / night

£2337 - £3186 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
elegant house sleeps 16 people, so it is perfect for a large group of friends and is located in Tuscany Italy. This property is ideal if you seek a relaxing holiday. The villa features: a swimming Pool, air Conditioning, an internet Connection .  …see more

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