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100 Holiday homes in Castellina in Chianti

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100 Results  |  
24 Photos

Villa | 7 Bedrooms | sleeps 14

5 Nights min stay

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from £455 /night

£3185 - £3901 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages 5
  • 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

14 Photos

Apartment | 2 Bedrooms | sleeps 5

5 Nights min stay

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from £151 /night

£1052 - £1387 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages 5
  • 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

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £532 /night

£3720 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

Featured properties

24 Photos

Apartment | 2 Bedrooms | sleeps 8

3 Nights min stay

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from £87 /night

£606 - £665 / week

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Key info:

  • Nearest beach 90 km
  • Great for children of all ages 5
  • 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

5 Photos

Villa | 8 Bedrooms | sleeps 14

7 Nights min stay

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from £388 /night

£2714 - £5038 / week

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Key info:

  • Not suitable for children
  • No pets allowed
  • Private garden
The Piaggione of Serravalle is like a gateway entrance that protects an uncontaminated hill that seems lost in time and where nature apparently undisturbed articulates its own natural rhythms. Located on one of the highest summits of Chianti, in between Siena and Flore  …see more

20 Photos

Farmhouse | 3 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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from £182 /night

£1272 - £2067 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • No pets allowed
  • Private garden
Chianti - well situated farmhouse with beautiful views  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £222 /night

£1552 - £2572 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

24 Photos

Villa | 5 Bedrooms | sleeps 9

Excellent 5/5 

7 Nights min stay

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from £280 /night

£1960 - £3672 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

20 Photos

House | 4 Bedrooms | sleeps 5

Very Good 4/5 

3 Nights min stay

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from £87 /night

£603 - £1162 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages 5
  • 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

24 Photos

Farmhouse | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £73 /night

£509 - £1781 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
www.ilcellese.it  …see more

13 Photos

Farmhouse | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £73 /night

£509 - £1272 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Pets welcome
CHIANTI , TOSCANA , AGRITURISMO , WINE , COOKING CLASS , LANDSCAPE , VIEW , SWIMMING POOL  …see more

13 Photos

House | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £114 /night

£795 - £1007 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Italy, Tuscany, Chianti, Castellina in Chianti, Florence, swimming pool, tennis court, private garden, stunning views, Luxury interior designed, house, beautiful gardens, San Gimignano, Siena, Florence, Firenze.  …see more

10 Photos

Farmhouse | 1 Bedroom | sleeps 2

2 Nights min stay

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from £84 /night

£584 - £752 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Castellina In Chianti with 1 bedrooms sleeps 2  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 6

4 Nights min stay

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from £89 /night

£622 - £1044 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Castellina In Chianti with 3 bedrooms sleeps 6  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 5

3 Nights min stay

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from £116 /night

£807 - £1356 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
Carming apartments in a medieval hamlet in heart of Tuscany, all the apartments have been carefully restored, swimming pool  …see more

11 Photos

Farmhouse | 6 Bedrooms | sleeps 14

5 Nights min stay

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from £310 /night

£2169 - £4909 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Villaandnbsp;Silvioandnbsp;is located atop a hill in midst of theandnbsp;ChiantiClassico regionandnbsp;in Tuscany.andnbsp;Villa Silvio consists of a structure withandnbsp;two levels.andnbsp; On theandnbsp;ground floorandnbsp;there is aandnbsp;large living  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 8

7 Nights min stay

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from £457 /night

£3199 - £4653 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Luxury holiday house for 8 persons, with swimming pool , in Chianti  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £47 /night

£323 - £409 / week

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Key info:

  • Not suitable for children
  • No pets allowed
This wonderful holiday accommodation is situated on the site of the former 12th century castle of Monte Gonzi. Occupying a strategic location between Florence and Siena, the castle once dominated this part of the Chianti region. In the construction of the current hou...  …see more

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £73 /night

£506 - £880 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Castellina In Chianti with 2 bedrooms sleeps 4  …see more

12 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £52 /night

£360 - £600 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
  • Private garden
Apartment / Condo in Castellina In Chianti with 2 bedrooms sleeps 4  …see more

16 Photos

Apartment | 2 Bedrooms | sleeps 5

7 Nights min stay

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from £68 /night

£470 - £783 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
  • Private garden
Attractive apartment for 5 persons, with swimming pool , in Chianti  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £96 /night

£672 - £1124 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
Apartment for 4 persons, with swimming pool , in Chianti  …see more

14 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

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from £58 /night

£404 - £476 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
Casa Sibilla F is an apartment in the characteristic style of the Tuscan countryside. It sleeps two people. It is appoximately 40 square meters (430 square feet). It features a shared swimming pool, a shared garden and winter heating. You will be roughly 3 km (1  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 7

7 Nights min stay

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from £74 /night

£517 - £689 / week

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Key info:

  • Not suitable for children
  • No pets allowed
This wonderful holiday accommodation is situated on the site of the former 12th century castle of Montegonzi. Thanks to its strategic location between Florence and Siena, the castle once dominated this part of the Chianti region. In the construction of the current ho...  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 7

7 Nights min stay

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from £65 /night

£453 - £645 / week

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Key info:

  • Not suitable for children
  • No pets allowed
This former farm, where at the end of the 19th century pasta was produced and sold, is a green oasis in the rural village of Greve, in Chianti. Situated not far from restaurants, cafes, shops and the historic square of the village, you can enjoy its tranquil garden w...  …see more

13 Photos

Villa | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £167 /night

£1165 - £1744 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Holiday house for 6 persons, with swimming pool , in Chianti  …see more

24 Photos

Cottage | 2 Bedrooms | sleeps 4

5 Nights min stay

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from £101 /night

£703 - £1075 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • Pets welcome
Cottage Rosemaryandnbsp;is a picturesque stone cottage in the magnificent Chianti hills and valleys. Surrounded by magnificent vineyards and silvery olive groves, the cottage expands on one level and can accommodate up toandnbsp;five peopleandnbsp;in its lovely  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 3

7 Nights min stay

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from £39 /night

£271 - £381 / week

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Key info:

  • Not suitable for children
  • No pets allowed
This wonderful holiday accommodation is situated on the site of the former 12th century castle of Monte Gonzi. Occupying a strategic location between Florence and Siena, the castle once dominated this part of the Chianti region. In the construction of the current hou...  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £96 /night

£672 - £1124 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
  • Private garden
Apartment for 4 persons, with swimming pool , in Chianti  …see more

16 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

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from £92 /night

£644 - £756 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
Casa Sibilla D is a cozy apartment in the characteristic style of the Tuscan countryside. It sleeps four people. It is appoximately 70 square meters (750 square feet). It features a shared swimming pool, a shared garden and winter heating  …see more

16 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

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from £86 /night

£596 - £700 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
Casa Sibilla C is a cozy apartment in the characteristic style of the Tuscan countryside. It sleeps four people. It is appoximately 55 square meters (590 square feet). It features a shared swimming pool, a shared garden and winter heating  …see more

11 Photos

Apartment | 1 Bedroom | sleeps 6

7 Nights min stay

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from £63 /night

£435 - £1010 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • Pets welcome
  • Private garden
Apartment for 6 persons, with swimming pool , in Chianti  …see more

20 Photos

House | 3 Bedrooms | sleeps 6

1 night min stay

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from £182 /night

£1270 - £1670 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

19 Photos

Apartment | 2 Bedrooms | sleeps 5

7 Nights min stay

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from £78 /night

£542 - £904 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
  • Private garden
Attractive apartment for 5 persons, with swimming pool , in Chianti  …see more

11 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

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from £86 /night

£596 - £700 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
Casa Sibilla B is a characteristic apartment surrounded by the vegetation. It sleeps four people. It is appoximately 60 square meters (645 square feet). It features a shared swimming pool, a shared garden and winter heating. You will be roughly 3 km (1  …see more

21 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £62 /night

£434 - £723 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
  • Private garden
Attractive apartment for 4 persons, with swimming pool , in Chianti  …see more

14 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

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from £58 /night

£404 - £476 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
Casa Sibilla E is a characteristic apartment in the characteristic style of the Tuscan countryside. It sleeps two people. It is appoximately 40 square meters (430 square feet). It features a shared swimming pool, a shared garden and winter heating  …see more

24 Photos

House | 2 Bedrooms | sleeps 5

7 Nights min stay

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from £94 /night

£658 - £848 / week

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Key info:

  • Not suitable for children
  • No pets allowed
This wonderful holiday accommodation is situated on the site of the former 12th century castle of Montegonzi. Thanks to its strategic location, between Florence and Siena, the castle once dominated this part of the Chianti region. In the construction of the current h...  …see more

11 Photos

Farmhouse | 1 Bedroom | sleeps 4

2 Nights min stay

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from £101 /night

£704 - £880 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Castellina In Chianti with 1 bedrooms sleeps 4  …see more

5 Photos

Farmhouse | 1 Bedroom | sleeps 2

2 Nights min stay

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from £59 /night

£408 - £504 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Castellina In Chianti with 1 bedrooms sleeps 2  …see more

22 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £78 /night

£545 - £950 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
  • Private garden
Apartment for 4 persons, with swimming pool , in Chianti  …see more

12 Photos

Farmhouse | 5 Bedrooms | sleeps 10

3 Nights min stay

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from £260 /night

£1816 - £2720 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Castellina In Chianti with 5 bedrooms sleeps 10  …see more

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £67 /night

£464 - £716 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Castellina In Chianti with 1 bedrooms sleeps 2  …see more

20 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £92 /night

£643 - £756 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Castellina In Chianti with 2 bedrooms sleeps 4  …see more

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

4 Nights min stay

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from £89 /night

£622 - £1044 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Castellina In Chianti with 2 bedrooms sleeps 4  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £47 /night

£329 - £430 / week

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Key info:

  • Not suitable for children
  • No pets allowed
This former farm - where at the end of the 19th century pasta was produced and sold - is a green oasis in the rural village of Greve, in Chianti. Situated not far from restaurants, cafes, shops and the historic square of the village, you can enjoy its tranquil garden...  …see more

14 Photos

Apartment | 3 Bedrooms | sleeps 6

1 night min stay

Add to shortlist

from £133 /night

£928 - £1092 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
Villa Sidonia is a pleasant and spacious apartment in the characteristic style of the Tuscan countryside. It sleeps six people. It is appoximately 90 square meters (970 square feet)  …see more

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £70 /night

£484 - £716 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Castellina In Chianti with 1 bedrooms sleeps 2  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 8

7 Nights min stay

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from £80 /night

£560 - £732 / week

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Key info:

  • Not suitable for children
  • No pets allowed
This wonderful holiday accommodation is situated on the site of the former 12th century castle of Montegonzi. Occupying a strategic location between Florence and Siena, the castle once dominated this part of the Chianti region. In the construction of the current hous...  …see more

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £73 /night

£508 - £780 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Castellina In Chianti with 1 bedrooms sleeps 2  …see more