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74 Holiday homes in Castellina in Chianti

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74 Results  |  
24 Photos

Villa | 7 Bedrooms | sleeps 14

5 Nights min stay

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from £459 /night

£3210 - £3933 / 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 £152 /night

£1060 - £1398 / 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

Apartment | 2 Bedrooms | sleeps 8

3 Nights min stay

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from £88 /night

£611 - £671 / 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

Featured properties

21 Photos

Villa | 8 Bedrooms | sleeps 14

7 Nights min stay

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from £391 /night

£2736 - £5078 / 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 £224 /night

£1565 - £2017 / 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 £283 /night

£1976 - £2492 / 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

13 Photos

Farmhouse | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £74 /night

£513 - £1026 / 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

24 Photos

Farmhouse | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £74 /night

£513 - £1496 / 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

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

12 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £283 /night

£1976 - £3065 / week

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Key info:

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

19 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £85 /night

£589 - £759 / 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 5

3 Nights min stay

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from £117 /night

£813 - £1124 / 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

24 Photos

Apartment | 1 Bedroom | sleeps 2

3 Nights min stay

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from £89 /night

£621 - £881 / 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

16 Photos

Villa | 6 Bedrooms | sleeps 11

2 Nights min stay

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from £428 /night

£2995 - £4718 / week

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Key info:

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

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £67 /night

£468 - £585 / 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

14 Photos

Apartment | 3 Bedrooms | sleeps 6

1 night min stay

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from £134 /night

£936 - £1101 / 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

24 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £49 /night

£341 - £446 / 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

11 Photos

Apartment | 1 Bedroom | sleeps 6

7 Nights min stay

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from £63 /night

£435 - £666 / 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 - £723 / 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

16 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

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from £86 /night

£600 - £706 / 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

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £74 /night

£513 - £589 / 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 | 1 Bedroom | sleeps 3

7 Nights min stay

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from £41 /night

£281 - £396 / 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 | 3 Bedrooms | sleeps 5

3 Nights min stay

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from £122 /night

£851 - £984 / 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 3 bedrooms sleeps 5  …see more

23 Photos

Farmhouse | 1 Bedroom | sleeps 4

3 Nights min stay

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from £112 /night

£783 - £968 / 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

14 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

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from £59 /night

£408 - £480 / 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 £77 /night

£536 - £702 / 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

14 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

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from £59 /night

£408 - £480 / 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

20 Photos

Villa | 7 Bedrooms | sleeps 14

2 Nights min stay

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from £295 /night

£2061 - £3845 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Some pets are welcome - please contact the owner
Villa Solara is a beautiful, modern villa, offering spectacular views of the surrounding countryside. Set within well-kept, private grounds and with easy access to local amenities, the villa is a perfect place for family or cultural holidays.  …see more

24 Photos

House | 2 Bedrooms | sleeps 5

7 Nights min stay

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from £98 /night

£682 - £880 / 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

24 Photos

Apartment | 2 Bedrooms | sleeps 8

7 Nights min stay

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from £83 /night

£581 - £759 / 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

11 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

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from £86 /night

£600 - £706 / 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

11 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £59 /night

£412 - £509 / 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

16 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

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from £93 /night

£649 - £763 / 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

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

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

13 Photos

Villa | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £167 /night

£1165 / 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

20 Photos

House | 2 Bedrooms | sleeps 4

1 night min stay

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from £125 /night

£870 - £1330 / week

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Key info:

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

24 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £64 /night

£446 - £536 / 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

16 Photos

Apartment | 2 Bedrooms | sleeps 5

7 Nights min stay

Add to shortlist

from £68 /night

£470 - £627 / 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

10 Photos

Apartment | 3 Bedrooms | sleeps 5

7 Nights min stay

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from £56 /night

£389 - £600 / 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 5 persons, with swimming pool , in Chianti  …see more

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £111 /night

£771 - £888 / 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

21 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £62 /night

£434 - £578 / 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

24 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £48 /night

£335 - £424 / 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 7

7 Nights min stay

Add to shortlist

from £67 /night

£469 - £669 / 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

12 Photos

Farmhouse | 5 Bedrooms | sleeps 10

3 Nights min stay

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from £262 /night

£1831 - £2742 / 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

17 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £140 /night

£976 - £1708 / week

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Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
Lovely house in the heart of the Chianti area, just 15 km from Siena, situated in peaceful position even though a secondary road passes 50m away. The property is partly fenced-in and the swimming pool, just below the house ground, has a lovely view over the va...  …see more

15 Photos

Apartment | 1 Bedroom | sleeps 3

1 night min stay

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from £59 /night

£408 - £480 / 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 G is an apartment in the characteristic style of the Tuscan countryside. It sleeps three 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

15 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

Add to shortlist

from £86 /night

£600 - £706 / 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 A is an apartment in the characteristic style of the Tuscan countryside. 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  …see more