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51 Holiday homes in Castellina in Chianti

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51 Results  |  
24 Photos

Apartment | 2 Bedrooms | sleeps 8

3 Nights min stay

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from £90 /night

£626 - £687 / week

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Key info:

  • Nearest beach 90 km
  • Suitable 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

14 Photos

Apartment | 2 Bedrooms | sleeps 5

5 Nights min stay

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from £156 /night

£1087 - £1433 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable 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

24 Photos

Villa | 7 Bedrooms | sleeps 14

5 Nights min stay

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from £470 /night

£3290 - £3965 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Suitable 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

Featured properties

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

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £549 /night

£3843 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Everything about this property is classically Tuscan. Misty hills covered in precision lines of vineyards, olive groves, gravel roads and driveways shadily lined with pointy cypress trees, and grand villas with green shutters.  …see more

20 Photos

Farmhouse | 6 Bedrooms | sleeps 12

Min stay varies

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from £470 /night

£3290 - £5777 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Conveniently located in the heart of Chianti close to Siena. Practical layout. Fantastic views. Helpful owners available for assistance.  …see more

24 Photos

Farmhouse | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £63 /night

£439 - £1840 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
www.ilcellese.it  …see more

18 Photos

Farmhouse | 1 Bedroom | sleeps 3

Min stay varies

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from £51 /night

£351 - £1052 / week

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Key info:

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

9 Photos

Farmhouse | 2 Bedrooms | sleeps 4

Min stay varies

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from £76 /night

£526 - £1315 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • No pets allowed
WINE , CHIANTI , VIEW , LANDSCAPE , COOKING CLASS , CASTELLINA IN CHIANTI  …see more

13 Photos

Farmhouse | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £76 /night

£526 - £1315 / week

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Late Deal: save up to €402 (approx. £332)

Key info:

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

14 Photos

Farmhouse | 2 Bedrooms | sleeps 7

Min stay varies

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from £101 /night

£701 - £1577 / week

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Key info:

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

11 Photos

Villa | 4 Bedrooms | sleeps 7

3 Nights min stay

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from £183 /night

£1281 - £2067 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Il Torrino is a wonderful 4 bedroom villa set within a small and perfectly kept Tuscan medieval village and situated atop a hill with stunning views over the Chianti vineyards. Once a Medieval watch tower, the property oozes character and charm, but has been completely renovated to an extremely high standard providing holidaymakers with all the mod cons they could possibly want and need. Outside, the property is surrounded by a large field offering guests complete privacy. Guests also have a private garden equipped with table and chairs and parasol and enjoy use of a shared infinity swimming pool.  …see more

12 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £290 /night

£2025 - £3141 / week

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Key info:

  • Swimming pool
  • Suitable 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

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
  • Suitable for children of all ages
  • 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 5

3 Nights min stay

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from £120 /night

£834 - £1400 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Carming apartments in a medieval hamlet in heart of Tuscany, all the apartments have been carefully restored, swimming pool  …see more

20 Photos

Villa | 7 Bedrooms | sleeps 14

2 Nights min stay

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from £304 /night

£2123 - £3961 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
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

11 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

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from £88 /night

£615 - £724 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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

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
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
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 £88 /night

£615 - £724 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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

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
  • Suitable for children of all ages
  • 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 £95 /night

£665 - £781 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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

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
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
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 £60 /night

£418 - £492 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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

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
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Attractive apartment for 4 persons, with swimming pool , in Chianti  …see more

13 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £143 /night

£1000 - £1713 / week

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Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Suitable for children of all ages
  • 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 4

1 night min stay

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from £88 /night

£615 - £724 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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

14 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

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from £60 /night

£418 - £492 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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

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
  • Suitable for children of all ages
  • 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
  • Suitable for children of all ages
  • Car not necessary
  • 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

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

15 Photos

Apartment | 1 Bedroom | sleeps 3

1 night min stay

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from £60 /night

£418 - £492 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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

16 Photos

Villa | 6 Bedrooms | sleeps 11

2 Nights min stay

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from £445 /night

£3115 - £4907 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
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

11 Photos

Farmhouse | 6 Bedrooms | sleeps 14

3 Nights min stay

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from £321 /night

£2241 - £5072 / 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

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
  • Suitable for children of all ages
  • Car not necessary
  • 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

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

16 Photos

Villa | 4 Bedrooms | sleeps 8

2 Nights min stay

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from £263 /night

£1838 - £3349 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
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

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
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Apartment for 4 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 - £798 / week

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Key info:

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

14 Photos

Apartment | 3 Bedrooms | sleeps 6

1 night min stay

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from £137 /night

£959 - £1129 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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 2

3 Nights min stay

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from £91 /night

£637 - £1065 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

Villa | 5 Bedrooms | sleeps 12

7 Nights min stay

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from £333 /night

£2326 - £4362 / week

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Key info:

  • Nearest beach 85 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

21 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £262 /night

£1834 - £3976 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Set in Tuscany Italy, this lovely house is the perfect place for your holidays. The house has a swimming pool and an internet connection.  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £159 /night

£1111 - £1805 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Carming apartments in a medieval hamlet in heart of Tuscany, all the apartments have been carefully restored, swimming pool  …see more

17 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £262 /night

£1834 - £3976 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This gorgeous house, with 5 bedrooms and 6 bathrooms can host 10 people, so it is ideal for a large group of friends. Located in Tuscany Italy, this house has a swimming pool.  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £181 /night

£1267 - £2060 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

Villa | 8 Bedrooms | sleeps 16

7 Nights min stay

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from £375 /night

£2620 - £3496 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

24 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £439 /night

£3069 - £4463 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This luxury villa for 8 in beautiful Chianti is ideally located between Florence and Siena. It is a truly stunning property set in peaceful grounds including a swimming pool, gardens and olive grove. Inside it is just attractive featuring 4 large en  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

3 Nights min stay

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from £269 /night

£1877 - £2810 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

24 Photos

Villa | 5 Bedrooms | sleeps 9

Excellent 5/5 

7 Nights min stay

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from £290 /night

£2025 - £3794 / week

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Key info:

  • Swimming pool
  • Suitable 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

24 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £230 /night

£1604 - £2658 / week

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Key info:

  • Swimming pool
  • Suitable 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