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72 Holiday homes in Castellina In Chianti

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72 Results  |  
24 Photos

Villa | 7 Bedrooms | sleeps 14

Excellent 5/5 

5 Nights min stay

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from £484 /night

£3384 - £3710 / 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

20 Photos

Farmhouse | 3 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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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

20 Photos

House | 4 Bedrooms | sleeps 5

Very Good 4/5 

Min stay varies

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Pricing unknown

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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

Featured properties

24 Photos

Villa | 4 Bedrooms | sleeps 7

3 Nights min stay

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from £168 /night

£1170 - £2017 / week

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Key info:

  • Great for children of all ages
  • Car essential
  • 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

22 Photos

Villa | 6 Bedrooms | sleeps 10

7 Nights min stay

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from £521 /night

£3642 - £5815 / 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

18 Photos

Apartment | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £85 /night

£593 - £706 / 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

24 Photos

Apartment | 2 Bedrooms | sleeps 8

3 Nights min stay

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from £89 /night

£621 - £644 / 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

17 Photos

Apartment | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £85 /night

£593 - £706 / 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

24 Photos

Apartment | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £134 /night

£932 - £1101 / 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

18 Photos

Apartment | 1 Bedroom | sleeps 4

3 Nights min stay

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from £85 /night

£593 - £706 / 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

18 Photos

Apartment | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £93 /night

£650 - £763 / 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, 70 sqm, a kitchen and TV, 2 double bedrooms, 2 bathrooms with shower. Access to people with disabilities. On the ground floor front with table, chairs and umbrella.  …see more

15 Photos

Apartment | 1 Bedroom | sleeps 2

3 Nights min stay

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from £57 /night

£396 - £480 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Bed and bathroom linen and kitchen teatowels, hairdryer, water, gas and electric consumption, central heating, final cleaning, pool use, car park, ping pong, barbecues, washing machine for common use, wi-fi in common area, 6 bikes for adults, on request iron and ironing  …see more

23 Photos

Apartment | 1 Bedroom | sleeps 2

3 Nights min stay

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from £57 /night

£396 - £480 / 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

15 Photos

Apartment | 1 Bedroom | sleeps 2

3 Nights min stay

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from £57 /night

£396 - £480 / 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

18 Photos

Apartment | 1 Bedroom | sleeps 2

3 Nights min stay

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from £57 /night

£396 - £480 / 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

18 Photos

Apartment | 1 Bedroom | sleeps 2

3 Nights min stay

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from £73 /night

£509 - £593 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Bed and bathroom linen and kitchen teatowels, hairdryer, water, gas and electric consumption, central heating, final cleaning, pool use, car park, ping pong, barbecues, washing machine for common use, wi-fi in common area, 6 bikes for adults, on request iron  …see more

13 Photos

Farmhouse | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £70 /night

£484 - £1210 / 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

13 Photos

House | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £108 /night

£750 - £950 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • 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

24 Photos

Cottage | 2 Bedrooms | sleeps 4

4 Nights min stay

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from £64 /night

£444 / week

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Key info:

  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
La Capanna delle Cozzole is located close to Castellina in Chianti, only a 30 minute drive from Siena, Florence and San Gimignano. It is set perfectly in the lush countryside between ancient woods, olive trees and enchanting hills. Pets by arrangement. Not included: county tax 1,5 euro per person per day (up to seven days)  …see more

14 Photos

Apartment | 2 Bedrooms | sleeps 5

5 Nights min stay

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from £143 /night

£1000 - £1319 / 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

14 Photos

Farmhouse | 1 Bedroom | sleeps 4

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
WINE , CHIANTI CLASSICO , CHIANTI , COOKING CLASS , VIEWS , LANDSCAPE  …see more

9 Photos

Farmhouse | 2 Bedrooms | sleeps 4

Min stay varies

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Pricing unknown

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Key info:

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

14 Photos

Farmhouse | 2 Bedrooms | sleeps 7

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
WINE , CHIANTI , DOCG, VIEW , LANDSCAPE , AGRITURISMO  …see more

18 Photos

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

24 Photos

Farmhouse | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £58 /night

£404 - £1694 / 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

23 Photos

Farmhouse | 2 Bedrooms | sleeps 5

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 not necessary
  • Pets welcome
  • Private garden
CHIANTI , WINE , COOKING CLASS , AGRITURISMO , LANDSCAPE , VIEW  …see more

16 Photos

Condo | 9 Bedrooms | sleeps 16

Short stays welcome

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from £404 /night

£2823 / 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

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
  • 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

22 Photos

Villa | 5 Bedrooms | sleeps 9

Excellent 5/5 

7 Nights min stay

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from £306 /night

£2138 - £3863 / 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

24 Photos

Apartment | 2 Bedrooms | sleeps 4

Very Good 4.5/5 

3 Nights min stay

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from £53 /night

£367 - £612 / week

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Key info:

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

20 Photos

Farmhouse | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £459 /night

£3210 - £5638 / 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

24 Photos

Apartment | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £169 /night

£1180 - £2010 / week

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Key info:

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

21 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £256 /night

£1790 - £3951 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • 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

Farmhouse | 3 Bedrooms | sleeps 6

4 Nights min stay

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from £91 /night

£634 - £1063 / week

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Key info:

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

10 Photos

Apartment | 3 Bedrooms | sleeps 5

7 Nights min stay

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from £54 /night

£377 - £772 / week

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Key info:

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

405 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
  • 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

24 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £222 /night

£1549 - £2581 / 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

16 Photos

Castle | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £30 /night

£204 - £1084 / 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

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £536 /night

£3750 / 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

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
  • 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 £433 /night

£3025 - £4399 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Located in Tuscany Italy, this gorgeous accommodation is the perfect place for your holidays. The accommodation features: a swimming Pool, air Conditioning .  …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
  • 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

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
  • 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 | 5 Bedrooms | sleeps 8

7 Nights min stay

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from £433 /night

£3025 - £4399 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Castellina In Chianti with 5 bedrooms sleeps 8  …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
  • 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

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
  • 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

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
  • 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

Farmhouse | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £150 /night

£1049 - £1574 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Castellina In Chianti with 2 bedrooms sleeps 6  …see more

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