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48 Holiday homes in Castellina in Chianti

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48 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
  • 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

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
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • 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

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
  • 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

Featured properties

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
  • Suitable 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

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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Late Deal: save up to £469

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 | 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
  • 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

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
  • 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

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
  • Suitable for children of all ages
  • 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
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
CHIANTI , TOSCANA , AGRITURISMO , WINE , COOKING CLASS , LANDSCAPE , VIEW , SWIMMING POOL  …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
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
Apartment / Condo in Castellina In Chianti with 2 bedrooms sleeps 4  …see more

12 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £280 /night

£1960 - £3040 / 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

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £73 /night

£508 - £780 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Villa / Farmhouse / Home in Castellina In Chianti with 1 bedrooms sleeps 2  …see more

12 Photos

Farmhouse | 8 Bedrooms | sleeps 16

7 Nights min stay

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from £378 /night

£2640 - £3360 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
Villa / Farmhouse / Home in Castellina In Chianti with 8 bedrooms sleeps 16  …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

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

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
  • Suitable for children of all ages
  • May take pets – please enquire
Villa / Farmhouse / Home in Castellina In Chianti with 1 bedrooms sleeps 2  …see more

20 Photos

Villa | 7 Bedrooms | sleeps 14

2 Nights min stay

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from £291 /night

£2035 - £3795 / 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

12 Photos

Farmhouse | 6 Bedrooms | sleeps 13

7 Nights min stay

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from £500 /night

£3500 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
Villa / Farmhouse / Home in Castellina In Chianti with 6 bedrooms sleeps 13  …see more

24 Photos

Farmhouse | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £147 /night

£1027 - £1351 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • Pets welcome
Offering accommodations in a gorgeous ancient building formerly used as a monastery, this beautiful Tuscan villa features aandnbsp;large dining room, a fireplace, and simple kitchen.andnbsp; It can accommodate up toandnbsp;8 peopleandnbsp;with itsandnbsp;four bedrooms  …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
  • 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

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
  • Suitable for children of all ages
  • May take pets – please enquire
Villa / Farmhouse / Home in Castellina In Chianti with 1 bedrooms sleeps 4  …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
  • Suitable for children of all ages
  • May take pets – please enquire
  • 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 £139 /night

£968 - £1658 / 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

12 Photos

Farmhouse | 5 Bedrooms | sleeps 8

7 Nights min stay

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from £425 /night

£2971 - £4320 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
Villa / Farmhouse / Home in Castellina In Chianti with 5 bedrooms sleeps 8  …see more

12 Photos

Farmhouse | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £455 /night

£3184 - £5592 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • May take pets – please enquire
  • Private garden
Villa / Farmhouse / Home in Monteriggioni with 6 bedrooms sleeps 12  …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

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
  • 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

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £110 /night

£764 - £1176 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Villa / Farmhouse / Home in Castellina In Chianti with 2 bedrooms sleeps 4  …see more

12 Photos

Farmhouse | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £138 /night

£960 - £1472 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Villa / Farmhouse / Home in Castellina In Chianti with 4 bedrooms sleeps 8  …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

11 Photos

Farmhouse | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £155 /night

£1080 - £1620 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
Villa / Farmhouse / Home in Castellina In Chianti with 2 bedrooms sleeps 6  …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

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

12 Photos

Farmhouse | 3 Bedrooms | sleeps 5

3 Nights min stay

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from £121 /night

£844 - £1300 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
Villa / Farmhouse / Home in Castellina In Chianti with 3 bedrooms sleeps 5  …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
  • Suitable for children of all ages
  • May take pets – please enquire
Villa / Farmhouse / Home in Castellina In Chianti with 1 bedrooms sleeps 2  …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

24 Photos

Villa | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £155 /night

£1080 - £1620 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
This elegant house, with 2 bedrooms and 3 bathrooms can accomodate 6 people, so it is perfect for a large group of friends. Located in Tuscany Italy, this house offers a swimming Pool, air Conditioning .  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 8

7 Nights min stay

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from £425 /night

£2971 - £4320 / week

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Key info:

  • Swimming pool
  • Suitable 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

24 Photos

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

24 Photos

Villa | 5 Bedrooms | sleeps 12

7 Nights min stay

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from £322 /night

£2252 - £4223 / week

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Key info:

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

24 Photos

Villa | 8 Bedrooms | sleeps 16

7 Nights min stay

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from £378 /night

£2640 - £3360 / week

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Key info:

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

16 Photos

Castle | 2 Bedrooms | sleeps 4

1 night min stay

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from £29 /night

£202 - £1367 / week

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Key info:

  • Swimming pool
  • Suitable 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

Cottage | 2 Bedrooms | sleeps 4

1 night min stay

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from £67 /night

£467 - £552 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • 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

16 Photos

Condo | 9 Bedrooms | sleeps 16

Short stays welcome

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from £424 /night

£2968 / week

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Key info:

  • Swimming pool
  • Suitable 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

18 Photos

Farmhouse | 1 Bedroom | sleeps 3

Min stay varies

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from £49 /night

£340 - £1018 / 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

14 Photos

Farmhouse | 1 Bedroom | sleeps 4

Min stay varies

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from £73 /night

£509 - £1230 / 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 CLASSICO , CHIANTI , COOKING CLASS , VIEWS , LANDSCAPE  …see more

23 Photos

Farmhouse | 2 Bedrooms | sleeps 5

Min stay varies

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from £85 /night

£594 - £1357 / week

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Key info:

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

14 Photos

Farmhouse | 2 Bedrooms | sleeps 7

Min stay varies

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from £97 /night

£679 - £1527 / 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