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71 Holiday homes in Castellina in Chianti

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71 Results  |  
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 | 7 Bedrooms | sleeps 14

Excellent 5/5 

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
  • 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

Cottage | 2 Bedrooms | sleeps 4

4 Nights min stay

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from £68 /night

£471 / 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

Featured properties

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

21 Photos

Villa | 8 Bedrooms | sleeps 10

7 Nights min stay

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from £254 /night

£1775 - £5270 / week

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Key info:

  • Nearest beach 40 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • 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

15 Photos

Apartment | 2 Bedrooms | sleeps 3

1 night min stay

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from £51 /night

£355 / week

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Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
We are in the nature close to a river but at the same time near the village where you will find supermarket, shops and restaurants. In 20 mins walking distance you can also reach a public swimming pool of the village. Large garden all around and a spacius terrace with parasol, sunbeds sun chairs and table Free car parking!  …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

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

20 Photos

Farmhouse | 3 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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from £189 /night

£1320 - £2145 / 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

14 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £60 /night

£417 - £514 / 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 1 bedrooms sleeps 2  …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

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

11 Photos

Apartment | 1 Bedroom | sleeps 6

7 Nights min stay

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from £62 /night

£428 - £992 / week

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Key info:

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

24 Photos

Farmhouse | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £148 /night

£1035 - £1362 / 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

Villa | 7 Bedrooms | sleeps 14

2 Nights min stay

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from £294 /night

£2052 - £3829 / 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
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

Farmhouse | 1 Bedroom | sleeps 4

3 Nights min stay

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from £113 /night

£791 - £978 / 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 1 bedrooms sleeps 4  …see more

24 Photos

Farmhouse | 5 Bedrooms | sleeps 10

3 Nights min stay

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from £265 /night

£1850 - £2770 / 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 10  …see more

10 Photos

Apartment | 3 Bedrooms | sleeps 5

7 Nights min stay

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from £55 /night

£383 - £785 / 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

24 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

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

15 Photos

Apartment | 1 Bedroom | 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 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

24 Photos

Farmhouse | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £74 /night

£516 - £896 / 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 4  …see more

24 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
  • Not suitable for children
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in San Leonino with 6 bedrooms sleeps 12  …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

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

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
  • 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

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

24 Photos

Farmhouse | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £118 /night

£825 - £1447 / 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 4  …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

Farmhouse | 2 Bedrooms | sleeps 4

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
  • Private garden
Villa / Farmhouse / Home in Castellina In Chianti with 2 bedrooms sleeps 4  …see more

20 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £86 /night

£596 - £767 / 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 1 bedrooms sleeps 2  …see more

24 Photos

Farmhouse | 2 Bedrooms | sleeps 4

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
  • Private garden
Villa / Farmhouse / Home in Castellina In Chianti with 2 bedrooms sleeps 4  …see more

24 Photos

Farmhouse | 8 Bedrooms | sleeps 16

7 Nights min stay

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from £367 /night

£2563 - £3495 / 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 8 bedrooms sleeps 16  …see more

16 Photos

Villa | 6 Bedrooms | sleeps 11

2 Nights min stay

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from £431 /night

£3011 - £4743 / 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

16 Photos

Villa | 4 Bedrooms | sleeps 8

2 Nights min stay

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from £254 /night

£1777 - £3238 / 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
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

24 Photos

Cottage | 2 Bedrooms | sleeps 4

5 Nights min stay

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from £102 /night

£709 - £1084 / 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 | 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

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

11 Photos

Farmhouse | 6 Bedrooms | sleeps 14

5 Nights min stay

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from £313 /night

£2187 - £3791 / week

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Key info:

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

24 Photos

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 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

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

4 Photos

House | 2 Bedrooms | sleeps 5

1 night min stay

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from £178 /night

£1242 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • No pets allowed
  • Private garden
Countryside house with pool surrounding, wignards and olive trees for a really relaxing holidays , located in a strategic position in the middle of Tuscany: thanks to it is easy to visit in 30 minutes/ 1 hour the main important centre of turist attractio of Tuscany  …see more

6 Photos

House | 4 Bedrooms | sleeps 9

7 Nights min stay

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from £174 /night

£1216 - £2486 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Once a fine old 17th century Tuscan barn, this beautiful, restored property has its own private swimming pool. The house lies in its own grounds with views over Tuscany, and on a clear day the towers of San Gimignano are visible on the horizon. There is a small villa...  …see more

24 Photos

Villa | 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
  • 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 10

3 Nights min stay

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from £265 /night

£1850 - £2770 / week

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Key info:

  • Swimming pool
  • Great 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

13 Photos

House | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £74 /night

£516 - £1066 / week

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Key info:

  • Not suitable for children
  • No pets allowed
This property is made up of three great apartments, with independent entrances, one of which is inhabited by the owners, in a beautiful and characteristic farmhouse in the heart of the Chianti Classico, set in a landscape rich in vineyards and olive groves. From here...  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £428 /night

£2995 - £4517 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • 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 | 8 Bedrooms | sleeps 16

7 Nights min stay

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from £367 /night

£2563 - £3495 / week

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Key info:

  • Swimming pool
  • Great 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

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