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73 Holiday homes in Gaiole in Chianti

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73 Results  |  
18 Photos

Villa | 4 Bedrooms | sleeps 8

Short stays welcome

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from £122 /night

£848 - £1696 / week

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Key info:

  • Swimming pool
  • Suitable for over 5s only
  • Car essential
  • May take pets – please enquire
  • Private garden
Tuscany. Heart of Chiant.iExclusive use of private swimming pool. The Villa accommodates up to 8/9 people. Beautiful views of the country side. Only a few other farmhouses are visible in the distance. Outdoor dining area. Fontecaresino, located in the hills of Chianti, in the heart of Tuscany. Breathtaking views.  …see more

24 Photos

Apartment | 3 Bedrooms | sleeps 6

Very Good 4/5 

Min stay varies

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
L'appartamento " Brunello " è l'ideale per un unico nucleo familiare con bambini Max.6 px. L'Appartamento è composto da tre camere che sono disposte in sequenza e perciò comunicanti e di passo una dopo l'altra. L'appartamento dispone di un bagno con vasca/doccia, lavabo  …see more

17 Photos

Villa | 6 Bedrooms | sleeps 12

Very Good 4/5 

7 Nights min stay

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from £216 /night

£1512 - £3320 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
The building of Villa Brolio was originally an old XII century watchtower later transformed into a mill and finally restored to become a villa.  …see more

Featured properties

24 Photos

Apartment | 3 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

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from £84 /night

£582 - £1235 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
"BACCHINO IN THE CHIANTI" is located in the center of the Chianti geographic area where they produce the famous and superb wine Chianti Gallo Nero, between Gaiole in Chianti (5 km), Radda in Chianti (7 km) and Castellina in Chianti.  …see more

24 Photos

House | 1 Bedroom | sleeps 3

2 Nights min stay

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from £49 /night

£340 - £679 / week

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Late Deal: save up to €240 (approx. £192)

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
The house, composed of 5 delightful apartments, has as it's main objective the idea of offering guests the opportunity to enjoy the calm, the beauty and all the pleasures our region has to offer. Our apartments have been renovated with respect for tradition.  …see more

10 Photos

Villa | 2 Bedrooms | sleeps 5

2 Nights min stay

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from £67 /night

£467 - £933 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
The Chianti As You Always Dreamed It. A charming Medieval borgo in the heart of Chianti Classico, 15 km far from Siena. Relax and discovery hour incredible landes. The charme of an ancient Medieval borgo in the heart of Chianti Classico  …see more

24 Photos

Castle | 6 Bedrooms | sleeps 14

Short stays welcome

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from £111 /night

£772 - £3477 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Castle, tuscany, italy, swimmingpool, bed and breakfast, gaiole in chianti, events, wedding, private castle, private villa, Yoga, wine  …see more

12 Photos

Farmhouse | 4 Bedrooms | sleeps 7

2 Nights min stay

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from £223 /night

£1560 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
Villa / Farmhouse / Home in Gaiole In Chianti with 4 bedrooms sleeps 7  …see more

8 Photos

Farmhouse | 1 Bedroom | sleeps 2

1 night min stay

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from £108 /night

£756 - £924 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
Villa / Farmhouse / Home in Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £79 /night

£550 - £644 / week

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Key info:

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

24 Photos

Apartment | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £60 /night

£416 - £752 / week

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Key info:

  • Nearest beach 105 km
  • Swimming pool
  • Suitable for over 5s only
  • Car advised
  • Air conditioning
  • May take pets – please enquire
Ideal location for couples and families, set within walking distance of Gaiole in Chianti with the typical Tuscan lifestyle at your doorstep. Perfect place to unwind and come back to after a cycle, a walk, or discovering the artistic and historic cities of Tuscany. Gaiole is in the Chianti Classico area, ideal to taste and enjoy the best wines and olive oil in Italy.  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £112 /night

£784 - £904 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Gaiole In Chianti with 3 bedrooms sleeps 6  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £371 /night

£2596 - £3894 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
Luxury holiday house for 8 persons, with swimming pool , in Chianti  …see more

10 Photos

B&B | 1 Bedroom | sleeps 2

1 night min stay

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from £75 /night

£524 - £616 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • May take pets – please enquire
Bed & Breakfast in Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 5

3 Nights min stay

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from £134 /night

£936 - £1130 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Villa / Farmhouse / Home in Vagliagli with 3 bedrooms sleeps 5  …see more

11 Photos

Farmhouse | 2 Bedrooms | sleeps 7

4 Nights min stay

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from £138 /night

£960 - £1920 / 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 Lecchi with 2 bedrooms sleeps 7  …see more

12 Photos

Farmhouse | 4 Bedrooms | sleeps 6

2 Nights min stay

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from £206 /night

£1440 - £1680 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
Villa / Farmhouse / Home in Gaiole In Chianti with 4 bedrooms sleeps 6  …see more

19 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

2 Nights min stay

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from £547 /night

£3824 - £5873 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
This beautiful, rustic villa is built on the side of a hill and surrounded by vineyards and woods. The villa is at the heart of an agricultural estate that produces organic wine and extra virgin olive oil. Good food, wine and relaxation await you in the heart of Tuscany  …see more

10 Photos

B&B | 1 Bedroom | sleeps 2

1 night min stay

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from £82 /night

£572 - £712 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • May take pets – please enquire
Bed & Breakfast in Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

11 Photos

Farmhouse | 1 Bedroom | sleeps 2

1 night min stay

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from £120 /night

£840 - £1008 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • May take pets – please enquire
Villa / Farmhouse / Home in Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £83 /night

£579 - £679 / week

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Key info:

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

24 Photos

Villa | 7 Bedrooms | sleeps 18

5 Nights min stay

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from £183 /night

£1280 - £4592 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • Pets welcome
Villa Il Giglio is a charming private villa located in the Chianti Senese area surrounded by a spacious 6000 sq mt parkland which is completely fenced in though giving access through an electronic gate. The villa has a lovely swimming pool ( 6 x 12 mts) with a  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 8

4 Nights min stay

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from £182 /night

£1272 - £2632 / 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 Lecchi with 3 bedrooms sleeps 8  …see more

9 Photos

Farmhouse | 1 Bedroom | sleeps 2

1 night min stay

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from £120 /night

£840 - £1008 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
Villa / Farmhouse / Home in Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

11 Photos

Farmhouse | 1 Bedroom | sleeps 2

1 night min stay

Add to shortlist

from £120 /night

£840 - £1008 / week

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Key info:

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

12 Photos

Farmhouse | 5 Bedrooms | sleeps 10

3 Nights min stay

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from £212 /night

£1480 - £1960 / week

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Key info:

  • Suitable for children of all ages
  • May take pets – please enquire
Villa / Farmhouse / Home in Lecchi with 5 bedrooms sleeps 10  …see more

10 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £112 /night

£784 - £904 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Gaiole In Chianti with 3 bedrooms sleeps 6  …see more

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

1 night min stay

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from £141 /night

£986 - £1176 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • May take pets – please enquire
Villa / Farmhouse / Home in Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

12 Photos

Apartment | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £138 /night

£960 - £1600 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • May take pets – please enquire
  • Private garden
Apartment / Condo in Lecchi with 3 bedrooms sleeps 6  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £152 /night

£1059 - £1512 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Villa / Farmhouse / Home in Gaiole In Chianti with 3 bedrooms sleeps 6  …see more

11 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £116 /night

£807 - £1109 / 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 Gaiole In Chianti with 2 bedrooms sleeps 4  …see more

10 Photos

B&B | 1 Bedroom | sleeps 4

1 night min stay

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from £102 /night

£712 - £904 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Bed & Breakfast in Gaiole In Chianti with 1 bedrooms sleeps 4  …see more

17 Photos

Farmhouse | 4 Bedrooms | sleeps 8

2 Nights min stay

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from £136 /night

£950 - £2301 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • May take pets – please enquire
This beautiful, detached farmhouse has been carefully restored by the architect owner to the highest standards. He has maintained the original structure, while adding modern design ideas.  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 8

Very Good 4.5/5 

Short stays welcome

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from £79 /night

£548 - £1248 / week

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Key info:

  • Nearest beach 107 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Located within walking distance of the village of Gaiole in Chianti, the villa offers the perfect setting to explore the Chianti Classico region, enjoy the breathtaking views of the vineyards and olive groves, and experience the charming Tuscan lifestyle. Beautiful villa located within walking distance of the village of Gaiole in Chianti, near Siena, Tuscany  …see more

10 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £108 /night

£756 - £1059 / week

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Key info:

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

10 Photos

Farmhouse | 1 Bedroom | sleeps 2

1 night min stay

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from £141 /night

£986 - £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 Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £111 /night

£773 - £872 / week

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Key info:

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

24 Photos

Apartment | 1 Bedroom | sleeps 3

7 Nights min stay

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from £46 /night

£316 - £580 / week

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Key info:

  • Nearest beach 105 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
Ideal location for couples and families, set within walking distance of Gaiole in Chianti with the typical Tuscan lifestyle at your doorstep. Perfect place to unwind and come back to after a cycle, a walk, or discovering the artistic and historic cities of Tuscany. Gaiole is in the Chianti Classico area, ideal to taste and enjoy the best wines and olive oil in Italy.  …see more

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £116 /night

£807 - £1109 / 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 Gaiole 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 £345 /night

£2412 - £3619 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Gaiole In Chianti with 4 bedrooms sleeps 8  …see more

9 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £103 /night

£720 - £832 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
Villa / Farmhouse / Home in Gaiole In Chianti with 2 bedrooms sleeps 4  …see more

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £74 /night

£516 - £615 / week

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Key info:

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

10 Photos

B&B | 1 Bedroom | sleeps 2

1 night min stay

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from £82 /night

£572 - £712 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Bed & Breakfast in Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

10 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £152 /night

£1059 - £1512 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
Villa / Farmhouse / Home in Gaiole In Chianti with 3 bedrooms sleeps 6  …see more

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £103 /night

£720 - £832 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Gaiole In Chianti with 2 bedrooms sleeps 4  …see more

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £155 /night

£1080 - £1280 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
Villa / Farmhouse / Home in Gaiole In Chianti with 2 bedrooms sleeps 4  …see more

12 Photos

Farmhouse | 1 Bedroom | sleeps 3

2 Nights min stay

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from £132 /night

£920 - £1080 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
Villa / Farmhouse / Home in Gaiole In Chianti with 1 bedrooms sleeps 3  …see more

10 Photos

Farmhouse | 1 Bedroom | sleeps 2

1 night min stay

Add to shortlist

from £141 /night

£986 - £1176 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
Villa / Farmhouse / Home in Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £152 /night

£1059 - £1512 / 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 Gaiole In Chianti with 3 bedrooms sleeps 6  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 12

2 Nights min stay

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from £567 /night

£3964 - £5491 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
Villa Stefano dates back to the 10th century and was originally a traditional stone water mill. With all the comforts of a modern villa, many of the original features including meter thick walls, wood beamed and tiled ceilings, and cotto floors still remain.  …see more