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135 Holiday homes in Gaiole in Chianti

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135 Results  |  
9 Photos

Farmhouse | 1 Bedroom | sleeps 2

1 night min stay

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from £121 /night

£847 - £1017 / week

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Key info:

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

21 Photos

Villa | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £277 /night

£1936 - £4537 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Villa Enrichettaandnbsp;is located in a charming medieval hamlet set in one of the most idyllic Tuscan scenery, surrounded by gently rolling, green hills and vineyards. The villa in authentic Chianti style is linear, luminous, almost a sculpture built onandnbsp;three  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 8

1 night min stay

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from £346 /night

£2420 - £3630 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Eracle is a bright and elegant three-story villa surrounded by vineyards and olive groves. It sleeps eight people. From Villa Eracle you will enjoy a fascinating view of the Chianti hills and of the vineyards  …see more

Featured properties

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

1 night min stay

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from £142 /night

£994 - £1186 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

10 Photos

B&B | 1 Bedroom | sleeps 2

1 night min stay

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from £83 /night

£577 - £718 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Some pets are welcome - please contact the owner
Bed & Breakfast in Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 18

5 Nights min stay

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from £185 /night

£1291 - £3500 / 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

17 Photos

Farmhouse | 4 Bedrooms | sleeps 8

2 Nights min stay

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from £135 /night

£943 - £2286 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • Some pets are welcome - please contact the owner
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

10 Photos

Farmhouse | 1 Bedroom | sleeps 2

1 night min stay

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from £142 /night

£994 - £1186 / 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 Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

22 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £48 /night

£335 - £505 / week

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Key info:

  • Nearest beach 105 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • Some pets are welcome - please contact the owner
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 wine and food in Italy.  …see more

16 Photos

House | 5 Bedrooms | sleeps 12

7 Nights min stay

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from £537 /night

£3759 - £4815 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
La Maccinaia is a beautiful property located in a very quiet location, in the heart of the Chianti region, between Gaiole and Castelnuovo Berardenga. The main villa dates to the 17th century, and has been immaculately restored by its Belgian owner who combined modern  …see more

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £80 /night

£555 - £649 / 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 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 £83 /night

£577 - £718 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Some pets are welcome - please contact the owner
Bed & Breakfast in Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £345 /night

£2412 - £3468 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Gaiole In Chianti with 3 bedrooms sleeps 6  …see more

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £80 /night

£555 - £649 / 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 Vagliagli with 1 bedrooms sleeps 2  …see more

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £75 /night

£520 - £620 / 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 Vagliagli with 1 bedrooms sleeps 2  …see more

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £112 /night

£780 - £879 / 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 Vagliagli with 2 bedrooms sleeps 4  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 8

4 Nights min stay

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from £184 /night

£1283 - £2654 / 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 Lecchi with 3 bedrooms sleeps 8  …see more

20 Photos

Apartment | 3 Bedrooms | sleeps 5

7 Nights min stay

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from £143 /night

£998 - £1205 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Apartment for 5 persons, with swimming pool , in Siena  …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
  • Great 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 £76 /night

£529 - £621 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Some pets are welcome - please contact the owner
Bed & Breakfast in Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

9 Photos

B&B | 1 Bedroom | sleeps 2

4 Nights min stay

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from £84 /night

£588 - £1307 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Apartmentandnbsp;Barnandnbsp;is located in splendid Chianti country side on the ground floor, can comfortably accommodate andnbsp;twoandnbsp;people.andnbsp; There is aandnbsp;double bed roomandnbsp;with open fireplace,andnbsp;small kitchen, bath room with hydro  …see more

16 Photos

Apartment | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £162 /night

£1130 - £1612 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
Apartment for 6 persons, with swimming pool , in Chianti  …see more

16 Photos

House | 5 Bedrooms | sleeps 9

7 Nights min stay

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from £492 /night

£3444 - £3565 / week

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Key info:

  • Great for children of all ages
  • No pets allowed
  • Private garden
Il Colombaio is a peaceful oasis in the heart of Chianti Classico, with expansive views on rolling hills and rows of vineyards. The location, near the village of Gaiole in Chianti, is perfect for visiting the several hilltop villages such as Radda, Castellina and Greve  …see more

12 Photos

Farmhouse | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £348 /night

£2432 - £3648 / week

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Key info:

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

10 Photos

Farmhouse | 1 Bedroom | sleeps 2

1 night min stay

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from £142 /night

£994 - £1186 / 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

8 Photos

B&B | 2 Bedrooms | sleeps 2

4 Nights min stay

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from £84 /night

£588 - £1307 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Apartment Archesandnbsp;is ideally located inandnbsp;Chianti countryside. It is on theandnbsp;ground floor, aboutandnbsp;80 m2, can comfortably sleepandnbsp;3andnbsp;people.andnbsp; There is aandnbsp;living roomandnbsp;with open fireplace,andnbsp;dining room,  …see more

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £84 /night

£584 - £684 / 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 Vagliagli with 1 bedrooms sleeps 2  …see more

12 Photos

Apartment | 3 Bedrooms | sleeps 6

4 Nights min stay

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from £117 /night

£813 - £2069 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Gaiole-Apartment Ventoandnbsp;is a andnbsp;threeandnbsp;bedroom rental countryside apartment in the hamlet of Gaiole in theandnbsp;Chianti region of Siena, Tuscany. San Gimignano, a small walled hill town in the province of Siena, is famous for itsandnbsp;medieval  …see more

10 Photos

B&B | 1 Bedroom | sleeps 4

1 night min stay

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from £103 /night

£718 - £912 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Bed & Breakfast in Gaiole In Chianti with 1 bedrooms sleeps 4  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 5

2 Nights min stay

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from £208 /night

£1452 - £1694 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
Villa / Farmhouse / Home in Gaiole In Chianti with 3 bedrooms sleeps 5  …see more

12 Photos

Apartment | 2 Bedrooms | sleeps 4

4 Nights min stay

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from £91 /night

£633 - £1471 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Gaiole -Apartment Yardandnbsp;is a rental holiday apartment inandnbsp;Gaiole, Chianti, in the province of Siena, Tuscany . The Chianti area is spread across the provinces of Florence and Siena and includes the municipalities ofandnbsp;Greve, Panzano, Radda, Gaiole and  …see more

19 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

2 Nights min stay

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from £539 /night

£3767 - £5786 / 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, 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

12 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £153 /night

£1067 - £1525 / 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 Gaiole In Chianti with 3 bedrooms sleeps 6  …see more

16 Photos

House | 7 Bedrooms | sleeps 13

7 Nights min stay

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from £689 /night

£4823 - £5073 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Il Colombaio is a peaceful oasis in the heart of Chianti Classico, with expansive views on rolling hills and rows of vineyards. The location, near the village of Gaiole in Chianti, is perfect for visiting the several hilltop villages such as Radda, Castellina and Greve,  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 3

Excellent 5/5 

7 Nights min stay

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from £46 /night

£319 - £464 / week

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Key info:

  • Nearest beach 105 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
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

16 Photos

Villa | 7 Bedrooms | sleeps 18

7 Nights min stay

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from £689 /night

£4823 - £6283 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
La Maccinaia is a beautiful property located in a very quiet location, in the heart of the Chianti region, between Gaiole and Castelnuovo Berardenga. The main villa dates to the 17th century, and has been immaculately restored by its Belgian owner who combined modern  …see more

12 Photos

Farmhouse | 4 Bedrooms | sleeps 6

2 Nights min stay

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from £208 /night

£1452 - £1694 / week

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Key info:

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

16 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

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from £85 /night

£591 - £689 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Apartment for 2 persons, with swimming pool , in Siena  …see more

9 Photos

Farmhouse | 1 Bedroom | sleeps 2

1 night min stay

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from £121 /night

£847 - £1017 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
Villa / Farmhouse / Home in Gaiole In Chianti 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

£420 - £638 / week

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Key info:

  • Nearest beach 105 km
  • Swimming pool
  • Suitable for children over
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
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

8 Photos

Apartment | 4 Bedrooms | sleeps 6

4 Nights min stay

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from £117 /night

£813 - £2069 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Gaiole-Apartment Canopyandnbsp;is a Tuscany rental in the municipality ofandnbsp;Gaiole, Chianti, in Siena, Tuscany. Gaiole in Chianti is a striking little township and rated as one of Europe's most idyllic places to live in. 'Leroica', a bicycle race is held here  …see more

12 Photos

Apartment | 1 Bedroom | sleeps 2

4 Nights min stay

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from £84 /night

£588 - £1307 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Apartment Wavesandnbsp;is provided withandnbsp;private terrace, air conditioning, panoramic living roomandnbsp;with open fireplace, aandnbsp;fully furnished kitchen and dining room, a double bedroomandnbsp;withandnbsp;queen size bed, beautifully tiled bathroom with  …see more

10 Photos

B&B | 1 Bedroom | sleeps 4

1 night min stay

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from £103 /night

£718 - £912 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Some pets are welcome - please contact the owner
Bed & Breakfast in Gaiole In Chianti with 1 bedrooms sleeps 4  …see more

7 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

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from £48 /night

£330 - £370 / week

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Key info:

  • Great for children of all ages
  • No pets allowed
'Prugnolino n°7', 1-room apartment 25 m2, on the ground floor: 1 double bedroom with satellite-TV. Kitchen (2 hotplates) with dining table. Shower/WC. Maximum 1 pet/ dog allowed. Private outdoor area, 6 m2, furnished with 2 loungers and sunbed. Farm hou  …see more

6 Photos

Apartment | 1 Bedroom | sleeps 3

1 night min stay

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from £57 /night

£395 - £504 / week

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Key info:

  • Great for children of all ages
  • No pets allowed
'Trebbiano n°5', 2-room apartment 40 m2, on the lower ground floor: living/dining room with satellite-TV. 1 double bedroom with 1 bed and 1 double bed. Kitchenette. Shower/WC. Maximum 1 pet/ dog allowed. Farm house Ensoli, approx 1600, has been recently  …see more

11 Photos

Apartment | 2 Bedrooms | sleeps 6

1 night min stay

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from £70 /night

£488 - £699 / week

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Key info:

  • Great for children of all ages
  • No pets allowed
'La Farfalla n°5', 3-room apartment 75 m2 on 2 levels, on the ground floor: living/dining room with 1 double sofa bed (160 cm), satellite-TV. Kitchenette (4 hotplates). Sep. WC. Upper floor: 1 double bedroom. 1 room with 2 beds. Shower/bidet/WC. Small patio. T  …see more

12 Photos

Townhouse | 1 Bedroom | sleeps 2

1 night min stay

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from £51 /night

£355 - £441 / week

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Key info:

  • Not suitable for children
  • No pets allowed

"Cerbiatto n°5A", 2-room apartment 35 m2 on 2 levels, on the ground floor: living/dining room with satellite-TV. Kitchenette (4 hotplates). On the lower ground floor: 1 double bedroom. Shower/bidet/WC. Small patio. Terrace furniture. Please note: only 1 dog accepted. The showwer  …see more

9 Photos

Apartment | 3 Bedrooms | sleeps 6

1 night min stay

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from £87 /night

£606 - £777 / week

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Key info:

  • Great for children of all ages
  • No pets allowed
'San Giovese n°4', 4-room apartment 105 m2, on the upper ground floor: living room with satellite-TV. 1 room with 1 bed and 1 double bed. 1 double bedroom. 1 room with 1 bed. Kitchen (4 hotplates, dishwasher) with open fireplace and dining table. Shower/WC, sh  …see more

13 Photos

Apartment | 2 Bedrooms | sleeps 6

1 night min stay

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from £69 /night

£482 - £777 / week

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Key info:

  • Great for children of all ages
  • No pets allowed
'La Colomba n°4', 3-room apartment 75 m2 on 2 levels, on the ground floor: living room with 1 double sofa bed (160 cm), satellite-TV. Kitchenette (4 hotplates). Shower/WC. Upper floor: 1 double bedroom. 1 room with 2 beds. Shower/bidet/WC. Small patio. Terrace  …see more

12 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

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from £67 /night

£463 - £600 / week

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Key info:

  • Great for children of all ages
  • No pets allowed
'Il Pettirosso n°7', 2-room apartment 55 m2 on 2 levels, on the ground floor: kitchen (4 hotplates) with dining table and satellite-TV. Upper floor: 1 double bedroom. 1 room with 2 beds. Shower/bidet/WC. Small patio. Terrace furniture. Maximum 1 pet/ dog allow  …see more