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68 Holiday homes in Gaiole in Chianti

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68 Results  |  
20 Photos

Apartment | 2 Bedrooms | sleeps 6

Excellent 5/5 

2 Nights min stay

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from £40 /night

£275 - £682 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
With beautiful views over the village, this ground floor, comfortable apartment is the perfect spot! Modern facilities including a Swimming pool a gym, and table tennis. The apartment has 2 bedrooms, a well equipped kitchen, a dining terrace, and underground parking. The multinational users are generally quiet and friendly, respectful of the natural ambience of the Borgo.  …see more

13 Photos

B&B | 1 Bedroom | sleeps 2

1 night min stay

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from £77 /night

£533 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Borgo in genuine Chianti town. Scenery perfect for hiking and biking. Proximity to Siena and Florence alongside other cultural and historical Chianti villages. Excellent local dining and wine tasting. Property provides easy access to spacious terrace and pool area.  …see more

23 Photos

Apartment | 3 Bedrooms | sleeps 8

Excellent 5/5 

4 Nights min stay

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from £143 /night

£1000 - £1500 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
A bright roomy south facing 3 bed/2 bath apartment with panaramic views over Gaiole and the hills beyond. Enjoy al fresco dining on the terrace or doze in a wisteria shaded hammock. Relax by the pool, take a cycle ride or just stroll down to the village restuarants. Maggiore is ideally situated to enjoy the areas premier events including Siena Palio and Gaiole Eroica.  …see more

Featured properties

24 Photos

Apartment | 4 Bedrooms | sleeps 12

Excellent 5/5 

4 Nights min stay

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from £229 /night

£1600 - £2100 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
A spacious townhouse complex on two levels well suited to sharing families in easy strolling distance of restaurants, delicatessens, bars etc; large pool, gym, free bicycle hire and plenty of private outdoor space with lovely views offers something for all the family.  …see more

22 Photos

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

4 Nights min stay

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from £70 /night

£490 - £725 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
A spacious 1 bed apartment with garden and bbq terrace, in a picturesque setting, only a short walk to local services. Enjoy free use of cycles & gym or just relax by the pool. Launderette & internet services add home comforts and a glass of wine greets you on arrival. Minore is ideally situated to enjoy the areas premier events including Siena Palio & Gaiole Eroica.  …see more

17 Photos

Villa | 6 Bedrooms | sleeps 12

Very Good 4/5 

7 Nights min stay

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from £218 /night

£1525 - £3347 / week

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Key info:

  • Nearest beach 125 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • 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

24 Photos

Farmhouse | 6 Bedrooms | sleeps 12

2 Nights min stay

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from £362 /night

£2530 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Podere Scopeto, a former hill farm on sunset-facing slopes of the Chianti in the heart of the wine-region. Main House sleeps 10 and separately available self-contained studio for 2 in its own 30 acres of woodland. 15m saltwater pool on terraces with spectacular views.  …see more

41 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £672 /night

£4702 - £5557 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
VILLA DEL SOLE is a lovely Tuscan villa near the popular towns of Gaiole and Radda in Chianti. This wonderful villa comprises of the main house which is spread over three floors and a separate ground floor villa which is aproximately 50 metres away.  …see more

15 Photos

Farmhouse | 5 Bedrooms | sleeps 9

7 Nights min stay

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from £492 /night

£3444 - £5057 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Breathtaking views over the Chianti Classico valleys. Attractive and panoramic terrace.  …see more

17 Photos

Farmhouse | 7 Bedrooms | sleeps 18

7 Nights min stay

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from £537 /night

£3759 - £6444 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Modern design combined to the original structure. Modern facilities including air conditioning. Very peaceful and secluded position in the Chianti region. Optional guest house.  …see more

16 Photos

Farmhouse | 6 Bedrooms | sleeps 11

7 Nights min stay

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from £596 /night

£4170 - £6130 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Breathtaking views over the Chianti Classico valleys. Attractive and panoramic terrace.  …see more

16 Photos

Farmhouse | 7 Bedrooms | sleeps 13

7 Nights min stay

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from £689 /night

£4823 - £7194 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Breathtaking views over the Chianti Classico valleys. Attractive and panoramic terrace.  …see more

19 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £69 /night

£480 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
This is a quiet and peaceful corner of the property idea for relaxing after sighseeing or for cooling off after the warm Tuscan day. Pool fenced - a 16x6 mtr pool open from mid-May to mid-September (weather permitting)  …see more

10 Photos

Villa | 2 Bedrooms | sleeps 5

2 Nights min stay

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from £70 /night

£488 - £879 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great 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

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

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

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

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

13 Photos

Apartment | 7 Bedrooms | sleeps 16

1 night min stay

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from £173 /night

£1209 - £1410 / week

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Key info:

  • Great for children of all ages
  • No pets allowed
'Il Gufo n°1', 9-room apartment 180 m2 on 2 levels on 1st floor: living/dining room with open fireplace. Small living room with 1 double sofa bed (160 cm), satellite-TV. 1 double bedroom. Kitchenette (4 hotplates, dishwasher, micro wave). Shower/WC. Upper floo  …see more

11 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

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from £59 /night

£407 - £522 / week

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Key info:

  • Great for children of all ages
  • No pets allowed
'Pulcino n°3', 2-room apartment 32 m2, on the ground floor: living/dining room with 1 double sofa bed (160 cm), satellite-TV. 1 small double bedroom. Kitchenette. Shower/WC. Small patio. Maximum 1 pet/ dog allowed. Località la Massa 15 km from Gaiole in  …see more

6 Photos

Apartment | 2 Bedrooms | sleeps 6

1 night min stay

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from £69 /night

£482 / week

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Key info:

  • Great for children of all ages
  • No pets allowed
'Malvasia n°6', 3-room apartment 60 m2, on the lower ground floor: living/dining room with 1 double sofa bed and satellite-TV. 1 double bedroom. 1 room with 1 x 2 bunk beds. Kitchenette. Shower/bidet/WC. Maximum 1 pet/ dog allowed. Farm house Ensoli, ap  …see more

9 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

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from £93 /night

£646 - £786 / week

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Key info:

  • Great for children of all ages
  • No pets allowed
'Casa Selvolini', 4-room apartment 80 m2 on 1st floor, comfortable furnishings: open living/dining room with open fireplace, digital TV and air-conditioning. Exit to the terrace. 1 double bedroom. 1 room with 2 beds. Small lounge. Kitchenette (4 hotplates, ove  …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

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

11 Photos

Apartment | 2 Bedrooms | sleeps 6

1 night min stay

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from £70 /night

£488 - £646 / week

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Key info:

  • Great for children of all ages
  • No pets allowed
'Coccinella n°6', 3-room apartment 50 m2, on the upper ground floor: living/dining room with 1 double sofa bed (160 cm), satellite-TV. 1 double bedroom. 1 room with 2 beds. Kitchenette (4 hotplates). Shower/bidet/WC. Small patio. Terrace furniture. Maximum 1 p  …see more

24 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £155 /night

£1079 - £1540 / 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 | 6 Bedrooms | sleeps 11

7 Nights min stay

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from £596 /night

£4170 - £4275 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
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

24 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £74 /night

£517 - £656 / 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

24 Photos

Farmhouse | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £335 /night

£2339 - £3670 / 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 Selvole with 3 bedrooms sleeps 6  …see more

24 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £74 /night

£517 - £656 / 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

24 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £78 /night

£545 - £692 / 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

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

24 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £70 /night

£484 - £626 / 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

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

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

24 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £104 /night

£727 - £888 / 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

20 Photos

House | 4 Bedrooms | sleeps 7

1 night min stay

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from £426 /night

£2980 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Villa Diora F is a splendid sixteenth-century apartment that is part of a villa in the characteristic style of the Tuscan countryside. It sleeps seven people. From Villa Diora F you will enjoy an enchanting view of the Chianti hills and of the vineyards  …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

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

24 Photos

Farmhouse | 3 Bedrooms | sleeps 5

3 Nights min stay

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from £126 /night

£880 - £1151 / 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 3 bedrooms sleeps 5  …see more

20 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £155 /night

£1079 - £1540 / 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

24 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £118 /night

£822 - £1130 / 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 Gaiole In Chianti with 2 bedrooms sleeps 4  …see more

22 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £118 /night

£822 - £1130 / 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 Gaiole In Chianti with 2 bedrooms sleeps 4  …see more

24 Photos

Farmhouse | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £351 /night

£2457 - £3685 / 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

24 Photos

Farmhouse | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £344 /night

£2404 - £2952 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
This particular and fascinating farmhouse is located in the heart of Chianti, a region renowned worldwide for its wine production. The property has a great and particular charm and although maintaining the rural character of the structure and the classic style typical  …see more

17 Photos

Farmhouse | 4 Bedrooms | sleeps 8

2 Nights min stay

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from £136 /night

£949 - £2299 / 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

24 Photos

Farmhouse | 5 Bedrooms | sleeps 10

3 Nights min stay

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from £216 /night

£1508 - £1996 / week

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Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Lecchi with 5 bedrooms sleeps 10  …see more

24 Photos

Farmhouse | 3 Bedrooms | sleeps 8

3 Nights min stay

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from £168 /night

£1174 - £1955 / 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 San Sano with 3 bedrooms sleeps 8  …see more

24 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £155 /night

£1079 - £1540 / 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 Gaiole In Chianti with 3 bedrooms sleeps 6  …see more