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58 Results  |  
100 Photos

Farmhouse / 5 Bedrooms / sleeps 18

Excellent 5/5 

7 Nights min stay

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from £352 / night

£2464 - £3551 / week

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Key info:

  • Great for children of all ages
  • Car essential
  • No pets allowed
This is a traditional 5 bedroom villa situated between the towns of Gaiole in Chianti and Radda in Chianti. Accommodating up to 18 guests in total as additional apartments are available within the grounds, it's an ideal base for a stay with family or friends. The wonderful gardens and exceptionally large private swimming pool will mean it's hard to drag yourself away to see the sights of Tuscany. However, for those that do want to enjoy some sightseeing during their stay, the property is perfectly placed for exploring the best that this region has to offer.  …see more

20 Photos

Apartment / 2 Bedrooms / sleeps 6

Excellent 5/5 

2 Nights min stay

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from £65 / night

£450 - £800 / 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

24 Photos

Castle / 6 Bedrooms / sleeps 16

Short stays welcome

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from £311 / night

£2174 - £3116 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Castle, tuscany, italy, swimmingpool, bed and breakfast, gaiole in chianti, events, wedding, private castle, private villa, Yoga, wine  …see more

Featured properties

24 Photos

Apartment / 2 Bedrooms / sleeps 5

3 Nights min stay

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from £65 / night

£453 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
This lovely 11th century castle for holiday rental in the Chianti Classico area is a tiny, medieval hamlet located at 10 km from Gaiole in Chianti.  …see more

13 Photos

B&B / 1 Bedroom / sleeps 2

1 night min stay

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from £63 / night

£435 / 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

12 Photos

Townhouse / 1 Bedroom / sleeps 2

2 Nights min stay

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from £40 / night

£274 - £649 / 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

15 Photos

Villa / 6 Bedrooms / sleeps 12

1 night min stay

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from £156 / night

£1087 - £1667 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Tranquilla Confortevole Cibo Cucina Salumi Vino Olio Piscina Palestra Panorama Chianti Castello  …see more

9 Photos

Apartment / 3 Bedrooms / sleeps 6

2 Nights min stay

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from £64 / night

£448 - £1047 / 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

2 Nights min stay

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from £54 / night

£375 - £948 / 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

9 Photos

Apartment / 2 Bedrooms / sleeps 4

3 Nights min stay

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from £47 / night

£326 - £622 / 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

2 Nights min stay

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from £50 / night

£349 - £724 / 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

11 Photos

Apartment / 2 Bedrooms / sleeps 6

2 Nights min stay

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from £54 / night

£375 - £922 / 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

11 Photos

Apartment / 1 Bedroom / sleeps 4

2 Nights min stay

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from £47 / night

£326 - £672 / 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

11 Photos

Apartment / 2 Bedrooms / sleeps 6

2 Nights min stay

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from £54 / night

£375 - £823 / 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

6 Photos

Apartment / 1 Bedroom / sleeps 3

2 Nights min stay

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from £40 / night

£274 - £573 / 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

6 Photos

Apartment / 2 Bedrooms / sleeps 6

2 Nights min stay

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from £54 / night

£375 - £747 / 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

7 Photos

Apartment / 1 Bedroom / sleeps 2

2 Nights min stay

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from £36 / night

£250 - £500 / 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

13 Photos

Apartment / 7 Bedrooms / sleeps 16

2 Nights min stay

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from £136 / night

£948 - £1941 / 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

19 Photos

Apartment / 1 Bedroom / sleeps 4

7 Nights min stay

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from £57 / night

£393 - £551 / 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

9 Photos

Villa / 2 Bedrooms / sleeps 5

5 Nights min stay

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from £57 / night

£399 - £798 / 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

45 Photos

Villa / 5 Bedrooms / sleeps 10

7 Nights min stay

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from £570 / night

£3986 - £4711 / 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

18 Photos

Villa / 6 Bedrooms / sleeps 14

Short stays welcome

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from £192 / night

£1341 - £2319 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
The "Molino della Carpinese" is located in the municipality of Gaiole in Chianti. The peace and silence characterize the environment that makes it particularly suitable for a relaxing vacation that helps you to forget the stress of those who live in big cities. The Mill of Carpinese is located in the municipality of Gaiole in Chianti, Province of Siena. The peace and  …see more

24 Photos

Villa / 5 Bedrooms / sleeps 10

Excellent 5/5 

7 Nights min stay

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from £176 / night

£1229 - £2722 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
This comfortably furnished country style Tuscan villa sleeps up to ten persons. Set amongst a mature well tended garden with its own private swimming pool. The property is in a great location only five minutes away from Gaiole.  …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

17 Photos

Villa / 6 Bedrooms / sleeps 12

Very Good 4/5 

7 Nights min stay

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from £196 / night

£1370 - £3008 / 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

Villa / 6 Bedrooms / sleeps 12

Excellent 5/5 

7 Nights min stay

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from £311 / night

£2171 - £4000 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Private Villa with pool in Gaiole in Chianti in Tuscany sleeping up to 12 people with 5 beds 5 baths in main house and a barn conversion with a separate one bedroomed apartment in the grounds. A great property for large families or groups travelling together.  …see more

22 Photos

Apartment / 1 Bedroom / sleeps 4

Excellent 5/5 

4 Nights min stay

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from £75 / night

£525 - £725 / week

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Late Deal: save up to £128

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

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

12 Photos

Farmhouse / 3 Bedrooms / sleeps 6

7 Nights min stay

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from £301 / night

£2102 - £3298 / 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

16 Photos

Farmhouse / 7 Bedrooms / sleeps 13

7 Nights min stay

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from £620 / night

£4334 - £6464 / 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

20 Photos

House / 2 Bedrooms / sleeps 4

7 Nights min stay

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from £129 / night

£900 - £1040 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Villa Diora D is a characteristic and welcoming independent house surrounded by vineyards and olive groves. It sleeps four people. From Villa Diora D you will enjoy an enchanting view of the Tuscan hills and of the Chianti valley  …see more

24 Photos

Villa / 5 Bedrooms / sleeps 10

3 Nights min stay

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from £782 / night

£5472 - £6993 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
This exclusive and luxurious villa in Chianti affords 5 bedrooms, dining room, 2 sitting rooms, kitchen, gym, games room and a fabulous infinity swimming pool.  …see more

22 Photos

Farmhouse / 5 Bedrooms / sleeps 10

Min stay varies

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Pricing unknown

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Le Diacce, an enchanting 18th century old farmhouse, belonging to Podere Ciona, 40 hectares of vineyards and woodland, enjoys a unique view on the surrounding hills covered with vineyards, olive groves and woods with Siena in the far distance.  …see more

22 Photos

Apartment / 1 Bedroom / sleeps 4

7 Nights min stay

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from £41 / night

£287 - £548 / 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

24 Photos

Farmhouse / 3 Bedrooms / sleeps 8

3 Nights min stay

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from £151 / night

£1055 - £1757 / 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

20 Photos

Farmhouse / 3 Bedrooms / sleeps 6

3 Nights min stay

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from £139 / night

£969 - £1384 / 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 / 1 Bedroom / sleeps 2

3 Nights min stay

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from £67 / night

£465 - £545 / 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

3 Nights min stay

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from £139 / night

£969 - £1384 / 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

24 Photos

Farmhouse / 1 Bedroom / sleeps 2

3 Nights min stay

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from £70 / night

£490 - £574 / 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 / 5 Bedrooms / sleeps 10

3 Nights min stay

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from £194 / night

£1355 - £1794 / 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 / 1 Bedroom / sleeps 2

3 Nights min stay

Add to shortlist

from £67 / night

£465 - £545 / 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 / 2 Bedrooms / sleeps 4

3 Nights min stay

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from £106 / night

£739 - £1015 / 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

20 Photos

Farmhouse / 1 Bedroom / sleeps 2

3 Nights min stay

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from £99 / night

£693 - £969 / 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

24 Photos

Farmhouse / 4 Bedrooms / sleeps 8

3 Nights min stay

Add to shortlist

from £316 / night

£2208 - £3311 / 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 / 3 Bedrooms / sleeps 5

3 Nights min stay

Add to shortlist

from £113 / night

£791 - £956 / 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

24 Photos

Farmhouse / 3 Bedrooms / sleeps 6

3 Nights min stay

Add to shortlist

from £139 / night

£969 - £1384 / 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 / 1 Bedroom / sleeps 2

3 Nights min stay

Add to shortlist

from £63 / night

£435 - £520 / 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 / 2 Bedrooms / sleeps 4

3 Nights min stay

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from £94 / night

£653 - £737 / 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

22 Photos

Farmhouse / 2 Bedrooms / sleeps 4

3 Nights min stay

Add to shortlist

from £106 / night

£739 - £1015 / 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

16 Photos

Farmhouse / 6 Bedrooms / sleeps 11

7 Nights min stay

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from £536 / night

£3747 - £5508 / 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

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