Gaiole in Chianti apartment or villa with a log fire | Holiday Lettings

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54 Holiday homes

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Travellers going to Gaiole in Chianti are booking September dates now. Secure your holiday home today and have the perfect trip.

1 / 15

Province of Siena / Gaiole in Chianti

2 5 7 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
 …see more

from £62 / night

£428 / week

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from £62 / night

(2) Excellent 

1 / 18

Province of Siena / Gaiole in Chianti

2 2 7 nights min stay

  • 2 bedrooms
  • Sleeps 2
  • 7 nights min stay
Key info: Swimming pool; Suitable for children age 5+; Pet friendly;
 …see more

from £77 / night

£539 / week

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from £77 / night

1 / 15

Province of Siena / Gaiole in Chianti

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Swimming pool; Child friendly ; Pet friendly;
 …see more

from £189 / night

£1283 - £1624 / week

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from £189 / night

1 / 20

Province of Siena / Gaiole in Chianti

3 5 7 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Swimming pool; Suitable for children age 5+; Ask about pets;
 …see more

from £80 / night

£556 / week

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from £80 / night

1 / 20

Villa Fontecaresino 2 - Montegrossi house sleeps 4

Gaiole in Chianti / Montegrossi

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Child friendly ; Ask about pets; Private garden;
Fontecaresino, located in the hills of Chianti, in the heart of Tuscany, with ready access to the culinary, cultural and artistic heritage of this region, is only 4 km from Gaiole in Chianti 10 km from Radda in Chianti, 35 km from Siena, 45 km from Arezzo and 55 km from  …see more

from £73 / night

£941 / week

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from £73 / night

(1) Excellent 

1 / 22

Le Diacce - Montegrossi farmhouse sleeps 10

Gaiole in Chianti / Montegrossi

5 10 5 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min stay
Key info: Nearest beach 100 km; Swimming pool; Child friendly ;
Le Diacce villa, benefits of a total privacy and enjoys splendid sunsets and a beautiful pool. The living room and kitchen open onto spacious terraces fully equipped for outdoor dining and surrounded by lawns, gardens and ancient trees.Ideal for families or a group of f  …see more

from £129 / night

£3419 / week

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from £129 / night

1 / 19

Province of Siena / Gaiole in Chianti

2 5 2 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min stay
Key info: Suitable for children age 5+; Car advised; Air conditioning;
 …see more

from £359 / night

£1283 / week

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from £359 / night

1 / 12

Province of Siena / Gaiole in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Not suitable for children; Car essential; Ask about pets;
 …see more

from £59 / night

£513 - £727 / week

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from £59 / night

1 / 14

Province of Siena / Gaiole in Chianti

1 4 2 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 2 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
 …see more

from £79 / night

£551 / week

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from £79 / night

1 / 48

Province of Siena / Gaiole in Chianti

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Nearest beach 100 km; Swimming pool; Child friendly ;
 …see more

from £90 / night

£624 - £791 / week

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from £90 / night

1 / 24

Ancient castle in the heart of Tuscany, 6 bedrooms - Lecchi castle sleeps 14

Gaiole in Chianti / Lecchi

6 14 7 nights min stay

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
A dive into an ancient culture in the heart of Tuscany, the Chianti Classico.Il Castello Medievale is situated in a medieval hamlet, constructed of white stone, built around 1000AD, surrounded by forests and olive groves, immersed in a magical atmosphere of tranquility.  …see more

from £411 / night

£2872 - £4419 / week

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from £411 / night

1 / 39

Province of Siena / Gaiole in Chianti

3 7 7 nights min stay

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
 …see more

from £114 / night

£795 - £953 / week

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from £114 / night

(11) Very Good 

1 / 24

Villa PetrAlexa, Tuscany cottage in Chianti area - Gaiole in Chianti villa sleeps 7

Province of Siena / Gaiole in Chianti

3 7 7 nights min stay

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min stay
Key info: Nearest beach 110 km; Swimming pool; Child friendly ;
September with Low Season prices instead of Middle Season prices: 1.440 Euro instead of 1.920 Euro! Come to enjoy the typical architecture of Tuscany houses! Villa PetrAlexa is an antic, now renovated barn, with natural stone, original beam ceilings and glass doors wh  …see more

from £176 / night

£1231 - £2052 / week

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from £176 / night

1 / 48

Bed & Breakfast La Cerreta - Gaiole in Chianti b&b sleeps 10

Province of Siena / Gaiole in Chianti

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Ask owner if suitable for children; Ask about pets;
This beautifull restructured 16th century house sits on a hillside and dominates the sorrounding countryside as far as the eye can see. Nestled in the heart of Chianti our B&B is perfectly located for the week-end break, walking or cycling holidays as well as trekking a  …see more

from £60 / night

£419 / week

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from £60 / night

1 / 27

La Pieve Marsina - Gaiole in Chianti villa sleeps 5

Province of Siena / Gaiole in Chianti

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 70 km; Swimming pool; Child friendly ;
In the top of a hill set in the patchwork of vineyards that characterizes the area of Chianti Classico, in the heart of an ancient medieval village, was born a few years ago Pieve Marsina.The structure, made up of nice apartments, has as principal objective to allow our  …see more

from £120 / night

£838 - £1137 / week

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from £120 / night

1 / 25

Podere Scopeto - Gaiole in Chianti farmhouse sleeps 12

Province of Siena / Gaiole in Chianti

6 12 3 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
Podere Scopeto is a former Chianti hill farm on the west-facing slopes of the Montagni di Chianti. The present owners bought it some 15 years ago and restored the farmhouse and a separate self-contained studio for family holidays. It has kept its family feel and charm.  …see more

from £350 / night

£2300 - £2800 / week

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from £350 / night

1 / 15

Pievasciata - 44263005 - Lecchi farmhouse sleeps 5

Gaiole in Chianti / Lecchi

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Swimming pool; Child friendly ; Ask about pets;
Ancient farmhouse with adjoining barn situated on a large and renowned farming estate producing excellent wine and olive oil. This property has been carefully restored and turned into 6 comfortable apartments, all of which offering nice interiors furnished in a rustic s  …see more

from £151 / night

£959 - £1140 / week

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from £151 / night

1 / 12

Pievasciata - 44263003 - Lecchi farmhouse sleeps 2

Gaiole in Chianti / Lecchi

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Child friendly ; Ask about pets;
Ancient farmhouse with adjoining barn situated on a large and renowned farming estate producing excellent wine and olive oil. This property has been carefully restored and turned into 6 comfortable apartments, all of which offering nice interiors furnished in a rustic s  …see more

from £95 / night

£613 - £708 / week

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from £95 / night

(1) Good 

1 / 25

castello in Chianti ginestra - Lecchi apartment sleeps 5

Gaiole in Chianti / Lecchi

2 5 3 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
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. Built around the year 1000 by the noble family of Guidi, today it is an esteemed wine estate with self catering holiday ap  …see more

from £86 / night

£445 - £573 / week

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from £86 / night

(1) Very Good 

1 / 11

Province of Siena / Gaiole in Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Child friendly ; No pets allowed;
 …see more

from £69 / night

£411 - £642 / week

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from £69 / night

(1) Excellent 

1 / 22

Province of Siena / Gaiole in Chianti

6 14 7 nights min stay

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
 …see more

from £245 / night

£1710 - £2736 / week

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from £245 / night

1 / 23

Radda In Chianti - 41968001 - Lecchi farmhouse sleeps 10

Gaiole in Chianti / Lecchi

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Child friendly ; Ask about pets;
The Villa Gallo Nero is a lovely home offering 5 bedrooms and 5 baths and is situated in the village of Casanuova di Ama. The village is comprised of a small cluster of houses surrounded by vineyards of wine and oil-producing farmers. Centered between the medieval towns  …see more

from £289 / night

£1683 - £2115 / week

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from £289 / night

(1) Very Good 

1 / 17

Villa Brolio - Gaiole in Chianti villa sleeps 12

Province of Siena / Gaiole in Chianti

6 12 7 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Nearest beach 125 km; Swimming pool; Child friendly ;
The building of Villa Brolio was originally an old XII century watchtower later transformed into a mill and finally restored to become a villa. The restoration works have been done preserving carefully all the ancient characteristics such as the outside stones, the vau  …see more

from £231 / night

£1616 - £3548 / week

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from £231 / night

(11) Excellent 

1 / 28

Villa LisiDor, luxury Tuscany cottage in Chianti - Gaiole in Chianti villa sleeps 10

Province of Siena / Gaiole in Chianti

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Nearest beach 110 km; Swimming pool; Child friendly ;
* 17-24 September has Low Season price instead of Middle Season price: 3.315 Euro instead of 3.900 Euro! * SPECIAL PRICE for a SHORT BREAK: 3-8 October at 2.000€ VILLA LISIDOR: FULLY RENOVATED WITH ALL NEW AMENITIES. The habitable area is doubled: from 150 square  …see more

from £342 / night

£2834 - £4359 / week

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from £342 / night

(9) Very Good 

1 / 58

Villa Albizi Holidayhome Gaiole in Chianti Tuscany - Montefienali villa sleeps 18

Gaiole in Chianti / Montefienali

7 18 Min stay varies

  • 7 bedrooms
  • Sleeps 18
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
NEW MANAGEMENT from Summer 2015 Villa Albizi Tuscany life and more….for groups of friends or large families Villa Albizi is normally rented on a villa-only weekly basis and are ideal for those seeking independence and privacy. We have created a formula designed to  …see more

from £308 / night

£2137 - £4445 / week

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from £308 / night

1 / 15

Pievasciata - 44263001 - Lecchi farmhouse sleeps 2

Gaiole in Chianti / Lecchi

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Child friendly ; Ask about pets;
Ancient farmhouse with adjoining barn situated on a large and renowned farming estate producing excellent wine and olive oil. This property has been carefully restored and turned into 6 comfortable apartments, all of which offering nice interiors furnished in a rustic s  …see more

from £95 / night

£613 - £708 / week

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from £95 / night

1 / 12

Pievasciata - 44263006 - Lecchi farmhouse sleeps 2

Gaiole in Chianti / Lecchi

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Child friendly ; Ask about pets;
Ancient farmhouse with adjoining barn situated on a large and renowned farming estate producing excellent wine and olive oil. This property has been carefully restored and turned into 6 comfortable apartments, all of which offering nice interiors furnished in a rustic s  …see more

from £91 / night

£574 - £682 / week

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from £91 / night

1 / 14

Pievasciata - 44263002 - Lecchi farmhouse sleeps 4

Gaiole in Chianti / Lecchi

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Child friendly ; Ask about pets;
Ancient farmhouse with adjoining barn situated on a large and renowned farming estate producing excellent wine and olive oil. This property has been carefully restored and turned into 6 comfortable apartments, all of which offering nice interiors furnished in a rustic s  …see more

from £125 / night

£812 - £915 / week

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from £125 / night

1 / 19

Gaiole In Chianti - 27123003 - Gaiole in Chianti farmhouse sleeps 6

Province of Siena / Gaiole in Chianti

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Child friendly ; Ask about pets;
Beautiful stone hamlet recently restored situated in quiet and panoramic location on the Chianti Classico hills offering extensive views over the surrounding vineyards. This charming hamlet comprises 6 nice apartments (and 9 double bedrooms) all of which furnished in a  …see more

from £182 / night

£1142 - £1631 / week

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from £182 / night

1 / 24

Casa Lecchi - Gaiole in Chianti apartment sleeps 4

Province of Siena / Gaiole in Chianti

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Pet friendly;
Casa Lecchi is a spacious two bedroom apartment facing on to the main piazza of Montefiorile which is a small hamlet of 14 villas situated in a quiet position in the heart of the Chianti Classico wine producing area. The hamlet is on a hillside and the houses enjoy st  …see more

from £63 / night

£436 - £958 / week

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from £63 / night

1 / 26

Province of Siena / Gaiole in Chianti

1 2 7 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
 …see more

from £66 / night

£462 - £539 / week

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from £66 / night

1 / 15

Gaiole In Chianti - 27123002 - Gaiole in Chianti farmhouse sleeps 2

Province of Siena / Gaiole in Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Child friendly ; Ask about pets;
Beautiful stone hamlet recently restored situated in quiet and panoramic location on the Chianti Classico hills offering extensive views over the surrounding vineyards. This charming hamlet comprises 6 nice apartments (and 9 double bedrooms) all of which furnished in a  …see more

from £130 / night

£816 - £1142 / week

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from £130 / night

1 / 27

Fontecaresino Property (1 & 2) - Montegrossi house sleeps 14

Gaiole in Chianti / Montegrossi

6 14 7 nights min stay

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Child friendly ; No pets allowed;
2 Villas (1 FONTECARESINO and 2 FONTECARESINO), located in the hills of Chianti, in the heart of Tuscany, with ready access to the culinary, cultural and artistic heritage of this region, is only 4 km from Gaiole in Chianti 10 km from Radda in Chianti, 35 km from Siena,  …see more

from £308 / night

£2906 / week

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from £308 / night

1 / 21

San Sano - 86210001 - Lecchi farmhouse sleeps 8

Gaiole in Chianti / Lecchi

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Child friendly ; Ask about pets;
Independent house with private pool in the Chianti Classico, in an old hamlet of houses surrounded by vineyards, olive groves and woods. The town of Gaiole in Chianti is just 10 km away and the other villages of the Chianti Classico (Radda, Castellina, Greve, etc.) are  …see more

from £213 / night

£1243 - £2072 / week

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from £213 / night

1 / 13

Gaiole In Chianti - 27123007 - Gaiole in Chianti farmhouse sleeps 4

Province of Siena / Gaiole in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Child friendly ; Ask about pets;
Beautiful stone hamlet recently restored situated in quiet and panoramic location on the Chianti Classico hills offering extensive views over the surrounding vineyards. This charming hamlet comprises 6 nice apartments (and 9 double bedrooms) all of which furnished in a  …see more

from £137 / night

£871 - £1196 / week

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from £137 / night

1 / 14

Pievasciata - 44263004 - Lecchi farmhouse sleeps 2

Gaiole in Chianti / Lecchi

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Child friendly ; Ask about pets;
Ancient farmhouse with adjoining barn situated on a large and renowned farming estate producing excellent wine and olive oil. This property has been carefully restored and turned into 6 comfortable apartments, all of which offering nice interiors furnished in a rustic s  …see more

from £91 / night

£574 - £682 / week

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from £91 / night

1 / 20

Badia Coltibuono - 82374003 - Montegrossi castle sleeps 6

Gaiole in Chianti / Montegrossi

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Child friendly ; Pet friendly;
Badia a Coltibuono is the first wine resort in Chianti, opening it's doors to travellers and visitors who want to share a truly unique experience. Here it is possible to encounter the magic of a venue, to observe the slow yet intense rhythm of a 1000 year old abbey and  …see more

from £243 / night

£1554 - £1813 / week

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from £243 / night

1 / 17

Gaiole In Chianti - 27123005 - Gaiole in Chianti farmhouse sleeps 6

Province of Siena / Gaiole in Chianti

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Child friendly ; Ask about pets;
Beautiful stone hamlet recently restored situated in quiet and panoramic location on the Chianti Classico hills offering extensive views over the surrounding vineyards. This charming hamlet comprises 6 nice apartments (and 9 double bedrooms) all of which furnished in a  …see more

from £182 / night

£1142 - £1631 / week

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from £182 / night

1 / 20

Vertine - 125393001 - Lecchi villa sleeps 10

Gaiole in Chianti / Lecchi

5 10 7 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Ask about pets;
Independent villa, surrounded by olive groves and vineyards; the villa is reachable by passing through the historical Hamlet of Vertine. We do not recommend the use of a van and minibus. Villa Vertine is only 2.5 km from Gaiole in Chianti, in the real heart of Chiant  …see more

from £370 / night

£2590 - £6043 / week

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from £370 / night

1 / 24

Badia Coltibuono - 82374004 - Montegrossi castle sleeps 7

Gaiole in Chianti / Montegrossi

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
Key info: Swimming pool; Child friendly ; Pet friendly;
Badia a Coltibuono is the first wine resort in Chianti, opening it's doors to travellers and visitors who want to share a truly unique experience. Here it is possible to encounter the magic of a venue, to observe the slow yet intense rhythm of a 1000 year old abbey and  …see more

from £224 / night

£1426 - £1686 / week

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from £224 / night

Top Destination reviews

A HOLIDAY IN THE HEART OF CHIANTI
Authentic unspoiled Italian charm!

My family and I stayed at this beautiful property and had a relaxed and wonderful holiday. Gaiole in Chianti is a small village totally unspoilt by tourism and the location of this property is ideal if you hire a car and travel to all the surrounding … see more
Villa PetrAlexa, Tuscany cottage in Chianti area
Villa PetrAlexa - excellent leisure facility

This years stay was even better than our stay last year. Despite the fact we arrived late at night due to repeated traffic jams on the motorway because of terrible weather conditions, everything was perfectly prepared. The house was heated up and foo … see more
Perfect, beautifil little place in tuscany

A beautiful place full of happines, were you can stay The time you want for a very very good price ,there's a beautiful view, is very relaxing and you can enjoy The animals and nature … see more

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