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61 Holiday homes

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

(32) Excellent 

1 / 24

LUXURY APARTMENT WITH PRIVATE GARDEN & VIEWS - Gaiole in Chianti apartment sleeps 2

Province of Siena / Gaiole in Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Not suitable for children; Car advised;
Ideal for couples looking for a relaxing romantic holiday, we provide everything you need in our fully equipped and tastefully decorated apartment, see our reviews. FREE WI-FI Walking distance to local restaurants. The large private garden for your exclusive use overlo  …see more

from £60 / night

£420 - £630 / week

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from £60 / night

(6) Excellent 

1 / 26

Just 5 minutes from the centre of the Gaiolie, wonderful apartment with pool and breathtaking terrace, sleeps 6 - Gaiole in Chianti apartment sleeps 6

Province of Siena / Gaiole in Chianti

2 6 7 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
The apartment is just 5 minutes walk from the center of Gaiole, where you will find all the services you need. Like restaurants, bars, wineshops, banks, food shop, hairdressers etc.Gaiole is one of several traditional Chianti villages in the region. Others worth visitin  …see more

from £85 / night

£590 - £936 / week

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from £85 / night

(14) Excellent 

1 / 22

Casacorvo Minore *Late Booking Discounts* - Gaiole in Chianti apartment sleeps 4

Province of Siena / Gaiole in Chianti

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 80 km; Swimming pool; Child friendly ;
Set in the Chianti Hills just 30 mins from Siena is Borgo di Gaiole, situated on the edge of Gaiole in Chianti, one of the historic 'Chianti League' townships.The Borgo comprises the best of old and new. Built in traditional Tuscan architectural style with sol  …see more

from £85 / night

£525 - £725 / week

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from £85 / night

(1) Excellent 

1 / 24

Casacorvo Grande *Group Discounts* - Gaiole in Chianti apartment sleeps 10

Province of Siena / Gaiole in Chianti

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Nearest beach 80 km; Swimming pool; Child friendly ;
Casacorvo Grande is a townhouse that sits on the edge of the unique development of Borgo di Gaiole overlooking the Chianti Hills. It is a perfect location for a holiday. The accommodation comprises of two apartments, one 1bed/1bath and one 3bed/2bath, that can be combi  …see more

from £250 / night

£1600 - £2100 / week

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from £250 / night

1 / 17

Galassia 22 - Gaiole in Chianti apartment sleeps 4

Province of Siena / Gaiole in Chianti

2 4 6 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
The natural extension of the existing village of Gaiole in Chianti. The 'village-inside-the village' concept that is unique of its kind. The village concept that becomes an integral part of Gaiole in Chianti. Details and the architecture are carefully planned.  …see more

from £113 / night

£682 / week

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from £113 / 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 £60 / night

£518 - £733 / week

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from £60 / night

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

£432 / week

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from £62 / 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 £363 / night

£1294 / week

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from £363 / night

(12) Excellent 

1 / 23

Casacorvo Maggiore: *Eroica Weekend Available* - Gaiole in Chianti apartment sleeps 8

Province of Siena / Gaiole in Chianti

3 8 4 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
A spacious well furnished three double bedroom, two bathroom apartment with an eight seating dining room and large lounge, just a few minutes stroll from the restaurants, cafes and wide range of services provided by Gaiole village. Outside, enjoy a game of boules in the  …see more

from £165 / night

£1000 - £1500 / week

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from £165 / night

(6) Excellent 

1 / 20

2 bedroom apartment in traditional Tuscan complex in village of Gaiole, sleeps 6, shared pool - Gaiole in Chianti apartment sleeps 6

Province of Siena / Gaiole in Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
A fabulous place to relax, this apartment is at the edge of the Borgo furthest from the road. Designed in a traditional style incorporating a range of modern comforts and facilities, the apartment is the best of both worlds. Stone tiled floors with chestnut beams overhe  …see more

from £70 / night

£500 - £700 / week

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from £70 / night

1 / 14

Province of Siena / Gaiole in Chianti

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
 …see more

from £80 / night

£556 / week

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from £80 / 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 £190 / night

£1294 - £1983 / week

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from £190 / night

1 / 28

Appartamento Gaiole 13 - Gaiole in Chianti apartment 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 ; Air conditioning;
Appartamento Gaiole 13 is a wonderful apartment in the heart of Chianti. This area is famous all over the world for its typical products and its superb wines. The apartment is located in Borgo di Gaiole, an ancient Borgo recently renovated that enjoys a magnificent view  …see more

from £61 / night

£423 - £513 / week

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from £61 / night

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 / 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 / 21

Gaiole in Chianti / Lecchi

1 5 1 night min stay

  • 1 bedroom
  • Sleeps 5
  • 1 night min stay
Key info: Child friendly ; No pets allowed;
 …see more

from £61 / night

£388 - £660 / week

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from £61 / night

(5) Very Good 

1 / 23

Spacious Chianti apartment with pool access, terrace and outdoor dining area - Gaiole in Chianti apartment sleeps 6

Province of Siena / Gaiole in Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 0 km; Swimming pool; Child friendly ;
This is a spacious fully furnished 2 bedroom apartment in Borgo di Gaiole in the village of Gaiole in Chianti. Gaiole is in the heart of the Chianti Classico Region of Tuscany.The property has stunning views over the village and to the vineyards overlooking the village  …see more

from £100 / night

£600 - £850 / week

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from £100 / 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 / 13

Casa Ciaccheri - Gaiole in Chianti apartment sleeps 4

Province of Siena / Gaiole in Chianti

2 4 3 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
The house is located in the heart of the Chianti Classico, inside the town of Gaiole in Chianti (all kinds of shops). The apartment is on the ground floor and is part of a building where the owners reside.Outside a portion of an equipped courtyard is available for the e  …see more

from £69 / night

£302 / week

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from £69 / night

1 / 19

Gaiole in Chianti / Lecchi

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Suitable for children age 5+; Ask about pets;
 …see more

from £63 / night

£440 - £897 / week

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from £63 / 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 / 33

Appartamento Gaiole 40 - Gaiole in Chianti apartment 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 ; Air conditioning;
Appartamento Gaiole 40 is a wonderful apartment in the heart of Chianti. This area is famous all over the world for its typical products and its superb wines. The apartment is located in Borgo di Gaiole, an ancient Borgo recently renovated that enjoys a magnificent view  …see more

from £92 / night

£640 - £737 / week

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from £92 / 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 £115 / night

£802 - £1194 / week

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from £115 / 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 / 18

Province of Siena / Gaiole in Chianti

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Child friendly ; Car advised; Ask about pets;
 …see more

from £48 / night

£311 - £518 / week

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from £48 / 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 / 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 / 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

(3) Very Good 

1 / 24

Villa Gaiole - Gaiole in Chianti villa sleeps 8

Province of Siena / Gaiole in Chianti

3 8 7 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Nearest beach 107 km; Swimming pool; Child friendly ;
Beautiful Family Villa in Borgo di Gaiole, surrounded by the Chianti hills covered in vineyards and olive groves, just a 100 meters walk from the quiet village of Gaiole in Chianti, a typical Tuscan hamlet with restaurants, shops and amenities, an ideally located betwee  …see more

from £84 / night

£582 - £1394 / week

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from £84 / 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 £247 / night

£1725 - £2759 / week

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from £247 / 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

(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 ;
Safe 380 Euro for booking from 10-17 and 17-24 September! 20% discounted rate: 1.536 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  …see more

from £176 / night

£1231 - £2052 / week

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from £176 / night

(2) Excellent 

1 / 45

Province of Siena / Gaiole in Chianti

3 6 7 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 75 km; Swimming pool; Child friendly ;
 …see more

from £198 / night

£1380 - £1897 / week

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from £198 / 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 £61 / night

£423 / week

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from £61 / 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 ;
Safe 585 Euro for booking from 10-17 and 17-24 September: 15% OFF ! 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 meters to 300 square meters. On GROUN  …see more

from £342 / night

£2834 - £4359 / week

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from £342 / night

(1) Good 

1 / 23

castello in Chianti conte - 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; Suitable for children age 5+; 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 £87 / night

£449 - £595 / week

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from £87 / 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

(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

£414 - £647 / week

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from £69 / night

1 / 16

Holidayhome Casa Isa, Borgo San Vincenti,Tuscany - Gaiole in Chianti house sleeps 5

Province of Siena / Gaiole in Chianti

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
A dream home set in the heart of Chianti. Relax, landscapes, nature, good food, wine ... for a unique holiday! Borgo San Vincenti is composed not only from Casa Isabella: Casa Guia( 4guests);Casa Eolo( 4 guests); Casa Monte Cristo (4 guests) , Casa Maestrale (8 guests)  …see more

from £113 / night

£785 - £1268 / week

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from £113 / night

Top Destination reviews

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
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

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