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79 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 

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
  • Swimming pool
  • Air conditioning
  • Private garden
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 - £665 / week

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from £60 / night

(13) Excellent 

23

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

Province of Siena / Gaiole in Chianti

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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

17

Galassia 22 - Gaiole in Chianti apartment sleeps 4

Province of Siena / Gaiole in Chianti

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min
  • 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

(6) Excellent 

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 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 / week

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from £70 / night

(15) Excellent 

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
  • 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

(5) Very Good 

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
  • 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

39

Province of Siena / Gaiole in Chianti

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from £115 / night

£802 - £962 / week

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from £115 / night

15

Province of Siena / Gaiole in Chianti

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £62 / night

£432 / week

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from £62 / night

(11) Excellent 

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
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
* 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 GROUND FLOOR, which is at garden level, is a large sitting room with Tv  …see more

from £345 / night

£2858 - £4397 / week

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from £345 / night

(6) Excellent 

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

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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

£595 - £944 / week

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from £85 / night

18

Province of Siena / Gaiole in Chianti

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden

 …see more

from £48 / night

£311 - £518 / week

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from £48 / night

12

Province of Siena / Gaiole in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about pets

 …see more

from £60 / night

£518 - £733 / week

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from £60 / night

(1) Very Good 

11

Province of Siena / Gaiole in Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly

 …see more

from £69 / night

£414 - £647 / week

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from £69 / night

(1) Excellent 

22

Province of Siena / Gaiole in Chianti

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £247 / night

£1725 - £2759 / week

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from £247 / night

(1) Good 

25

castello in Chianti ginestra - Lecchi apartment sleeps 5

Gaiole in Chianti / Lecchi

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
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 - £578 / week

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from £87 / night

(1) Good 

23

castello in Chianti conte - Lecchi apartment sleeps 5

Gaiole in Chianti / Lecchi

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Pet friendly
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 - £585 / week

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from £87 / night

24

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

Gaiole in Chianti / Lecchi

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • 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 £414 / night

£2897 - £3345 / week

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from £414 / night

25

Podere Scopeto - Gaiole in Chianti farmhouse sleeps 12

Province of Siena / Gaiole in Chianti

6 12 3 nights min

  • 6 bedrooms
  • Sleeps 12
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
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 - £2500 / week

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from £350 / night

(1) Good 

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
  • 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 - £981 / week

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from £92 / night

(1) Excellent 

22

Le Diacce - Montegrossi farmhouse sleeps 10

Gaiole in Chianti / Montegrossi

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • 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 £130 / night

£3449 / week

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from £130 / night

19

Province of Siena / Gaiole in Chianti

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Ask about pets

 …see more

from £363 / night

£1294 / week

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from £363 / night

100

Gaiole In Chianti 70247 - Gaiole in Chianti villa sleeps 8

Province of Siena / Gaiole in Chianti

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful independent villa with private pool situated in the heart of the Chianti region, a short distance away from the town of Gaiole in Chianti. This villa, nestling deep in quiet position among vineyards and woods, offers full privacy and is the ideal place for tho  …see more

from £436 / night

£2625 - £3938 / week

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from £436 / night

13

Casa Ciaccheri - Gaiole in Chianti apartment sleeps 4

Province of Siena / Gaiole in Chianti

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • 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 £35 / night

£302 / week

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from £35 / night

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
  • 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 £104 / night

£815 - £1147 / week

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from £104 / night

(3) Very Good 

24

Villa Gaiole - Gaiole in Chianti villa sleeps 8

Province of Siena / Gaiole in Chianti

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • 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

£587 - £1406 / week

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from £84 / night

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
  • 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

14

Province of Siena / Gaiole in Chianti

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £80 / night

£556 / week

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from £80 / night

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
  • Swimming pool
  • Child friendly
  • Ask about pets
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 - £1121 / week

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from £113 / night

19

Gaiole in Chianti / Lecchi

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets

 …see more

from £63 / night

£440 - £664 / week

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from £63 / night

21

Gaiole in Chianti / Lecchi

1 5 1 night min

  • 1 bedroom
  • Sleeps 5
  • 1 night min
  • Child friendly

 …see more

from £61 / night

£388 - £660 / week

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from £61 / night

(2) Excellent 

45

Province of Siena / Gaiole in Chianti

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly

 …see more

from £197 / night

£1380 - £1897 / week

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from £197 / night

(11) Very Good 

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

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
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 which offer a pleasing mix in a comfortable, spacious environment spread over two floors with a wide at  …see more

from £178 / night

£1242 - £2069 / week

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from £178 / night

(1) Very Good 

17

Villa Brolio - Gaiole in Chianti villa sleeps 12

Province of Siena / Gaiole in Chianti

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • 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 £233 / night

£1630 - £3578 / week

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from £233 / night

(1) Excellent 

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
  • 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

15

Province of Siena / Gaiole in Chianti

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £190 / night

£1294 - £1638 / week

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from £190 / night

24

Casa Lecchi - Gaiole in Chianti apartment sleeps 4

Province of Siena / Gaiole in Chianti

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • 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

£440 - £966 / week

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from £63 / night

(10) Very Good 

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
  • Swimming pool
  • Child friendly
  • Air conditioning
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 £311 / night

£2156 - £4483 / week

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from £311 / night

15

Pievasciata - 44263001 - Lecchi farmhouse sleeps 2

Gaiole in Chianti / Lecchi

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • 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 £97 / night

£620 - £716 / week

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from £97 / night

12

Pievasciata - 44263006 - Lecchi farmhouse sleeps 2

Gaiole in Chianti / Lecchi

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • 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 £92 / night

£582 - £690 / week

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from £92 / night

27

Appartamento Gaiole 15 - Gaiole in Chianti apartment sleeps 2

Province of Siena / Gaiole in Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Appartamento Gaiole 15 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 - £608 / week

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from £61 / 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
Villa Podere Earthly
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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