Air conditioned apartments and villas to rent in Gaiole in Chianti

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  • Italy
  • Tuscany
  • Province of Siena
  • Gaiole in Chianti

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  • Lecchi (2)
  • Montefienali (1)

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54 Holiday homes

Filters applied: Air conditioning (54)

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

(32) Excellent 

1 / 24

1 bedroom luxury apartment with Private Garden, Gaiole in Chianti

Tuscany / Province of Siena / Gaiole in Chianti

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Not suitable for children; Car advised;
Surrounded by the famous rolling hills covered with vineyards and olive groves, which give the name to some of the most prestigious Chianti wine is Borgo di Gaiole. The apartment is on the ground floor as you enter the Borgo, private and self contained around 60sq meter  …see more

from £90 / night

£630 - £770 / week

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from £90 / night

(5) Very Good 

1 / 23

Spacious Chianti apartment with pool access, terrace and outdoor dining area

Tuscany / Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 0 km; Swimming pool; Great for children of all ages ;
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

(14) Excellent 

1 / 22

Casacorvo Minore *Late Booking Discounts*

Tuscany / Province of Siena / Gaiole in Chianti

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 80 km; Swimming pool; Great for children of all ages ;
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 / 65

Tuscany / Province of Siena / Gaiole in Chianti

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £351 / night

£2455 - £3617 / week

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from £351 / night

(11) Excellent 

1 / 27

Villa LisiDor, luxury Tuscany cottage in Chianti

Tuscany / Province of Siena / Gaiole in Chianti

4 bedroomsSleeps 107 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Nearest beach 110 km; Swimming pool; Great for children of all ages ;
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 Sat area, a dining room in front of the pool, a professional  …see more

from £395 / night

£2763 - £4250 / week

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from £395 / night

1 / 24

Casa Chianti - Gaiole in Chianti apartment sleeps 3

Tuscany / Province of Siena / Gaiole in Chianti

1 bedroomSleeps 37 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 7 nights min stay
Key info: Nearest beach 105 km; Swimming pool; Great for children of all ages ;
A cosy and lovingly furnished 1 bedroom apartment located in the spectacular Borgo di Gaiole, a popular hamlet just a short walk from the centre of the renown Gaiole in Chianti, right in the heart of the Chianti region, and only 20 minutes away from the wonderful SienaT  …see more

from £43 / night

£300 - £517 / week

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from £43 / night

1 / 100

Gaiole In Chianti 70247 - Gaiole in Chianti villa sleeps 8

Tuscany / Province of Siena / Gaiole in Chianti

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; 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 £421 / night

£2538 - £3807 / week

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from £421 / night

1 / 33

Appartamento Gaiole 40 - Gaiole in Chianti apartment sleeps 4

Tuscany / Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; 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 £89 / night

£619 - £945 / week

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from £89 / night

(6) Excellent 

1 / 26

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

Tuscany / Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; 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 £83 / night

£575 - £913 / week

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from £83 / night

(1) Good 

1 / 10

H 9 - Gaiole in Chianti apartment sleeps 5

Tuscany / Province of Siena / Gaiole in Chianti

3 bedroomsSleeps 51 night min stay

  • 3 bedrooms
  • Sleeps 5
  • 1 night min stay
Key info: Swimming pool; Great for children of all ages ; 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 £84 / night

£375 / week

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from £84 / night

1 / 20

Tuscany / Province of Siena / Gaiole in Chianti

1 bedroomSleeps 23 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Swimming pool; Suitable for children age 5+; Air conditioning;
 …see more

from £90 / night

£625 - £1045 / week

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from £90 / night

1 / 22

Casa Borgo - Gaiole in Chianti apartment sleeps 4

Tuscany / Province of Siena / Gaiole in Chianti

1 bedroomSleeps 47 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 7 nights min stay
Key info: Nearest beach 105 km; Swimming pool; Great for children of all ages ;
This beautiful and tastefully furnished 1 bedroom apartment is located in the spectacular Borgo di Gaiole, a popular hamlet just a short walk from the centre of the renown Gaiole in Chianti, right in the heart of the Chianti region, and only 20 minutes away from the won  …see more

from £43 / night

£300 - £575 / week

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from £43 / night

1 / 24

Casa Corte - Gaiole in Chianti apartment sleeps 6

Tuscany / Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 105 km; Swimming pool; Suitable for children age 5+;
This beautiful and tastefully furnished 2 bedroom apartment is located in the spectacular Borgo di Gaiole, a popular hamlet just a short walk from the centre of the renown Gaiole in Chianti, right in the heart of the Chianti region, and only 20 minutes away from the won  …see more

from £47 / night

£325 - £692 / week

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from £47 / night

1 / 20

Tuscany / Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 43 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Swimming pool; Suitable for children age 5+; Air conditioning;
 …see more

from £107 / night

£747 - £1103 / week

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from £107 / night

(12) Excellent 

1 / 23

Casacorvo Maggiore: *Eroica Weekend Available*

Tuscany / Province of Siena / Gaiole in Chianti

3 bedroomsSleeps 84 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min stay
Key info: Swimming pool; Great for children of all ages ; 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

(3) Very Good 

1 / 24

Villa Gaiole - Gaiole in Chianti villa sleeps 8

Tuscany / Province of Siena / Gaiole in Chianti

3 bedroomsSleeps 87 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Nearest beach 107 km; Swimming pool; Great for children of all ages ;
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 £81 / night

£567 - £1359 / week

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from £81 / night

1 / 17

Galassia 22 - Gaiole in Chianti apartment sleeps 4

Tuscany / Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 46 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min stay
Key info: Swimming pool; Great for children of all ages ; 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 £109 / night

£659 / week

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from £109 / night

(1) Excellent 

1 / 20

Casa Giardino - Gaiole in Chianti apartment sleeps 3

Tuscany / Province of Siena / Gaiole in Chianti

1 bedroomSleeps 37 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 7 nights min stay
Key info: Nearest beach 105 km; Swimming pool; Great for children of all ages ;
A cosy and lovingly furnished 1 bedroom apartment located in the spectacular Borgo di Gaiole, a popular hamlet just a short walk from the centre of the renown Gaiole in Chianti, right in the heart of the Chianti region, and only 20 minutes away from the wonderful SienaT  …see more

from £43 / night

£300 - £517 / week

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from £43 / night

1 / 9

Gaiole Suites 8 - Gaiole in Chianti apartment sleeps 4

Tuscany / Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
Gaiole Suites is a compound of terraced houses, just renewed, situated 500m away from Gaiole in Chianti center, in a quiet zone, silent and not familiar with rush hour since the traffic is very little. It is surrounded by the green Tuscany hills. The beautiful apartmen  …see more

from £40 / night

£280 - £455 / week

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from £40 / night

1 / 18

galassia 18 - Gaiole in Chianti apartment sleeps 3

Tuscany / Province of Siena / Gaiole in Chianti

1 bedroomSleeps 32 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 2 nights min stay
Key info: Nearest beach 120 km; Swimming pool; Not suitable for children;
appartamento, 2 - 3 persone, 2 vano/vani, 1 camera/e da letto, 1 bagno/bagni, ca. 44 m², 1 piano/piani, alloggio al piano terra. Accesso all'alloggio indipendente.TerrenoPorzione privata del terreno, giardino, lastre.Parcheggio: 1 x posto macchina in garage sotter  …see more

from £66 / night

£334 / week

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from £66 / night

1 / 24

Ancient castle in the heart of Tuscany, 6 bedrooms

Tuscany / Province of Siena / Gaiole in Chianti / Lecchi

6 bedroomsSleeps 147 nights min stay

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; 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 £400 / night

£2800 - £4309 / week

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from £400 / night

1 / 45

Tuscany / Province of Siena / Gaiole in Chianti

11 bedroomsSleeps 223 nights min stay

  • 11 bedrooms
  • Sleeps 22
  • 3 nights min stay
Key info: Swimming pool; Suitable for children age 5+; Air conditioning;
 …see more

from £486 / night

£3401 - £5303 / week

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from £486 / night

1 / 8

Gaiole Suites 4 - Gaiole in Chianti apartment sleeps 6

Tuscany / Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
Gaiole Suites is a compound of terraced houses, just renewed, situated 500m away from Gaiole in Chianti center, in a quiet zone, silent and not familiar with rush hour since the traffic is very little. It is surrounded by the green Tuscany hills. The beautiful apartmen  …see more

from £42 / night

£292 - £578 / week

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from £42 / night

1 / 9

Gaiole Suites 1 - Gaiole in Chianti apartment sleeps 6

Tuscany / Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
Borgo di Gaiole, is an ancient town in the heart of Chianti hills. This area is famous all over the world for the typical products and therefore known destination for wine tourism. Here, also, there are all finds of shops and restaurants. Siena, the wonderful city that  …see more

from £42 / night

£292 - £578 / week

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from £42 / night

1 / 28

Appartamento Gaiole 13 - Gaiole in Chianti apartment sleeps 2

Tuscany / Province of Siena / Gaiole in Chianti

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; 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 £59 / night

£409 - £584 / week

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from £59 / night

(14) Excellent 

1 / 13

Tuscany / Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Ask owner if suitable for children; Air conditioning;
 …see more

from £209 / night

£500 - £913 / week

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from £209 / night

1 / 100

Itaca - Gaiole in Chianti villa sleeps 10

Tuscany / Province of Siena / Gaiole in Chianti

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
ExteriorsThis exclusive and luxurious villa in Chianti is a very short distance away from other Tuscan cities, such as Florence and Siena. Chianti has always been very famous for its exquisite wine. But apart from that, it holds many more experiences, ruled by  …see more

from £1131 / night

£7917 / week

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from £1131 / night

(9) Very Good 

1 / 58

Villa Albizi Holidayhome Gaiole in Chianti Tuscany

Tuscany / Province of Siena / Gaiole in Chianti / Montefienali

7 bedroomsSleeps 18Min stay varies

  • 7 bedrooms
  • Sleeps 18
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; 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 £300 / night

£2084 - £4917 / week

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from £300 / night

(6) Excellent 

1 / 20

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

Tuscany / Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; 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 / 16

Il Borghetto, Gaiole-in-Chianti - Lecchi b&b sleeps 2

Tuscany / Province of Siena / Gaiole in Chianti / Lecchi

1 bedroomSleeps 21 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Nearest beach 95 km; Swimming pool; Not suitable for children;
Adjacent apartment with terra-cotta floors and furnished with a double Chianti iron bed (subsequently with a madonna picture above), a large armadio and an en suite bathroom. Through French doors the room leads to a 55 square meter terrace with an antique iron sofa, a f  …see more

from £92 / night

£500 / week

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from £92 / night

1 / 9

Gaiole Suites 9 - Gaiole in Chianti apartment sleeps 6

Tuscany / Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
Gaiole Suites is a compound of terraced houses, just renewed, situated 500m away from Gaiole in Chianti center, in a quiet zone, silent and not familiar with rush hour since the traffic is very little. It is surrounded by the green Tuscany hills. The beautiful apartmen  …see more

from £45 / night

£310 - £514 / week

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from £45 / night

1 / 10

Gaiole suites 2 - Gaiole in Chianti apartment sleeps 6

Tuscany / Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
Gaiole Suites is a compound of terraced houses, just renewed, situated 500m away from Gaiole in Chianti center, in a quiet zone, silent and not familiar with rush hour since the traffic is very little. It is surrounded by the green Tuscany hills. The beautiful apartmen  …see more

from £42 / night

£292 - £578 / week

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from £42 / night

1 / 13

Casa Ciaccheri - Gaiole in Chianti apartment sleeps 4

Tuscany / Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 43 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; 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 £67 / night

£292 / week

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from £67 / night

1 / 9

Tuscany / Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 63 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £70 / night

£500 / week

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from £70 / night

(1) Excellent 

1 / 24

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

Tuscany / Province of Siena / Gaiole in Chianti

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Nearest beach 80 km; Swimming pool; Great for children of all ages ;
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 / 16

Galassia H - Gaiole in Chianti house sleeps 5

Tuscany / Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 51 night min stay

  • 2 bedrooms
  • Sleeps 5
  • 1 night min stay
Key info: Swimming pool; Not suitable for children; 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 £84 / night

£417 / week

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from £84 / night

1 / 19

Tuscany / Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 52 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 £350 / night

£1250 / week

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from £350 / night

1 / 21

Tuscany / Province of Siena / Gaiole in Chianti

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Suitable for children age 5+; Air conditioning;
 …see more

from £381 / night

£2666 - £3751 / week

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from £381 / night

1 / 20

Tuscany / Province of Siena / Gaiole in Chianti

1 bedroomSleeps 23 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Swimming pool; Suitable for children age 5+; Air conditioning;
 …see more

from £90 / night

£625 - £1045 / week

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from £90 / night

1 / 20

Tuscany / Province of Siena / Gaiole in Chianti

3 bedroomsSleeps 63 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Swimming pool; Suitable for children age 5+; Air conditioning;
 …see more

from £155 / night

£1080 - £1628 / week

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from £155 / 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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