Gaiole in Chianti apartment or villa with a private pool area | Holiday Lettings

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31 Holiday homes

Filters applied: Private pool (31)

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

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) Excellent 

1 / 12

Il Mulinaccio - Gaiole in Chianti farmhouse sleeps 18

Province of Siena / Gaiole in Chianti

5 18 Min stay varies

  • 5 bedrooms
  • Sleeps 18
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
On entering the property, guests will find a welcoming living area, furnished with sofas around a traditional, focal fireplace. The kitchen is adjacent to this room. The kitchen is a typical Tuscan kitchen, well-equipped with plenty of pots and pans for those that enjoy  …see more

from £477 / night

£3334 - £4616 / week

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from £477 / night

(1) Excellent 

1 / 17

Province of Siena / Gaiole in Chianti

2 6 Min stay varies

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

from £104 / night

£518 - £1121 / week

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from £104 / 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

(4) Very Good 

1 / 43

Chianti house, Florence, Siena, Jacuzzi, Tuscany

Gaiole in Chianti / Montefienali

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Child friendly ; Pet friendly;
Recently renovated, is located in a scenic hillside location in a picturesque village nestled in the heart of Chianti, strategic point to reach in a short time two beautiful cities such as Siena and Florence. Moreover, you can go trekking in the beautiful trails and na  …see more

from £47 / night

£269 - £604 / week

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from £47 / night

1 / 24

Ancient castle in the heart of Tuscany, 6 bedrooms

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 £414 / night

£2897 - £4457 / week

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from £414 / night

1 / 100

Gaiole - Gaiole in Chianti villa sleeps 8

Province of Siena / Gaiole in Chianti

4 8 3 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; No pets allowed;
ExteriorsVilla Gaiole is an authentic Sienese-style retreat with total privacy and comfort. Located in a natural environment of absolute privacy Villa Gaiole has recently  been remodeled and elegantly furnished. All rooms and bedrooms are air conditioned to allow a  …see more

from £428 / night

£2565 - £3847 / week

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from £428 / 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) 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

(11) Very Good 

1 / 24

Villa PetrAlexa, Tuscany cottage in Chianti area

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 £178 / night

£1242 - £2069 / week

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from £178 / 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

(11) Excellent 

1 / 28

Villa LisiDor, luxury Tuscany cottage in Chianti

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 £345 / night

£2858 - £4397 / week

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from £345 / night

1 / 18

Villa Fontecaresino 1 - Montegrossi villa sleeps 9

Gaiole in Chianti / Montegrossi

4 9 7 nights min stay

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min stay
Key info: Swimming pool; Suitable for children age 5+; Car essential;
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, 35 km from Siena, 45 km from Arezzo and 55 km from Florence. Our close proximi  …see more

from £111 / night

£776 - £1983 / week

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from £111 / 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 £233 / night

£1630 - £3578 / week

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from £233 / night

1 / 100

Itaca - Gaiole in Chianti villa sleeps 10

Province of Siena / Gaiole in Chianti

5 10 7 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; 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 £1160 / night

£8120 / week

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from £1160 / night

1 / 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
Key info: 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 £432 / night

£2603 - £3905 / week

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from £432 / night

(9) Very Good 

1 / 58

Villa Albizi Holidayhome Gaiole in Chianti Tuscany

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 £311 / night

£2156 - £5087 / week

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from £311 / 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 £374 / night

£2613 - £6095 / week

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from £374 / night

1 / 20

Gaiole In Chianti - 70247001 - Gaiole in Chianti farmhouse sleeps 8

Province of Siena / Gaiole in Chianti

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Child friendly ; Pet friendly;
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

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 £215 / night

£1254 - £2090 / week

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from £215 / night

1 / 32

Province of Siena / Gaiole in Chianti

7 14 3 nights min stay

  • 7 bedrooms
  • Sleeps 14
  • 3 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Car essential;
 …see more

from £1983 / night

£11207 / week

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from £1983 / night

1 / 22

Province of Siena / Gaiole in Chianti

7 13 3 nights min stay

  • 7 bedrooms
  • Sleeps 13
  • 3 nights min stay
Key info: Swimming pool; Not suitable for children; Car essential;
 …see more

from £1207 / night

£8449 / week

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from £1207 / night

1 / 12

Province of Siena / Gaiole in Chianti

5 18 7 nights min stay

  • 5 bedrooms
  • Sleeps 18
  • 7 nights min stay
Key info: Swimming pool; Not suitable for children; Car not necessary;
 …see more

from £481 / night

£3363 - £4656 / week

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from £481 / night

(4) Very Good 

1 / 20

Province of Siena / Gaiole in Chianti

2 7 7 nights min stay

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Ask about pets;
 …see more

from £219 / night

£1529 - £2547 / week

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from £219 / night

1 / 102

Province of Siena / Gaiole in Chianti

7 13 Min stay varies

  • 7 bedrooms
  • Sleeps 13
  • Min stay varies
Key info: Swimming pool; Ask owner if suitable for children; Ask about pets;
 …see more

from £1035 / night

£7242 - £8449 / week

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from £1035 / night

1 / 45

Province of Siena / Gaiole in Chianti

11 22 3 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 £503 / night

£3519 - £5486 / week

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from £503 / night

(1) Excellent 

1 / 36

Province of Siena / Gaiole in Chianti

4 8 7 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Air conditioning;
 …see more

from £370 / night

£2587 - £3880 / week

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from £370 / night

1 / 18

Province of Siena / Gaiole in Chianti

3 6 7 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; No pets allowed;
 …see more

from £358 / night

£2500 - £3923 / week

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from £358 / night

1 / 21

Province of Siena / Gaiole in Chianti

4 8 7 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 £394 / night

£2758 - £3881 / week

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from £394 / night

1 / 21

Province of Siena / Gaiole in Chianti

3 6 7 nights min stay

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

from £148 / night

£1032 - £1726 / week

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from £148 / night

1 / 30

Province of Siena / Gaiole in Chianti

7 14 7 nights min stay

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Nearest beach 100 km; Swimming pool; Child friendly ;
 …see more

from £382 / night

£2671 - £3561 / week

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from £382 / 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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