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

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30 Holiday homes

Filters applied: Private pool (30)

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

(4) Excellent 

17

Province of Siena / Gaiole in Chianti

2 6 Min stay varies

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

 …see more

from £104 / night

£518 - £1121 / week

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from £104 / night

(6) Very Good 

43

Chianti house, Florence, Jacuzzi, Tuscany up to 6p - Montefienali house sleeps 6

Gaiole in Chianti / Montefienali

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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

(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

18

Villa Fontecaresino 1 - Montegrossi villa sleeps 9

Gaiole in Chianti / Montegrossi

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets
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) 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

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

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

100

Gaiole - Gaiole in Chianti villa sleeps 8

Province of Siena / Gaiole in Chianti

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
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 £397 / night

£2759 - £3880 / week

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from £397 / night

(1) Excellent 

12

Il Mulinaccio - Gaiole in Chianti farmhouse sleeps 16

Province of Siena / Gaiole in Chianti

5 16 Min stay varies

  • 5 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
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 £432 / night

£3018 - £4656 / week

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from £432 / 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

(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

(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

(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

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

(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

100

Itaca - Gaiole in Chianti villa sleeps 10

Province of Siena / Gaiole in Chianti

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • 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

Pricing unknown

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Pricing unknown

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
  • 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 £438 / night

£2633 - £3950 / week

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from £438 / night

20

Vertine - 125393001 - Lecchi villa sleeps 10

Gaiole in Chianti / Lecchi

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • 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 £412 / night

£2882 - £6811 / week

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from £412 / night

21

San Sano - 86210001 - Lecchi farmhouse sleeps 8

Gaiole in Chianti / Lecchi

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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 £216 / night

£1258 - £2096 / week

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from £216 / night

(1) Excellent 

36

Province of Siena / Gaiole in Chianti

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • 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

32

Province of Siena / Gaiole in Chianti

7 14 3 nights min

  • 7 bedrooms
  • Sleeps 14
  • 3 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Ask about pets

 …see more

from £1983 / night

£11207 / week

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from £1983 / night

22

Province of Siena / Gaiole in Chianti

7 13 3 nights min

  • 7 bedrooms
  • Sleeps 13
  • 3 nights min
  • Swimming pool

 …see more

from £1207 / night

£8449 / week

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from £1207 / night

12

Province of Siena / Gaiole in Chianti

5 18 7 nights min

  • 5 bedrooms
  • Sleeps 18
  • 7 nights min
  • Swimming pool
  • Car not necessary
  • Ask about pets

 …see more

from £432 / night

£3018 - £4311 / week

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from £432 / night

(4) Very Good 

20

Province of Siena / Gaiole in Chianti

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Ask about pets

 …see more

from £222 / night

£1552 - £2586 / week

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from £222 / night

45

Province of Siena / Gaiole in Chianti

11 22 3 nights min

  • 11 bedrooms
  • Sleeps 22
  • 3 nights min
  • 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 

30

Province of Siena / Gaiole in Chianti

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

 …see more

from £385 / night

£2691 - £3588 / week

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from £385 / night

21

Province of Siena / Gaiole in Chianti

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

 …see more

from £394 / night

£2758 - £3881 / week

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from £394 / night

21

Province of Siena / Gaiole in Chianti

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

 …see more

from £148 / night

£1032 - £1726 / week

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from £148 / night

18

Province of Siena / Gaiole in Chianti

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children

 …see more

from £358 / night

£2500 - £3923 / week

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from £358 / 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 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
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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