Villas in Gaiole in Chianti: Rent luxury villas in Gaiole in Chianti

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33 Holiday homes

Filters applied: Villa (33)

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

(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

(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

(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

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

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

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

(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

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

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

24

Province of Siena / Gaiole in Chianti

7 13 7 nights min

  • 7 bedrooms
  • Sleeps 13
  • 7 nights min
  • Suitable for children age 5+

 …see more

from £670 / night

£4685 - £7547 / week

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from £670 / night

(2) Excellent 

27

Province of Siena / Gaiole in Chianti

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Pet friendly

 …see more

from £111 / night

£776 - £1147 / week

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from £111 / night

29

Province of Siena / Gaiole in Chianti

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Suitable for children age 5+

 …see more

from £2693 / night

£18847 - £26897 / week

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from £2693 / 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

54

Province of Siena / Gaiole in Chianti

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly

 …see more

from £113 / night

£785 / week

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from £113 / 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

26

Province of Siena / Gaiole in Chianti

7 13 3 nights min

  • 7 bedrooms
  • Sleeps 13
  • 3 nights min
  • Ask owner if suitable for children
  • Ask about pets

 …see more

from £1035 / night

£7242 - £16897 / week

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from £1035 / 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

29

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 £423 / night

£2955 - £4818 / week

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from £423 / 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 £388 / night

£2712 - £3616 / week

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from £388 / night

16

Province of Siena / Gaiole in Chianti

5 9 7 nights min

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min
  • Ask owner if suitable for children
  • Ask about pets

 …see more

from £490 / night

£3428 - £5673 / week

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from £490 / night

16

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+
  • Ask about pets

 …see more

from £401 / night

£2806 - £4402 / week

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from £401 / night

30

Province of Siena / Gaiole in Chianti

11 22 7 nights min

  • 11 bedrooms
  • Sleeps 22
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

 …see more

from £544 / night

£3805 - £6467 / week

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from £544 / night

16

Province of Siena / Gaiole in Chianti

6 11 7 nights min

  • 6 bedrooms
  • Sleeps 11
  • 7 nights min
  • Ask owner if suitable for children
  • Ask about pets

 …see more

from £601 / night

£4207 - £6880 / week

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from £601 / night

30

Province of Siena / Gaiole in Chianti

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Suitable for children age 5+
  • Ask about pets

 …see more

from £273 / night

£1911 - £2400 / week

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from £273 / night

19

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 £427 / night

£2983 - £4197 / week

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from £427 / night

31

Province of Siena / Gaiole in Chianti

6 17 7 nights min

  • 6 bedrooms
  • Sleeps 17
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets

 …see more

from £190 / night

£1324 - £4228 / week

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from £190 / night

0

Province of Siena / Gaiole in Chianti

4 8 7 nights min

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

 …see more

from £428 / night

£2994 - £4490 / week

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from £428 / 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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