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

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Gaiole in Chianti

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33 Holiday homes

Filters applied: Villa (33)

18

Villa rental in Montegrossi with swimming pool

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 £109 / night

£757 - £1933 / week

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from £109 / night

(12) Excellent 

78

Holiday villa with swimming pool, tennis court in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
“Perfect holiday location” Our family group of 8 adults spent 5 nights at Villa LisiDor - a perfect location for both relaxing & a great base for exploring the local region. The roads in Chianti can be narrow & windy but worth the drive to villages lik  …see more

from £398 / night

£2786 - £4286 / week

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from £398 / 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 £241 / night

£1681 - £2690 / week

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from £241 / night

100

Gaiole in Chianti holiday villa rental

Province of Siena / Gaiole in Chianti

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 130 km
  • Swimming pool
  • Child friendly
Villa Gaiole features all the comforts and a wonderful panoramic Tuscan Villa in Chianti between Siena and Florence, with private pool, air conditioning, total privacy, and a lovely park.  …see more

from £387 / night

£2690 - £3782 / week

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from £387 / night

(4) Excellent 

17

Province of Siena / Gaiole in Chianti

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £101 / night

£505 / week

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from £101 / night

100

Gaiole in Chianti holiday villa rental

Province of Siena / Gaiole in Chianti

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This stunning villa, with 4 bedrooms and 4 bathrooms can accomodate 8 people, so it is ideal for a large group of friends. Located in Tuscany Italy, this villa offers a swimming Pool, air Conditioning, an internet Connection, a pet friendly space .  …see more

from £550 / night

£3850 / week

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from £550 / night

27

Villa rental in Gaiole in Chianti with shared pool

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
The Chianti As You Always Dreamed It. A charming Medieval borgo in the heart of Chianti Classico, 15 km far from Siena. Relax and discovery hour incredible landes.The charme of an ancient Medieval borgo in the heart of Chianti Classico  …see more

from £127 / night

£795 - £1118 / week

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from £127 / night

(3) Very Good 

24

Holiday villa with shared pool in Gaiole in Chianti

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
Located within walking distance of the village of Gaiole in Chianti, the villa offers the perfect setting to explore the Chianti Classico region, enjoy the breathtaking views of the vineyards and olive groves, and experience the charming Tuscan lifestyle.Beautiful villa  …see more

from £82 / night

£572 - £654 / week

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from £82 / night

(11) Very Good 

50

Holiday villa with indoor pool, golf nearby in Montefienali

Gaiole in Chianti / Montefienali

7 18 Min stay varies

  • 7 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
SERVICES INCLUDED • Cleaning pre-arrival and post-departure • Meet and greet by local member of staff • Daily cleaning Monday to Friday: 2 hours per day • Complete change of all sheets and towels every Saturday (a full spare set of bathroom towels is provided each week  …see more

from £303 / night

£2101 - £7030 / week

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from £303 / night

(12) Very Good 

28

Holiday villa with swimming pool, tennis court in Gaiole in Chianti

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
“Toscany at its best at Radda in Chianti property Villa PetrAlexa” The property itself is wonderfully placed between woods and a vinery in the picturesque Chianti area near Radda. The hospitality we have experienced was outstanding in the mean that you  …see more

from £173 / night

£1211 - £2017 / week

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from £173 / night

(1) Very Good 

17

Villa rental in Gaiole in Chianti with swimming pool

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 £227 / night

£1589 - £3488 / week

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from £227 / night

100

Holiday villa with swimming pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
This exclusive and luxurious villa in Chianti affords 5 bedrooms, dining room, 2 sitting rooms, kitchen, gym, games room and a fabulous infinity swimming pool.  …see more

Pricing unknown

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Pricing unknown

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 £353 / night

£1261 / week

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from £353 / night

24

Holiday villa with swimming pool in Lecchi

Gaiole in Chianti / Lecchi

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Villa in Vertine with 5 bedrooms sleeps 10  …see more

from £397 / night

£2774 - £6555 / week

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from £397 / 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 £135 / night

£757 - £1009 / week

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from £135 / 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 £227 / night

£1589 - £2647 / week

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from £227 / 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 £110 / night

£765 / week

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from £110 / night

29

Province of Siena / Gaiole in Chianti

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly

 …see more

from £2756 / night

£19292 - £27532 / week

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from £2756 / 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 £1849 / night

£12942 - £16471 / week

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from £1849 / 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 £1933 / night

£10925 / week

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from £1933 / 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 £1177 / night

£8236 / week

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from £1177 / 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 £397 / night

£2776 - £3701 / week

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from £397 / night

30

Province of Siena / Gaiole in Chianti

11 22 7 nights min

  • 11 bedrooms
  • Sleeps 22
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £530 / night

£3705 - £6297 / week

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from £530 / 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 £586 / night

£4100 - £6383 / week

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from £586 / night

16

Province of Siena / Gaiole in Chianti

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly

 …see more

from £356 / night

£2493 - £3910 / week

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from £356 / 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 £478 / night

£3342 - £5265 / week

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from £478 / night

19

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 £415 / night

£2904 - £4087 / week

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from £415 / night

23

Province of Siena / Gaiole in Chianti

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Suitable for children age 5+
  • Pet friendly

 …see more

from £421 / night

£2534 - £3801 / week

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from £421 / night

31

Province of Siena / Gaiole in Chianti

6 17 7 nights min

  • 6 bedrooms
  • Sleeps 17
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £190 / night

£1324 - £4228 / week

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from £190 / night

30

Province of Siena / Gaiole in Chianti

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
  • Ask about pets

 …see more

from £263 / night

£1837 - £2308 / week

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from £263 / night

16

Province of Siena / Gaiole in Chianti

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £391 / night

£2732 - £4522 / week

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from £391 / night

44

Province of Siena / Gaiole in Chianti

5 10 7 nights min

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

 …see more

from £397 / night

£2774 - £6555 / week

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from £397 / night

23

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 £417 / night

£2916 - £4373 / week

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from £417 / night

Top Destination reviews

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
Agriturismo Podere Terrena Appartamento "Papavero"
We found what we were looking for: beauty and relax

I was looking for a beautiful place to relax with my husband and certainly found it in this beautiful borghetto. The apartment is very comfortable and well equipped with everything you need to feel at home itself. Italian typical breakfast was ideal … see more
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