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

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Gaiole in Chianti

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28 Holiday homes

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

(12) Excellent 

69

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 £405 / night

£2834 - £4359 / week

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from £405 / 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 £176 / night

£1231 - £2052 / week

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from £176 / night

18

Villa rental in Gaiole in Chianti with swimming pool

Province of Siena / Gaiole in Chianti

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • 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 £165 / night

£1368 - £2398 / week

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from £165 / 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.<br />Bea  …see more

from £76 / night

£530 - £1513 / week

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from £76 / 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 £103 / night

£513 / week

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from £103 / 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.<br />The charme of an ancient Medieval borgo in the heart of Chianti Classico  …see more

from £129 / night

£808 - £966 / week

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from £129 / 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 £245 / night

£1710 - £2736 / week

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from £245 / night

(12) Excellent 

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 i  …see more

from £693 / night

£4847 - £7150 / week

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from £693 / 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 £359 / night

£1283 / week

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from £359 / night

24

Holiday villa with swimming pool in Lecchi

Gaiole in Chianti / Lecchi

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Villa in Vertine with 5 bedrooms sleeps 10  …see more

from £953 / night

£2821 - £6667 / week

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from £953 / 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 £1197 / night

£8377 / week

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from £1197 / 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 £137 / night

£770 - £1026 / week

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from £137 / night

29

Province of Siena / Gaiole in Chianti

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Child friendly

 …see more

from £2908 / night

£20351 - £28198 / week

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from £2908 / 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 £112 / night

£778 / week

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from £112 / night

16

Province of Siena / Gaiole in Chianti

Studio 9 7 nights min

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

 …see more

from £486 / night

£3399 - £5355 / week

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from £486 / night

16

Province of Siena / Gaiole in Chianti

Studio 11 7 nights min

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

 …see more

from £596 / night

£4171 - £6492 / week

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from £596 / 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 £375 / night

£2623 - £4005 / week

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from £375 / 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 £420 / night

£2937 - £4133 / week

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from £420 / night

(4) Very Good 

30

Province of Siena / Gaiole in Chianti

Studio 7 7 nights min

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

 …see more

from £233 / night

£1627 - £2711 / week

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from £233 / 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

(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 £407 / night

£2843 - £3791 / week

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from £407 / 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 £295 / night

£2063 - £6368 / week

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from £295 / night

30

Province of Siena / Gaiole in Chianti

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £436 / night

£3051 - £7211 / week

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from £436 / night

44

Province of Siena / Gaiole in Chianti

5 10 Min stay varies

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

 …see more

from £953 / night

£2821 - £6667 / week

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from £953 / night

15

Province of Siena / Gaiole in Chianti

5 10 7 nights min

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

 …see more

from £76 / night

£526 - £2566 / week

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from £76 / 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 £266 / night

£1858 - £2334 / week

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from £266 / 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 £395 / night

£2763 - £4573 / week

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from £395 / 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 £425 / night

£2969 / week

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from £425 / night