Apartments in Gaiole in Chianti and Villas – Holiday Lettings - Holiday Rentals Gaiole in Chianti

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Gaiole in Chianti

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5,252 Holiday homes

24

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Suitable for children age 5+

from £62 / night

£428 - £888 / week

Enquire View

from £62 / night

(16) Excellent 

22

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Charming accommodations and beautiful surroundings!” My husband and I stayed for four nights in this wonderful and clean apartment in the heart of Chianti. Phil was extremely responsive and helpful throughout the booking process and our stay even goin
…see more

from £110 / night

£560 - £760 / week

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from £110 / night

(39) Excellent 

24

Gaiole in Chianti holiday apartment accommodation

Province of Siena / Gaiole in Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden
“Highly Recommended” Apartment - Gaiole in Chianti This apartment is located in a small traditional Tuscan village, right in the heart of Chianti country. The village is surrounded by vineyards on all sides, so you have no excuse not to sample the w
…see more

from £90 / night

£630 / week

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Responds fast!
avg. 1 hour 52 minutes

from £90 / night

24

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 125 km
  • Swimming pool
  • Child friendly

from £140 / night

£979 / week

Enquire View

from £140 / night

11

Gaiole in Chianti holiday apartment rental

Province of Siena / Gaiole in Chianti

3 5 1 night min

  • 3 bedrooms
  • Sleeps 5
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £193 / night

£1,181 / week

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Responds fast!
avg. 2 hours 27 minutes

from £193 / night

(7) Very Good 

Certificate of Excellence

43

Montefienali holiday home accommodation

Gaiole in Chianti / Montefienali

3 6 Min stay varies

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

Certificate of Excellence

from £48 / night

£273 - £656 / week

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Responds fast!
avg. 1 hour 23 minutes

from £48 / night

24

Holiday apartment in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 107 km
  • Swimming pool
  • Child friendly

from £52 / night

£359 - £768 / week

Enquire View

from £52 / night

(1) Very Good 

15

Gaiole in Chianti holiday home rental

Province of Siena / Gaiole in Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly

from £66 / night

£420 - £567 / week

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from £66 / night

(12) Excellent 

70

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 £455 / night

£1,738 - £4,898 / week

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from £455 / night

(13) Excellent 

24

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Perfect and plaisant location to explore Tuscany” We were 4 people staying in this very nice apartment : comfortable, clean, modern, well equipped. We loved the location. I never heard of Gaiole before, but it was a nice discovery. Quiet village, but
…see more

from £175 / night

£1,100 - £1,600 / week

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from £175 / night

44

Holiday home with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

from £98 / night

£681 - £1,205 / week

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from £98 / night

18

Gaiole in Chianti holiday condo rental

Province of Siena / Gaiole in Chianti

3 5 1 night min

  • 3 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

from £48 / night

£315 / week

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from £48 / night

(4) Excellent 

28

Gaiole in Chianti holiday barn let

Province of Siena / Gaiole in Chianti

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £97 / night

£612 / week

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from £97 / night

(1) Excellent 

4

Holiday b&b in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

from £70 / night

£437 - £525 / week

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from £70 / night

(14) Very Good 

30

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

Province of Siena / Gaiole in Chianti

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 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 £108 / night

£756 - £2,098 / week

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from £108 / night

(2) Average 

23

Lecchi holiday apartment rental

Gaiole in Chianti / Lecchi

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Pet friendly

from £88 / night

£498 - £638 / week

Book View

Responds fast!
avg. 2 hours 41 minutes

from £88 / night

(6) Excellent 

26

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £87 / night

£603 - £957 / week

Book View

Responds fast!
avg. 1 hour 36 minutes

from £87 / night

6

Gaiole in Chianti holiday farmhouse rental

Province of Siena / Gaiole in Chianti

2 2 3 nights min

  • 2 bedrooms
  • Sleeps 2
  • 3 nights min
  • Nearest beach 127 km
  • Child friendly
  • Pet friendly

from £75 / night

£498 - £533 / week

Book View

from £75 / night

(4) Excellent 

17

Holiday villa rental

Province of Siena / Gaiole in Chianti

2 6 1 night min

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

from £105 / night

£525 / week

Book View

Responds fast!
avg. 2 hours 0 minutes

from £105 / night

22

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Child friendly

from £49 / night

£341 - £717 / week

Enquire View

from £49 / night

15

Gaiole in Chianti holiday farmhouse rental

Province of Siena / Gaiole in Chianti

9 22 1 night min

  • 9 bedrooms
  • Sleeps 22
  • 1 night min
  • Child friendly
  • Private garden

from £67 / night

£437 / week

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from £67 / night

24

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Child friendly

from £49 / night

£341 - £643 / week

Enquire View

from £49 / night

(1) Average 

25

Lecchi holiday apartment rental

Gaiole in Chianti / Lecchi

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £96 / night

£550 - £699 / week

Book View

Responds fast!
avg. 2 hours 42 minutes

from £96 / night

47

Gaiole in Chianti holiday apartment rental

Province of Siena / Gaiole in Chianti

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 100 km
  • Child friendly
  • Private garden

from £123 / night

£857 / week

Book View

from £123 / night

(1) Excellent 

20

Gaiole in Chianti holiday apartment rental

Province of Siena / Gaiole in Chianti

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Child friendly

from £49 / night

£341 - £643 / week

Enquire View

from £49 / 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

from £145 / night

£1,009 / week

Book View

from £145 / night

(7) Very Good 

20

Apartment accommodation in Gaiole in Chianti with shared pool

Province of Siena / Gaiole in Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Comfortable new apartment in a traditional style, highly recommended.” The apartment has a lovely view over the town and the hills beyond. It's an easy walk down into the town centre which has bars, restaurants and a pizza cafe, though it's uphill (an
…see more

from £70 / night

£500 - £700 / week

Book View

from £70 / night

(6) Very Good 

23

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
“Peaceful taste of Tuscany!!!!” Stayed here for a lovely, idyllic, December week. Amazing apartment with all home comforts. Loved walking through the village, stopping for pizza and fine wines :-) The views over the hills and vineyards are incredibly i
…see more

from £150 / night

£600 / week

Book View

Responds fast!
avg. 2 hours 49 minutes

from £150 / night

(2) Very Good 

13

Holiday apartment with swimming pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £44 / night

£306 - £551 / week

Book View

from £44 / night

(1) Excellent 

24

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Fabulous place to stay with a group of friends or family.” My Husband and I stayed here with a group of our friends for a week. It was the perfect size and location. Great for day trips to the hill towns of Tuscany or just hanging out in the cute to
…see more

from £300 / night

£1,500 - £2,000 / week

Enquire View

from £300 / night

7

Holiday apartment in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

from £118 / night

£809 - £830 / week

Book View

from £118 / night

22

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Nearest beach 107 km
  • Swimming pool
  • Child friendly

from £49 / night

£341 - £372 / week

Enquire View

from £49 / night

19

Holiday cottage with shared pool in Lecchi

Gaiole in Chianti / Lecchi

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets

from £83 / night

£586 - £909 / week

Book View

from £83 / night

21

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Nearest beach 107 km
  • Swimming pool
  • Child friendly

from £49 / night

£341 - £372 / week

Enquire View

from £49 / night

(2) Excellent 

45

Holiday farmhouse with swimming pool in Gaiole in Chianti

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

from £187 / night

£1,307 - £2,010 / week

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from £187 / night

25

Apartment rental in Gaiole in Chianti with shared pool, golf nearby

Province of Siena / Gaiole in Chianti

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 107 km
  • Swimming pool
  • Child friendly

from £62 / night

£428 - £802 / week

Enquire View

from £62 / 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
  • Nearest beach 130 km
  • Swimming pool
  • Child friendly

from £400 / night

£2,796 - £4,107 / week

Enquire View

from £400 / night

21

Holiday guest house in Montefienali

Gaiole in Chianti / Montefienali

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden

from £48 / night

£306 - £656 / week

Book View

Responds fast!
avg. 1 hour 23 minutes

from £48 / night

23

Holiday home with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Swimming pool
  • Child friendly

from £241 / night

£1,573 - £1,695 / week

Book View

from £241 / night

(3) Average 

12

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £74 / night

£516 / week

Book View

from £74 / night