Apartments and villas with a balcony in Gaiole in Chianti | Holiday Lettings UK

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Gaiole in Chianti

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49 Holiday homes

Filters applied: Balcony or terrace

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

(15) Excellent 

22

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • 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 £100 / night

£560 - £760 / week

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from £100 / night

(1) Excellent 

24

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

4 10 4 nights min

  • 4 bedrooms
  • Sleeps 10
  • 4 nights min
  • 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

£1500 - £2000 / week

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from £300 / night

(2) Excellent 

18

Province of Siena / Gaiole in Chianti

2 2 7 nights min

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

 …see more

from £77 / night

£539 / week

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from £77 / night

18

Province of Siena / Gaiole in Chianti

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £48 / night

£308 - £368 / week

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from £48 / night

(13) Excellent 

23

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • 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

£1100 - £1600 / week

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from £175 / 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
Ideal location for couples and families, set within walking distance of Gaiole in Chianti with the typical Tuscan lifestyle at your doorstep. Perfect place to unwind and come back to after a cycle, a walk, or discovering the artistic and historic cities of Tuscany.<b  …see more

from £44 / night

£308 - £338 / week

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from £44 / night

(32) 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
“A Little Corner of Heaven” This was our fourth visit to Gaiole in Chianti and our third stay in this apartment. The apartment is modern, well furnished and equipped and spotlessly clean. The garden is beautiful and a real bonus. It is a wonderful  …see more

from £60 / night

£420 - £665 / week

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from £60 / night

(6) Excellent 

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 £65 / night

£400 - £800 / week

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from £65 / 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

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
Ideal location for couples and families, set within walking distance of Gaiole in Chianti with the typical Tuscan lifestyle at your doorstep. Perfect place to unwind and come back to after a cycle, a walk, or discovering the artistic and historic cities of Tuscany.<b  …see more

from £44 / night

£308 - £338 / week

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from £44 / night

(1) Average 

23

Gaiole in Chianti holiday apartment rental

Gaiole in Chianti / Lecchi

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Pet friendly
This lovely 11th century castle for holiday rental in the Chianti Classico area is a tiny, medieval hamlet located at 10 km from Gaiole in Chianti  …see more

from £86 / night

£385 - £580 / week

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from £86 / night

20

Province of Siena / Gaiole in Chianti

3 5 7 nights min

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

 …see more

from £80 / night

£556 / week

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from £80 / 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

(2) Excellent 

45

Province of Siena / Gaiole in Chianti

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly

 …see more

from £195 / night

£1368 - £1881 / week

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from £195 / 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

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from £150 / night

(1) Average 

25

Gaiole in Chianti holiday apartment rental

Gaiole in Chianti / Lecchi

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
This lovely 11th century castle for holiday rental in the Chianti Classico area is a tiny, medieval hamlet located at 10 km from Gaiole in Chianti.  …see more

from £86 / night

£385 - £573 / week

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from £86 / night

44

Province of Siena / Gaiole in Chianti

3 7 7 nights min

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

 …see more

from £114 / night

£795 - £1184 / week

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from £114 / night

17

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The natural extension of the existing village of Gaiole in Chianti. The 'village-inside-the village' concept that is unique of its kind. The village concept that becomes an integral part of Gaiole in Chianti. l  …see more

from £112 / night

£676 / week

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from £112 / 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

16

Home rental in Gaiole in Chianti with shared pool

Province of Siena / Gaiole in Chianti

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Behind steep hills but harmonious, furrowed largely by rows vineyards that produce a highly renowned wine.  …see more

from £112 / night

£778 / week

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from £112 / 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

21

Gaiole in Chianti / Lecchi

1 5 2 nights min

  • 1 bedroom
  • Sleeps 5
  • 2 nights min
  • Child friendly

 …see more

from £60 / night

£385 - £654 / week

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from £60 / night

11

Province of Siena / Gaiole in Chianti

3 5 1 night min

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

 …see more

from £189 / night

£1155 - £1371 / week

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from £189 / 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
A fantastic apartment, 2 bedrooms, 2 bathrooms and livingroom/kitchen. The apartment is one of the towers in beautiful Borgo Gaoile. From the livingroom/kitchen there is a wonderful view over Gaiole and the valley. The wall in the living/kitchen is a glasfoldingdoor.&l  …see more

from £85 / night

£590 - £936 / week

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from £85 / night

16

Holiday b&b rental

Gaiole in Chianti / Lecchi

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 95 km
  • Swimming pool
  • Car not necessary
Adjacent apartment with terra-cotta floors and furnished with a double Chianti iron bed (subsequently with a madonna picture above), a large armadio and an en suite bathroom. Through French doors the room leads to a 55 square meter terrace with an antique iron sofa, a f  …see more

from £95 / night

£513 / week

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from £95 / night

(1) Excellent 

22

Holiday farmhouse in Gaiole in Chianti

Gaiole in Chianti / Montegrossi

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Le Diacce, an enchanting 18th century old farmhouse, belonging to Podere Ciona, 40 hectares of vineyards and woodland, enjoys a unique view on the surrounding hills covered with vineyards, olive groves and woods with Siena in the far distance.  …see more

from £129 / night

£3419 / week

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from £129 / 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
Casa Lecchi is a spacious two bedroom apartment facing on to the main piazza of Montefiorile which is a small hamlet of 14 villas situated in a quiet position in the heart of the Chianti Classico wine producing area. The hamlet is on a hillside and the houses enjoy st  …see more

from £73 / night

£505 - £958 / week

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from £73 / night

23

Apartment rental in Gaiole in Chianti with shared pool

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
This cosy and comfortable 2-bedroom apartment is ideally located in the hamlet and develops on one level on the first floor, with independent access via an external staircase, with views overlooking the village and countryside. It avails of a private south facing garde  …see more

from £64 / night

£445 - £785 / week

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from £64 / 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

27

Gaiole in Chianti holiday home rental

Gaiole in Chianti / Montegrossi

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Child friendly
2 Villas (1 FONTECARESINO and 2 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 10 km from Radda in Chianti, 35 km from Siena,  …see more

from £308 / night

£2317 - £3979 / week

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from £308 / night

48

Province of Siena / Gaiole in Chianti

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

 …see more

from £90 / night

£624 / week

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from £90 / 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
This cosy and comfortable 2-bedroom apartment sits nestled within the hamlet of Giaole. An open plan kitchen/living room allows for easy preparation of meals and the dining area with table and chairs hosts up to 5 people, a Satellite TV and side unit finish this room. A  …see more

from £64 / night

£445 - £785 / week

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from £64 / night

38

Holiday home in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Private garden
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 10 km from Radda in Chianti, 35 km from Siena, 45 km from Arezzo and 55 km from  …see more

from £119 / night

£834 - £1492 / week

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from £119 / night

29

Province of Siena / Gaiole in Chianti

1 2 7 nights min

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

 …see more

from £66 / night

£462 - £539 / week

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from £66 / 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

(14) Excellent 

21

Province of Siena / Gaiole in Chianti

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £89 / night

£620 - £936 / week

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from £89 / 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 £428 / night

£2992 - £4274 / week

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from £428 / 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 £391 / night

£2736 - £3847 / week

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from £391 / night