Holiday rentals in Gaiole in Chianti: Villas, Cottages and Apartments

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Gaiole in Chianti

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157 Holiday homes

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

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

£518 / 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 £130 / night

£3449 / week

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from £130 / night

(1) Excellent 

12

Holiday farmhouse rental

Province of Siena / Gaiole in Chianti

5 16 Min stay varies

  • 5 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
This is a traditional 5 bedroom villa situated between the towns of Gaiole in Chianti and Radda in Chianti. Accommodating up to 18 guests in total as additional apartments are available within the grounds, it's an ideal base for a stay with family or friends. The w  …see more

from £432 / night

£3018 - £4656 / week

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from £432 / night

19

Gaiole in Chianti / Lecchi

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets

 …see more

from £63 / night

£440 / week

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from £63 / 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 £699 / night

£4888 - £7212 / week

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from £699 / 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 £397 / night

£2759 - £3880 / week

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from £397 / night

7

Province of Siena / Gaiole in Chianti

2 6 3 nights min

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

 …see more

from £87 / night

£544 / week

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from £87 / night

(1) Excellent 

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
The house is located in the heart of the Chianti Classico, inside the town of Gaiole in Chianti (all kinds of shops). The apartment is on the ground floor and is part of a building where the owners reside.Outside a portion of an equipped courtyard is available for t  …see more

from £35 / night

£302 / week

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from £35 / night

(1) Very Good 

16

Gaiole in Chianti holiday home rental

Province of Siena / Gaiole in Chianti

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Swimming pool
  • Air conditioning
  • Private garden
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. Details and the architecture are carefully planned.  …see more

from £87 / night

£432 / week

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from £87 / 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 £120 / night

£841 - £1505 / week

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from £120 / 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 £113 / night

£785 / week

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from £113 / 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 £311 / night

£2337 - £4013 / week

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from £311 / night

33

Gaiole in Chianti holiday home rental

Province of Siena / Gaiole in Chianti

13 25 3 nights min

  • 13 bedrooms
  • Sleeps 25
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden
The Borgo San Vincenti is a Homelidays in Tuscany; is a beautiful stone house in a prestigious estate of 500 acres of forest in the hills above Gaiole in Chianti, a short distance from Siena. The large farmhouse has been restored by the owners. They used their experienc  …see more

from £539 / night

£3772 / week

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from £539 / 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

23

Home letting in Gaiole in Chianti with shared pool

Province of Siena / Gaiole in Chianti

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
The house, composed of 5 delightful apartments, has as it's main objective the idea of offering guests the opportunity to enjoy the calm, the beauty and all the pleasures our region has to offer.Our apartments have been renovated with respect for tradition.  …see more

from £78 / night

£489 - £707 / week

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from £78 / night

100

Gaiole in Chianti holiday villa rental

Province of Siena / Gaiole in Chianti

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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

Pricing unknown

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Pricing unknown

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 £67 / night

£466 - £544 / week

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from £67 / night

7

Province of Siena / Gaiole in Chianti

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden

 …see more

from £493 / night

£3449 / week

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from £493 / night

5

Province of Siena / Gaiole in Chianti

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £65 / night

£423 / week

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from £65 / night

4

Province of Siena / Gaiole in Chianti

2 4 3 nights min

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

 …see more

from £173 / night

£1207 / week

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from £173 / night

6

Province of Siena / Gaiole in Chianti

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Private garden

 …see more

from £87 / night

£544 / week

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from £87 / 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 £962 / night

£2845 - £6725 / week

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from £962 / night

6

Holiday home with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Casa Maestrale is a holiday home immersed in the most idyllic Chiantishire: surrounded by vineyards producing world-class red wine, overlooking the rolling hills of Tuscany and is located in the village of San Vincenti, with its stone houses and clay roof tiles. The vil  …see more

from £130 / night

£906 / week

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from £130 / night

18

Holiday home with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Casa Montecristo is immersed in the most idyllic Chiantishire: surrounded by vineyards producing world-class red wine, overlooking the rolling hills of Tuscany and is located in the village of San Vincenti, with its stone houses and clay roof tiles. The village has been  …see more

from £95 / night

£664 / week

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from £95 / night

14

Holiday home with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Casa Eolo is immersed in the most idyllic Chiantishire: surrounded by vineyards producing world-class red wine, overlooking the rolling hills of Tuscany and is located in the village of San Vincenti, with its stone houses and clay roof tiles. The village has been comple  …see more

from £95 / night

£664 / week

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from £95 / night

24

Gaiole in Chianti holiday farmhouse rental

Gaiole in Chianti / Lecchi

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Villa in San Sano with 3 bedrooms sleeps 8  …see more

from £213 / night

£1242 - £2069 / week

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from £213 / night

20

Holiday farmhouse with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about pets
  • Private garden
Villa in Selvole with 3 bedrooms sleeps 6  …see more

from £367 / night

£2569 - £4138 / week

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from £367 / night

9

Province of Siena / Gaiole in Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £60 / night

£400 - £800 / week

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from £60 / 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 £138 / night

£776 - £1035 / week

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from £138 / 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 £2931 / night

£20517 - £28427 / week

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from £2931 / night

21

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 £394 / night

£2758 - £3881 / week

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from £394 / night

26

Province of Siena / Gaiole in Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Pet friendly

 …see more

from £61 / night

£462 - £664 / week

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from £61 / 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 £1897 / night

£13276 - £16897 / week

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from £1897 / 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 £90 / night

£625 - £944 / week

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from £90 / night

26

Province of Siena / Gaiole in Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £87 / night

£509 - £871 / week

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from £87 / 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 £370 / night

£2587 - £3880 / week

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from £370 / night

16

Gaiole in Chianti / Lecchi

5 18 Min stay varies

  • 5 bedrooms
  • Sleeps 18
  • Min stay varies
  • Nearest beach 130 km
  • Swimming pool
  • Child friendly

 …see more

from £238 / night

£1638 - £2673 / week

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from £238 / 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

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 £432 / night

£3018 - £4311 / week

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from £432 / night

20

Province of Siena / Gaiole in Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £93 / night

£646 - £1081 / week

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from £93 / night