Air conditioned apartments and villas to rent in Gaiole in Chianti

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Gaiole in Chianti

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42 Holiday homes

Filters applied: Air conditioning (42)

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

(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

(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

(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 £45 / night

£311 - £341 / week

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from £45 / night

(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 £409 / night

£2858 - £4397 / week

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from £409 / 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 £113 / night

£682 / week

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from £113 / 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 £45 / night

£311 - £341 / week

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from £45 / 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

18

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Air conditioning
appartamento, 2 - 3 persone, 2 vano/vani, 1 camera/e da letto, 1 bagno/bagni, ca. 44 m², 1 piano/piani, alloggio al piano terra. Accesso all'alloggio indipendente.TerrenoPorzione privata del terreno, giardino, lastre.Parcheggio: 1 x posto macchina in g  …see more

from £69 / night

£345 / week

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from £69 / 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

(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 

10

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
  • 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. Details and the architecture are carefully planned.  …see more

from £87 / night

£388 / week

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from £87 / night

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+
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 £49 / night

£337 - £457 / week

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from £49 / night

100

Holiday villa with swimming pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • 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

from £1170 / night

£8190 - £10345 / week

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from £1170 / 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
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 £45 / night

£311 - £371 / week

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from £45 / 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 £77 / night

£535 - £1526 / week

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from £77 / 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

(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

(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

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

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

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

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

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

66

Province of Siena / Gaiole in Chianti

4 7 7 nights min

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

 …see more

from £288 / night

£2009 - £3526 / week

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from £288 / 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

(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

(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

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

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

20

Province of Siena / Gaiole in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

 …see more

from £111 / night

£773 - £1141 / week

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from £111 / night

45

Province of Siena / Gaiole in Chianti

11 22 Min stay varies

  • 11 bedrooms
  • Sleeps 22
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

 …see more

from £503 / night

£3519 - £5486 / week

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from £503 / night

21

Province of Siena / Gaiole in Chianti

3 6 7 nights min

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

 …see more

from £148 / night

£1032 - £1726 / week

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from £148 / night

20

Province of Siena / Gaiole in Chianti

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

 …see more

from £152 / night

£1063 - £1684 / week

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from £152 / night

20

Province of Siena / Gaiole in Chianti

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

 …see more

from £160 / night

£1117 - £1684 / week

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from £160 / 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 £300 / night

£2099 - £6479 / week

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from £300 / night

14

Province of Siena / Gaiole in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask owner if suitable for children
  • Air conditioning
  • Ask about pets

 …see more

from £82 / night

£574 - £696 / week

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from £82 / night

26

Province of Siena / Gaiole in Chianti

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £47 / night

£328 - £737 / week

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from £47 / night

20

Province of Siena / Gaiole in Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

 …see more

from £93 / night

£646 - £1081 / week

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from £93 / 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 £427 / night

£2988 - £4204 / week

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from £427 / night