Horse riding holiday villas and apartments Gaiole in Chianti | Holiday Lettings

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Gaiole in Chianti

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45 Holiday homes

Filters applied: Horse riding

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

(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
“Very comfortable home away from home” Casacorvo Minore is a very comfortable apartment well located in the heart of Chianti. It has great views from its veranda which fostered perfect starts for each day as we had breakfast sitting in the morning sun.  …see more

from £100 / night

£560 - £760 / week

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from £100 / 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

(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

(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
“A hidden gem.” We stayed at Villa LisiDor at the end of May with family. We made the trip to Tuscany by train to Florence from the UK and hired a car from there. We arrived during an unseasonably chilly spell and in torrential rain after a very l  …see more

from £402 / night

£2810 - £4323 / week

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from £402 / 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 £47 / night

£306 - £365 / week

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from £47 / 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 £111 / night

£670 / week

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from £111 / 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

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 £128 / night

£801 - £958 / week

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from £128 / 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) 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 £424 / night

£2967 - £4577 / week

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from £424 / 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

£534 / week

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from £77 / 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

(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 £243 / night

£1695 - £2712 / week

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from £243 / 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

£306 - £335 / week

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from £44 / night

(1) Very Good 

11

Province of Siena / Gaiole in Chianti

2 6 Min stay varies

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

 …see more

from £68 / night

£407 - £814 / week

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from £68 / 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 £194 / night

£1356 - £1865 / week

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from £194 / 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 £79 / night

£551 / week

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from £79 / 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

£526 - £1500 / week

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from £76 / 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
“Villa PetrAlexa - excellent leisure facility” This years stay was even better than our stay last year. Despite the fact we arrived late at night due to repeated traffic jams on the motorway because of terrible weather conditions, everything was perfec  …see more

from £175 / night

£1221 - £2034 / week

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from £175 / 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 £687 / night

£4806 - £7089 / week

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from £687 / 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 £128 / night

£3390 / week

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from £128 / 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 £72 / night

£500 - £950 / week

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from £72 / 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

£306 - £335 / week

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from £44 / night

19

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

 …see more

from £62 / night

£433 - £882 / week

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from £62 / night

(7) Very Good 

45

Holiday villa with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
“Our Dream Villa in Tuscany” We traveled to Tuscany because it was my daughter's dream vacation to celebrate her 50th birthday. Her family of 2 boys and husband, myself and we were later joined by her brother and spouse. We spent two weeks at La Casa i  …see more

from £170 / night

£933 - £2187 / week

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from £170 / 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 £48 / night

£331 - £450 / week

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from £48 / 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 £85 / night

£382 - £575 / week

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from £85 / 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 £111 / night

£772 / week

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from £111 / 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 £85 / night

£382 - £568 / week

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from £85 / 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 £89 / night

£619 / week

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from £89 / 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 £44 / night

£306 - £365 / week

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from £44 / 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 £356 / night

£1272 / week

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from £356 / 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 £34 / night

£297 / week

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from £34 / night

20

Gaiole in Chianti holiday apartment rental

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. There is independent access via an external staircase and views over the village and countryside. It avails of a private terraced garden outside  …see more

from £63 / night

£441 - £778 / week

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from £63 / 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 £63 / night

£441 - £778 / week

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from £63 / night

22

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 107 km
  • Swimming pool
  • Child friendly
A charming stone staircase leads up to the entrance of this first-floor apartment which opens directly in to the large kitchen/living room. The living area consists of a wooden table and chairs which seats up to 3 people, a Satellite TV and side unit, comfortable sofa t  …see more

from £51 / night

£356 - £624 / week

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from £51 / 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 £63 / night

£441 - £778 / week

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from £63 / 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 £77 / night

£481 - £695 / week

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from £77 / night

18

Gaiole in Chianti holiday apartment rental

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 Gaiole. 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 £63 / night

£441 - £778 / week

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from £63 / 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
This cosy and comfortable first-floor 2-bedroom apartment sits overlooking the rest of the hamlet, also with views over the pool. The entrance leads into the spacious living room where crisscrossed terracotta tiling runs seamlessly throughout the apartment, whilst Chest  …see more

from £51 / night

£356 - £636 / week

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from £51 / night