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

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Gaiole in Chianti

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130 Holiday homes

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

(6) Very Good 

43

Gaiole in Chianti 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
Recently renovated, is located in a scenic hillside location in a picturesque village nestled in the heart of Chianti, strategic point to reach in a short time two beautiful cities such as Siena and Florence. Moreover, you can go trekking in the beautiful trails and na  …see more

from £47 / night

£267 - £599 / week

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from £47 / 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

(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

(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 

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 £428 / night

£2992 - £4616 / week

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from £428 / 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

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

(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

(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

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
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, 35 km from Siena, 45 km from Arezzo and 55 km from Florence. Our close proximi  …see more

from £165 / night

£1368 - £2398 / week

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from £165 / 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

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

(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 £69 / night

£411 - £821 / week

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from £69 / 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

42

Holiday home in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

6 13 3 nights min

  • 6 bedrooms
  • Sleeps 13
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Nestled in the lush nature of the Chianti region, this charming manor built in the early 1900s lovingly embraces and preserves the romance of bygone times. It is an ideal place for relaxing in the surrounding nature while enjoying the area’s superb foods and wines  …see more

from £283 / night

£1778 - £2740 / week

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from £283 / 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
La naturale estensione del paese di Gaiole in Chianti. Il concetto del “villaggio - nel - villaggio” unico nel suo genere. Il concetto del borgo che diventa parte integrante del villaggio. Una cura maniacale dell' architettura e dei materiali. Disponibi  …see more

from £68 / night

£342 / week

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from £68 / 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

(4) Excellent 

17

Province of Siena / Gaiole in Chianti

2 6 1 night min

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

 …see more

from £103 / night

£513 / week

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from £103 / 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

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

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

£334 - £453 / week

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from £48 / 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

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

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

£308 - £368 / week

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from £44 / 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 £86 / night

£385 / week

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from £86 / 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

(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) 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 £86 / night

£428 / week

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from £86 / night

22

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
Homelidays "Casa Guia " 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  …see more

from £107 / night

£748 / week

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from £107 / 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 £64 / night

£445 - £785 / week

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from £64 / 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

33

Gaiole in Chianti holiday home rental

Province of Siena / Gaiole in Chianti

13 40 4 nights min

  • 13 bedrooms
  • Sleeps 40
  • 4 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 £3419 / night

£21368 / week

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from £3419 / 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

(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

(1) Excellent 

4

Province of Siena / Gaiole in Chianti

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Ask about pets
  • Private garden

 …see more

from £65 / night

£455 / week

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from £65 / 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

Top Destination reviews

Villa Podere Earthly
Perfect, beautifil little place in tuscany

A beautiful place full of happines, were you can stay The time you want for a very very good price ,there's a beautiful view, is very relaxing and you can enjoy The animals and nature … see more
A HOLIDAY IN THE HEART OF CHIANTI
Authentic unspoiled Italian charm!

My family and I stayed at this beautiful property and had a relaxed and wonderful holiday. Gaiole in Chianti is a small village totally unspoilt by tourism and the location of this property is ideal if you hire a car and travel to all the surrounding … see more