Gaiole in Chianti apartment or villa with a log fire | Holiday Lettings

Close

View larger map

Also consider

Coastal Cottages
222 properties
Apartments Sardinia
478 properties
Apartments Tuscany
3181 properties
Apartments Lake Garda Area
103 properties
Apartments Lake Como Area
494 properties
Apartments Sicily
634 properties
Lecchi
16 properties
Montegrossi
9 properties
Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

54 Holiday homes

Filters applied: Fireplace (54)

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

12

Province of Siena / Gaiole in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about pets

 …see more

from £60 / night

£518 - £733 / week

Book View

from £60 / night

(6) Very Good 

43

Chianti house, Florence, Jacuzzi, Tuscany up to 6p - Montefienali house sleeps 6

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

£269 - £604 / week

Book View

from £47 / 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 £78 / night

£544 / week

Book View

from £78 / night

(11) Excellent 

28

Villa LisiDor, luxury Tuscany cottage in Chianti - Gaiole in Chianti villa sleeps 10

Province of Siena / Gaiole in Chianti

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
* SPECIAL PRICE for a SHORT BREAK: 3-8 October at 2.000€ VILLA LISIDOR: FULLY RENOVATED WITH ALL NEW AMENITIES. The habitable area is doubled: from 150 square meters to 300 square meters. On GROUND FLOOR, which is at garden level, is a large sitting room with Tv  …see more

from £345 / night

£2858 - £4397 / week

Book View

from £345 / 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

£414 - £647 / week

Book View

from £69 / night

39

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 £115 / night

£802 - £962 / week

Book View

from £115 / night

27

La Pieve Marsina - Gaiole in Chianti villa sleeps 5

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
In the top of a hill set in the patchwork of vineyards that characterizes the area of Chianti Classico, in the heart of an ancient medieval village, was born a few years ago Pieve Marsina.The structure, made up of nice apartments, has as principal objective to allow our  …see more

from £104 / night

£815 - £1147 / week

Book View

from £104 / 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 £247 / night

£1725 - £2759 / week

Book View

from £247 / night

24

Ancient castle in the heart of Tuscany, 6 bedrooms - Lecchi castle sleeps 14

Gaiole in Chianti / Lecchi

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
A dive into an ancient culture in the heart of Tuscany, the Chianti Classico.Il Castello Medievale is situated in a medieval hamlet, constructed of white stone, built around 1000AD, surrounded by forests and olive groves, immersed in a magical atmosphere of tranquility.  …see more

from £414 / night

£2897 - £3345 / week

Book View

from £414 / night

(1) Good 

25

castello in Chianti ginestra - Lecchi apartment sleeps 5

Gaiole in Chianti / Lecchi

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • 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. Built around the year 1000 by the noble family of Guidi, today it is an esteemed wine estate with self catering holiday ap  …see more

from £87 / night

£449 - £578 / week

Book View

from £87 / night

48

Bed & Breakfast La Cerreta - Gaiole in Chianti b&b sleeps 10

Province of Siena / Gaiole in Chianti

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask owner if suitable for children
  • Ask about pets
This beautifull restructured 16th century house sits on a hillside and dominates the sorrounding countryside as far as the eye can see. Nestled in the heart of Chianti our B&B is perfectly located for the week-end break, walking or cycling holidays as well as trekking a  …see more

from £61 / night

£423 / week

Book View

from £61 / 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 £81 / night

£561 / week

Book View

from £81 / night

20

Villa Fontecaresino 2 - Montegrossi house sleeps 4

Gaiole in Chianti / Montegrossi

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
  • Ask about pets
  • 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 £74 / night

£513 / week

Book View

from £74 / night

(1) Excellent 

22

Le Diacce - Montegrossi farmhouse sleeps 10

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 villa, benefits of a total privacy and enjoys splendid sunsets and a beautiful pool. The living room and kitchen open onto spacious terraces fully equipped for outdoor dining and surrounded by lawns, gardens and ancient trees.Ideal for families or a group of f  …see more

from £130 / night

£3449 / week

Book View

from £130 / night

(11) Very Good 

24

Villa PetrAlexa, Tuscany cottage in Chianti area - Gaiole in Chianti villa sleeps 7

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
Come to enjoy the typical architecture of Tuscany houses! Villa PetrAlexa is an antic, now renovated barn, with natural stone, original beam ceilings and glass doors which offer a pleasing mix in a comfortable, spacious environment spread over two floors with a wide at  …see more

from £178 / night

£1242 - £2069 / week

Book View

from £178 / 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

Book View

from £363 / night

14

Province of Siena / Gaiole in Chianti

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £80 / night

£556 / week

Book View

from £80 / 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

£630 - £651 / week

Book View

from £90 / night

(1) Very Good 

17

Villa Brolio - Gaiole in Chianti villa sleeps 12

Province of Siena / Gaiole in Chianti

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 125 km
  • Swimming pool
  • Child friendly
The building of Villa Brolio was originally an old XII century watchtower later transformed into a mill and finally restored to become a villa. The restoration works have been done preserving carefully all the ancient characteristics such as the outside stones, the vau  …see more

from £233 / night

£1630 - £3578 / week

Enquire View

from £233 / night

25

Podere Scopeto - Gaiole in Chianti farmhouse sleeps 12

Province of Siena / Gaiole in Chianti

6 12 3 nights min

  • 6 bedrooms
  • Sleeps 12
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Podere Scopeto is a former Chianti hill farm on the west-facing slopes of the Montagni di Chianti. The present owners bought it some 15 years ago and restored the farmhouse and a separate self-contained studio for family holidays. It has kept its family feel and charm.  …see more

from £350 / night

£2300 - £2500 / week

Book View

from £350 / night

15

Province of Siena / Gaiole in Chianti

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £190 / night

£1294 - £1638 / week

Book View

from £190 / night

(10) Very Good 

58

Villa Albizi Holidayhome Gaiole in Chianti Tuscany - Montefienali villa sleeps 18

Gaiole in Chianti / Montefienali

7 18 Min stay varies

  • 7 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
NEW MANAGEMENT from Summer 2015 Villa Albizi Tuscany life and more….for groups of friends or large families Villa Albizi is normally rented on a villa-only weekly basis and are ideal for those seeking independence and privacy. We have created a formula designed to  …see more

from £311 / night

£2156 - £4483 / week

Book View

from £311 / night

15

Province of Siena / Gaiole in Chianti

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £62 / night

£432 / week

Book View

from £62 / night

24

Casa Lecchi - Gaiole in Chianti apartment sleeps 4

Province of Siena / Gaiole in Chianti

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet 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 £63 / night

£440 - £966 / week

Enquire View

from £63 / night

23

Radda In Chianti - 41968001 - Lecchi farmhouse sleeps 10

Gaiole in Chianti / Lecchi

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Ask about pets
The Villa Gallo Nero is a lovely home offering 5 bedrooms and 5 baths and is situated in the village of Casanuova di Ama. The village is comprised of a small cluster of houses surrounded by vineyards of wine and oil-producing farmers. Centered between the medieval towns  …see more

from £293 / night

£1703 - £2139 / week

Enquire View

from £293 / night

45

Casale Le Fonti - Gaiole in Chianti - Gaiole in Chianti house sleeps 13

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. T  …see more

from £268 / night

£1682 - £2625 / week

Book View

from £268 / night

15

Pievasciata - 44263001 - Lecchi farmhouse sleeps 2

Gaiole in Chianti / Lecchi

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Ancient farmhouse with adjoining barn situated on a large and renowned farming estate producing excellent wine and olive oil. This property has been carefully restored and turned into 6 comfortable apartments, all of which offering nice interiors furnished in a rustic s  …see more

from £97 / night

£620 - £716 / week

Enquire View

from £97 / night

19

Gaiole In Chianti - 27123003 - Gaiole in Chianti farmhouse sleeps 6

Province of Siena / Gaiole in Chianti

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Beautiful stone hamlet recently restored situated in quiet and panoramic location on the Chianti Classico hills offering extensive views over the surrounding vineyards. This charming hamlet comprises 6 nice apartments (and 9 double bedrooms) all of which furnished in a  …see more

from £184 / night

£1156 - £1651 / week

Enquire View

from £184 / night

12

Pievasciata - 44263003 - Lecchi farmhouse sleeps 2

Gaiole in Chianti / Lecchi

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Ancient farmhouse with adjoining barn situated on a large and renowned farming estate producing excellent wine and olive oil. This property has been carefully restored and turned into 6 comfortable apartments, all of which offering nice interiors furnished in a rustic s  …see more

from £96 / night

£620 - £716 / week

Enquire View

from £96 / night

12

Pievasciata - 44263006 - Lecchi farmhouse sleeps 2

Gaiole in Chianti / Lecchi

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Ancient farmhouse with adjoining barn situated on a large and renowned farming estate producing excellent wine and olive oil. This property has been carefully restored and turned into 6 comfortable apartments, all of which offering nice interiors furnished in a rustic s  …see more

from £92 / night

£582 - £690 / week

Enquire View

from £92 / night

26

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

Book View

from £67 / night

14

Pievasciata - 44263002 - Lecchi farmhouse sleeps 4

Gaiole in Chianti / Lecchi

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Ancient farmhouse with adjoining barn situated on a large and renowned farming estate producing excellent wine and olive oil. This property has been carefully restored and turned into 6 comfortable apartments, all of which offering nice interiors furnished in a rustic s  …see more

from £126 / night

£820 - £926 / week

Enquire View

from £126 / night

27

Fontecaresino Property (1 & 2) - Montegrossi house sleeps 14

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

£2173 / week

Book View

from £311 / 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 £247 / night

£1725 - £3449 / week

Book View

from £247 / night

15

Pievasciata - 44263005 - Lecchi farmhouse sleeps 5

Gaiole in Chianti / Lecchi

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Ancient farmhouse with adjoining barn situated on a large and renowned farming estate producing excellent wine and olive oil. This property has been carefully restored and turned into 6 comfortable apartments, all of which offering nice interiors furnished in a rustic s  …see more

from £154 / night

£969 - £1152 / week

Enquire View

from £154 / night

20

Gaiole In Chianti - 70247001 - Gaiole in Chianti farmhouse sleeps 8

Province of Siena / Gaiole in Chianti

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Beautiful independent villa with private pool situated in the heart of the Chianti region, a short distance away from the town of Gaiole in Chianti. This villa, nestling deep in quiet position among vineyards and woods, offers full privacy and is the ideal place for tho  …see more

from £438 / night

£2633 - £3950 / week

Enquire View

from £438 / night

15

Gaiole In Chianti - 27123002 - Gaiole in Chianti farmhouse sleeps 2

Province of Siena / Gaiole in Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Beautiful stone hamlet recently restored situated in quiet and panoramic location on the Chianti Classico hills offering extensive views over the surrounding vineyards. This charming hamlet comprises 6 nice apartments (and 9 double bedrooms) all of which furnished in a  …see more

from £132 / night

£826 - £1156 / week

Enquire View

from £132 / night

14

Pievasciata - 44263004 - Lecchi farmhouse sleeps 2

Gaiole in Chianti / Lecchi

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Ancient farmhouse with adjoining barn situated on a large and renowned farming estate producing excellent wine and olive oil. This property has been carefully restored and turned into 6 comfortable apartments, all of which offering nice interiors furnished in a rustic s  …see more

from £92 / night

£582 - £690 / week

Enquire View

from £92 / night

11

Gaiole In Chianti - 27123001 - Gaiole in Chianti farmhouse sleeps 6

Province of Siena / Gaiole in Chianti

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Beautiful stone hamlet recently restored situated in quiet and panoramic location on the Chianti Classico hills offering extensive views over the surrounding vineyards. This charming hamlet comprises 6 nice apartments (and 9 double bedrooms) all of which furnished in a  …see more

from £184 / night

£1156 - £1651 / week

Enquire View

from £184 / night

20

Badia Coltibuono - 82374003 - Montegrossi castle sleeps 6

Gaiole in Chianti / Montegrossi

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Badia a Coltibuono is the first wine resort in Chianti, opening it's doors to travellers and visitors who want to share a truly unique experience. Here it is possible to encounter the magic of a venue, to observe the slow yet intense rhythm of a 1000 year old abbey and  …see more

from £246 / night

£1572 - £1833 / week

Enquire View

from £246 / night

Top Destination reviews

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
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
Villa PetrAlexa, Tuscany cottage in Chianti area
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 perfectly prepared. The house was heated up and foo … see more
Agriturismo Podere Terrena Appartamento "Papavero"
We found what we were looking for: beauty and relax

I was looking for a beautiful place to relax with my husband and certainly found it in this beautiful borghetto. The apartment is very comfortable and well equipped with everything you need to feel at home itself. Italian typical breakfast was ideal … see more

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page