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62 Holiday homes in San Casciano Val di Pesa

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24 Photos

Cottage | 3 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

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from £101 /night

£701 - £789 / week

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Key info:

  • Nearest beach 120 km
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
In the heart of Chianti, half way between Florence and Siena. An old farmhouse which has recently been restored is situated in an hamlet dating back to the 1400's. Surrounded by vineyards and olive groves offering uniquely picturesque views. A place to feel at peace and tranquil making it ideal for a family looking to relax in contact with nature.  …see more

23 Photos

Villa | 4 Bedrooms | sleeps 12

Excellent 5/5 

3 Nights min stay

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from £190 /night

£1327 - £2322 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Villa "Casale San Casciano" is a 200 sqm independent villa with private pool and garden (sleeps up to 12 people). The Villa is located in the typical context of the Chianti area, surrounded by vineyards, olive-trees and small woods.  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £398 /night

£2781 - £4339 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Originally a farmhouse owned by the Medici family, and dating back to the early fifteenth century. Villa Il Portico is perfectly positioned between Florence and Siena.  …see more

Featured properties

19 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £414 /night

£2897 - £3901 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Enjoy noble splendor in this gracious antique villa which is both close to Florence and immersed in tranquility.  …see more

24 Photos

Villa | 11 Bedrooms | sleeps 20

7 Nights min stay

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from £886 /night

£6199 - £8720 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
In the heart of the Chianti region, 15 minutes drive from Florence, stands Castello Buondelmonti set on a hillside overlooking the valley of the river Pesa.  …see more

20 Photos

Farmhouse | 5 Bedrooms | sleeps 10

Min stay varies

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from £430 /night

£3009 - £4934 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
In the Chianti Gallo Classico, very close to Florence. Large living area. Air conditioning in the first floor bedrooms.  …see more

23 Photos

Castle | 11 Bedrooms | sleeps 20

Short stays welcome

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from £939 /night

£6571 - £7710 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Tuscany Castle/Villa Chianti San Casciano Florence Italy The love for the past together with modern comfort make your stay unforgettable..  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 7

7 Nights min stay

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from £177 /night

£1236 - £2145 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Luxurious smaller Villa. On a unique estate 10 ha. Swimmingpool. Chianti Classico. 30 minutes Florence Airconditioned. Large livingroom, very complete kitchen. 3 bedrooms, 2 marble bathrooms Tuscan colors, terracotta floors,beam ceilings. Nice for children. Great views Situated on one of the finest estates in Chianti. Classical gardens.  …see more

21 Photos

Guest house | 3 Bedrooms | sleeps 6

Very Good 4.5/5 

2 Nights min stay

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from £66 /night

£460 - £552 / week

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Key info:

  • Suitable for over 5s only
  • Car not necessary
  • May take pets – please enquire
Un posto mágico, inmerso nella campagna.Pace assoluta. Relax. Prodotti naturali del nostro campo. Corsi di cucina e cene ad hoc per i nostri ospiti. Un posto di charm. Accoglienza curata e familiare. Tranquillity only half an hour from Florence. Artists, foodies and sybarites will be in heaven!  …see more

6 Photos

Barn | 2 Bedrooms | sleeps 5

Min stay varies

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from £61 /night

£424 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Trattasi di un fienile immerso nelle colline del Chianti, completamente ristrutturato, su 2 livelli, 80 mq, con pergolato esterno . Al pian terreno: sala, cucina, bagno con doccia. Al piano superiore 2 camere doppie con la possibilità di aggiungere un lettino  …see more

24 Photos

Farmhouse | 6 Bedrooms | sleeps 12

Short stays welcome

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from £220 /night

£1534 - £2278 / week

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Key info:

  • Nearest beach 150 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
The medieval fortified farmhouse "Corzanello" strides a hill covered in vineyards, olive trees and an oak wood. Situated on the renowned farm Fattoria Corzano e Paterno. Wine and cheese tasting on appointment.  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 4

Short stays welcome

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from £53 /night

£368 - £526 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Beautiful country house surrounded by vineyards and olive groves. We offer on request welcome dinner, cooking lessons, lunch and diinner,  …see more

21 Photos

House | 2 Bedrooms | sleeps 5

Short stays welcome

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from £79 /night

£552 - £789 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
A beautiful farmhouse built at the beginning of the 15th century, lying in the middle of the Chianti Hills; The house is surrounded by garden, lawn and woods, as well as a covered terrace overlooking vineyards, olive groves and villages topping the surrounding hills.  …see more

17 Photos

Villa | 6 Bedrooms | sleeps 12

2 Nights min stay

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from £227 /night

£1585 - £2354 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
The historic Casa Erta, acquired from the Machiavelli family, together with the other farm houses on the property, have been restored with great care to their original form.  …see more

16 Photos

Villa | 6 Bedrooms | sleeps 12

2 Nights min stay

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from £227 /night

£1585 - £2354 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
The historic Casa Corza, belonged to the legendary Cavalcanti and Niccolini families, Florentine nobility and together with the other farm houses on the property, have been restored with great care to their original form.  …see more

17 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £157 /night

£1095 - £1559 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
Apartment for 4 persons, with swimming pool , in Chianti  …see more

17 Photos

Farmhouse | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £430 /night

£3009 - £4934 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
About our villas in italy Mezzola is a typical stone-built Tuscan farmhouse, located on an estate producing Chianti wine, only 1 kilometre from Cerbaia and 18 kilometres from the centre of Florence. Until a few years ago, it was the home of the owner, an antique dealer  …see more

12 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

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from £61 /night

£423 - £603 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Apartment for 2 persons, with swimming pool , in Chianti  …see more

15 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £56 /night

£388 - £568 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Apartment for 4 persons, with swimming pool , in Chianti  …see more

22 Photos

Apartment | 1 Bedroom | sleeps 3

7 Nights min stay

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from £146 /night

£1020 - £1287 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Apartment for 3 persons, with swimming pool , in Florentine Hills  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 12

7 Nights min stay

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from £186 /night

£1300 - £2329 / week

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Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Independent villa set in the typical context of Chianti, surrounded by vineyards, olive-groves and small woods. The villa rises in a dominant position upon a little lake. The property, now completely restored, dates back to the beginning of the XIX century...  …see more

8 Photos

Villa | 11 Bedrooms | sleeps 15

7 Nights min stay

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from £1069 /night

£7480 - £8781 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
this is a beautiful example of a tuscan medieval castle situated on a panoramic hilltop in the chianti classico district, around 10 km from san casciano val di pesa. Built by the buondelmonti family on the foundations of a 10th century roman construction, the castle was converted into a villa in the 15th century. The castle is now more than 1,000 years old and has been recently renovated by the current owners and turned into a summer residence. most of the furniture consists of restored antique pieces. Inside the fortified walls, there is a large terrace with a loggia offering panoramic views of the surrounding valley, and a swimming pool for the exclusive use of guests with deckchairs and sun loungers. The castle has a lift/elevator for reaching the torre (tower) area, a laundry room, internet connection, a dishwasher and a barbecue. the nearest town, bargino, has food stores and a restaurant. All types of services can be found in san casciano val di pesa, which is 10 km away. The best known places in the chianti district – san gimignano, siena and florence - are approximately 30 minutes away by car. the surrounding area has many restaurants that offer excellent traditional tuscan cuisine as well as farms where special wine tastings can be arranged and it is possible to purchase some excellent chianti wines.  …see more

10 Photos

Villa | 4 Bedrooms | sleeps 12

7 Nights min stay

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from £165 /night

£1153 - £2622 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
Attractive holiday house for 12 persons, with swimming pool , in Chianti  …see more

21 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £60 /night

£417 - £695 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Apartment for 4 persons, with swimming pool , in Chianti  …see more

21 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £60 /night

£417 - £695 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Apartment for 4 persons, with swimming pool , in Chianti  …see more

23 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £75 /night

£522 - £730 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Apartment for 4 persons, with swimming pool , in Chianti  …see more

21 Photos

Apartment | 4 Bedrooms | sleeps 11

7 Nights min stay

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from £120 /night

£834 - £1385 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Apartment for 11 persons, with swimming pool , in Chianti  …see more

20 Photos

House | 1 Bedroom | sleeps 2

1 night min stay

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from £48 /night

£331 - £455 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Appartamento Marvena B is a characteristic ancient house surrounded by the vegetation. It sleeps two people. From Appartamento Marvena B you will enjoy an enchanting view of the Chianti hills and of the surrounding countryside  …see more

11 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £70 /night

£488 - £706 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Apartment for 4 persons in Florentine Hills  …see more

8 Photos

Villa | 4 Bedrooms | sleeps 7

7 Nights min stay

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from £331 /night

£2312 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
this splendid stone farmhouse is situated in a beautiful, peaceful valley, surrounded by fields and vineyards, just a short distance away from mercatale val di pesa, in the heart of the chianti classico district. The house is located on a farm that produces excellent wines and olive oil which can be sampled in the winery. The indoor areas have been tastefully furnished. It has a comfortable, modern, well-equipped kitchen. Outdoors there are large terraces and a beautiful loggia furnished with tables and chairs for enjoying wonderful “al fresco” meals. Across the lawn, separated by a hedge, is a 6 x 12 meter swimming pool. the position of this property makes it possible to easily organize trips around the chianti classico area, from the splendid towers of san gimignano, to the beautiful medieval town of monteriggioni or the art cities of florence and siena, all of which are no more than thirty minutes away by car. However, this property stands out in particular for its peace and tranquility, offering guests the chance to enjoy a truly unique and completely relaxing vacation. internet connection in the winery which is around 300 meters away from the house. the maximum occupancy of the house is 7 people including children.  …see more

21 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £189 /night

£1317 - £1456 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
In the heart of Chianti, halfway between Florence and Siena The farmhouse I Greppi Di Silli located 300 mt above sea level. rises and looks out over a green valley, surrounded on all sides by cultivated hills covered in olive groves and vineyards. Alongsi...  …see more

18 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £46 /night

£319 - £481 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Attractive apartment for 4 persons, with swimming pool , in Chianti  …see more

12 Photos

Apartment | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £84 /night

£585 - £1223 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Attractive apartment for 6 persons, with swimming pool , in Chianti  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £168 /night

£1176 - £1460 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Apartment for 4 persons, with swimming pool , in Florentine Hills  …see more

20 Photos

Cottage | 1 Bedroom | sleeps 2

1 night min stay

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from £54 /night

£372 - £496 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Appartamento Edmondo B is a romantic and welcoming cottage surrounded by the vegetation. It sleeps two people. From Appartamento Edmondo B you will enjoy an enchanting view of the Chianti hills and of the surrounding countryside  …see more

8 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £450 /night

£3144 - £5035 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Lying in the splendid backdrop of the gentle hills that characterize the Chianti region, is Villa La Colombaia. Just 4 kms from the town of San Casciano and little more than 20 kms from Florence, it has the structure of a typical tuscan country house, solid and restrained, and goes back the 1400s and was once part of the Medici family estates. From where it stands it dominates a little valley, hushed and unspoilt, and at the bottom runs a river. It has been renovated with great care and ability by the current owners and has been made into a very comfortable and spacious home, where each and every element of the furnishings has been carefully selected, revealing their enthusiasm and good taste. Around the house, in the grounds of 3 hectacres, completely enclosed, is a large, panoramic garden with a large swimming-pool (7 x 17m), offering guests peace and quiet in particularly beautiful countryside. The villa is reached along an untarred road of about 900 metres. Internet wi-fi system.  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 3

7 Nights min stay

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from £154 /night

£1076 - £1232 / week

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Key info:

  • Nearest beach 127 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
These apartments will guarantee that you have a wonderful holiday in Chianti. The Giotto Apartment can accomodate up to 3 guests, while the Leonardo can accomodate up to 5 guests.  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 2

2 Nights min stay

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from £101 /night

£703 - £1158 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
These Chianti vacation homes offer accommodation for 2 to 6 guests, 1 to 3 double bedrooms, bathroom with shower or bathtub, living area and fully fitted kitchen.  …see more

24 Photos

Apartment | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £189 /night

£1323 - £2232 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
These Chianti vacation homes offer accommodation for 2 to 6 guests, 1 to 3 double bedrooms, bathroom with shower or bathtub, living area and fully fitted kitchen.  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 2

2 Nights min stay

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from £77 /night

£538 - £1034 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
These Chianti vacation homes offer accommodation for 2 to 6 guests, 1 to 3 double bedrooms, bathroom with shower or bathtub, living area and fully fitted kitchen.  …see more

15 Photos

Villa | 8 Bedrooms | sleeps 15

7 Nights min stay

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from £473 /night

£3306 - £4794 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
This delightful farmhouse for 15 in a grand estate would make the ideal accommodation for a wide variety of guests- a family or group on holiday, attendees at a conference, or guests at one of the special events or weddings held at the villa.  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £166 /night

£1158 - £2025 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
These Chianti vacation homes offer accommodation for 2 to 6 guests, 1 to 3 double bedrooms, bathroom with shower or bathtub, living area and fully fitted kitchen.  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £102 /night

£711 - £901 / week

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Key info:

  • Nearest beach 95 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
These apartments guarantee a totally Tuscan experience with the Chianti hills as the perfect backdrop, modern comforts and antiques in every corner, and the kind hospitality of this former castle's staff.  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £124 /night

£868 - £1116 / week

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Key info:

  • Nearest beach 95 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
These apartments guarantee a totally Tuscan experience with the Chianti hills as the perfect backdrop, modern comforts and antiques in every corner, and the kind hospitality of this former castle's staff.  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

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from £69 /night

£480 - £587 / week

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Key info:

  • Nearest beach 95 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
These apartments guarantee a totally Tuscan experience with the Chianti hills as the perfect backdrop, modern comforts and antiques in every corner, and the kind hospitality of this former castle's staff.  …see more

21 Photos

Villa | 1 Bedroom | sleeps 2

7 Nights min stay

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from £78 /night

£546 - £661 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Vacation house sleeps 2 people, so it is perfect for romantic breaks and is located in Tuscany Italy. This property is ideal if you seek a memorable experience. The villa offers an internet connection .  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £88 /night

£612 - £753 / week

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Key info:

  • Nearest beach 95 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
These apartments guarantee a totally Tuscan experience with the Chianti hills as the perfect backdrop, modern comforts and antiques in every corner, and the kind hospitality of this former castle's staff.  …see more

24 Photos

Apartment | 3 Bedrooms | sleeps 5

7 Nights min stay

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from £176 /night

£1228 - £1399 / week

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Key info:

  • Nearest beach 127 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
These apartments will guarantee that you have a wonderful holiday in Chianti. The Giotto Apartment can accomodate up to 3 guests, while the Leonardo can accomodate up to 5 guests.  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 16

7 Nights min stay

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from £603 /night

£4215 - £5538 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
The La Corte estate stretches out over a hillside covered with vineyards, olive trees and woodland.  …see more

13 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £247 /night

£1728 - £2141 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This is the perfect starting point to explore Tuscany. Located in the heart of Chianti, Borgo in Rosa is just 20 minutes from Florence  …see more