Holiday rentals in San Casciano in Val di Pesa: Villas, Cottages and Apartments

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218 Holiday homes

Travellers going to San Casciano in Val di Pesa are booking October dates now. Secure your holiday home today and have the perfect trip.

(4) Very Good 

14

San Casciano in Val di Pesa / Montefiridolfi

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Private garden

 …see more

from £61 / night

£366 / week

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from £61 / night

(2) Excellent 

39

Lavish 8BR Villa w pool only 10 Miles to Florence! - San Casciano in Val di Pesa villa sleeps 16

Province of Florence / San Casciano in Val di Pesa

8 16 1 night min

  • 8 bedrooms
  • Sleeps 16
  • 1 night min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
This wonderful 8 BR – 8 BA villa is located in the beautiful village of San Casciano val di pesa, just about 8 miles away from the beginning of the historic district of the city of Florence. The villa traces back its origins to the early XVI century and is considere  …see more

from £1174 / night

£8674 - £9740 / week

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from £1174 / night

(1) Excellent 

23

Appartamento villa I Chisci - San Casciano in Val di Pesa apartment sleeps 4

Province of Florence / San Casciano in Val di Pesa

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
The apartment that we rent is part of a villa. The apartment is about 100 square meters, can accommodate 4 people. It can be available, in addition to the 4 sleeps in the two bedrooms air Conditioning Room, a double sofa bed in the living room. The apartment is on two f  …see more

from £66 / night

£457 - £640 / week

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from £66 / night

24

I5.3324 - Holiday apartmen... - Montefiridolfi apartment sleeps 4

San Casciano in Val di Pesa / Montefiridolfi

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
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. Alongside the bor  …see more

from £179 / night

£1253 - £1540 / week

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from £179 / night

(14) Excellent 

25

Villa Sole in Chianti :D - San Casciano in Val di Pesa villa sleeps 6

Province of Florence / San Casciano in Val di Pesa

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 84 km
  • Swimming pool
A few minutes drive from Ponte Vecchio, among olivetrees and vineyards of the famous Chianti Wine, the villa is part of an ancient stone farmhouse, (13th century) carefully renovated.The Villa has a wonderful panoramic location, facing the incomparable Tuscany sunset.Th  …see more

from £261 / night

£957 - £1914 / week

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from £261 / night

100

Il Principe - 2+2 pax - San Casciano in Val di Pesa apartment sleeps 4

Province of Florence / San Casciano in Val di Pesa

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly
These two family apartments are equipped with antique furniture and beautiful carpets, and they boast a very traditional atmosphere. One of them is located on the ground floor, and the other one is on the first floor, and they both afford a kitchen area, a living room w  …see more

from £140 / night

£644 - £792 / week

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from £140 / night

26

Castello di Pergolato - San Casciano in Val di Pesa villa sleeps 26

Province of Florence / San Casciano in Val di Pesa

11 26 Min stay varies

  • 11 bedrooms
  • Sleeps 26
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Originally a Medieval feudal castle, the property was converted to a villa between 1450 and 1500. As you would expect, it is steeped in history and is a fascinating place to spend a holiday in this wonderful part of Tuscany. The property is divided into two main sectio  …see more

from £1035 / night

£6466 - £8104 / week

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from £1035 / night

25

Province of Florence / San Casciano in Val di Pesa

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £105 / night

£731 - £914 / week

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from £105 / night

(15) Excellent 

20

Candida's Chianti House B&B - Neri Room - San Casciano in Val di Pesa b&b sleeps 2

Province of Florence / San Casciano in Val di Pesa

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Suitable for children age 5+
  • Ask about pets
  • Private garden
This listing is for the first of the three double bedrooms at " Candida's Chianti House", the NERI ROOM. If you wish to book 2 or 3 rooms at the same time, please contact me for a quote on any of the rooms (Neri, Mattia or Martina) and in the notes ask for a full quote.  …see more

from £74 / night

£487 - £548 / week

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from £74 / night

27

Castello Buondelmonti - San Casciano in Val di Pesa villa sleeps 15

Province of Florence / San Casciano in Val di Pesa

11 15 Min stay varies

  • 11 bedrooms
  • Sleeps 15
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
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. This extraordinary example of Tuscan medieval castle was built, on the foundations of a Roman Settlement, in the  …see more

from £1131 / night

£6522 - £8174 / week

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from £1131 / night

(2) Excellent 

23

Villa Casale San Casciano - San Casciano in Val di Pesa villa sleeps 12

Province of Florence / San Casciano in Val di Pesa

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa "Casale San Casciano" is a 200 sqm independent villa, which can comfortably accommodate up to 12 people. The Villa overlooks a little lake beside the property and it is located in the typical context of the Chianti area, surrounded by vineyards, olive-trees and s  …see more

from £227 / night

£1435 - £2479 / week

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from £227 / night

(1) Very Good 

10

Province of Florence / San Casciano in Val di Pesa

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Ask about pets

 …see more

from £78 / night

£540 / week

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from £78 / night

(27) Excellent 

25

Il Visciolo - San Casciano in Val di Pesa farmhouse sleeps 4

Province of Florence / San Casciano in Val di Pesa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 83 km
  • Suitable for children age 5+
  • Car not necessary
The holiday house is located 300 metres from San Casciano in Val di Pesa centre. Facing the open country from a dominant position, it offers the comforts of a town life and the beauty of the Chianti landscape opening on hills with vineyards and olive trees. There are no  …see more

from £74 / night

£479 - £821 / week

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from £74 / night

(1) Very Good 

16

Delicious country house in Chianti 2 - San Casciano in Val di Pesa apartment sleeps 2

Province of Florence / San Casciano in Val di Pesa

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 nights min
  • Nearest beach 100 km
  • Child friendly
  • Air conditioning
Living Chianti. Staying in an environment of the most beautiful that nature can offer. The beautiful Tuscan countryside, with its gentle hills dotted by the regular geometry of vineyards and olive groves . With the noble patrician villas and rustic cottages nestled in s  …see more

from £48 / night

£314 / week

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from £48 / night

(1) Excellent 

21

San Casciano in Val di Pesa / Campoli in Chianti

2 6 3 nights min

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

 …see more

from £109 / night

£653 / week

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from £109 / night

100

I marchesi - Trilo Deluxe - San Casciano in Val di Pesa apartment sleeps 4

Province of Florence / San Casciano in Val di Pesa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Furnishings of Chianti air and ancient walls dating back to the Middle Ages are enchanting features of these vacation homes for 4 people. Guests can relish a sunset while tasting some regional wine in the garden or porch which the apartment affords. These apartments hav  …see more

from £235 / night

£1409 - £2192 / week

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from £235 / night

(1) Very Good 

23

Province of Florence / San Casciano in Val di Pesa

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Ask about pets

 …see more

from £57 / night

£357 / week

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from £57 / night

(1) Very Good 

19

LINDA Apartment with POOL - Campoli in Chianti apartment sleeps 6

San Casciano in Val di Pesa / Campoli in Chianti

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
LINDA is an apartment (WITH PRIVATE SWIMMING POOL USED ONLY by WHOM RENTING LINDA!!!) that sleep up to 5 or 6 people, placed in the village of Campoli, in the heart of Chianti, only 12 km far from the famous town of Greve in Chianti and 13,5 km far from Panzano in Chian  …see more

from £148 / night

£957 - £1857 / week

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from £148 / night

96

San Casciano in Val di Pesa / Chiesanuova

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

 …see more

from £162 / night

£1131 - £1914 / week

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from £162 / night

(4) Excellent 

14

Candida's Chianti House B&B - Mattia Room - San Casciano in Val di Pesa b&b sleeps 2

Province of Florence / San Casciano in Val di Pesa

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Suitable for children age 5+
  • Car not necessary
  • Ask about pets
This is the second of the three double bedrooms at " Candida's Chianti House", the MATTIA ROOM. If you wish to book 2 or 3 rooms at the same time, please contact me for a quote on any of the rooms (Neri, Mattia or Martina) and in the notes ask for a full quote. I will b  …see more

from £74 / night

£518 / week

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from £74 / night

(2) Excellent 

20

Villa Il Portico - San Casciano in Val di Pesa villa sleeps 10

Province of Florence / San Casciano in Val di Pesa

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
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. This large holiday rental property was originally a farmhouse owned by the Medici family and dates ba  …see more

from £419 / night

£2927 - £4566 / week

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from £419 / night

(1) Very Good 

21

San Casciano in Val di Pesa / Chiesanuova

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from £61 / night

£345 / week

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from £61 / night

100

Il Principe - 4+2 pax - San Casciano in Val di Pesa apartment sleeps 6

Province of Florence / San Casciano in Val di Pesa

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly
These four large apartments are between 79 and 119sqm big, and they sleep up to 6 people each. They all boast antique furniture and beautiful carpets, fully equipped kitchens and bathrooms with Jacuzzi.One of them is located on a first floor, so it features a lovel  …see more

from £192 / night

£914 - £1174 / week

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from £192 / night

(2) Excellent 

15

Chiantihouse "Il Poderino" - San Casciano in Val di Pesa apartment sleeps 4

Province of Florence / San Casciano in Val di Pesa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Private garden
Our lovely , nearly 1000 years old farmhouse is situated in the hills "CHIANTISHIRE" : olivetrees and vineyards , ca. 15 km south of Florence in direction Siena.The house has been completely restored. We offer the Apartment "Bougainville": ideal for  …see more

from £50 / night

£347 - £433 / week

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from £50 / night

100

I marchesi - House 6 Pax - San Casciano in Val di Pesa apartment sleeps 6

Province of Florence / San Casciano in Val di Pesa

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
These vacation homes for 6 people brims over with the style of Chianti. To enjoy sipping a glass of wine outdoors, the apartments have a large porch and its garden area. These apartments affords a living room with a fireplace. Its fully fitted kitchen features its dinin  …see more

from £270 / night

£1618 - £2435 / week

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from £270 / night

8

Province of Florence / San Casciano in Val di Pesa

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Swimming pool
  • Private garden

 …see more

from £87 / night

£435 / week

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from £87 / night

21

Province of Florence / San Casciano in Val di Pesa

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

 …see more

from £293 / night

£2047 / week

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from £293 / night

9

San Casciano in Val di Pesa / Campoli in Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets

 …see more

from £53 / night

£366 / week

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from £53 / night

(6) Excellent 

30

Province of Florence / San Casciano in Val di Pesa

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 65 km
  • Child friendly
  • Ask about pets

 …see more

from £87 / night

£479 - £874 / week

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from £87 / night

20

Villetta - Mercatale di Val di Pesa villa sleeps 7

San Casciano in Val di Pesa / Mercatale di Val di Pesa

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome to Villetta. This is a freestanding smaller type of Villa with its private garden of 3000 m2 ....in the Chianti Classico. With spacious living and tastefully decorated. We offer 2 double and 1 single bedroom. Sofabed for 2 persons. 2 marble bathrooms. Villett  …see more

from £1243 / night

£8696 / week

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from £1243 / night

24

Old House in Chianti Near Florence - San Casciano in Val di Pesa farmhouse sleeps 4

Province of Florence / San Casciano in Val di Pesa

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The Torriano is located at the highest point of the scenic road that leads to the Castle of Bibbione Montefiridolfi. The characteristic landscape of Chianti and sunsets that you enjoy are unforgettable. The house is surrounded by a beautiful lawn with fruit trees and ol  …see more

from £114 / night

£522 / week

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from £114 / night

9

34477-Apartment Chianti - Montefiridolfi apartment sleeps 6

San Casciano in Val di Pesa / Montefiridolfi

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
The Fattoria Montignana is made up of well furnished apartments and a relaxing informal garden. In total, Fattoria Montignana offers 11 apartments which have been carefully restored and furnished following the typical Tuscan style. It is located where the vines of the  …see more

from £87 / night

£607 / week

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from £87 / night

13

Province of Florence / San Casciano in Val di Pesa

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

 …see more

from £44 / night

£305 - £427 / week

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from £44 / night

24

Villa Corti - San Casciano in Val di Pesa villa sleeps 12

Province of Florence / San Casciano in Val di Pesa

4 12 7 nights min

  • 4 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 115 km
  • Swimming pool
  • Child friendly
This is an independent villa, covering 200 square metres, and extending over two storeys, plus the traditional Tuscan dovecot on its rooftop, now converted into a luxurious bathroom. Although recently fully renovated, the interiors nonetheless retain many typical charac  …see more

from £131 / night

£914 - £2261 / week

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from £131 / night

(1) Excellent 

20

Casa delle Rose - Mercatale di Val di Pesa villa sleeps 10

San Casciano in Val di Pesa / Mercatale di Val di Pesa

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Casa delle Rose is a wonderful villa with its private rose garden,fountain and private traverin swimming pool. In Chianti Classico You find here a fine living room, 5 tastefully decorated bedrooms with double beds (200x200cm), 4 marble bathrooms.....a very complete Tu  …see more

from £1243 / night

£8696 / week

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from £1243 / night

(1) Excellent 

57

Il Nespolo - Campoli in Chianti cottage sleeps 6

San Casciano in Val di Pesa / Campoli in Chianti

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 120 km
  • Child friendly
  • Ask about pets
The house is split over two levels.On the ground floor there is a large dining-room with a working large open fire place and spacious modern kitchen.The upper level is the living area consisting of 2 double bedrooms and 1 bedroom with 2 single beds, a large lounge with  …see more

from £114 / night

£757 / week

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from £114 / night

0

Province of Florence / San Casciano in Val di Pesa

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Pet friendly

 …see more

from £314 / night

£2192 - £3987 / week

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from £314 / night

24

Province of Florence / San Casciano in Val di Pesa

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

Pricing unknown

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Pricing unknown

11

Province of Florence / San Casciano in Val di Pesa

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Private garden

 …see more

from £69 / night

£479 / week

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from £69 / night

17

San Casciano in Val di Pesa / Campoli in Chianti

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £79 / night

£435 / week

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from £79 / night

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