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

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129 Holiday homes

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

1 / 16

Province of Florence / San Casciano in Val di Pesa

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Nearest beach 100 km; Swimming pool; Not suitable for children;
 …see more

from £56 / night

£334 - £359 / week

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from £56 / night

1 / 46

Tuscan Villa on top of hill Panoramic Gorgeous Vie - San Casciano in Val di Pesa farmhouse sleeps 6

Province of Florence / San Casciano in Val di Pesa

2 6 1 night min stay

  • 2 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
700 yr-old FarmHouse renovated to Western standards.Sits on top of a gorgeous pano hillside, saltpool,a/c.Directly off Chianti Classico wine road.5 min walk to Le Corti Winery.17 mins drive to Florence, Piazza Michelangelo. PerfectLocation! Stunning! It is considered a  …see more

from £385 / night

£1624 / week

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from £385 / night

(4) Excellent 

1 / 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 stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: 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 £73 / night

£509 / week

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from £73 / night

1 / 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
Key info: 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 £189 / night

£898 - £1154 / week

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from £189 / night

(1) Very Good 

1 / 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 stay

  • 1 bedroom
  • Sleeps 2
  • 4 nights min stay
Key info: Nearest beach 100 km; Child friendly ; Car essential;
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

£308 / week

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from £48 / night

1 / 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
Key info: 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 £231 / night

£1385 - £2154 / week

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from £231 / night

1 / 101

Incantesimo - Leonardo - San Casciano in Val di Pesa apartment sleeps 5

Province of Florence / San Casciano in Val di Pesa

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 127 km; Swimming pool; Child friendly ;
Leonardo is a roomy and luminous apartment in the heart of Chianti. It is located on the second floor and is easily accessible by an elevator. You'll find a large and cozy living-cum-dining room with its own fireplace, a double bed and a bathroom with a shower.&nbs  …see more

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1 / 18

Province of Florence / San Casciano in Val di Pesa

2 5 7 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Nearest beach 100 km; Child friendly ; Car advised;
 …see more

from £55 / night

£385 / week

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from £55 / night

(1) Excellent 

1 / 24

Province of Florence / San Casciano in Val di Pesa

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
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from £119 / night

£830 / week

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from £119 / night

1 / 15

Chianti luxury villa, 5 bedrooms, pool, view - San Casciano in Val di Pesa villa sleeps 11

Province of Florence / San Casciano in Val di Pesa

5 11 7 nights min stay

  • 5 bedrooms
  • Sleeps 11
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; No pets allowed;
Luxury home near Florence, San Giminiano, Siena; sleeps 11 + 2 children The house belonged to the florentine families of Strozzi and Cavalcanti in 16th century. It was restored preserving the structure from the Renaissance, with its high ceilings and stone capitals. Co  …see more

from £428 / night

£2992 / week

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from £428 / night

(4) Excellent 

1 / 30

Province of Florence / San Casciano in Val di Pesa

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
Key info: Nearest beach 65 km; Child friendly ; Car advised;
 …see more

from £86 / night

£471 - £859 / week

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from £86 / night

1 / 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
Key info: 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 £146 / night

£941 - £1825 / week

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from £146 / night

1 / 20

67560006 - San Casciano In Val - Mercatale di Val di Pesa farmhouse sleeps 10

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

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Child friendly ; Pet friendly;
Beautiful farming estate comprising 6 restored units situated on the Chianti hills, a short distance from the village of Mercatale (with general stores) and 22 km from Florence away. This property offers large outdoor areas and a nice panoramic pool with splendid views  …see more

from £149 / night

£875 - £1366 / week

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from £149 / night

1 / 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 stay

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
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 £1222 / night

£8548 / week

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from £1222 / night

1 / 8

Province of Florence / San Casciano in Val di Pesa

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Swimming pool; Not suitable for children; No pets allowed;
 …see more

from £86 / night

£428 - £513 / week

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from £86 / night

(1) Excellent 

1 / 57

Il Nespolo - Campoli in Chianti cottage sleeps 6

San Casciano in Val di Pesa / Campoli in Chianti

3 6 3 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Nearest beach 120 km; Child friendly ; Car essential;
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 £112 / night

£744 / week

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from £112 / night

(1) Very Good 

1 / 21

San Casciano in Val di Pesa / Chiesanuova

1 3 2 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 2 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
 …see more

from £60 / night

£342 / week

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from £60 / night

(15) Excellent 

1 / 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 stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: 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 £73 / night

£479 - £539 / week

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from £73 / night

1 / 13

Province of Florence / San Casciano in Val di Pesa

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Child friendly ; Ask about pets; Private garden;
 …see more

from £77 / night

£445 / week

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from £77 / night

1 / 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
Key info: 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 £265 / night

£1590 - £2394 / week

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from £265 / night

(2) Excellent 

1 / 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
Key info: Swimming pool; Child friendly ; Car essential;
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 £223 / night

£1411 - £2436 / week

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from £223 / night

1 / 23

Province of Florence / San Casciano in Val di Pesa

1 4 3 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay
Key info: Child friendly ; Ask about pets;
 …see more

from £56 / night

£351 / week

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from £56 / night

(2) Excellent 

1 / 23

Province of Florence / San Casciano in Val di Pesa

2 6 1 night min stay

  • 2 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Swimming pool; Child friendly ; Ask about pets;
 …see more

from £86 / night

£513 / week

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from £86 / night

1 / 4

Province of Florence / San Casciano in Val di Pesa

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Nearest beach 110 km; Child friendly ; Car advised;
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from £82 / night

£556 / week

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from £82 / night

(1) Excellent 

1 / 21

Province of Florence / San Casciano in Val di Pesa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Child friendly ; Car advised; Ask about pets;
 …see more

from £120 / night

£659 - £727 / week

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from £120 / night

1 / 29

Province of Florence / San Casciano in Val di Pesa

1 4 1 night min stay

  • 1 bedroom
  • Sleeps 4
  • 1 night min stay
Key info: Child friendly ; No pets allowed;
 …see more

from £52 / night

£300 - £479 / week

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from £52 / night

(2) Excellent 

1 / 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
Key info: Not suitable for children; Car advised; No pets allowed;
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 £49 / night

£342 - £425 / week

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from £49 / night

1 / 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 stay

  • 4 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: 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 £129 / night

£898 - £2223 / week

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from £129 / night

1 / 20

Appartamento Villa I Chisci - 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
Key info: Child friendly ; Air conditioning; Pet friendly;
2BR apartment in a prestigious villa located close to village centre. Car is not required. Florence easy to reach by bus. WiFi included. TV Sat. Private parking. Spacious garden, BBQ. Owners on site. Minimum stay 4 nights, change over day Saturday or Sunday. The apartm  …see more

from £69 / night

£479 - £659 / week

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from £69 / night

(1) Excellent 

1 / 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 stay

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min stay
Key info: 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 £65 / night

£449 - £629 / week

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from £65 / night

(3) Excellent 

1 / 15

Province of Florence / San Casciano in Val di Pesa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
 …see more

from £73 / night

£509 - £850 / week

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from £73 / night

(1) Excellent 

1 / 32

Province of Florence / San Casciano in Val di Pesa

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
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from £214 / night

£1112 - £4274 / week

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from £214 / night

1 / 20

Stunning Villa in the Chianti - San Casciano in Val di Pesa villa sleeps 9

Province of Florence / San Casciano in Val di Pesa

5 9 Min stay varies

  • 5 bedrooms
  • Sleeps 9
  • Min stay varies
Key info: Child friendly ; Car advised; No pets allowed;
This stunning holiday villa in Chianti is located near the village of San Casciano Val di Pesa (2 km), a tiny medieval hamlet at 15 km from Florence, renowned for its Chianti Classico red wine and olive oil. The villa is an historical listed mansion built during the sec  …see more

from £428 / night

£1966 - £2778 / week

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from £428 / night

1 / 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
Key info: 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 £1112 / night

£6411 - £7607 / week

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from £1112 / night

(1) Excellent 

1 / 21

San Casciano in Val di Pesa / Campoli in Chianti

2 6 3 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
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from £107 / night

£642 - £812 / week

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from £107 / night

1 / 17

San Casciano in Val di Pesa / Campoli in Chianti

1 3 3 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
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from £77 / night

£428 - £599 / week

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from £77 / night

1 / 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
Key info: Swimming pool; Child friendly ; Car essential;
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 £1112 / night

£6411 - £7607 / week

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from £1112 / night

1 / 14

15685001 - San Casciano In Val - San Casciano in Val di Pesa farmhouse sleeps 4

Province of Florence / San Casciano in Val di Pesa

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Child friendly ; Pet friendly;
One of the charming villas in Chianti region. Nice farmhouse completely restored situated in quiet and panoramic location affording extensive views over the Chianti Classico hills. The villa comprises 3 spacious and comfortable apartments offering tastefully decorated i  …see more

from £53 / night

£311 - £483 / week

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from £53 / night

1 / 37

Province of Florence / San Casciano in Val di Pesa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 60 km; Child friendly ; Pet friendly;
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from £30 / night

£210 / week

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from £30 / night

1 / 19

Cerbaia - 63582001 - San Casciano in Val di Pesa farmhouse sleeps 5

Province of Florence / San Casciano in Val di Pesa

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Child friendly ; Ask about pets; Private garden;
Charming independent, recently-restored house situated in the Chianti Classico area on the road connecting the medieval village of San Casciano to the village of Cerbaia. The house is welcoming and tastefully furnished with a mix of modern and traditional furniture pre  …see more

from £98 / night

£570 - £945 / week

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from £98 / night

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