Cycling holiday villas and apartments San Casciano in Val di Pesa | Holiday Lettings

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44 Holiday homes

Filters applied: Cycling holidays (44)

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

(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

(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

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

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 

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) 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

(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

(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

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

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

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

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

  • 5 bedrooms
  • Sleeps 11
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
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 £435 / night

£3044 / week

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from £435 / night

(4) Excellent 

22

Delicious country house - San Casciano in Val di Pesa apartment sleeps 3

Province of Florence / San Casciano in Val di Pesa

1 3 4 nights min

  • 1 bedroom
  • Sleeps 3
  • 4 nights min
  • Child friendly
  • Air conditioning
  • Private garden
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 £53 / night

£348 / week

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from £53 / night

47

Province of Florence / San Casciano in Val di Pesa

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 60 km
  • Child friendly
  • Pet friendly

 …see more

from £31 / night

£214 / week

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from £31 / night

(1) Excellent 

21

Province of Florence / San Casciano in Val di Pesa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden

 …see more

from £122 / night

£670 - £740 / week

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from £122 / night

17

Province of Florence / San Casciano in Val di Pesa

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Air conditioning
  • Pet friendly
  • Private garden

 …see more

from £40 / night

£287 / week

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from £40 / night

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

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • 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 £392 / night

£1653 / week

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from £392 / night

(3) Excellent 

15

Province of Florence / San Casciano in Val di Pesa

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £74 / night

£518 / week

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from £74 / night

18

Province of Florence / San Casciano in Val di Pesa

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 100 km
  • Child friendly
  • Air conditioning

 …see more

from £56 / night

£392 / week

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from £56 / night

(1) Excellent 

16

Atelier 2 - Mercatale di Val di Pesa apartment sleeps 4

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

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Atelier 2 is the smaller of our Atelier Apartments. 80 m in the Chianti Classico. The apartment has a tastefully decorated double bedroom and a very large marble bathroom. The large Atelier of the famous Dutch painter Karel Apple (member of COBRA group) who owned the e  …see more

from £1243 / night

£8696 / week

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from £1243 / night

(2) Excellent 

19

Atelier 1 - Mercatale di Val di Pesa apartment sleeps 6

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

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Atelier 1 is the largest of our Atelier apartments. in the Chianti Classico With 2 tastefully colored double bedrooms and 2 marble bathrooms. The large Atelier of the famous Dutch painter Karel Appel (member of COBRA group) who owned the estate Villa Licia and worked  …see more

from £1243 / night

£8696 / week

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from £1243 / night

(2) Excellent 

23

Province of Florence / San Casciano in Val di Pesa

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £87 / night

£522 / week

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from £87 / night

(2) Excellent 

32

Province of Florence / San Casciano in Val di Pesa

6 12 4 nights min

  • 6 bedrooms
  • Sleeps 12
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £218 / night

£1131 - £3427 / week

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from £218 / night

11

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

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

 …see more

from £192 / night

£1305 / week

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from £192 / night

24

Province of Florence / San Casciano in Val di Pesa

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly

 …see more

from £61 / night

£348 / week

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from £61 / night

4

Province of Florence / San Casciano in Val di Pesa

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 110 km
  • Child friendly

 …see more

from £83 / night

£566 / week

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from £83 / night

(2) Excellent 

35

San Casciano in Val di Pesa / Montefiridolfi

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

 …see more

from £105 / night

£609 / week

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from £105 / night

13

Province of Florence / San Casciano in Val di Pesa

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden

 …see more

from £78 / night

£453 / week

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from £78 / night

7

Chianti Views, WIFI, Perfect for exploring - Mercatale di Val di Pesa apartment sleeps 5

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

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Suitable for children age 5+
This loving decorated home set up in the Chianti hills will have you feeling welcome and serene. It has views that extend right up to the mountains with flowing vines and olive groves. It is an ideal place to stay for tranquility or exploration.....The SpaceThis is a to  …see more

Pricing unknown

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Pricing unknown

(1) Excellent 

18

Fattoria Marzocco 4 - Mercatale di Val di Pesa apartment sleeps 6

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

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Fattoria Marzocco 4 is a spacious apartment, in the Chianti Classico. With nice living, 2 tastefully decorated bedrooms of which one is a grand suite bedroom. 2marble bathrooms. The old Fattoria, renovated during 2 years according to the rules and supervision of the "B  …see more

from £1243 / night

£8696 / week

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from £1243 / night

17

Atelier 3 - Mercatale di Val di Pesa apartment sleeps 6

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

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Atelier 3 is one of our finest Atelier apartments, in the Chianti Classico. With 2 tastefully coloured double bedrooms and 2 marble bathrooms. The large Atelier of the famous Dutch painter Karel Appel (member of COBRA group) who owned the estate Villa Licia and worked  …see more

from £1243 / night

£8696 / week

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from £1243 / night

(1) Terrible 

28

Province of Florence / San Casciano in Val di Pesa

8 25 1 night min

  • 8 bedrooms
  • Sleeps 25
  • 1 night min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

 …see more

from £870 / night

£6087 / week

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from £870 / night

14

B&B ART - San Casciano in Val di Pesa b&b sleeps 16

Province of Florence / San Casciano in Val di Pesa

8 16 1 night min

  • 8 bedrooms
  • Sleeps 16
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
B&B ART; a warm piece of Tuscany in the heart of the Chianti region B&B ART is a charming bed & breakfast conveniently situated in the city centre of San Casciano Val di Pesa, an ancient roman city located in the heart of the Chianti region, close to Florenc  …see more

from £79 / night

£79 / week

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from £79 / night

7

La Palagina - Talente apartment sleeps 5

San Casciano in Val di Pesa / Talente

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Air conditioning
  • Ask about pets
Our home is just 12km from Florence, in the middle of the Tuscany hills. 30min from the towers of San Gimignano, 45min from Siena and the etruscan town of Volterra. It is the ideal place for your family to fully enjoy our Tuscany.The apartment is a fully-renovated flat  …see more

from £174 / night

£1218 / week

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from £174 / night

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