50 Best Vacation Rentals in San Casciano in Val di Pesa - Holiday Lettings - Cabins

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San Casciano in Val di Pesa

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244 Vacation rentals

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24

Villa rental in San Casciano in Val di Pesa with swimming pool

Province of Florence / San Casciano in Val di Pesa

4 12 7 nights min

  • 4 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 115 mi
  • 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 $228 / night

$1590 - $2756 / week

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from $228 / night

(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 $75 / night

$446 / week

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from $75 / night

(2) Excellent 

24

San Casciano in Val di Pesa Vacation villa rental

Province of Florence / San Casciano in Val di Pesa

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 80 mi
  • 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 $532 / night

$3720 - $5464 / week

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from $532 / night

(3) Excellent 

39

Vacation villa rental

Province of Florence / San Casciano in Val di Pesa

8 16 1 night min

  • 8 bedrooms
  • Sleeps 16
  • 1 night min
  • Nearest beach 90 mi
  • 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 consi  …see more

from $1431 / night

$10572 - $11871 / week

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from $1431 / night

27

Vacation villa with swimming pool in San Casciano in Val di Pesa

Province of Florence / San Casciano in Val di Pesa

11 15 7 nights min

  • 11 bedrooms
  • Sleeps 15
  • 7 nights min
  • Nearest beach 120 mi
  • 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 $1197 / night

$8373 - $9963 / week

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from $1197 / night

24

Vacation apartment with swimming pool in Montefiridolfi

San Casciano in Val di Pesa / Montefiridolfi

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 90 mi
  • 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 $243 / night

$1696 - $1877 / week

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from $243 / night

26

Vacation villa accommodation

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 $1272 / night

$8373 - $9963 / week

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from $1272 / night

(15) Excellent 

20

Vacation b&b in San Casciano in Val di Pesa

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 fo  …see more

from $96 / night

$668 - $705 / week

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from $96 / night

(2) Excellent 

23

Villa rental in San Casciano in Val di Pesa with swimming pool

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-t  …see more

from $276 / night

$1749 - $3021 / week

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from $276 / night

(28) Excellent 

25

San Casciano in Val di Pesa Vacation farmhouse rental

Province of Florence / San Casciano in Val di Pesa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 83 mi
  • 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 $84 / night

$542 - $1001 / week

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from $84 / night

96

San Casciano in Val di Pesa / Chiesanuova

4 8 7 nights min

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

 …see more

from $197 / night

$1378 - $2332 / week

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from $197 / night

(4) Excellent 

14

San Casciano in Val di Pesa Vacation b&b rental

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 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  …see more

from $96 / night

$668 - $705 / week

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from $96 / night

8

Vacation apartment with shared pool in San Casciano in Val di Pesa

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
  • Pet friendly
Two floors apartment in the heart of Chianti Classico with private and equipped garden and free access to the main swimming pool of Villa Le Corti. The apartment is 100 metres far from Osteria and Wineshop Le Corti where guests are welcome for a lunch, guided tour of t  …see more

from $85 / night

$594 / week

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from $85 / 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 $133 / night

$795 - $1007 / week

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from $133 / night

(1) Excellent 

28

Vacation apartment in San Casciano in Val di Pesa

Province of Florence / San Casciano in Val di Pesa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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, a double sofa bed in the living room. The apartment is on two floors plus a large gar  …see more

from $85 / night

$594 - $817 / week

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from $85 / night

24

Vacation home rental

Province of Florence / San Casciano in Val di Pesa

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The La Corte estate stretches out over a hillside covered with vineyards, olive trees and woodland. It is set in the very heart of Chianti near the main road from Florence to Siena, only 16 km south of Florence. This lovely estate on the western fringe of Chianti is own  …see more

from $742 / night

$5194 - $6783 / week

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from $742 / night

19

Vacation farmhouse in San Casciano in Val di Pesa

Province of Florence / San Casciano in Val di Pesa

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • 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 $119 / night

$699 - $1160 / week

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from $119 / night

(2) Excellent 

23

Province of Florence / San Casciano in Val di Pesa

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from $75 / night

$583 - $848 / week

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from $75 / night

(1) Very Good 

19

Apartment rental in Campoli in Chianti with swimming pool

San Casciano in Val di Pesa / Campoli in Chianti

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 110 mi
  • 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 $181 / night

$1166 - $1936 / week

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from $181 / night

(4) Excellent 

22

Vacation apartment in San Casciano in Val di Pesa

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 $64 / night

$424 / week

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from $64 / night

(1) Very Good 

23

Vacation apartment in San Casciano in Val di Pesa

Province of Florence / San Casciano in Val di Pesa

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • 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 $85 / night

$594 - $817 / week

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from $85 / night

37

Province of Florence / San Casciano in Val di Pesa

2 4 1 night min

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

 …see more

from $38 / night

$260 / week

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from $38 / night

15

San Casciano in Val di Pesa Vacation home accommodation

Province of Florence / San Casciano in Val di Pesa

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This is the perfect starting point to explore Tuscany. Located in the heart of Chianti, Borgo in Rosa is just 20 minutes from Florence, 50 minutes from Siena, one hour from Lucca, and all of the beautiful hill towns of Chianti are within easy reach. The location couldn&  …see more

from $309 / night

$2163 - $2745 / week

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from $309 / night

23

Mercatale di Val di Pesa Vacation farmhouse rental

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

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • 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 $93 / night

$537 - $937 / week

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from $93 / night

19

Vacation villa with swimming pool in San Casciano in Val di Pesa

Province of Florence / San Casciano in Val di Pesa

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Surrounded by vineyards and olive groves, Casale Classico is perfect for five couples or an extended family, and the location couldn't be better. Located in the heart of Tuscany's Chianti Classico region and set on an idyllic hillside just 15 minutes from Flor  …see more

from $1151 / night

$8055 - $12506 / week

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from $1151 / 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 $69 / night

$435 / week

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from $69 / night

29

Province of Florence / San Casciano in Val di Pesa

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly

 …see more

from $64 / night

$371 - $594 / week

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from $64 / 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 $75 / night

$424 / week

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from $75 / night

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

Pricing unknown

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Pricing unknown

8

Province of Florence / San Casciano in Val di Pesa

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Private garden

 …see more

from $106 / night

$530 - $769 / week

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from $106 / 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
  • Pet friendly

 …see more

from $117 / night

$817 - $1188 / week

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from $117 / night

24

Vacation villa rental

Province of Florence / San Casciano in Val di Pesa

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The La Corte estate stretches out over a hillside covered with vineyards, olive trees and woodland. It is set in the very heart of Chianti near the main road from Florence to Siena, only 16 km south of Florence. This lovely estate on the western fringe of Chianti is own  …see more

from $773 / night

$5406 - $7313 / week

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from $773 / night

(1) Excellent 

57

Campoli in Chianti Vacation cottage rental

San Casciano in Val di Pesa / Campoli in Chianti

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 120 mi
  • 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  …see more

from $138 / night

$923 / week

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from $138 / 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 $371 / night

$1802 - $4176 / week

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from $371 / night

24

Vacation farmhouse with shared pool in Mercatale di Val di Pesa

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

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • 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 $184 / night

$1073 - $1880 / week

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from $184 / 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

San Casciano in Val di Pesa Vacation villa rental

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 $530 / night

$3710 / week

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from $530 / night

(1) Excellent 

24

Province of Florence / San Casciano in Val di Pesa

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from $105 / night

$732 - $1235 / week

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from $105 / night

(1) Excellent 

20

Vacation villa with shared pool in Mercatale di Val di Pesa

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 $1515 / night

$10599 / week

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from $1515 / 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 $95 / night

$658 / week

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from $95 / night