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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8,594 Vacation rentals

(4) Excellent 

45

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 considered …see more

from $1,760 / night

$12,348 - $14,694 / week

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from $1,760 / 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-trees and s …see more

from $321 / night

$2,034 - $3,514 / week

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from $321 / night

(3) Excellent 

15

San Casciano in Val di Pesa Vacation apartment rental

Province of Florence / San Casciano in Val di Pesa

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Nearest beach 90 mi
  • 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 3 adults or 2 adu …see more

from $81 / night

$555 - $611 / week

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from $81 / night

(4) Excellent 

51

San Casciano in Val di Pesa Vacation finca accommodation

Province of Florence / San Casciano in Val di Pesa

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly
Greve Podere is a beautiful recently renovated and in 2017 entered in the tourist circuit. large private pool (13x7) available from 08/07/2018. On the way Chiantigiana, that connects Florence with Siena passing through the evocative landscape of Chianti, Greve Podere is …see more

from $155 / night

$988 - $1,729 / week

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from $155 / night

10

Apartment rental in San Casciano in Val di Pesa

Province of Florence / San Casciano in Val di Pesa

1 5 1 night min

  • 1 bedroom
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Air conditioning
The B & B Art is born from the renovation of an old building of the early twentieth century, and still preserves the architecture and numerous stylish details. The building is now a wonderful bed and breakfast elegant and welcoming, where service and attention to detail …see more

from $124 / night

$222 / week

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from $124 / night

(1) Excellent 

32

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 air Conditioning Room. The apartment is on two floors plus a large garden. Independent …see more

from $105 / night

$692 - $951 / week

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from $105 / night

(1) Very Good 

21

Townhouse rental in Chiesanuova with shared pool

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
If you want luxury and sophisticated elegance, for change! At The Treggiaia you live a simple life in harmony with the surrounding countryside and the artistic beauty of the area, which are countless. You will be greeted with warmth and affection by the owners, who wil …see more

from $87 / night

$494 / week

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from $87 / night

15

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 $108 / night

$624 - $1,128 / week

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from $108 / night

(6) Excellent 

30

Vacation home rental

Province of Florence / San Casciano in Val di Pesa

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 65 mi
  • Child friendly
  • Pet friendly
Villa very spacious and comfortable, surrounded by green countryside of Tuscany, in the heart of Chianti Classico; in one of the most beautiful areas of Tuscany, surrounded by olive groves, vineyards and woods, close to historical and artistic sites.Country house suitab …see more

from $136 / night

$839 - $1,424 / week

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Responds fast!
avg. 3 hours 50 minutes

from $136 / night

13

Vacation b&b with shared pool in San Casciano in Val di Pesa

Province of Florence / San Casciano in Val di Pesa

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
13 years ago we decided to move in the beautiful green area of Chianti. It was definitely a great choice for quality of life. The restructuring of the farmhouse we have designed a part with Bed and Breakfast. We offer you an apartment with bedroom, bathroom, small kitch …see more

from $62 / night

$433 - $778 / week

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from $62 / night

(31) 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 $109 / night

$715 - $1,169 / week

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Responds fast!
avg. 1 hour 49 minutes

from $109 / night

(17) Excellent 

21

Vacation b&b in San Casciano in Val di Pesa

Province of Florence / San Casciano in Val di Pesa

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night 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 $105 / night

$692 / week

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from $105 / 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 $1,418 / night

$9,123 - $14,485 / week

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Responds fast!
avg. 3 hours 26 minutes

from $1,418 / night

17

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 $214 / night

$1,250 - $2,259 / week

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from $214 / night

(4) Excellent 

15

San Casciano in Val di Pesa Vacation b&b rental

Province of Florence / San Casciano in Val di Pesa

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night 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 quote. I will b …see more

from $105 / night

$692 / week

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from $105 / night

(1) Excellent 

21

Apartment rental in Campoli in Chianti with shared pool

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
Surrounded by the vineyards of the Chianti hills, not far from Florence and Siena, Villa Barberino has all the charm of the ancient Tuscan manor houses. In what were once the service spaces of the villa was once the apartment The Campolino she. In it you can find an eas …see more

from $155 / night

$926 - $1,173 / week

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from $155 / night

(1) Excellent 

29

San Casciano in Val di Pesa Vacation villa rental

Province of Florence / San Casciano in Val di Pesa

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
The apartment, part of a Villa, beautiful and with spacious garden is furnished with style and consists of a beautiful entrance, a double living room with big fireplace that opens onto a panoramic terrace, kitchen with fireplace and double bedroom with bathroom. Going d …see more

from $370 / night

$2,466 - $4,315 / week

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Responds fast!
avg. 3 hours 1 minutes

from $370 / night

12

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

Province of Florence / San Casciano in Val di Pesa

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 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 $99 / night

$692 / week

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from $99 / night

(3) Excellent 

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 $705 / night

$4,931 - $5,794 / week

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from $705 / night

(3) Very Good 

23

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

Province of Florence / San Casciano in Val di Pesa

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
2 bedrooms, 2 bathrooms, 1cucina-living room with courtyard, deck chairs, tables, barbecue The Blackthorn is located in Tuscany in the Chianti area, between San Casciano Val di Pesa and Mercatale vp IDEAL FOR FAMILY: GARDEN AND HOME SAFE FOR CHILDREN. Cultivated area al …see more

from $99 / night

$691 - $1,110 / week

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from $99 / 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 $161 / night

$1,075 / week

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from $161 / night

(3) Very Good 

24

Vacation townhouse with shared pool in Chiesanuova

San Casciano in Val di Pesa / Chiesanuova

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Apartment nestled in the green hills around Florence, just 9 kilometres from the city centre. You can enjoy the magnificent view over the Chianti hills and enjoy good wine and oil produced on the spot. The apartment is equipped with every comfort: air conditioning, tv, …see more

from $93 / night

$680 / week

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from $93 / night

18

San Casciano in Val di Pesa Vacation villa rental

Province of Florence / San Casciano in Val di Pesa

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 100 mi
  • Child friendly
  • Air conditioning
Villa of 150 sqm. with 850 m² shady garden with pines, and 3000 square metres of vineyards and olive trees, with two large bedrooms of 20 m2 each, and built-in closets, space accommodated in cots, carrycot. Studio with double bed, living room with fireplace, kitchen 20 …see more

from $80 / night

$556 / week

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Responds fast!
avg. 3 hours 12 minutes

from $80 / night

29

Vacation apartment in San Casciano in Val di Pesa

Province of Florence / San Casciano in Val di Pesa

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
Our apartment is unique for the spectacular views which can be enjoyed from the living room window and room overlooking the gentle slopes of the Chianti hills. We made even more special with a typical Tuscan décor with warm and cozy but comfortable and functional at the …see more

from $74 / night

$433 - $692 / week

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Responds fast!
avg. 1 hour 38 minutes

from $74 / night

(1) Very Good 

23

San Casciano in Val di Pesa Vacation finca rental

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
Apparatmento 4 beds in the heart of the Chianti hills apartment is located in a splendid position overlooking panorominca much of the Toscna strategy position to visit the most important cities of Tuscany, 30 minutes from Florence and Siena 40. It consists of a large li …see more

from $81 / night

$506 / week

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from $81 / night

27

Vacation b&b in San Casciano in Val di Pesa

Province of Florence / San Casciano in Val di Pesa

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
B & B Gepparino is located on the first floor of a building that has four units. Recently renovated, hardwood floors, cozy, airy rooms decorated with recycled materials. Large living room with terrace, where breakfast is served with local meats and cheeses, and homemade …see more

from $87 / night

$574 / week

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from $87 / 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 $1,392 / night

$9,739 - $11,588 / week

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from $1,392 / night

83

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 $265 / night

$1,850 - $3,206 / week

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from $265 / 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 $277 / night

$1,935 - $2,187 / week

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from $277 / night

19

San Casciano in Val di Pesa Vacation villa rental

Province of Florence / San Casciano in Val di Pesa

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Villa Giulia is an ancient residence of the eighteenth century, located in the hills near Florence, where is produced a fine Chianti Classico DOCG, we can sample directly in our cellar, accompanied by delicious cheeses of the surrounding dairy farms. The apartment in th …see more

from $470 / night

$3,285 / week

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from $470 / night

13

B&b rental in San Casciano in Val di Pesa

Province of Florence / San Casciano in Val di Pesa

1 10 3 nights min

  • 1 bedroom
  • Sleeps 10
  • 3 nights min
  • Nearest beach 90 mi
  • Child friendly
  • Pet friendly
Halfway between an apartment and a bed & breakfast, Acquapietra offers 5 beautiful rooms with private bathrooms and common areas such as the lounge, kitchen and terrace, in an old farmhouse nestled in the breathtaking scenery of vineyards and olive groves, with warm Tus …see more

from $111 / night

$728 / week

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from $111 / night

(2) Very Good 

10

Vacation apartment in San Casciano in Val di Pesa

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
Time Palace is one of the oldest buildings on the main street of San Casciano in Val di Pesa, a small medieval village on the outskirts of Florence. Is located in Via Machiavelli, the main street of the village, and features elegant and sober forms due at seventeenth an …see more

from $110 / night

$765 / week

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from $110 / night

(1) Excellent 

24

Vacation home with swimming pool 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
  • Swimming pool
  • Child friendly
  • Private garden
The property is located near San Casciano Val di Pesa, in the heart of Chianti, località VALIGONDOLI, at 500 mt sml, surrounded by greenery. Nearby you will find the best restaurants and places to visit at few kilometers (Florence, Sienna, Greve in Chianti, San Gimignan …see more

from $62 / night

$1,036 - $1,628 / week

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from $62 / night

(1) Very Good 

111

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 $210 / night

$1,359 - $2,124 / week

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from $210 / night

4

Vacation b&b rental

Province of Florence / San Casciano in Val di Pesa

4 3 1 night min

  • 4 bedrooms
  • Sleeps 3
  • 1 night min
  • Nearest beach 110 mi
  • Child friendly
  • Private garden
Poggiolato is an ancient residence of the noble family of Cavalcanti and dates from about the year 1000. Here it seems that he was born Guido Cavalcanti, Dante's friend and INSPIRER of the Dolce Stil Novo. The Poggiolato covers about 5.5 ha. and is surrounded by vineyar …see more

from $93 / night

$648 / week

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from $93 / 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 $74 / night

$494 / week

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from $74 / night

14

B&b rental in San Casciano in Val di Pesa

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 Florence. Sa …see more

from $93 / night

$649 / week

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from $93 / night

28

Vacation home in San Casciano in Val di Pesa

Province of Florence / San Casciano in Val di Pesa

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Located in San Casciano Val di Pesa, a town Mucciana, you must do 2 km of gravel road to reach this structure. The Casale FURNACE, consists of three apartments: - "La Villa" of 100 square meters, intimate, harvest, surrounded by garden - "La Grande" of 160 square meters …see more

from $88 / night

$617 - $1,231 / week

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from $88 / night

25

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

Province of Florence / San Casciano in Val di Pesa

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
San Casciano Val di Pesa - Canaiolo is an apartment of 85 square meters, part of a typical farmhouse recently renovated, Casale Le Lame, surrounded by the untouched countryside of Chianti among vineyards and olive groves. Composition of the apartment: - 1 Large living …see more

from $149 / night

$1,038 - $1,297 / week

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from $149 / 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 $802 / night

$5,614 - $7,057 / week

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from $802 / night