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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7,988 Vacation rentals

(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 $106 / night

$694 - $954 / week

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from $106 / night

(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 $1,766 / night

$12,390 - $14,744 / week

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from $1,766 / 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

$930 - $1,177 / week

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from $155 / 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 $323 / night

$2,045 - $3,531 / week

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from $323 / 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 $100 / night

$694 - $1,115 / week

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from $100 / 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
The Casale FURNACE, consists of three apartments: - "La Villa" of 100 square meters, intimate, harvest, surrounded by garden - "La Grande" of 160 square meters, located on the first floor of ancient building floor, spacious, with beautiful front lawn - "La Loggia" of 10 …see more

from $88 / night

$620 - $1,237 / week

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from $88 / night

(3) Excellent 

15

San Casciano in Val di Pesa Vacation apartment rental

Province of Florence / San Casciano in Val di Pesa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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 $71 / night

$496 - $564 / week

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from $71 / night

(5) Very Good 

14

Montefiridolfi Vacation home rental

San Casciano in Val di Pesa / Montefiridolfi

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Private garden
In the green hills of San Casciano Val di PESA, in the heart of Chianti between Florence and Siena, the comfort of a House recently renovated, a panoramic view, the relaxation of a large and quiet garden. Surrounded by farms of direct production of olive oil and wine, t …see more

from $62 / night

$384 - $645 / week

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from $62 / 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

$508 / week

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from $81 / 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 $278 / night

$1,942 - $2,195 / week

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from $278 / 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 $100 / night

$682 - $1,431 / week

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from $100 / 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 $372 / night

$2,478 - $4,337 / week

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Responds fast!
avg. 2 hours 42 minutes

from $372 / night

(30) 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

$694 - $1,175 / week

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Responds fast!
avg. 1 hour 42 minutes

from $109 / 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 $1,425 / night

$9,788 - $14,558 / week

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Responds fast!
avg. 2 hours 40 minutes

from $1,425 / 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 $75 / night

$434 - $694 / week

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Responds fast!
avg. 1 hour 38 minutes

from $75 / 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 $1,399 / night

$9,788 - $11,646 / week

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from $1,399 / night

24

Vacation apartment in San Casciano in Val di Pesa

Province of Florence / San Casciano in Val di Pesa

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
Modern and comfortable apartment for 2/4 persons with kitchen, living, bedroom, bathroom. Equipped with kitchenware, bed linen, bedroom and bathroom. Washing Machine. It is located in a strategic position in the Centre of San Casciano val di Pesa, a few km from Florenc …see more

from $87 / night

$496 / 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

$627 - $1,134 / week

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from $108 / 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 Florence (18 k …see more

from $1,381 / night

$9,664 - $14,620 / week

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from $1,381 / 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 $75 / night

$496 / week

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from $75 / 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 $471 / night

$3,296 / week

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from $471 / 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

$496 / week

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from $87 / night

20

San Casciano in Val di Pesa Vacation farmhouse rental

Province of Florence / San Casciano in Val di Pesa

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • 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 $77 / night

$538 - $894 / week

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from $77 / 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 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • 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

$434 / week

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from $62 / 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 $805 / night

$5,633 - $7,081 / week

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from $805 / 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 $266 / night

$1,859 - $3,222 / week

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from $266 / night

11

Apartment rental in San Casciano in Val di Pesa with shared pool

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
This 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. The lovely estate on the western fringe of Chianti is owned by one …see more

from $151 / night

$1,053 - $1,314 / week

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from $151 / 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 $100 / night

$694 / week

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from $100 / night

28

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

Province of Florence / San Casciano in Val di Pesa

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
The Casale FURNACE, consists of three apartments: - "La Villa" of 100 square meters, intimate, harvest, surrounded by garden - "La Grande" of 160 square meters, located on the first floor of ancient building floor, spacious, with beautiful front lawn - "La Loggia" of 10 …see more

from $80 / night

$558 - $1,052 / week

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from $80 / night

(3) Excellent 

15

Vacation farmhouse with swimming pool, tennis court 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
  • Pet friendly
Podere Caldio is a beautiful property located in the center of about 20 hectares of land, most of which consists of vineyards and olive groves, with direct sales of wine and oil production. Located in a panoramic position and well-ventilated, immersed in the peaceful gr …see more

from $106 / night

$738 - $1,177 / week

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from $106 / night

16

Vacation tower rental

Province of Florence / San Casciano in Val di Pesa

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Nearest beach 100 mi
  • Child friendly
  • Private garden
In the heart of Chianti, 20 Km from the center of Florence, spend your holidays or your weekend in Torre del Chianti, a 360 ° panoramic view, the view will range characteristic of vineyards and olive groves of the area. A few kilometers separate Siena, from this site. P …see more

from $112 / night

$682 / week

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from $112 / 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 $211 / night

$1,363 - $2,131 / week

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from $211 / 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 $708 / night

$4,956 - $5,823 / week

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from $708 / night

24

Vacation home rental

Province of Florence / San Casciano in Val di Pesa

8 14 7 nights min

  • 8 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 $885 / night

$6,195 - $8,413 / week

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from $885 / 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

$1,078 / week

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from $161 / night

24

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

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
  • 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 $119 / night

$835 - $1,756 / week

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from $119 / night

96

Vacation barn in Chiesanuova

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
Salve Regina is a pretty country style villa Florentine, a short distance from the Chianti town Tavernuzze. It's wonderful position not far from the main roads to Florence, Siena and into the Chianti, makes this a fantastic property for sight-seeing. There is also a res …see more

from $230 / night

$1,611 - $2,416 / week

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Responds fast!
avg. 2 hours 19 minutes

from $230 / 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

$651 / week

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from $93 / night

(2) Excellent 

19

Vacation apartment with shared pool in Mercatale di Val di Pesa

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 $1,770 / night

$12,390 / week

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from $1,770 / 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

$682 / week

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Responds fast!
avg. 3 hours 29 minutes

from $93 / night