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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193 Vacation rentals

(3) 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 $1504 / night

$11698 - $14583 / week

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from $1504 / night

(15) Excellent 

25

Vacation villa with swimming 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
  • Beach/lakeside relaxation
  • Nearest beach 84 mi
  • 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 $319 / night

$1226 - $2229 / week

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from $319 / night

(2) Excellent 

23

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

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
  • 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 $78 / night

$669 - $892 / week

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from $78 / 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 $290 / night

$1839 - $3175 / week

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from $290 / 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 $1282 / night

$8801 - $13090 / week

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Responds fast!
avg. 3 hours 28 minutes

from $1282 / night

7

Vacation apartment rental

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 Space …see more

Pricing unknown

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Pricing unknown

(4) 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 $65 / night

$424 - $591 / week

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from $65 / 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 $717 / night

$5014 - $5743 / week

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from $717 / night

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 $558 / night

$3900 - $5014 / week

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from $558 / night

(2) 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
  • 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 $64 / night

$446 - $554 / week

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from $64 / night

(16) 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 $95 / night

$624 / week

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Responds fast!
avg. 2 hours 36 minutes

from $95 / 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 $255 / night

$1783 - $1973 / week

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from $255 / 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 $130 / night

$751 - $1579 / week

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from $130 / night

8

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
  • Private garden
Imagine you are on top of a hill and you can dominate the two valleys and enjoy the sunsets of every ray, this is just a taste. the large garden, surrounded by tall trees and laurels perfectly framing the barn we totally restore from top to bottom with my family. The R …see more

from $112 / night

$558 - $808 / week

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Responds fast!
avg. 3 hours 20 minutes

from $112 / 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 $140 / night

$836 - $1059 / week

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from $140 / night

(29) 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 $94 / night

$613 - $1057 / week

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Responds fast!
avg. 1 hour 32 minutes

from $94 / night

(1) 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 $100 / night

$691 / week

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from $100 / night

20

Vacation villa with shared pool in Mercatale di Val di Pesa

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 $1592 / night

$11141 / week

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from $1592 / 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 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 $134 / night

$936 - $1248 / week

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from $134 / 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 $78 / night

$446 / week

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from $78 / 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 $95 / night

$624 / week

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Responds fast!
avg. 2 hours 36 minutes

from $95 / night

23

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 $125 / night

$735 - $1219 / week

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from $125 / night

16

Vacation home 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
  • Private garden
House "La Villa" is a small independent building free on 4 sides, completely renovated, with entrance, garden and private pool. It has two bedrooms for four comfortable seats, with the possibility of two additional beds on the sofa bed in the living room instead. It has …see more

from $101 / night

$613 - $1337 / week

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from $101 / 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 $1605 / night

$11229 / week

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from $1605 / night

11

San Casciano in Val di Pesa Vacation apartment rental

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 $325 / night

$2273 - $2886 / week

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from $325 / 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 $207 / night

$1449 - $2451 / week

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from $207 / 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 $73 / night

$457 / week

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from $73 / night

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 $239 / night

$1672 - $2897 / week

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from $239 / night

20

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 $193 / night

$1128 - $1976 / week

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from $193 / 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 $190 / night

$1226 - $1861 / week

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from $190 / 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 $67 / night

$446 / week

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from $67 / night

(2) 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 $1592 / night

$11141 / week

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from $1592 / 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 $95 / night

$624 - $858 / week

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from $95 / 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 $101 / night

$101 / week

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from $101 / 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 $101 / night

$613 / week

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from $101 / night

13

Vacation barn 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
  • Child friendly
  • Ask about pets
  • Private garden
It is a barn, completely renovated, on 2 levels, 80 sqm, with a Pergola outside where you can make beautiful outdoor breakfasts. On the ground floor: living room, kitchen, bathroom with shower. 2 bedrooms upstairs with large window overlooks the garden of 2000 sqm.In th …see more

Pricing unknown

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Pricing unknown

9

Vacation barn in Mercatale di Val di Pesa

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

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
This is a typical Tuscan barn completely renovated. Composed of two layers (80sqm): on the first floor, large living room, kitchen, bathroom with shower; the second two bedrooms and the ability to add a single bed in one of the two rooms. The House is immersed in …see more

Pricing unknown

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Pricing unknown

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 $780 / night

$5459 - $7130 / week

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from $780 / 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 $70 / night

$400 - $702 / week

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from $70 / night

(2) Excellent 

32

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

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
A beautiful villa in the Chianti Classico region, a private panoramic pool with salt system, stunning landscapes with vineyards and olive groves, a lot of original activities to do. All this and more you will find in Montrogoli, just a few minutes drive from all ameniti …see more

from $390 / night

$1894 - $4390 / week

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from $390 / night

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