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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211 Vacation rentals

(14) 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 $326 / night

$1194 - $2170 / week

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from $326 / 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
  • Private garden

from $76 / night

$651 - $868 / week

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from $76 / 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 for a full quote. …see more

from $98 / night

$684 - $722 / week

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from $98 / 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 $92 / night

$597 - $1024 / week

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from $92 / night

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

from $109 / night

$543 - $787 / week

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from $109 / 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 …see more

from $62 / night

$434 - $540 / week

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from $62 / night

(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 $1465 / night

$10821 - $12150 / week

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from $1465 / 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 $87 / night

$608 / week

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from $87 / 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

from $136 / night

$814 - $1031 / week

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from $136 / 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

from $67 / night

$434 - $456 / week

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from $67 / 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 $283 / night

$1790 - $3092 / week

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from $283 / 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 quote. I will b …see more

from $98 / night

$684 - $722 / week

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from $98 / 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 $1248 / night

$8570 - $12746 / week

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from $1248 / 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 $543 / night

$3797 - $4882 / week

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from $543 / 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 $248 / night

$1736 - $1922 / week

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from $248 / 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 $233 / night

$1628 - $2821 / week

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from $233 / 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

(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 $185 / night

$1194 - $1812 / week

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from $185 / night

17

Province of Florence / San Casciano in Val di Pesa

1 2 2 nights min

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

from $49 / night

$358 / week

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from $49 / 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 $122 / night

$715 - $1187 / week

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from $122 / night

(3) Very Good 

24

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

from $82 / night

$597 / week

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from $82 / 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 $188 / night

$1098 - $1924 / week

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from $188 / night

(1) Excellent 

16

Vacation apartment with shared pool in Mercatale di Val di Pesa

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

1 4 7 nights min

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

from $1550 / night

$10848 / week

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from $1550 / 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 $93 / night

$608 - $836 / week

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from $93 / 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 $760 / night

$5316 - $6943 / week

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from $760 / 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

from $107 / night

$749 - $1264 / week

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from $107 / night

14

Province of Florence / San Casciano in Val di Pesa

7 20 1 night min

  • 7 bedrooms
  • Sleeps 20
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $1085 / night

$7051 / week

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from $1085 / night

9

San Casciano in Val di Pesa Vacation farmhouse rental

Province of Florence / San Casciano in Val di Pesa

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 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 $166 / night

$1161 - $1302 / week

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from $166 / 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 $68 / night

$390 - $684 / week

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from $68 / 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

from $120 / night

$836 - $1215 / week

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from $120 / night

(3) Excellent 

15

Province of Florence / San Casciano in Val di Pesa

2 4 1 night min

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

from $93 / night

$646 / week

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from $93 / night

19

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 $95 / night

$549 - $959 / week

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from $95 / night

(1) Excellent 

21

Province of Florence / San Casciano in Val di Pesa

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Child friendly
  • Ask about pets
  • Private garden

from $163 / night

$836 / week

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from $163 / night

9

San Casciano in Val di Pesa / Campoli in Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets

Pricing unknown

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Pricing unknown

(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 $698 / night

$4882 - $5592 / week

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from $698 / night

16

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

from $98 / night

$597 / week

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from $98 / night

13

Province of Florence / San Casciano in Val di Pesa

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly

from $54 / night

$377 - $528 / week

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from $54 / 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 $791 / night

$5533 - $7485 / week

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from $791 / 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 $126 / night

$732 - $1538 / week

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from $126 / night

20

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

Province of Florence / San Casciano in Val di Pesa

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Villa Pisignano is a characteristic Tuscan country house (“Leopold style”) situated on the Florentine hills, approx. 3 kilometers away from the small town of San Casciano Val di Pesa. This villa, surrounded by beautiful olive groves and vineyards, is in quiet and panora …see more

from $345 / night

$2414 - $4123 / week

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from $345 / night

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