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

Close

View larger map

Also consider

Mercatale di Val di Pesa
24 properties
Campoli in Chianti
9 properties
Ponte di Gabbiano
7 properties
Chiesanuova
5 properties

San Casciano in Val di Pesa

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

230 Vacation rentals

Travelers going to San Casciano in Val di Pesa are booking April dates now. Secure your vacation rental today and have the perfect trip.

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 $1305 / night

$8587 - $10218 / week

Book View

from $1305 / night

(28) Excellent 

25

San Casciano in Val di Pesa Vacation farmhouse rental

Province of Florence / San Casciano in Val di Pesa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 83 mi
  • Suitable for children age 5+
  • Car not necessary
The holiday house is located 300 metres from San Casciano in Val di Pesa centre. Facing the open country from a dominant position, it offers the comforts of a town life and the beauty of the Chianti landscape opening on hills with vineyards and olive trees. There are no  …see more

from $92 / night

$598 - $1027 / week

Book View

from $92 / 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 $1553 / night

$10870 / week

Book View

from $1553 / night

Featured properties

(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 $327 / night

$1196 - $2392 / week

Book View

from $327 / night

(15) Excellent 

20

Vacation b&b in San Casciano in Val di Pesa

Province of Florence / San Casciano in Val di Pesa

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Suitable for children age 5+
  • Ask about pets
  • Private garden
This listing is for the first of the three double bedrooms at " Candida's Chianti House", the NERI ROOM. If you wish to book 2 or 3 rooms at the same time, please contact me for a quote on any of the rooms (Neri, Mattia or Martina) and in the notes ask fo  …see more

from $98 / night

$685 - $723 / week

Book View

from $98 / 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

$609 / week

Book View

from $87 / 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 $546 / night

$3816 - $5604 / week

Inquire View

from $546 / night

(4) Very Good 

14

San Casciano in Val di Pesa / Montefiridolfi

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Private garden

 …see more

from $79 / night

$457 / week

Book View

from $79 / 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 $249 / night

$1740 - $1925 / week

Inquire View

from $249 / night

17

San Casciano in Val di Pesa / Campoli in Chianti

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $98 / night

$544 / week

Book View

from $98 / night

(1) Excellent 

21

San Casciano in Val di Pesa / Campoli in Chianti

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $136 / night

$816 - $1033 / week

Book View

from $136 / night

(1) Very Good 

21

San Casciano in Val di Pesa / Chiesanuova

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from $76 / night

$432 / week

Book View

from $76 / 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 $127 / night

$733 - $1541 / week

Inquire View

from $127 / night

24

Province of Florence / San Casciano in Val di Pesa

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

Pricing unknown

Book View

Pricing unknown

(2) Excellent 

23

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

Province of Florence / San Casciano in Val di Pesa

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa "Casale San Casciano" is a 200 sqm independent villa, which can comfortably accommodate up to 12 people. The Villa overlooks a little lake beside the property and it is located in the typical context of the Chianti area, surrounded by vineyards, olive-t  …see more

from $283 / night

$1794 - $3098 / week

Book View

from $283 / 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 $1553 / night

$10870 / week

Book View

from $1553 / 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

$391 - $685 / week

Inquire View

from $68 / 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 $65 / night

$432 / week

Book View

from $65 / 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 $761 / night

$5327 - $6957 / week

Inquire View

from $761 / night

11

Province of Florence / San Casciano in Val di Pesa

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Private garden

 …see more

Pricing unknown

Book View

Pricing unknown

(2) Excellent 

23

Province of Florence / San Casciano in Val di Pesa

2 5 1 night min

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

 …see more

from $77 / night

$598 - $870 / week

Book View

from $77 / 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 $189 / night

$1100 - $1928 / week

Inquire View

from $189 / 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

 …see more

from $109 / night

$544 - $789 / week

Book View

from $109 / night

100

Vacation apartment 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
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
These vacation homes for 6 people brims over with the style of Chianti. To enjoy sipping a glass of wine outdoors, the apartments have a large porch and its garden area. These apartments affords a living room with a fireplace. Its fully fitted kitchen features its dinin  …see more

from $272 / night

$1631 - $3044 / week

Inquire View

from $272 / night

(4) Excellent 

14

San Casciano in Val di Pesa Vacation b&b rental

Province of Florence / San Casciano in Val di Pesa

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Suitable for children age 5+
  • Ask about pets
  • Private garden
This is the second of the three double bedrooms at " Candida's Chianti House", the MATTIA ROOM. If you wish to book 2 or 3 rooms at the same time, please contact me for a quote on any of the rooms (Neri, Mattia or Martina) and in the notes ask for a full  …see more

from $98 / night

$685 - $723 / week

Book View

from $98 / night

37

Province of Florence / San Casciano in Val di Pesa

2 4 1 night min

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

 …see more

from $174 / night

$1218 / week

Book View

from $174 / night

(1) Very Good 

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
  • Air conditioning
  • Pet friendly
2BR apartment in a prestigious villa located close to village centre. Car is not required. Florence easy to reach by bus. WiFi included. TV Sat. Private parking. Spacious garden, BBQ. Owners on site. Minimum stay 4 nights, change over day Saturday or Sunday. The apartm  …see more

from $93 / night

$609 - $837 / week

Book View

from $93 / 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 consi  …see more

from $1468 / night

$10843 - $12174 / week

Book View

from $1468 / 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

 …see more

from $49 / night

$359 / week

Book View

from $49 / 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

$1631 - $2827 / week

Inquire View

from $233 / night

100

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

Province of Florence / San Casciano in Val di Pesa

2 3 7 nights min

  • 2 bedrooms
  • Sleeps 3
  • 7 nights min
  • Nearest beach 127 mi
  • Swimming pool
  • Child friendly
Giotto This apartment is roomy and luminous with an elegance that is unmatched. It is located on the second floor and is easily reachable by an elevator. You'll find a large and cozy living-cum-dining room with its own fireplace.The apartment's fully equi  …see more

from $193 / night

$1349 - $1702 / week

Inquire View

from $193 / 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

 …see more

from $82 / night

$598 / week

Book View

from $82 / night

100

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
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Furnishings of Chianti air and ancient walls dating back to the Middle Ages are enchanting features of these vacation homes for 4 people. Guests can relish a sunset while tasting some regional wine in the garden or porch which the apartment affords. These apartments hav  …see more

from $207 / night

$1174 - $2218 / week

Inquire View

from $207 / night

96

San Casciano in Val di Pesa / Chiesanuova

4 8 7 nights min

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

 …see more

from $202 / night

$1414 - $2392 / week

Book View

from $202 / 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, a double sofa bed in the living room. The apartment is on two floors plus a large gar  …see more

from $93 / night

$609 - $837 / week

Book View

from $93 / night

(2) Excellent 

7

Province of Florence / San Casciano in Val di Pesa

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly

 …see more

Pricing unknown

Book View

Pricing unknown

(2) Excellent 

32

Province of Florence / San Casciano in Val di Pesa

6 12 4 nights min

  • 6 bedrooms
  • Sleeps 12
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from $381 / night

$1848 - $4283 / week

Book View

from $381 / night

(1) Very Good 

10

Province of Florence / San Casciano in Val di Pesa

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Ask about pets

 …see more

from $97 / night

$674 / week

Book View

from $97 / 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 $317 / night

$2218 - $2816 / week

Inquire View

from $317 / 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 $1553 / night

$10870 / week

Book View

from $1553 / night

1