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45 Results   |  

from £160 / night

£1116 - £2051 / week

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Excellent 5/5 

23 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 4 Bedrooms / sleeps 12

Excellent 5/5 

4 Nights min stay

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from £160 / night

£1116 - £2051 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Villa "Casale San Casciano" is a 200 sqm independent villa with private pool and garden (sleeps up to 12 people). The Villa is located in the typical context of the Chianti area, surrounded by vineyards, olive-trees and small woods.  …see more

from £219 / night

£1533 - £3337 / week

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28 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

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from £219 / night

£1533 - £3337 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome

10-room house 400 m2 on 2 levels, on the ground floor, tasteful and stylish furnishings: entrance hall. Lounge with open fireplace and satellite-TV. Living room with 1 double sofa bed. Exit to the garden. Open dining room. Kitchen (4 hotplates, oven, dishwasher, micr  …see more

from £151 / night

£1051 - £2195 / week

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22 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 5 Bedrooms / sleeps 10

7 Nights min stay

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from £151 / night

£1051 - £2195 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Gorgeous Villa with swimming pool in the Chianti, near San Casciano Val di Pesa, a medieval hamlet between Florence and Siena  …see more

Featured properties

from £216 / night

£1511 - £2375 / week

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20 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 5 Bedrooms / sleeps 9

7 Nights min stay

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from £216 / night

£1511 - £2375 / week

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Key info:

  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Stunning villa in the Chianti, walking distance from San Casciano village  …see more

from £175 / night

£1224 - £3641 / week

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Excellent 5/5 

25 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 6 Bedrooms / sleeps 12

Excellent 5/5 

6 Nights min stay

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from £175 / night

£1224 - £3641 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • Some pets are welcome - please contact the owner
 …see more

from £146 / night

£1021 - £1899 / week

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28 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 4 Bedrooms / sleeps 10

7 Nights min stay

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from £146 / night

£1021 - £1899 / week

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Key info:

  • Not suitable for children
  • Some pets are welcome - please contact the owner
 …see more

from £172 / night

£1200 - £2065 / week

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18 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 4 Bedrooms / sleeps 12

7 Nights min stay

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from £172 / night

£1200 - £2065 / week

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Key info:

  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Chianti Classico, recently renovated, is a nineteenth century villa originally belonging to the “Conti Bandini”. The villa with a swimming pool and Jacuzzi can comfortably accommodate up tp 12 people. Check-in : 11.00 am - 7 pm (For late check-in could be requ  …see more

from £175 / night

£1224 - £2231 / week

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23 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 4 Bedrooms / sleeps 10

7 Nights min stay

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from £175 / night

£1224 - £2231 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
This pretty country house, set in the typical context of Chianti Classico, surrounded by vineyards, olive-groves and small woods, rises in a dominant position upon a little lake.  …see more

from £155 / night

£1080 - £1439 / week

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Excellent 5/5 

23 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 3 Bedrooms / sleeps 7

Excellent 5/5 

3 Nights min stay

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from £155 / night

£1080 - £1439 / week

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Late Deal: save up to €495 (approx. £356)

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children over 5
  • Air conditioning
  • Pets welcome
  • Private garden
Property Type: Villa Highlights: garden, olive oil field, parking,swimming pool Location: Chianti Hills Ideal for: base to relax and visit Florence, Pisa, Siena, Chianti playing sports: golf, horse riding, mountain biking, tennis ect. Sleeps: 6+1  …see more

from £191 / night

£1331 - £2015 / week

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Excellent 5/5 

24 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 4 Bedrooms / sleeps 8

Excellent 5/5 

3 Nights min stay

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from £191 / night

£1331 - £2015 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Beautiful rutic and cozy tuscan villa  …see more

from £189 / night

£1319 - £2272 / week

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19 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 4 Bedrooms / sleeps 12

7 Nights min stay

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from £189 / night

£1319 - £2272 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
Villa Chianti Classico, recently renovated, is a XIX century villa originally belonging to the “Counti Bandini”. This beautiful villa with a swimming pool and Jacuzzi is for max 12 people. Villa Chianti Classico is located in San Casciano, a wonderful area of Chiant  …see more

from £124 / night

£864 - £2806 / week

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Excellent 5/5 

24 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 6 Bedrooms / sleeps 12

Excellent 5/5 

4 Nights min stay

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from £124 / night

£864 - £2806 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Charming Chianti Holiday Home. 5 bedrooms. Stunning landscapes. Private panoramic salt swimming pool. Perfect Location: 30 min from Florence, 50 min from Siena, 10 min from Greve in Chianti. We organise wine Tours & other activities. Extra Virgin Olive Oil producers. C  …see more

from £165 / night

£1152 - £2303 / week

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23 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 5 Bedrooms / sleeps 9

1 night min stay

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from £165 / night

£1152 - £2303 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children over 5
  • Car advised
  • No pets allowed
  • Private garden
Tuscan Historical Villa with stunning hill views, just 25 minutes south of Florence in the Chianti wine region. Private pool, garden, courthouse for pleasant breakfasts, dining. Ideal for seeking real Tuscan elegant taste. A registered 19th century villa. A registered  …see more

from £134 / night

£936 - £2087 / week

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20 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 5 Bedrooms / sleeps 11

1 night min stay

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from £134 / night

£936 - £2087 / week

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Key info:

  • Not suitable for children
  • No pets allowed
 …see more

from £229 / night

£1599 - £2000 / week

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22 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 4 Bedrooms / sleeps 8

4 Nights min stay

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from £229 / night

£1599 - £2000 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
 …see more

from £47 / night

£324 - £360 / week

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18 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 2 Bedrooms / sleeps 5

7 Nights min stay

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from £47 / night

£324 - £360 / week

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Key info:

  • Nearest beach 100 km
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Vacanza tranquilla in campagna, passeggiate neile pinete, a 40 km da Siena, 20 da San Gimignano, Volterra, e altre città turistiche. Ottimi ristoranti, negozi e pizzerie anche a 3 km ( San Casciano). Visite a siti etruschi della zona a pochi chilometri. I proprie  …see more

from £1028 / night

£7195 - £12231 / week

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6 Photos

San Casciano in Val di Pesa / Chiesanuova

Villa / 8 Bedrooms / sleeps 16

Min stay varies

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from £1028 / night

£7195 - £12231 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Ski
  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
Prices: per week High (March 23rd-Apr 5th/June1st-Sept.29th/Dec 14th-Jan3rd 2014) €17.000 Mid (April 6th-May 31st/Sept 30th-Oct 25th) € 12.000 Low (Jan 5th-March 22nd/Oct 26th-Dec 13th) € 10.000 All prices p.w. must be considered less 10% in case of 2/3 weeks  …see more

from £346 / night

£2421 - £3777 / week

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Excellent 5/5 

20 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 5 Bedrooms / sleeps 10

Excellent 5/5 

7 Nights min stay

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from £346 / night

£2421 - £3777 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
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.  …see more

from £360 / night

£2515 - £3303 / week

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20 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 5 Bedrooms / sleeps 10

7 Nights min stay

Add to shortlist

from £360 / night

£2515 - £3303 / week

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Key info:

  • Nearest beach 121 km
  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
Villa Il Turco is an elegant, aristocratic, sixteenth-century country estate which once belonged to a noble family named Rosselli Del Turco. Enjoy noble splendour in this gracious antique villa which is both close to Florence and immersed in tranquillity. Complete with  …see more

from £194 / night

£1358 - £2017 / week

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17 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 6 Bedrooms / sleeps 12

2 Nights min stay

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from £194 / night

£1358 - £2017 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
The historic Casa Erta, acquired from the Machiavelli family, together with the other farm houses on the property, have been restored with great care to their original form.  …see more

from £197 / night

£1376 - £2044 / week

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16 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 6 Bedrooms / sleeps 12

2 Nights min stay

Add to shortlist

from £197 / night

£1376 - £2044 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
The historic Casa Corza, belonged to the legendary Cavalcanti and Niccolini families, Florentine nobility and together with the other farm houses on the property, have been restored with great care to their original form.  …see more

from £360 / night

£2515 - £2972 / week

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21 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 5 Bedrooms / sleeps 10

7 Nights min stay

Add to shortlist

from £360 / night

£2515 - £2972 / week

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Key info:

  • Nearest beach 75 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Enjoy noble splendor in this gracious antique villa which is both close to Florence and immersed in tranquility.  …see more

from £323 / night

£2257 - £3777 / week

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42 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 5 Bedrooms / sleeps 10

7 Nights min stay

Add to shortlist

from £323 / night

£2257 - £3777 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Splendid and characteristic Chianti villa (400 m2) that dates back to the early 15th century. Once belonging to the Medici family, it is situated in a small valley amid the Chianti hills and has been skilfully restored and transformed into a cosy country house. The vill  …see more

from £771 / night

£5396 - £6259 / week

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26 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 11 Bedrooms / sleeps 20

3 Nights min stay

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from £771 / night

£5396 - £6259 / week

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Key info:

  • Great for children of all ages
  • Car essential
  • No pets allowed
This is a fabulous Tuscan villa sleeping between 15 and 20 people. Set on a hillside overlooking the River Pesa valley, it is just 15 minutes from Florence in the heart of the Chianti region. The views from the property are simply stunning and it will be hard for guests  …see more

from £328 / night

£2295 - £2921 / week

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21 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 5 Bedrooms / sleeps 8

5 Nights min stay

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from £328 / night

£2295 - £2921 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
This charming farmhouse is located on the grounds of a famous medieval castle, and manuscripts documenting the life of the castle date back to the year 997. The castle is surrounded by ominous walls which in days gone by served as protection, now just add to the  …see more

from £412 / night

£2878 - £5425 / week

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15 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 7 Bedrooms / sleeps 14

5 Nights min stay

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from £412 / night

£2878 - £5425 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • Pets welcome
The robustandnbsp;Villa Marianaandnbsp;stands tall beside the towering Tuscan landscape. Theandnbsp;Chianti Classicoandnbsp;hills framework this villa thoroughly situated in the wine producing estate, Villa Mariana comfortably admit up toandnbsp;14 membersandnbsp;and  …see more

from £247 / night

£1728 - £3299 / week

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20 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 6 Bedrooms / sleeps 12

3 Nights min stay

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from £247 / night

£1728 - £3299 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
Characteristic Tuscan-style Chianti villa, independent and secluded, located in the heart of Tuscany, in the Chianti Classico region, a few kilometers from San Casciano Val di Pesa. The villa rental is surrounded by the Tuscan hills, olive groves and vineyards, in a qui  …see more

from £771 / night

£5396 - £7590 / week

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25 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 11 Bedrooms / sleeps 20

3 Nights min stay

Add to shortlist

from £771 / night

£5396 - £7590 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
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.  …see more

from £782 / night

£5470 - £6401 / week

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31 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 8 Bedrooms / sleeps 15

7 Nights min stay

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from £782 / night

£5470 - £6401 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
A typical example of a Tuscan medieval castle, dating to the 12th century, built by the architect Buondelmonti as a fortification to defend the feudal possessions. Transformed into a country villa in 1520, with large decorated rooms and elegant arcades, the castle is pe  …see more

from £329 / night

£2302 - £3526 / week

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44 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 4 Bedrooms / sleeps 12

7 Nights min stay

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from £329 / night

£2302 - £3526 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
Ancient farmhouse surrounded by olive groves and terraced areas and situated inside the Castello di Bibbione estate in the Chianti area. The castle dates back to the early 11th century, whereas the stone-built houses of the hamlet date back to the early 13th century.  …see more

from £835 / night

£5842 - £6990 / week

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57 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 11 Bedrooms / sleeps 22

7 Nights min stay

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from £835 / night

£5842 - £6990 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
Borgo Casciano offers a terrific setting for a large gathering or for smaller groups.  The entire villa is complete with five apartments that accommodate 22 guests and can be rented as one exclusive dwelling for a large group. The apartments can also be rented separate  …see more

from £708 / night

£4954 - £7623 / week

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43 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 6 Bedrooms / sleeps 17

7 Nights min stay

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from £708 / night

£4954 - £7623 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
Located in the heart of Tuscany's Chianti region, Casa Matteo is an outstanding villa with stunning views over characteristic olive groves, vineyards, forests and country estates.  This spacious independent country house, originally a small monastery, has five bedrooms  …see more

from £710 / night

£4965 - £7698 / week

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19 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 5 Bedrooms / sleeps 10

Min stay varies

Add to shortlist

from £710 / night

£4965 - £7698 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Surrounded by vineyards and olive groves, Casale Classico is perfect for five couples or an extended family, and the location couldn't be better.  …see more

from £458 / night

£3202 - £4029 / week

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24 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

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from £458 / night

£3202 - £4029 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
The La Corte estate stretches out over a hillside covered with vineyards, olive trees and woodland.  …see more

from £525 / night

£3670 - £4821 / week

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24 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 8 Bedrooms / sleeps 16

7 Nights min stay

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from £525 / night

£3670 - £4821 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
The La Corte estate stretches out over a hillside covered with vineyards, olive trees and woodland.  …see more

from £797 / night

£5575 - £6660 / week

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24 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 7 Bedrooms / sleeps 14

7 Nights min stay

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from £797 / night

£5575 - £6660 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden

Tuscan country farmhouse near Florence to rent – Casolare del Chianti is a traditional refurbished farmhouse sitting on a large rural estate, ideally located in the popular Chianti region, between Florence and San Gimignano.

 …see more

from £1542 / night

£10792 / week

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24 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 7 Bedrooms / sleeps 13

5 Nights min stay

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from £1542 / night

£10792 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
There are many beautiful villas in Tuscany andandnbsp;Villa Carlosandnbsp;is certainly one of them.andnbsp;Overlooking one of the most uncontaminated views, Villa Carlos is perched on a hill 300 mts above sea level, surrounded by vineyards, olive groves, dense forest  …see more

from £78 / night

£540 - £1015 / week

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Very Good 4.5/5 

36 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 3 Bedrooms / sleeps 8

Very Good 4.5/5 

7 Nights min stay

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from £78 / night

£540 - £1015 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Villa Gentile is an age-old 300-square-meter (about 3,229 square feet) countryside house in stone which sleeps eight people. It features a private garden and swimming-pool. It overlooks the valley. The house is located amidst the hills where the famous Chianti wine is p  …see more

from £422 / night

£2949 - £4514 / week

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Excellent 5/5 

70 Photos

San Casciano in Val di Pesa / Montefiridolfi

Villa / 4 Bedrooms / sleeps 11

Excellent 5/5 

7 Nights min stay

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from £422 / night

£2949 - £4514 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Some pets are welcome - please contact the owner
With traditional furnishings, a private swimming pool, and a fantastic location just south of Florence, this Tuscan villa for rent is right out of your Italian fantasies! This is not a bare hotel; this is a home, a Tuscany villa near Florence filled with character and e  …see more

from £78 / night

£540 - £1015 / week

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Excellent 5/5 

23 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 3 Bedrooms / sleeps 8

Excellent 5/5 

5 Nights min stay

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from £78 / night

£540 - £1015 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Villa Gentile is an age-old 300-square-meter (about 3,229 square feet) countryside house in stone which sleeps eight people. It features a private garden and swimming-pool. It overlooks the valley  …see more

from £484 / night

£3382 - £4605 / week

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15 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 8 Bedrooms / sleeps 16

1 night min stay

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from £484 / night

£3382 - £4605 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
This delightful farmhouse for 16 in a grand estate would make the ideal accommodation for a wide variety of guests- a family or group on holiday, attendees at a conference, or guests at one of the special events or weddings held at the villa.  …see more

from £329 / night

£2303 - £3526 / week

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18 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 4 Bedrooms / sleeps 12

7 Nights min stay

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from £329 / night

£2303 - £3526 / week

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Key info:

  • Nearest beach 95 km
  • Swimming pool
  • Great for children of all ages
  • No pets allowed
The stone walls and the ample spaces in this ancient villa in Tuscany welcomes its guests and comforts them with modern amenities, a warm atmosphere and enchanting views of the surroundings.  …see more

from £147 / night

£1026 - £1914 / week

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41 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 4 Bedrooms / sleeps 12

7 Nights min stay

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from £147 / night

£1026 - £1914 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
Villa Lacustre is a characteristic and welcoming two-story villa in the characteristic style of the Tuscan countryside. It sleeps 12 people. From Villa Lacustre you will enjoy a charming view of the greenery. Villa Lacustre is 185 square meters (1990 square feet). It fe  …see more

from £380 / night

£2654 - £4382 / week

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28 Photos

Province of Florence / San Casciano in Val di Pesa

Villa / 5 Bedrooms / sleeps 10

7 Nights min stay

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from £380 / night

£2654 - £4382 / week

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Key info:

  • Nearest beach 95 km
  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Surrounded by the marvelous Chianti hills, this ample and traditional farmhouse sleeps up to 10 people. A large swimming pool, several bedrooms and bathrooms, and a cozy atmosphere for those who long to experience Tuscan life in the countryside.  …see more

from £153 / night

£1069 - £1856 / week

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Province of Florence / San Casciano in Val di Pesa

Villa / 3 Bedrooms / sleeps 6

7 Nights min stay

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from £153 / night

£1069 - £1856 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Some pets are welcome - please contact the owner
Unwind after climbing through hilltop villages with a dip in the private pool, enjoy the spoils of your wine tasting excursion in this villa’s lush private garden, or just snuggle up next to the fireplace with family or friends. Set in a tranquil location in Tuscany  …see more

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