Province of Siena apartment or villa with a private pool area

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  • Italy
  • Tuscany
  • Province of Siena

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  • Asciano (9)
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  • Chiusi (17)
  • Colle di Val d'Elsa (8)
  • Gaiole in Chianti (32)
  • Gallina (2)
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952 Holiday homes

Filters applied: Private pool (952)

(1) Excellent 

1 / 24

Villa Montebello - Montalcinello villa sleeps 18

Chiusdino / Montalcinello

8 bedroomsSleeps 18Min stay varies

  • 8 bedrooms
  • Sleeps 18
  • Min stay varies
Key info: Nearest beach 55 km; Swimming pool; Great for children of all ages ;
Characteristic Tuscan stone farmhouse situated in a dominant position just 5 minutes’ walk from a magical medieval village 35 km west of Siena . The property has been completely renovated a few years ago and turned into a most cozy and comfortable luxury holiday vill  …see more

from £331 / night

£2101 - £3782 / week

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from £331 / night

(1) Excellent 

1 / 20

Villa Loreta - Casole d'Elsa villa sleeps 11

Province of Siena / Casole d'Elsa

5 bedroomsSleeps 11Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
Key info: Nearest beach 75 km; Swimming pool; Great for children of all ages ;
On the side of a green and sunny hill and a stone's throw away from the small medieval town of Casole d'Elsa is found this characteristic old Tuscan stone farmhouse transformed into a charming and comfortable holiday home. The villa, a luxurious haven for families and g  …see more

from £119 / night

£825 - £2450 / week

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from £119 / night

1 / 20

Casa Eleonora - Gallina villa sleeps 12

Castiglione D'Orcia / Gallina

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
Just South of Siena, The Val d'Orcia is UNESCO World Heritage. Its enchanting towns and villages like Montalcino and Pienza are surrounded by a sea of vines and olives whose slopes intermittently give way to deep forest of pines, chestnuts and oaks, cool and refreshing.  …see more

from £180 / night

£1250 - £2042 / week

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from £180 / night

(1) Excellent 

1 / 17

Tuscan hillside farmhouse with private pool, terrace and garden, great for family holidays

Province of Siena / San Gimignano

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 45 km; Swimming pool; Great for children of all ages ;
Podere Le Monache set on a hillside dominates one of the most picturesque and spectacular landscapes in Tuscany. With distant views over hills, out to sea towards Livorno and Pisa. Originally a convent wrapped in history Le Monache has a magical and spiritual atmosphere  …see more

from £61 / night

£413 - £917 / week

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from £61 / night

(1) Excellent 

1 / 20

Podere le Monache 1 - San Gimignano farmhouse sleeps 4

Province of Siena / San Gimignano

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 45 km; Swimming pool; Great for children of all ages ;
Podere Le Monache set on a hillside dominates one of the most picturesque and spectacular landscapes in Tuscany. With distant views over hills, out to sea towards Livorno and Pisa. Originally a convent wrapped in history Le Monache has a magical and spiritual atmosphere  …see more

from £55 / night

£367 - £792 / week

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from £55 / night

(4) Excellent 

1 / 23

Podere Lo Spadino - San Gimignano villa sleeps 9

Province of Siena / San Gimignano

4 bedroomsSleeps 9Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
The villa, on two floors, is just 5 km from the historic center of San Gimignano, in a secluded location is surrounded by large well kept garden and green, with lawn, where you can spend time and relax. The garden also features a gazebo with garden furniture, barbecue.  …see more

from £292 / night

£1292 - £2084 / week

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from £292 / night

(1) Excellent 

1 / 19

Farmhouse holiday rental with private pool and garden in San Gimignano

Province of Siena / San Gimignano

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 45 km; Swimming pool; Great for children of all ages ;
Podere Le Monache set on a hillside dominates one of the most picturesque and spectacular landscapes in Tuscany. With distant views over hills, out to sea towards Livorno and Pisa. Originally a convent wrapped in history Le Monache has a magical and spiritual atmosphere  …see more

from £67 / night

£459 - £959 / week

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from £67 / night

1 / 20

Villa Cafaggiola 3 bedroom villa with private pool

Province of Siena / San Gimignano

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 75 km; Swimming pool; Great for children of all ages ;
The Villa has been completely renovated from an old barn and materials have been used for its original restructuring terracotta floors and exposed beams on the ceilings. It 'a great place to spend a quiet holiday without sacrificing the various excursions just a short d  …see more

from £155 / night

£1084 - £1875 / week

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from £155 / night

1 / 100

Beata - Poggibonsi villa sleeps 12

Province of Siena / Poggibonsi

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Nearest beach 75 km; Swimming pool; Great for children of all ages ;
ExteriorThe fantastic location of this independant manor affords guests the pleasure of many great towns and cities nearby, all perfect for a day trip. Whether you want to explore Siena, Volterra , Florence or San Gimignano or the extremely close Poggibonsi, this p  …see more

from £525 / night

£3670 - £6335 / week

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from £525 / night

(5) Excellent 

1 / 20

Secluded villa with private pool Chianciano Terme

Province of Siena / Chianciano Terme

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
The villa lies at 3 kms from the town of Chianciano Terme, one of the most popular thermal Spas in Italy. The villa is located among the hills dividing Val d'Orcia and Valdichiana. The whole property is for your private use and not shared with any other person. The vill  …see more

from £209 / night

£1250 - £2209 / week

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from £209 / night

(1) Excellent 

1 / 24

24091-Holiday house Siena - Radicondoli villa sleeps 6

Province of Siena / Radicondoli

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car not necessary;
Situated at the edge of a park, just within 5 minutes walk to the mediaeval hilltop village of Radicondoli, the property enjoys an exceptional view over the Metallifere Hills and those of Chianti, taking in the towers of San Gimignano and stretching as far as the Apenni  …see more

from £73 / night

£509 - £1697 / week

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from £73 / night

(1) Excellent 

1 / 12

Villa Masseto - Castellina In Chianti villa sleeps 10

Province of Siena / Castellina In Chianti

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
Beautiful independent restored villa (400 sqm) sleeping 10 with private pool, astro turf tennis court, daily maid service, gardens. Located in panoramic position on a Chianti Hillside only 5km from Castellini in Chianti. The private swimming pool (6/10m) is situated on  …see more

from £393 / night

£2750 - £3167 / week

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from £393 / night

(1) Excellent 

1 / 16

Province of Siena / Sinalunga

2 bedroomsSleeps 7Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
Key info: Nearest beach 30 km; Swimming pool; Great for children of all ages ;
 …see more

from £150 / night

£992 - £1117 / week

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from £150 / night

1 / 24

Ancient castle in the heart of Tuscany, 6 bedrooms

Gaiole in Chianti / Lecchi

6 bedroomsSleeps 147 nights min stay

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
A dive into an ancient culture in the heart of Tuscany, the Chianti Classico.Il Castello Medievale is situated in a medieval hamlet, constructed of white stone, built around 1000AD, surrounded by forests and olive groves, immersed in a magical atmosphere of tranquility.  …see more

from £400 / night

£2800 - £4309 / week

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from £400 / night

1 / 24

23891-Holiday house San Gimign - Badia A Elmi villa sleeps 5

Siena / Badia A Elmi

2 bedroomsSleeps 57 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Nearest beach 65 km; Swimming pool; Great for children of all ages ;
Charming stone-built house located in a peaceful and panoramic position on the green, rolling hills near San Gimignano.<br><br>The villa is the result of a recent renovation which has transformed this ancient barn into a beautiful and comfortable detached vi  …see more

from £100 / night

£698 - £1745 / week

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from £100 / night

(2) Very Good 

1 / 100

Castellina In Chianti 81687 - Castellina In Chianti villa sleeps 10

Province of Siena / Castellina In Chianti

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
The villa dating back to the first 800 as is present in the Catasto Leopoldino (the first inventory in Tuscany), it has been restructured maintaining it Tuscan typical style with ceilings with beams in wood and floors in cooked and window "mandorlate" that the  …see more

from £327 / night

£1910 - £2862 / week

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from £327 / night

(5) Very Good 

1 / 24

Picturesque Tuscan villa in the hills near Siena features private garden, barbecue and swimming pool, sleeps 6

Radicondoli / Belforte

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 50 km; Swimming pool; Great for children of all ages ;
In the picturesque setting of the "Metallifere" hills, west from Siena, is located this characteristic stone built cottage, recently renovated in keeping with the traditional style and character, with wood beams and terracotta floors, furnished in a comfortabl  …see more

from £78 / night

£542 - £1459 / week

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from £78 / night

(5) Excellent 

1 / 33

Asciano / Crete Senesi

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 110 km; Swimming pool; Great for children of all ages ;
 …see more

from £59 / night

£409 - £667 / week

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from £59 / night

1 / 20

The Spring (v024) - Pienza villa sleeps 12

Province of Siena / Pienza

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
Situated on a farm of 150 hectares producing excellent extra virgin olive oil, the farmhouse is set on a kind of natural terrace overlooking the lovely valley below. The house, built in the first half of the eighteenth century, has been renovated carefully by the couple  …see more

from £472 / night

£3300 - £4375 / week

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from £472 / night

(13) Excellent 

1 / 24

Renovated 5 bedroom villa surrounded by Tuscan vineyards, fetures private pool, log fire and terrace

Province of Siena / San Gimignano

5 bedroomsSleeps 12Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Nearest beach 70 km; Swimming pool; Great for children of all ages ;
The completely renovated property occupies a panoramic position within an estate of olive groves and vineyards, boasting an entrancing view of the famous towers of San Gimignano 4 km away. The characteristic architecture enables guests to experience a specifically Tusc  …see more

from £334 / night

£1500 - £2667 / week

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from £334 / night

(5) Excellent 

1 / 46

Villa Sangimignano - Montauto farmhouse sleeps 5

San Gimignano / Montauto

2 bedroomsSleeps 53 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Nearest beach 80 km; Swimming pool; Great for children of all ages ;
The 200 sqm villa is a typical stone barn in an early '900 style, characterized by the tranquility of the Tuscan countryside of San Gimignano in which it is immersed.It can be accessed via a large private and completely fenced garden of 2,000 sqm.The house is the r  …see more

from £194 / night

£1417 - £1917 / week

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from £194 / night

(8) Excellent 

1 / 24

Delightful 2 bedroom farmhouse with beautiful private grounds and pool

Province of Siena / Sarteano

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
The Agriturismo Sferracavalli is the best way to enjoy Italian genuine food, which can be gathered in the back garden, and to feel compleatly plunged in peace and relax among Tuscany nature. Medieval villages complete the perfect Tuscany atmosphere all around, so that w  …see more

from £105 / night

£625 - £917 / week

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from £105 / night

(15) Excellent 

1 / 23

Podere Scopicciolo - Casole d'Elsa villa sleeps 12

Province of Siena / Casole d'Elsa

7 bedroomsSleeps 127 nights min stay

  • 7 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Nearest beach 75 km; Swimming pool; Great for children of all ages ;
Villa Podere Scopicciolo is located about 30 miles from Florence. It is 900 ft above sea level in the heart of Tuscany surruonded by cultivated farm land and well preserved forests. It is fully immersed in the countryside enjoying peace and tranquillity, yet convenientl  …see more

from £858 / night

£6000 - £8750 / week

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from £858 / night

1 / 17

Old Brick Farm (v034) - Radicofani farmhouse sleeps 8

Province of Siena / Radicofani

3 bedroomsSleeps 87 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
This beautifully renovated farmhouse is ideal positioned for touring the area.On the ground floor there is a living room with double sofa bed, a double room with door on to the garden, a small kitchen, a bathroom with shower. On the first floor there is another living r  …see more

from £120 / night

£834 - £1434 / week

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from £120 / night

(2) Very Good 

1 / 20

Lovely hillside cottage in the Province of Siena w

Radicondoli / Belforte

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 50 km; Swimming pool; Great for children of all ages ;
In the picturesque setting of the "Metallifere" hills, west from Siena, is located this characteristic stone built house, recently renovated in keeping with the traditional style and character, with wood beams and terra cotta floors, furnished in a comfortable, rustic s  …see more

from £60 / night

£417 - £1459 / week

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from £60 / night

1 / 20

Cypress Villa (v008) - Pienza farmhouse sleeps 13

Province of Siena / Pienza

6 bedroomsSleeps 137 nights min stay

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min stay
Key info: Nearest beach 44 km; Swimming pool; Great for children of all ages ;
Ground floor: a large living room with fireplace, small kitchen, a double bedroom with a separate entrance from the outside with an en-suite bathroom with washing machine.First floor: a double bedroom with Jacuzzi inside the room and en-suite bathroom with shower, a dou  …see more

from £343 / night

£2400 - £5734 / week

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from £343 / night

(1) Very Good 

1 / 17

Villa Brolio - Gaiole in Chianti villa sleeps 12

Province of Siena / Gaiole in Chianti

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Nearest beach 125 km; Swimming pool; Great for children of all ages ;
The building of Villa Brolio was originally an old XII century watchtower later transformed into a mill and finally restored to become a villa. The restoration works have been done preserving carefully all the ancient characteristics such as the outside stones, the vau  …see more

from £225 / night

£1575 - £3459 / week

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from £225 / night

1 / 100

Farnetella 56708 - Sinalunga villa sleeps 7

Province of Siena / Sinalunga

3 bedroomsSleeps 7Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; No pets allowed;
Old stone farmhouse restored with the 1700 conservative policy that has left intact the charm and beauty of the past. Located between the Val d'Orcia and the hills of Chianti, the farmhouse is divided on two floors: on the first floor is accessed by an ancient ston  …see more

from £231 / night

£1557 - £1852 / week

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from £231 / night

1 / 100

Castiglione D'orcia 62100 - Castiglione D'Orcia villa sleeps 19

Province of Siena / Castiglione D'Orcia

8 bedroomsSleeps 197 nights min stay

  • 8 bedrooms
  • Sleeps 19
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; No pets allowed;
Beautiful independent villa with private pool situated in the Orcia valley area, a splendid region south of Siena rich in charming villages and hamlets such us Montalcino, Pienza, San Quirico dOrcia, Castiglione dOrcia. This property has been recently restored and turne  …see more

from £275 / night

£1923 - £3540 / week

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from £275 / night

1 / 24

34184-Holiday house Chianti - Radda in Chianti villa sleeps 12

Province of Siena / Radda in Chianti

5 bedroomsSleeps 127 nights min stay

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car not necessary;
Beautiful and characteristic villa (330 m2) obtained from the renovation of an ancient farmhouse in the heart of the Chianti near Castellina in Chianti. The villa is situated inside a property that also includes other 6 apartments approximately 30 m away from the villa  …see more

from £318 / night

£2226 - £4173 / week

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from £318 / night

(2) Excellent 

1 / 35

Agriturismo Sammonti - Monteriggioni farmhouse sleeps 2

Province of Siena / Monteriggioni

1 bedroomSleeps 22 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: Nearest beach 80 km; Swimming pool; Great for children of all ages ;
The “borgo Sammonti” was built in the beginning of the 13th century as a fortress in the county of Scorgiano, and it is located near most beautiful and important tuscan cities. The structure is surrounded by woods and it offers many paths for walks and escursions.Th  …see more

from £63 / night

£417 - £625 / week

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from £63 / night

1 / 100

Foiano Della Chiana 15663 - Montepulciano villa sleeps 10

Province of Siena / Montepulciano

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; No pets allowed;
Beautiful 5-hectare estate in Tuscany, a villa for wedding celebration and holidays, comprising a farmhouse of 140 m2 and an outbuilding of 60 m2 which have been skilfully restored and turned into a delightful independent villa offering tastefully and refined furnished  …see more

from £154 / night

£1072 - £2111 / week

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from £154 / night

(4) Excellent 

1 / 24

Pretty Tuscan cottage surrounded by stunning hills with private pool and terrace, sleeps up to 5

Province of Siena / Casole d'Elsa

2 bedroomsSleeps 57 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Nearest beach 65 km; Swimming pool; Great for children of all ages ;
Stone cottage situated in the green, panoramic hills at 1.5 km from the hilltop town of Casole d'Elsa. Accommodation is offered on the elevated ground floor composed by a cosy leaving room with a double sofa bed and access onto a large panoramic terrace (50 m2), 1  …see more

from £78 / night

£542 - £1167 / week

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from £78 / night

(9) Excellent 

1 / 48

Glorious historic Tuscan villa , pool,WIFI,AC

Province of Siena / San Giovanni d'Asso

8 bedroomsSleeps 16Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
Key info: Nearest beach 120 km; Swimming pool; Great for children of all ages ;
A beautiful old historic family house with a large hanging garden and swimming pool (6x12) nestled in the middle of a tiny village, San Giovanni d'Asso, in the Siennese countryside: the comfort to be in a village and the privacy of a place hidden at the sight. Becoming  …see more

from £527 / night

£3900 - £5084 / week

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from £527 / night

(3) Very Good 

1 / 24

Splendid period farmhouse in the Tuscan countryside with 6 bedrooms, swimming pool and private garden

Province of Siena / San Gimignano

6 bedroomsSleeps 177 nights min stay

  • 6 bedrooms
  • Sleeps 17
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
Splendid period farmhouse dating back many centuries which was once a water tower and mill. Expertly converted offering accommodation of large proportions and only 4 kms from San Gimignano and close for excursions for both Florence and Siena. The property stands in seve  …see more

from £167 / night

£1167 - £2742 / week

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from £167 / night

(7) Very Good 

1 / 24

Just outside of medieval Tuscan village, beautiful 2 bedroom hillside cottage with private pool and garden

Province of Siena / Radicondoli

2 bedroomsSleeps 57 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Nearest beach 50 km; Swimming pool; Great for children of all ages ;
Situated below the mediaeval village of Radicondoli, west from Siena, is located this characteristic farm house, recently renovated in keeping with the traditional style and character, with wood beams and terra cotta floors, furnished in a comfortable, rustic style. In  …see more

from £48 / night

£334 - £1459 / week

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from £48 / night

(1) Excellent 

1 / 100

Tenuta di Papena - Chiusdino villa sleeps 19

Province of Siena / Chiusdino

10 bedroomsSleeps 191 night min stay

  • 10 bedrooms
  • Sleeps 19
  • 1 night min stay
Key info: Nearest beach 60 km; Swimming pool; Great for children of all ages ;
ExteriorThis property is a unique property with six separated apartments, set in an ancient hamlet very close to Siena, with a picturesque central square and a lovely garden where the guests can enjoy a pleasant stroll, a dive into the pool or a table tennis m  …see more

from £500 / night

£2917 - £3417 / week

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from £500 / night

1 / 20

Chapel Manor (v027) - Chiusi manor house sleeps 21

Province of Siena / Chiusi

8 bedroomsSleeps 217 nights min stay

  • 8 bedrooms
  • Sleeps 21
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 7 km; Swimming pool;
This large country house, located in the hills between Lake Chiusi and Lake Trasimeno is an ideal property for a large family or a group of friends that which to spend their holidays together in the beautiful Tuscan countryside.This property is particular suitable for p  …see more

from £297 / night

£2075 - £3109 / week

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from £297 / night

1 / 34

Podere Sant' Albino - Sant'Albino villa sleeps 14

Montepulciano / Sant'Albino

7 bedroomsSleeps 147 nights min stay

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Nearest beach 115 km; Swimming pool; Great for children of all ages ;
Podere Sant'Albino is a 16th century farmhouse built on Roman foundations, nestled between woods and olive groves. It has been turned into a residence of refined charm that retains an atmosphere of informal welcome. The landscape and environment of Montepulciano are amo  …see more

from £358 / night

£2500 - £5167 / week

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from £358 / night

(6) Very Good 

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Virgilius - Radicondoli villa sleeps 6

Province of Siena / Radicondoli

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 50 km; Swimming pool; Great for children of all ages ;
Situated below the mediaeval village of Radicondoli, this property enjoys an exceptional view over the Chianti hills, taking in the towers of San Gimignano and stretching as far as the Apennines.This self standing villa, surrounded by olives groves and fruit trees, has  …see more

from £60 / night

£417 - £1667 / week

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from £60 / night

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