Watersports holiday villas and apartments Province of Siena | Holiday Lettings

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  • Italy
  • Tuscany
  • Province of Siena

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  • Abbadia San Salvatore (1)
  • Casole d'Elsa (4)
  • Castellina In Chianti (2)
  • Castelnuovo Berardenga (2)
  • Cetona (10)
  • Chianciano Terme (3)
  • Chiusi (3)
  • Colle di Val d'Elsa (1)
  • Montepulciano (19)
  • Monteriggioni (7)
  • Monteroni d'Arbia (1)
  • Monticiano (2)
  • Murlo (1)
  • Piancastagnaio (1)
  • Pienza (5)
  • Poggibonsi (5)
  • Radda in Chianti (5)
  • Radicondoli (6)
  • Rapolano Terme (5)
  • San Casciano dei Bagni (1)
  • San Gimignano (6)
  • San Giovanni d'Asso (1)
  • Sarteano (2)
  • Siena (16)
  • Sinalunga (5)
  • Sovicille (1)
  • Torrita di Siena (1)

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116 Holiday homes

Filters applied: Water sports (116)

(18) Excellent 

1 / 49

3 bedroom holiday apartment near Tuscan cities, staffed property with outdoor pool

Tuscany / Province of Siena / San Gimignano / Castel San Gimignano

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 55 km; Swimming pool; Great for children of all ages ;
The apartment is placed in the hamlet of Castel San Gimignano, very near to the best famous cities as Siena, Firenze, San Gimignano, Volterra and the sea is reachable in less than an hour by car. You can also start from here for a relaxing walk or ride through the olive  …see more

from £84 / night

£459 - £709 / week

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from £84 / night

(1) Excellent 

1 / 14

New Casa Titta apt 3 bedrooms , amazing view

Tuscany / Province of Siena / San Gimignano / Castel San Gimignano

3 bedroomsSleeps 5Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 55 km; Great for children of all ages ; Car advised;
C asa Titta is our third apartment ,completely new ,really comfortable, placed on the first floor with three bedrooms for 5 people and a large open space living . A new kitchen equipped with dishwasher , fridge/freezer, microwave and electrical hoven. The bathroom has  …see more

from £84 / night

£459 - £709 / week

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from £84 / night

(30) Excellent 

1 / 25

Tuscan apartment in rural setting with easy access to nearby cities, property has private garden and shared pool

Tuscany / Province of Siena / San Gimignano / Castel San Gimignano

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 55 km; Swimming pool; Great for children of all ages ;
The apartment is located in the hamlet of Castel San Gimignano, very near to the best famous cities as Siena, Firenze, San Gimignano, Volterra and the sea is reachable in less than an hour by car. You can also start from here for a relaxing walk or ride through the oliv  …see more

from £84 / night

£459 - £709 / week

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from £84 / night

(54) Excellent 

1 / 52

Incredible, large Tuscan villa boasts jacuzzi, private outdoor pool, billiard room, tennis court, tripadvisor Certificate of Excellence

Tuscany / Province of Siena / Sinalunga

12 bedroomsSleeps 26Min stay varies

  • 12 bedrooms
  • Sleeps 26
  • Min stay varies
Key info: Nearest beach 170 km; Swimming pool; Great for children of all ages ;
Villa Scopetello is the perfect holiday home for large groups and families who wish to spend their holidays together. (Between September and May it is also possible to rent just a portion of the Villa or even one bedroom) The 1000 square meter large Villa with 12 bedro  …see more

from £331 / night

£2318 - £7500 / week

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from £331 / night

(41) Excellent 

1 / 21

La Casina Toscana, central with parking and wi-fi

Tuscany / Province of Siena / Montepulciano

3 bedroomsSleeps 53 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Nearest beach 158 km; Great for children of all ages ; Car advised;
Placed in the countryside of Montepulciano, near the most important historical towns such as Pienza, Montalcino and Bagno Vignoni, the Casina Toscana is a historical residence of the nineteenth century, which allows guests to enjoy the tranquility and relaxation that th  …see more

from £59 / night

£334 - £584 / week

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from £59 / night

(3) Excellent 

1 / 35

The Notary's House - Montepulciano apartment sleeps 6

Tuscany / Province of Siena / Montepulciano

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Great for children of all ages ; Car not necessary; Air conditioning;
Small charming flat, old residence of householder's great-grandfather, Notary in Montepulciano. Recently wholly restructured, very quiet, in a very beautiful position: in the centre of town, but facing the walls of the city, in a dominant position.Two nice bedrooms, sma  …see more

from £59 / night

£334 - £500 / week

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from £59 / night

1 / 38

Tuscany / Province of Siena / Montepulciano

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Great for children of all ages ; No pets allowed; Private garden;
 …see more

from £163 / night

£1137 - £1561 / week

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from £163 / night

1 / 20

Chapel Manor (v027) - Chiusi manor house sleeps 21

Tuscany / 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 / 36

Tuscany / Province of Siena / Montepulciano

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Great for children of all ages ; Car not necessary; Air conditioning;
 …see more

from £59 / night

£334 - £500 / week

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from £59 / night

(5) Excellent 

1 / 33

Torre Farmholiday Tuscan Chianti near Florence

Tuscany / Province of Siena / Radda in Chianti

2 bedroomsSleeps 35 nights min stay

  • 2 bedrooms
  • Sleeps 3
  • 5 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 120 km; Great for children of all ages ;
Farmholiday Agriturismo Podere Tegline is of a family from the Chianti region for many centuries, and always produce Chianti Classico wine and extra virgin olive oil organic.We restored the farmhouse of the 15th century and Giovanni has personally followed all the wor  …see more

from £59 / night

£350 - £467 / week

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from £59 / night

(2) Excellent 

1 / 22

Balz Tuscan farmholiday Chianti - Radda in Chianti farmhouse sleeps 3

Tuscany / Province of Siena / Radda in Chianti

2 bedroomsSleeps 35 nights min stay

  • 2 bedrooms
  • Sleeps 3
  • 5 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 120 km; Great for children of all ages ;
Farmholiday Agriturismo Podere Tegline is of a family from the Chianti region for many centuries, and always produce Chianti Classico wine and extra virgin olive oil organic.We restored the farmhouse of the 15th century and Giovanni has personally followed all the work  …see more

from £47 / night

£292 - £375 / week

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from £47 / night

(3) Excellent 

1 / 29

Tegline Chianti Tuscan holiday accomodation

Tuscany / Province of Siena / Radda in Chianti

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 120 km; Great for children of all ages ;
Farmholiday Agriturismo Podere Tegline is of a family from the Chianti region for many centuries, and always produce Chianti Classico wine and extra virgin olive oil organic. We restored the farmhouse of the 15th century and Giovanni has personally followed all the wor  …see more

from £67 / night

£417 - £542 / week

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from £67 / night

(7) Excellent 

1 / 41

Unique, charming farmhouse in Tuscany countryside with shared outdoor pool, sleeps up to 6

Tuscany / Province of Siena / Montepulciano

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 0 km; Swimming pool; Great for children of all ages ;
The main arched entrance leads past a utility room and downstairs bathroom into the open plan kitchen and dining room with dining table for 6 guests. The lounge has two sofa's one of which is a comfortable double sofa bed There is a wood burning stove in the lounge  …see more

from £72 / night

£500 - £890 / week

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from £72 / night

1 / 19

Forsythia Cottage (V041) - Sarteano cottage sleeps 8

Tuscany / Province of Siena / Sarteano

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
Typical country house, well restructured, Mount Amiata dominates the unique landscape surrounding this property. From the interiors which are refined but cosy, you understand the owners' passion. Very well furnished.On the first floor there is a living room with fi  …see more

from £179 / night

£1250 - £1900 / week

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from £179 / night

1 / 27

Agriturismo Ardene - Montepulciano villa sleeps 14

Tuscany / Province of Siena / Montepulciano

7 bedroomsSleeps 14Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 100 km; Swimming pool;
Villa Ardene provides its guests with high level services in a magical, peaceful and unforgettable atmosphere. All the suites and apartments are equipped with whirlpool bath, air conditioning, satellite TV, internet connection.The interior space in “arte povera” has  …see more

from £565 / night

£3956 - £6060 / week

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from £565 / night

(2) Excellent 

1 / 48

Tuscany / Province of Siena / Castellina In Chianti

2 bedroomsSleeps 44 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min stay
Key info: Nearest beach 150 km; Great for children of all ages ; Car essential;
 …see more

from £100 / night

£459 - £542 / week

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from £100 / night

(6) Very Good 

1 / 45

Tuscany / Province of Siena / Montepulciano

3 bedroomsSleeps 5Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Great for children of all ages ; Car advised; Some pets are welcome - please contact the owner;
 …see more

from £67 / night

£442 - £500 / week

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from £67 / night

1 / 20

Il castagno - Radicondoli apartment sleeps 9

Tuscany / Province of Siena / Radicondoli

4 bedroomsSleeps 9Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
Key info: Nearest beach 60 km; Swimming pool; Great for children of all ages ;
Located at 1,900mt from the Medieval town of Radicondoli with all its shops and restaurants yet peaceful and quiet surrounded by olive groves and the beautiful hills of the Siena countryside.60 kms from the Sea. 40 minutes from Siena, Volterra, San Gimignano. 1 hour fro  …see more

from £142 / night

£992 - £1167 / week

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from £142 / night

(3) Excellent 

1 / 23

Renovated antique apartment in Tuscan countryside

Tuscany / Province of Siena / Siena / Val di Merse

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 70 km; Great for children of all ages ;
The antique apartment have been reinvigorated, made more comfortable and personalized whilst using traditional local materials, rough stone, terracotta, wrought iron, wood.This elegant, well-appointed apartment is complete with stylish fitted bathroom and kitchen.It has  …see more

from £100 / night

£667 - £834 / week

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from £100 / night

(1) Excellent 

1 / 14

Apartment in the historic city center of Siena

Tuscany / Province of Siena / Siena

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 70 km; Great for children of all ages ; Some pets are welcome - please contact the owner;
This bright and modern apartment totally renovated by just one year, is situated in the charming historic centre of Siena.The apartment is part of a palace complex with other apartments and is located on the ground floor and consists of two floors.The apartment is so co  …see more

from £80 / night

£542 - £834 / week

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from £80 / night

1 / 11

Tuscany / Province of Siena / Siena

1 bedroomSleeps 41 night min stay

  • 1 bedroom
  • Sleeps 4
  • 1 night min stay
Key info: Nearest beach 95 km; Great for children of all ages ; Car not necessary;
 …see more

from £55 / night

£380 - £438 / week

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from £55 / night

(1) Excellent 

1 / 14

Tipica dimora toscana - Monticiano apartment sleeps 4

Tuscany / Province of Siena / Monticiano

2 bedroomsSleeps 44 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min stay
Key info: Nearest beach 60 km; Great for children of all ages ; Car essential;
This apartment is in the historical center of a beautiful town near Siena. Its name is Monticiano. It's composed by 2 bedrooms (for 4 gests), 1 bathroom (with a shower box), 1 indipendent kitchen and a great dining room. The apartment is 75 mq. In the centre of this vi  …see more

from £59 / night

£350 / week

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from £59 / night

1 / 24

Tuscany / Province of Siena / Poggibonsi / Staggia Senese

1 bedroomSleeps 5Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
Key info: Great for children of all ages ; Car advised; Some pets are welcome - please contact the owner;
 …see more

from £27 / night

£167 - £317 / week

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from £27 / night

(1) Excellent 

1 / 22

Villa Amedeo - Giotto - Val di Merse apartment sleeps 2

Tuscany / Province of Siena / Siena / Val di Merse

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 70 km; Great for children of all ages ;
The antique spaces of the apartment have been reinvigorated, made more comfortable and personalized whilst using traditional local materials, rough stone, terracotta, wrought iron, wood.Giotto is one of six complete and elegant, well-appointed apartments, complete with  …see more

from £59 / night

£375 - £459 / week

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from £59 / night

1 / 7

Il Casalone Apartment Oliveto - Montepulciano farmhouse sleeps 4

Tuscany / Province of Siena / Montepulciano

4 bedroomsSleeps 4Min stay varies

  • 4 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car advised;
Located in a panoramic position on a hill crest between the Val d'Orcia and Valdichiana near Montepulciano, Agriturismo Il Casalone offers a holiday unit tastefully furnished in Tuscan country style. One double bed room (king size), one bathroom and a living room w  …see more

from £50 / night

£225 - £409 / week

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from £50 / night

1 / 25

Lodge Melograno wonderful view in Val D'Orcia

Tuscany / Province of Siena / Pienza

1 bedroomSleeps 27 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 7 nights min stay
Key info: Nearest beach 100 km; Swimming pool; Not suitable for children;
Poggio ai Gelsi is located in the south of Tuscany between the hills of Val d'Orcia, Siena and halfway between Montepulciano and Pienza. The property enjoys a magnificent view over Montichiello and Pienza. The colours of the nature in this corner of Tuscany are bea  …see more

from £64 / night

£442 - £709 / week

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from £64 / night

(4) Excellent 

1 / 42

Tuscany / Province of Siena / Siena

2 bedroomsSleeps 52 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min stay
Key info: Great for children of all ages ; Car not necessary; Pets welcome;
 …see more

from £84 / night

£417 / week

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from £84 / night

(1) Excellent 

1 / 29

Tuscany / Province of Siena / Montepulciano

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Great for children of all ages ; Air conditioning; Pets welcome;
 …see more

from £225 / night

£1167 - £1959 / week

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from £225 / night

(1) Good 

1 / 27

MA13 - Belforte farmhouse sleeps 5

Tuscany / Province of Siena / Radicondoli / Belforte

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 55 km; Swimming pool; Great for children of all ages ;
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 £72 / night

£334 - £1417 / week

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from £72 / night

1 / 20

Tuscany / Province of Siena / Rapolano Terme

3 bedroomsSleeps 61 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Great for children of all ages ; Car advised; Air conditioning;
 …see more

from £46 / night

£167 - £876 / week

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from £46 / night

1 / 20

Orchard Manor (V056) - Chiusi manor house sleeps 20

Tuscany / Province of Siena / Chiusi

8 bedroomsSleeps 207 nights min stay

  • 8 bedrooms
  • Sleeps 20
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
An independent farmhouse built in stone and bricks with oak beams and terracotta floors, in the heart of a 35 hectare farming estate. The farmhouse is divided into 4 apartments and sleeps 17 + 3.Cypress (sleeps 7) on the first floor there is a living room with a firepla  …see more

from £254 / night

£1775 - £3017 / week

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from £254 / night

(2) Excellent 

1 / 32

Fonte Tuscany Holiday Apartment in Chianti Hill

Tuscany / Province of Siena / Radda in Chianti

1 bedroomSleeps 25 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 5 nights min stay
Key info: Nearest beach 120 km; Great for children of all ages ; Car advised;
Farmholiday Agriturismo Podere Tegline is of a family from the Chianti region for many centuries, and always produce organic Chianti Classico wine and extra virgin olive oil.We restored the farmhouse of the 15th century and Giovanni has personally followed all the work  …see more

from £55 / night

£334 - £400 / week

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from £55 / night

1 / 24

Tuscany / Province of Siena / Pienza

4 bedroomsSleeps 11Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
Key info: Nearest beach 95 km; Swimming pool; Great for children of all ages ;
 …see more

from £292 / night

£1750 - £2942 / week

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from £292 / night

1 / 27

Tuscany / Province of Siena / Siena

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Nearest beach 100 km; Swimming pool; Suitable for children age 5+;
 …see more

from £173 / night

£1209 - £2000 / week

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from £173 / night

1 / 10

Agriturismo Terrarossa 2 pax - Valiano apartment sleeps 2

Tuscany / Province of Siena / Montepulciano / Valiano

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car not necessary;
The apartment "Rosa" (2 persons), with furniture of epoch, is composed of a stay- kitchen with read couch, a double bedroom and a bathroom with shower. In bedroom: tv sat. The Terrarossa agriturism complex is situated on one of the most beautiful and panoramic  …see more

from £80 / night

£375 - £505 / week

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from £80 / night

1 / 20

Primrose Villa (V039) - Chiusi villa sleeps 8

Tuscany / Province of Siena / Chiusi

3 bedroomsSleeps 87 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
At Chiusi lake, this beautiful villa is a peaceful and cosy place for a holiday in close contact with nature. The restoration work, using environmentally friendly techniques paid attention to every detail, making the interiors light and comfortable. Extremely well furni  …see more

from £141 / night

£984 - £2492 / week

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from £141 / night

(5) Excellent 

1 / 24

Tuscany / Province of Siena / Montepulciano

1 bedroomSleeps 43 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay
Key info: Great for children of all ages ; Car advised; No pets allowed;
 …see more

from £65 / night

£384 / week

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from £65 / night

1 / 11

Tuscany / Province of Siena / Montepulciano

1 bedroomSleeps 22 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: Not suitable for children; Car advised; No pets allowed;
 …see more

from £59 / night

£367 / week

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from £59 / night

(3) Excellent 

1 / 13

Tuscany / Province of Siena / Poggibonsi / Staggia Senese

2 bedroomsSleeps 31 night min stay

  • 2 bedrooms
  • Sleeps 3
  • 1 night min stay
Key info: Nearest beach 74 km; Great for children of all ages ; Car advised;
 …see more

from £59 / night

£392 / week

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from £59 / night

(7) Excellent 

1 / 57

Poggio ai Gelsi - Pienza lodge sleeps 8

Tuscany / Province of Siena / Pienza

3 bedroomsSleeps 87 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Nearest beach 100 km; Swimming pool; Great for children of all ages ;
Poggio ai Gelsi is located in the south of Tuscany between the hills of Val d'Orcia, Siena and halfway between Montepulciano and Pienza. The property enjoys a magnificent view over Montichiello and Pienza. The colours of the nature in this corner of Tuscany are bea  …see more

from £193 / night

£1350 - £2459 / week

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from £193 / night

Top Destination reviews

Pink Holiday-apartment with pool in Chianti
Wanderful stayin

The location of the house is in a very typical Tuscan environment: hills, vineyards, olive trees. Even if you might thing to be in a faraway place, the location is very convenient to Siena, San Giminiano, Firenze, and to other spots, such as Pisa an … see more
COSOLI CHARMING HISTORICAL VILLA IN CHIANTI
Tuscan Heaven

Cosoli is a beautiful villa in a stunning location. It was a superb family holiday location. thanks. … see more
Villa Vianci
Best vacation ever!

Our entire experience at Villa Vianci was beyond expectations. We travelled with 4 generations, ages 3 1/2 to 85! The villa was spectacular, spacious & immaculate. The pictures on line don't do it justice. Tommasso & Chiara were the best, any que … see more
Perfect, beautifil little place in tuscany

A beautiful place full of happines, were you can stay The time you want for a very very good price ,there's a beautiful view, is very relaxing and you can enjoy The animals and nature … see more
The Beautiful Sun Apartment
Well maintained apartment and very helpful owner

Elias iwas most helpful meeting us on arrival and going through everything with us and all places to visit in the area even giving us a map with this all marked on The apartment is beautifully kept and everything we needed was there. All to a good s … see more
The Grifo Apartment
Perfect!!

The apartment is spacious and clean. It's inside the historical center and it's perfect to visit it. We had a quiet stay . … see more

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