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46 Holiday homes in Monticiano

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46 Results  |  
15 Photos

Farmhouse | 2 Bedrooms | sleeps 6

Min stay varies

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from £72 /night

£501 - £667 / week

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Key info:

  • Nearest beach 75 km
  • Suitable for over 5s only
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
The village is located in a strategic position, 25 km from Siena and 50 km from the seaside; along the way to the coast, the old Massetana way, you will have the chance to visit the extraordinary San Galgano Abbey, the Montesiepi hermitage, villages, ancient churches. Sail with us on board of Free Will to the Tuscan Archipelago, Sardinia, Corsica.  …see more

10 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £44 /night

£307 - £377 / week

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Key info:

  • Nearest beach 60 km
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
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.  …see more

24 Photos

Villa | 14 Bedrooms | sleeps 27

7 Nights min stay

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from £2630 /night

£18410 - £24546 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
This exclusive luxury villa nestled in the hills of the Tuscan countryside in the south of the province of Siena offers top-quality accommodation completed by first-class services and panoramic views in a natural biogenetic reserve in the Val di Merse.  …see more

Featured properties

20 Photos

Villa | 5 Bedrooms | sleeps 16

Min stay varies

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from £682 /night

£4769 - £7860 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Very stylish and beautiful villa in the heart of the famous Montalcino vine-yards. Featured in books and magazines.  …see more

19 Photos

Apartment | 1 Bedroom | sleeps 2

2 Nights min stay

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from £109 /night

£758 - £806 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
Romantic hideaway in Tuscan villa with chlorine free pool. Siena 25 minutes.All Tuscan art cities and seaside daily outings. Nature, art, peace and quiet.  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 2

2 Nights min stay

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from £109 /night

£758 - £806 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
Charming and romantic hideaway in Tuscan villa with chlorine free pool. Siena 25 minutes.All Tuscan art cities and seaside daily outings. Nature, art, peace and quiet.  …see more

17 Photos

Apartment | 1 Bedroom | sleeps 2

2 Nights min stay

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from £100 /night

£697 - £745 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
Romantic hideaway in Tuscan villa with chlorine free pool. All amenities in the nearby village, walking distance. Siena 25 minutes.All Tuscan art cities and seaside daily outings. Nature, art, peace and quiet.  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 2

2 Nights min stay

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from £97 /night

£675 - £723 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
Cozy hideaway in Tuscan villa with chlorine free pool. Siena 25 minutes.All Tuscan art cities and seaside daily outings. Nature, art, peace and quiet.  …see more

24 Photos

Villa | 9 Bedrooms | sleeps 18

Very Good 4/5 

2 Nights min stay

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from £808 /night

£5651 - £6089 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Ideal family and wedding Tuscan villa with private chlorine free pool. Tucked away yet not isolated. All amenities in the nearby village, walking distance. Siena 25 minutes.All Tuscan art cities and seaside daily outings. Nature, art, peace and quiet.  …see more

23 Photos

Villa | 9 Bedrooms | sleeps 9

2 Nights min stay

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from £871 /night

£6091 - £6563 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
Villa Leccio is a world apart set in a charming and peaceful place where guests can truly relax and rediscover a calmer pace of life, away from the city. Our area offers breathtaking panoramas, countless daily outings and still preserves an unspoiled wilderness.  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 7

Excellent 5/5 

2 Nights min stay

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from £69 /night

£482 - £570 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • Private garden
Monticiano is one of the most beautiful villages of the Val di Merse, a wild and unspoilt natural area, covered in woods and rich in rivers and hot springs, dotted with castles, abbeys, little countryside churches and ruins, countryside villas and small quiet hamlets.  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

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from £103 /night

£715 - £761 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Appartamento Larice E is a graceful apartment built on a hillside, surrounded by meadows and woods. It sleeps two people. From Appartamento Larice E you will enjoy a pleasant view of the garden and of the hills  …see more

20 Photos

Villa | 8 Bedrooms | sleeps 18

1 night min stay

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from £762 /night

£5331 - £5744 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa Larice Grande is a characteristic two-story age-old farm house made of stone. It sleeps 16 people. From Villa Larice Grande you will enjoy a fascinating view of the Valley and of the hills. Villa Larice Grande is 600 square meters (6460 square feet)  …see more

20 Photos

Apartment | 5 Bedrooms | sleeps 9

1 night min stay

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from £455 /night

£3182 - £3298 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Appartamento Larice A is a characteristic and welcoming two-story apartment surrounded by meadows and by green hills. It sleeps nine people. It is appoximately 150 square meters (1615 square feet)  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 3

1 night min stay

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from £60 /night

£414 - £604 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Casa Prospero E is a graceful apartment surrounded by the vegetation. It sleeps four people. From Casa Prospero E you will have a view of the swimming pool and of the garden and of the surrounding countryside. Casa Prospero E is 100 square meters (1076 square feet)  …see more

16 Photos

Villa | 5 Bedrooms | sleeps 16

7 Nights min stay

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from £682 /night

£4769 - £7860 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Fontanelle is without doubt one of our loveliest Tuscan properties. It is located to the west of Montalcino, an area renowned for its beauty and for its wines, especially the famous Brunello di Montalcino. The property is in a spectacular position, surrounded by viney  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 12

7 Nights min stay

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from £233 /night

£1627 - £2711 / week

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Key info:

  • Nearest beach 50 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Holiday house for 12 persons, with swimming pool , in Siena  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

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from £89 /night

£620 - £703 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Appartamento Larice C is a characteristic apartment surrounded by meadows and by green hills. It sleeps two people. It is appoximately 35 square meters (375 square feet). It features a shared swimming pool, a shared garden and winter heating  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

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from £76 /night

£529 - £777 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Appartamento Prosperina A is a characteristic two-story apartment created inside an ancient watch tower. It sleeps four people. From Appartamento Prosperina A you will have a pleasant view of the Valley and of the hills  …see more

16 Photos

Farmhouse | 6 Bedrooms | sleeps 16

7 Nights min stay

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from £551 /night

£3852 - £6439 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
This exceptionally beautiful property is located in a very quiet and spectacular position, just a few kilometres away from the lovely village of Montalcino. The views from the house are outstanding taking in the Val d'Orcia and Crete Senesi  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

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from £60 /night

£414 - £604 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Casa Prospero F is a characteristic apartment surrounded by the vegetation. It sleeps four people. It is appoximately 100 square meters (1076 square feet)  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 18

5 Nights min stay

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from £802 /night

£5614 - £6048 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • Pets welcome
Podere Monte is a luxury private Tuscany villa in the Val di Merse some 35 kilometers to the south of Siena, just north of the extensive Maremma area. The villa's building used to be an 18thbeautiful place for receiving guests. Although not as popular as other Chianti  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

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from £103 /night

£715 - £761 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Appartamento Larice D is a characteristic apartment surrounded by the vegetation. It sleeps two people. From Appartamento Larice D you will enjoy a pleasant view of the garden and of the surrounding countryside  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

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from £60 /night

£414 - £604 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Appartamento Prosperina B is a characteristic apartment created inside an ancient watch tower. It sleeps four people. From Appartamento Prosperina B you will have a fascinating view of the Valley. Appartamento Prosperina B is 100 square meters (1076 square feet)  …see more

14 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

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from £83 /night

£579 - £1075 / week

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Key info:

  • Swimming pool
  • Suitable for over 5s only
  • Car essential
  • No pets allowed
Lovely apartment on the exclusive wine estate dei Vini . Here you can taste some of the best wines of Italy, the house is surrounded by renowned vineyards. The apartment is suitable for 2 persons.  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

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from £60 /night

£414 - £604 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Casa Prospero C is a welcoming two-story apartment surrounded by the vegetation. It sleeps five people. From Casa Prospero C you will have a pleasant view of the Tuscan hills and of the surrounding countryside. Casa Prospero C is 60 square meters (645 square feet)  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

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from £91 /night

£637 - £682 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Appartamento Larice B is a welcoming apartment in the characteristic style of the Tuscan countryside. It sleeps two people. It is appoximately 35 square meters (375 square feet). It features a shared swimming pool, a shared garden and winter heating  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

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from £76 /night

£529 - £777 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Casa Prospero A is a pleasant and spacious apartment surrounded by meadows and by green hills. It sleeps four people. It is appoximately 50 square meters (540 square feet). It features a shared swimming pool, a shared garden and winter heating  …see more

17 Photos

Villa | 3 Bedrooms | sleeps 8

7 Nights min stay

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from £144 /night

£1008 - £1767 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Holiday house for 8 persons, with swimming pool , in Siena  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 3

1 night min stay

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from £60 /night

£414 - £604 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Casa Prospero D is a characteristic apartment surrounded by meadows and by green hills. It sleeps four people. From Casa Prospero D you will have a fascinating view of the Tuscan countryside and of the vineyards  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

Add to shortlist

from £60 /night

£414 - £604 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Casa Prospero B is a welcoming apartment surrounded by meadows and by green hills. It sleeps four people. It is appoximately 50 square meters (540 square feet). It features a shared swimming pool, a shared garden and winter heating. You will be roughly 6 km (3  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £60 /night

£417 - £810 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
These cheap apartments offer two panoramic swimming pools, living room, dining area, kitchen or kitchenette, one or three bedrooms and bathrooms with shower.  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

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from £60 /night

£417 - £810 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
These cheap apartments offer two panoramic swimming pools, living room, dining area, kitchen or kitchenette, one or three bedrooms and bathrooms with shower.  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 8

7 Nights min stay

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from £93 /night

£648 - £1273 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
These cheap apartments offer two panoramic swimming pools, living room, dining area, kitchen or kitchenette, one or three bedrooms and bathrooms with shower.  …see more

24 Photos

Villa | 9 Bedrooms | sleeps 18

2 Nights min stay

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from £762 /night

£5331 - £5744 / week

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Key info:

  • Nearest beach 50 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This villa has a swimming pool in its gardens and offers accommodation for 18 guests in a building with a living room, dining area, kitchenette, bedroom and bathroom each.  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 2

2 Nights min stay

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from £103 /night

£715 - £761 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
These apartments hosting from 1 to 9 guests offer a kitchenette, living room and 1 to 5 bedrooms with bathroom with shower.  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 2

2 Nights min stay

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from £103 /night

£715 - £761 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
These apartments hosting from 1 to 9 guests offer a kitchenette, living room and 1 to 5 bedrooms with bathroom with shower.  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £70 /night

£486 - £926 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
These cheap apartments offer two panoramic swimming pools, living room, dining area, kitchen or kitchenette, one or three bedrooms and bathrooms with shower.  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

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from £58 /night

£405 - £753 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
These cheap apartments offer two panoramic swimming pools, living room, dining area, kitchen or kitchenette, one or three bedrooms and bathrooms with shower.  …see more

24 Photos

Apartment | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £88 /night

£614 - £1215 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
These cheap apartments offer two panoramic swimming pools, living room, dining area, kitchen or kitchenette, one or three bedrooms and bathrooms with shower.  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 2

2 Nights min stay

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from £89 /night

£620 - £703 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
These apartments hosting from 1 to 9 guests offer a kitchenette, living room and 1 to 5 bedrooms with bathroom with shower.  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 2

2 Nights min stay

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from £91 /night

£637 - £682 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
These apartments hosting from 1 to 9 guests offer a kitchenette, living room and 1 to 5 bedrooms with bathroom with shower.  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £174 /night

£1215 - £1447 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
These apartments hosting from 1 to 9 guests offer a kitchenette, living room and 1 to 5 bedrooms with bathroom with shower.  …see more

22 Photos

Villa | 14 Bedrooms | sleeps 28

1 night min stay

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from £211 /night

£1472 - £21879 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
We also offer Cooking Classes, Italian Lessons, Dance Lessons, and many other activities. Since we are in Tuscany... cultural outings (opera, concerts, museums, exhibitions, theater...) are everyday emotions to be lived. Come to share with us the love for beauty and ou  …see more

24 Photos

Tower | 1 Bedroom | sleeps 5

3 Nights min stay

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from £94 /night

£658 - £745 / week

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Key info:

  • Nearest beach 39 km
  • Suitable for over 5s only
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Ubicato all'ingresso di un Borgo intatto del 1100 La Torre del Castello di Tocchi è diventato un appartamento su tre piani che conserva il fascino della sua storia ed il calore del passato. Il Castello di Tocchi dista solo 15' da Siena e 15' dalla bellissima ed unica Abbazia di San Galgano.  …see more

4 Photos

Farmhouse | 2 Bedrooms | sleeps 5

7 Nights min stay

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from £44 /night

£307 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Casale tipico immerso nel verde delle colline toscane. Ambiente rurale tipico a due passi dalla splendida Abbazia di San Galgano con l'autentica spada nella roccia. Possibilità di usufruire della piscina in agriturismo di lusso (ex Mulino Bianco) a circa 10 km.  …see more