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677 Holiday homes in Siena Province

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677 Results  |  
24 Photos

Villa | 2 Bedrooms | sleeps 5

7 Nights min stay

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from £173 /night

£1210 - £2138 / week

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Key info:

  • Nearest beach 95 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
A cypress tree lined road will lead you to Villino le Tortore and it represents a perfect introduction to this amazing Tuscany villa located just 15 minutes walking from Piazza del Campo, the very heart of Siena.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 8

3 Nights min stay

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from £461 /night

£3226 - £5242 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
This comfortable, cosy villa nestles on a sheltered incline among gently rolling hills. These are covered in Brunello wine-producing vineyards, which border the lower pool-terrace. The San Giuseppe winery, from which the house takes its name, is situated nearby.  …see more

21 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £139 /night

£968 - £1936 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Immersed in the green countryside on the outskirts of Siena, Villa Palio offers all the quiet of its natural setting just a stone throw from the very center of the town of Siena.  …see more

Featured properties

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £346 /night

£2420 - £3630 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
This elegant villa, with cream-washed external walls, dates back to the late 16th century, when it served as the summer residence and hunting lodge of the noble Tolomei family.  …see more

25 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £484 /night

£3388 - £4517 / week

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Key info:

  • Nearest beach 110 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Senese is an ancient mansion dating back to the eighteenth century, located in the heart of Chianti Senese, just 17 km away from Siena and 45 Km from Florence.  …see more

24 Photos

Villa | 14 Bedrooms | sleeps 27

7 Nights min stay

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from £1723 /night

£12057 - £23952 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great 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

15 Photos

Townhouse | 2 Bedrooms | sleeps 5

3 Nights min stay

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from £101 /night

£706 - £908 / week

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Key info:

  • Nearest beach 100 km
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
In the very center of a lovely ancient medieval village stands Casa Marelli. Recently carefully restored preserving all the traditional Tuscan characteristics of the building such as wooden beamed ceilings and brick work arches.  …see more

17 Photos

Villa | 6 Bedrooms | sleeps 12

Very Good 4/5 

7 Nights min stay

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from £218 /night

£1525 - £3347 / week

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Key info:

  • Nearest beach 125 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
The building of Villa Brolio was originally an old XII century watchtower later transformed into a mill and finally restored to become a villa.  …see more

21 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £80 /night

£557 - £847 / week

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Key info:

  • Nearest beach 95 km
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
This Tuscan 17th century farmhouse with 2 bedrooms, Villa Arpicella, is located very close to Pienza and it enjoys the stunning countryside setting with spectacular wide open views.  …see more

23 Photos

Villa | 7 Bedrooms | sleeps 14

7 Nights min stay

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from £289 /night

£2017 - £4839 / week

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Key info:

  • Nearest beach 115 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Podere Sant'Albino is a 16th century farmhouse built on Roman foundations, nestled between woods and olive groves.  …see more

25 Photos

Villa | 8 Bedrooms | sleeps 16

4 Nights min stay

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from £490 /night

£3428 - £3952 / week

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Key info:

  • Nearest beach 115 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Villa Bossona is an impressive villa which dates back to the eighteenth century. Ideal for quiet and relaxing holidays it is located in the sweet Montepulciano hills few minutes from the town.  …see more

22 Photos

Villa | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £120 /night

£839 - £1311 / week

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Key info:

  • Nearest beach 115 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Colonica Gigli is a portion of a typical Tuscan farmhouse immersed in the green Chianti hills covered with vineyards and olive groves. Recently restored the original stone building stands in a well tended green lawn.  …see more

21 Photos

Villa | 2 Bedrooms | sleeps 5

Excellent 5/5 

7 Nights min stay

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from £98 /night

£686 - £984 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Villino Montisi is a splendid two-story ancient farmhouse surrounded by meadows with breathtaking views over the sweet hills of Tuscany. Recently restored following the architectural Tuscan style with the pale Tuscan stone of the façade.  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 16

7 Nights min stay

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from £392 /night

£2742 - £4759 / week

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Key info:

  • Nearest beach 110 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Villa La Torre is a medieval lookout tower, built more than 8 centuries ago on Etruscan foundations, and at a later date incorporated into the farmhouse structure.  …see more

23 Photos

Apartment | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £29 /night

£202 - £799 / week

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Key info:

  • Nearest beach 115 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
I Tigli is a splendid apartment with two bedrooms and two bathrooms which is part of a property with a total of 6 apartments sharing a pool.  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £145 /night

£1009 - £3025 / week

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Key info:

  • Nearest beach 130 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Demata is the beloved holiday home of a Florentine family with strong American connections as well as a great appreciation for the Tuscan country side and it's pleasures.  …see more

16 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

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from £74 /night

£513 - £684 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Il Pozzo is an apartment which is part of a converted farmhouse from the eighteenth-century, entirely in stone, that was recently the subject of a careful and passionate restoration. A park of three hectares surrounds the property. There is also a swimming pool on-site  …see more

16 Photos

Farmhouse | 8 Bedrooms | sleeps 19

2 Nights min stay

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from £278 /night

£1941 - £2548 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
A 17th century stone hamlet situated in one of the most wonderful positions of Tuscany. Four apartments and two bedrooms furnished with big taste and with exclusive period furniture, fireplace Sky TV independent heating external private space. Parking, scenic pool  …see more

19 Photos

Farmhouse | 2 Bedrooms | sleeps 7

Excellent 5/5 

2 Nights min stay

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from £80 /night

£556 - £770 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
A 17th century stone hamlet situated in one of the most wonderful position of Tuscany. The apartment is characterised by good taste and warmth, equipped with a fireplace and elegantly furnished with furniture from the era. Park, scenic swimming pool.  …see more

16 Photos

Farmhouse | 2 Bedrooms | sleeps 4

Excellent 5/5 

2 Nights min stay

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from £68 /night

£471 - £625 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
A 17th century stone hamlet situated in one of the most wonderful position of Tuscany. The apartment is furnished tastefully and with exclusive period furniture, fireplace, Sky TV, independent heating, external private space. Park, scenic swimming pool.  …see more

5 Photos

Apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £49 /night

£342 - £556 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Pets welcome
The natural extension of the existing village of Gaiole in Chianti. The 'village-inside-the village' concept that is unique of its kind. The village concept that becomes an integral part of Gaiole in Chianti. l  …see more

13 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £46 /night

£317 - £556 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
The apartment "La Casina" comes from the restructuring of the rural outbuildings of the main building, it has been done with care leaving unchanged the characteristics of the original structure, highlighting the architectural value.  …see more

21 Photos

Apartment | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £104 /night

£727 - £1283 / week

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Key info:

  • Not suitable for children
  • Car advised
  • No pets allowed
Experience life as a local in this magnificent property in the main square of Cetona. Located in an historic "palazzo" from the 1700s, but updated to offer every convenience, this three bedroom, two bathroom flat puts you right in the heart of daily life. Frescoed walls and ceilings, beautiful furnishings set this property apart.  …see more

4 Photos

Apartment | 1 Bedroom | sleeps 3

2 Nights min stay

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from £37 /night

£257 - £385 / week

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Key info:

  • Nearest beach 75 km
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
ADDITIONAL SERVICES AVAILABLE ARE: CHILDREN UNDER 3 YEARS FREE in cot (from 4 years € 15 per night in an armchair bed) STROLLER € 5 a day BABYSITTING both day and night BREAKFAST housewife € 5 a day DINNER WITH THE FAMILY you can taste typical dishes of Tuscan ho TOUR GUIDE arrange personalized excursions in the countryside and in the city.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 12

1 night min stay

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from £206 /night

£1437 - £2065 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Farmhouse Casa Orcia is situated in the province of Siena in the peaceful heart of Val d'Orcia, a beautiful landscape of UNESCO patrimony.  …see more

15 Photos

Apartment | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £53 /night

£366 / week

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Key info:

  • Nearest beach 35 km
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
A place where where you can find, good temperature, nature, relax and fantastic italian food!! distances: - 30 km from Pescara (sea) - 20 km from the National Park of Gran Sasso/Monti della Laga, AQ - 40 km from the Majella National Park, Sulmona, AQ - 190 km from Rome Private entrance, parking, 2 double bedrooms + 1 single bedroom / study, living room / kitchen with fireplac  …see more

10 Photos

Apartment | 5 Bedrooms | sleeps 9

2 Nights min stay

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from £92 /night

£642 - £1026 / week

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Key info:

  • Nearest beach 95 km
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
A simple old house, functional and warm with manifold opportunities to fully enjoy the Tuscan atmosphere. The terrace with garden in the West side and the olive tree grove on the East, allow you to choose separate locations for your relax. Free in/outside wifi.  …see more

10 Photos

Villa | 4 Bedrooms | sleeps 4

Excellent 5/5 

Short stays welcome

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from £74 /night

£513 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden
Si godono scorci pittoreschi degli Edifici Storici e gli ampi spazi del panorama Toscano . Per gli amanti di MountainBikes , del Relax nei Laghi ,del Wellness alle Terme, ,della cucina Toscana e della arguta simpatia e della cordialita' dei Toscani. Vicinissima a Ristorants,Bar,Farmacia,Banche, Musei Concerti ? Se siete fortunati anche Concerti !!!!!  …see more

24 Photos

Farmhouse | 2 Bedrooms | sleeps 6

2 Nights min stay

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from £75 /night

£525 - £638 / week

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Key info:

  • Nearest beach 40 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
In Tuscany in an Old Mill fine restructured typical apartments with private patio, pool garden and wonderful panorama, near Siena and San Gimignano.  …see more

21 Photos

Villa | 15 Bedrooms | sleeps 37

3 Nights min stay

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from £1383 /night

£9678 - £11291 / week

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Key info:

  • Nearest beach 45 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Luxury Villa seventeenth century, Private Chapel , private pool 10x20, sauna,Kitchen pool area Ideal location for weddings and parties Luxury villa, Ideal location for weddings and parties  …see more

24 Photos

Farmhouse | 5 Bedrooms | sleeps 10

Excellent 5/5 

Short stays welcome

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from £228 /night

£1590 - £2095 / week

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Key info:

  • Nearest beach 200 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Due to the central geographical position of Villa Pietra del Diavolo you can spend a day touring famous cities rich in history, culture, architecture and artistic works such as Siena (km 45), Arezzo (km 50), Firenze (km 110), Perugia (km 70), Roma (km 150). Croce di Febo take care of our land according to the traditions of organic agricolture respecting the soil.  …see more

12 Photos

Villa | 8 Bedrooms | sleeps 25

7 Nights min stay

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from £98 /night

£684 - £2992 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Tuscany, Toscana, Casale, Piscina, Vigneto, Corsi cucina, Caccia al tartufo, Villa, Casa Vacanze, Italia, Equitazione, Matrimonio, matrimoni, eventi, lusso, Catering ;Tastings and Wine Tour's; Truffle Hunting ;Cooking Classes; Excursions; Horse Riding  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

7 Nights min stay

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from £215 /night

£1500 - £2350 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Charming country house in idyllic setting, stunning views in unique landscape, real family home. Beautifully restored, lovely private pool in delightful gardens and olive groves, village 1 km, nearby Montalcino and Pienza  …see more

20 Photos

Farmhouse | 2 Bedrooms | sleeps 5

2 Nights min stay

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from £49 /night

£342 - £599 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Summer holiday rental, self-catering, romantic view, villa in Tuscany, city of art, Siena, Florence, Pisa, San Gimignano, Volterra, Monteriggioni, Certaldo,Radicondoli, Belforte,San Galgano, Massa Marittima, Populonia, Montepulciano, Montalcino, Pienza, Cortona.  …see more

13 Photos

Villa | 5 Bedrooms | sleeps 10

Very Good 4/5 

Short stays welcome

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from £81 /night

£561 - £803 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Located on a hill overlooking the Val D'Orcia Tuscany's only Unesco heritage site is truly beautiful. A stay here will relax body and mind. We now offer excellent home cooked food within your house in the traditional tuscan style and cater for large or small groups.  …see more

19 Photos

Villa | 4 Bedrooms | sleeps 7

Very Good 4.5/5 

3 Nights min stay

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from £78 /night

£541 - £984 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
Gorgeous holiday villa in Siena, just 5 minutes walking from the town. blloming garden, shared swimming pool, private car parking, internet (with flash drive), laundry room, chef for dinner or meal on request  …see more

10 Photos

Farmhouse | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £62 /night

£428 - £513 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Not suitable for children
  • Car essential
  • No pets allowed
  • Private garden
An old Tuscan farmhouse nestled in a typical hilly tuscan landscape away from chaos and city traffic, but easy reachable. Swimming-pool, nice private gardens, solarium-terrace, fitness-room, barbecue-area, free wi-fi unlimited connection. The property is located very close to the characteristic medieval towns of San Gimignano and Volterra.  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 5

Excellent 5/5 

4 Nights min stay

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from £58 /night

£400 - £600 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
Tuscan style apartment with pool, ideally situated on the outskirts of the medieval town of Cetona, with panoramic views. Two minute walk from local amenities. Perfect for exploring cultural Tuscany.  …see more

24 Photos

Farmhouse | 11 Bedrooms | sleeps 24

Short stays welcome

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from £786 /night

£5500 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
1700's farmhouse with breathtaking views over the Siena hills with a pool overlooking miles of countryside  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 12

Excellent 5/5 

3 Nights min stay

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from £185 /night

£1291 - £2380 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Self-catering Tuscan villa with private pool ideal for 8-12 persons. Each room with ensuite bathroom Private infinity swimming pool The skilful renovation of the premises has fully preserved the typical rustic Tuscan style.  …see more

24 Photos

House | 1 Bedroom | sleeps 5

Very Good 4.5/5 

3 Nights min stay

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from £49 /night

£339 - £428 / week

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Key info:

  • Nearest beach 50 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Tuscany, near Siena. Lovely small villa in the beautiful countryside, with large garden, veranda and private pool. Ideal for a relaxing holiday in full nature as well as for interesting visits to the sites of art in the area. The house is really cosy, situated in a very central and tranquil location. Siena is only 20 min. drive.  …see more

25 Photos

Villa | 5 Bedrooms | sleeps 12

6 Nights min stay

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from £180 /night

£1259 - £2259 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Luxurious detached villa in hilly and quiet location with a beautiful panorama in southern Tuscany. Pool, Jacuzzi (all for private use of the tenant).  …see more

21 Photos

Villa | 9 Bedrooms | sleeps 21

7 Nights min stay

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from £404 /night

£2823 - £3952 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Detached villa with private pool 35 km eastern of Siena. It is an expansive property providing a high standard of accommodation. Tasteful furnished. Hilly and quiet location. The whole property is for private use of the tenant. 9 bedrooms, 17+4 sleeps. Billiard room.  …see more

24 Photos

Farmhouse | 1 Bedroom | sleeps 4

Very Good 4.5/5 

2 Nights min stay

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from £45 /night

£315 - £363 / week

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Key info:

  • Nearest beach 40 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Typical Apartment sleeping 2/4 with private patio, garden, pool, parking, panorama in charming Resindence in Old Mill in the heart of Tuscany between Siena and San Gimignano  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £162 /night

£1130 - £2138 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Detached villa with private pool in southern Tuscany. 4 bedrooms up to 10 sleeps.  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 6

Excellent 5/5 

4 Nights min stay

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from £147 /night

£1026 / week

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Key info:

  • Nearest beach 65 km
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Completely restored old country villa surrounded by private garden with superb views on one of the most pristine parts of Tuscany.  …see more

23 Photos

Apartment | 1 Bedroom | sleeps 2

Excellent 5/5 

2 Nights min stay

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from £57 /night

£396 - £424 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Not suitable for children
  • Car advised
  • Pets welcome
Casanova di Lucignano is an old farmhouse completely restored and set in the Crete Senesi. It is an ideal place to relax, admire the landscape and enjoy many outdoor activities or for a short romantic getaway. Experience the homely atmosphere of the Tuscan countryside.  …see more

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House | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £289 /night

£2017 - £2662 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children over
  • Car advised
  • Some pets are welcome - please contact the owner
If you are searching for something very special, with charm, history and love for details- thats the place to be. It it the perfect hub to discover the jewels of tuscany (if you want to stay in lovely apartments with your friends) or to celebrate a ferry tale wedding-  …see more

8 Photos

Farmhouse | 6 Bedrooms | sleeps 12

3 Nights min stay

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from £346 /night

£2420 - £3710 / 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
The Farm house Tinaione is an ideal locations for a riunion of big family or for a group holiday as it has all the comfort in the rustic simple tuscan way for 12 persons, the appartament is very charmy and the owner knows exately how to look after you. The infinity pool with the stunning views of the tuscan landscape is the perfect setting holiday!  …see more

10 Photos

House | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £139 /night

£968 - £1291 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Make Stomemmano the destination, not just the base for your Tuscan holiday!  …see more