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598 Holiday homes in Siena Province

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Filters applied: Private pool (598)

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598 Results  |  
24 Photos

Villa | 6 Bedrooms | sleeps 12

3 Nights min stay

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from £404 /night

£2823 - £5242 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Luxury air-conditioned villa with pool, Jacuzzi and sauna close to San Gimignano – sleeps 12 From 3500€ to 6500€ a week  …see more

14 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
  • Some pets are welcome - please contact the owner
  • Private garden
Large mansion with private pool to rent near Monteroni d'Arbia - sleeps 11 From 3000€ to 4500€ a week  …see more

21 Photos

Villa | 8 Bedrooms | sleeps 12

Short stays welcome

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from £391 /night

£2736 - £5078 / week

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Key info:

  • Nearest beach 45 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
The Piaggione of Serravalle is like a gateway entrance that protects an uncontaminated hill that seems lost in time and where nature apparently undisturbed articulates its own natural rhythms. Located on one of the highest summits of Chianti, in between Siena and Floren  …see more

Featured properties

23 Photos

Villa | 5 Bedrooms | sleeps 9

7 Nights min stay

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from £208 /night

£1452 - £2904 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Holiday villa with private pool and sauna within walking distance from Cetona – sleeps 9 From 1800€ to 3600€ a week  …see more

20 Photos

Farmhouse | 5 Bedrooms | sleeps 9

Short stays welcome

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from £125 /night

£871 - £1678 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Comfortable country house with private pool to rent near San Casciano dei Bagni – sleeps 9 From 1080€ to 2040€ a week  …see more

27 Photos

Lodge | 3 Bedrooms | sleeps 8

Excellent 5/5 

7 Nights min stay

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from £198 /night

£1385 - £2522 / 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
Modern and tastefully decorated cottages with an infinity swimming pool where you can totally relaxed surrounded by the typical tuscany landscape: a fantastic view. Perfect for families, couples or groups of friends to enjoy cultural, art, good wine and italian food.  …see more

24 Photos

Farmhouse | 3 Bedrooms | sleeps 7

3 Nights min stay

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from £178 /night

£1240 - £1496 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • No pets allowed
  • Private garden
Charming farmhouse in Tuscany, the ideal starting point to visit the Val di Chiana and Val d'Orcia with its wonderful medieval towns such as Cortona, Montepulciano, San Quirico d'Orcia, Pienza, as well as Montalcino and San Gimignano and the beautiful art town of Siena. Situated in the heart of Tuscany, near the centre of the little town of Sinalunga.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 7

3 Nights min stay

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from £178 /night

£1240 - £1582 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Thanks to its superb location the farmhouse is the ideal starting point to visit the Val di Chiana and Val d'Orcia with its wonderful medieval towns such as Cortona, Montepulciano, San Quirico d'Orcia, Pienza, as well as Montalcino and San Gimignano and the beautiful ar An ideal place for a relaxing holiday and visiting the most beautiful and striking sites of Tuscany.  …see more

14 Photos

Villa | 5 Bedrooms | sleeps 10

2 Nights min stay

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from £128 /night

£893 - £2522 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
Le fonti di santa Lucia e una bella villa in posizione panoramica a San Gimignano. Da questa villa isolata e possibile facilmente raggiungere le città di Siena, Firenze, Pisa . la casa situata sulla Via Francigena dove e possibile fare trekking su percorsi segnalati. la casa è stata costruita per permettere una comoda vacanza a 10 persone con tutti i confort  …see more

19 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £225 /night

£1573 - £3750 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Elegant air-conditioned villa with private pool to rent close to Montepulciano – sleeps 8 From 2300€ to 4650€ a week  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £489 /night

£3420 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Ancient and noble mansion of the XVIII century overlooking Chianti hills, for a luxury and leisure stay in the hearth of Tuscany... Its location in the centre of Tuscany, a few km from the highway Firenze-Siena.  …see more

21 Photos

Castle | 6 Bedrooms | sleeps 16

7 Nights min stay

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from £415 /night

£2904 - £3105 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Romantic castle with pool to rent near Montepulciano – sleeps 14+2 From 3300€ to 3850€ a week  …see more

21 Photos

Apartment | 4 Bedrooms | sleeps 9

Excellent 5/5 

1 night min stay

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from £226 /night

£1582 - £1881 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
An amazing holiday in the moast beautiful area of Tuscany, in the natural park of the Val d'Orcia, near Montalcino, Pienza, Siena, Montichiello, Bagno Vignoni. A quiete, relaxing garden with swimming pool, a charming, cosy and comfortable apartment in an ancient villa.  …see more

20 Photos

Villa | 2 Bedrooms | sleeps 6

Excellent 5/5 

4 Nights min stay

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from £116 /night

£807 - £1855 / week

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Key info:

  • Nearest beach 75 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Villa La chiesina is ideal for families, for groups of friends and for all those who prefer to spend their holidays in well-appointed, welcoming and private surroundings. They offer an exclusive peaceful location that makes each stay in Tuscany pleasant and relaxing. The villa and the pool are let with the exclusive use  …see more

22 Photos

Villa | 5 Bedrooms | sleeps 14

3 Nights min stay

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from £72 /night

£500 - £2400 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Italy, Tuscany, Siena , beautiful villa with swimming pool. Incredible views, perfect holiday location.  …see more

24 Photos

Villa | 9 Bedrooms | sleeps 18

7 Nights min stay

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from £1009 /night

£7057 - £12380 / week

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Key info:

  • Nearest beach 85 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Set on a large estate with extensive views over the Crete Senesi and Siena countryside, this villa is just perfect for family reunions or large group of friends. Built in stone and brick, this Tuscany villa consists of a main villa and a dependence.  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 14

Excellent 5/5 

7 Nights min stay

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from £542 /night

£3791 - £6371 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
This spacious, stylishly furnished villa is set in extensive grounds, which offer a choice of venues for outdoor relaxation and dining. It is tucked away in a very secluded spot, amid gently rolling wooded hills.  …see more

24 Photos

Villa | 10 Bedrooms | sleeps 20

7 Nights min stay

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from £634 /night

£4436 - £6291 / week

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Key info:

  • Nearest beach 85 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
The large 800 sqm villa is an ancient historical residence. Villa Siena, an 18th century villa, rises within a secluded parkland in the hills of Tuscany.  …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

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

24 Photos

Villa | 4 Bedrooms | sleeps 10

7 Nights min stay

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from £39 /night

£271 - £1896 / week

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Key info:

  • Nearest beach 125 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden
Villa Abbadia is an ancient country house located in the village of Abbadia di Montepulciano about 10 km from Montepulciano. The villa is immersed in its green manicured garden with shady mature trees and pots of flowers.  …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

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £392 /night

£2742 - £4839 / 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 Corte is a large farmhouse from the early 15th century, built around a thousand-year-old lookout Lombard tower and set inside six hectares of private grounds amidst the hills covered in vineyards and olive trees, just outside of San Gimignano.  …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 | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £536 /night

£3750 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Just 4 km from Castellina in Chianti Villa Rosa boasts unique views over the Chianti countryside from its romantic terrace and from whole of the villa. The classically furnished interior complete the picture.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £265 /night

£1855 - £2984 / week

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Key info:

  • Nearest beach 55 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
The villa is located in a natural reserve and offers walking paths and mountain bike trails, horse riding , historical churches and villas, refreshing dips in the rivers and small lakes.  …see more

24 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

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

22 Photos

Villa | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £121 /night

£847 - £1210 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
This little, two-storey, converted Tuscany farmhouse has been meticulously restored in a simple, rustic style, employing high-quality traditional materials.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

3 Nights min stay

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from £312 /night

£2178 - £3630 / week

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Key info:

  • Nearest beach 95 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • 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

22 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £152 /night

£1061 - £2138 / week

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Key info:

  • Nearest beach 115 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
This compact, two-storey, converted Tuscan farmhouse has been extensively renovated, employing in its restoration solely products certified as ecologically friendly.  …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

23 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £219 /night

£1533 - £2904 / week

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Key info:

  • Nearest beach 115 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Villa Croce, recently restored, is situated on one of the most beautiful and panoramic hills around Montepulciano.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £138 /night

£960 - £2057 / week

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Key info:

  • Nearest beach 95 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
It is the most photographed house in the area, a symbol of the Tuscany countryside, featured on many postcards and calendars simply because it has maintained the charm of the old farmhouse and the surrounding fields, without any new buildings as far as the eye can see.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £346 /night

£2420 - £3186 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Villa Nuti is an elegant XVII century manor only 3 km from the center of Siena. From its unique terrace it enjoys privileged magnificent views of the town with its famous bell towers.  …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

24 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £392 /night

£2742 - £3831 / 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
Casa Oliveto is the guest villa, and sits at the end of an olive grove known for producing one of Italy's premier extra virgin olive oils. The villa, the pool & the gardens are totally private - separated from the main house by a large expanse of olive grove.  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 7

3 Nights min stay

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from £202 /night

£1412 - £1775 / week

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Key info:

  • Nearest beach 130 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Villa Farnetella is an old farmhouse dating back to the XVII century, which has been carefully restored respecting all the traditional architectural characteristics, preserving the stone walls, the original wooden beamed ceilings and the terracotta floors.  …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

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £217 /night

£1513 - £2097 / week

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Key info:

  • Nearest beach 95 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Everybody who loves Tuscan tradition, excellent cuisine, biological food and, why not, horse riding and biking, besides a relaxing visit to thermal spas will be enchanted by this area.  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 16

3 Nights min stay

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from £505 /night

£3529 - £5545 / week

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Key info:

  • Nearest beach 115 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Villa San Biagio is situated close to Montepulciano. This magnificent country house is known for being the most exclusive and stunning farmhouse you can find in this area. It is the perfect choice if you are looking for a peaceful and relaxing holiday.  …see more

19 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £127 /night

£888 - £2009 / week

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Key info:

  • Nearest beach 105 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden
Villa Le Tolfe is so close to Siena you can almost touch it (only 3 kilometres away). With stunning views and beautiful antique gardens this villa is perfect for relaxed stress free holidays.  …see more

18 Photos

Villa | 7 Bedrooms | sleeps 14

7 Nights min stay

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from £281 /night

£1967 / week

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Key info:

  • Nearest beach 150 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
The villa is located 800 meters from a traditional Tuscan restaurant and four kilometers from the nearest village of Montepulciano where you'll find a few shops, restaurants, and a market. Nearby: Pienza, Montefollonico, Bagno Vignoni, Cortona, Orvieto, Castiglion del Lago, S.Quirico, Montalcino  …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

5 Photos

Villa | 4 Bedrooms | sleeps 8

6 Nights min stay

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from £171 /night

£1197 - £2424 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Immersa nelle colline della Valdichiana, in posizione panoramica e strategica per i collegamenti alle grandi città d'arte Siena,Firenze,Arezzo,Cortona,Pienza,Montepulciano,Montalcino,Chianti, tutte a circa un'ora di distanza.  …see more

4 Photos

Apartment | 2 Bedrooms | sleeps 8

2 Nights min stay

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from £55 /night

£385 - £684 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
agriturismo laura  …see more

41 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £672 /night

£4702 - £5557 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
VILLA DEL SOLE is a lovely Tuscan villa near the popular towns of Gaiole and Radda in Chianti. This wonderful villa comprises of the main house which is spread over three floors and a separate ground floor villa which is aproximately 50 metres away.  …see more

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Townhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £129 /night

£898 - £1197 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Ospitato in un'antica casa colonica il delizioso agriturismo "Collosodo" è circondato da un vasto giardino, in cui, nei periodi estivi, é possibile mangiare o fare un bagno in piscina immersi negli scenari incontaminati della Val d'Orcia. L'attenzione all'ospite nella nostra struttura è molto curata.  …see more

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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