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617 Holiday homes in Siena Province

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Filters applied: Private pool (617)

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617 Results  |  
24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £355 /night

£2480 - £3720 / week

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Key info:

  • Swimming pool
  • Suitable 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

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £355 /night

£2480 - £3265 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable 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

24 Photos

Villa | 8 Bedrooms | sleeps 16

7 Nights min stay

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from £532 /night

£3720 - £4546 / week

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Key info:

  • Nearest beach 115 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • 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

Featured properties

24 Photos

Villa | 7 Bedrooms | sleeps 16

7 Nights min stay

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from £517 /night

£3616 - £5682 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • 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

21 Photos

Villa | 2 Bedrooms | sleeps 5

Excellent 5/5 

7 Nights min stay

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from £101 /night

£703 - £1009 / week

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Key info:

  • Swimming pool
  • Suitable 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 £222 /night

£1550 - £1934 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • 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

22 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £225 /night

£1571 - £2976 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Villa Croce, recently restored, is situated on one of the most beautiful and panoramic hills around Montepulciano.  …see more

21 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £142 /night

£992 - £1612 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable 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

22 Photos

Villa | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £124 /night

£868 - £1240 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • 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

17 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £107 /night

£744 - £2058 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • 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

24 Photos

Villa | 7 Bedrooms | sleeps 14

Excellent 5/5 

7 Nights min stay

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from £555 /night

£3885 - £6529 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Suitable 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

20 Photos

Villa | 3 Bedrooms | sleeps 7

7 Nights min stay

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from £183 /night

£1281 - £1529 / week

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Key info:

  • Nearest beach 130 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • 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

24 Photos

Villa | 9 Bedrooms | sleeps 18

7 Nights min stay

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from £1034 /night

£7232 - £12686 / week

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Key info:

  • Swimming pool
  • Suitable 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

19 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £402 /night

£2810 - £4463 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • 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

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £549 /night

£3843 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • 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

20 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £141 /night

£984 - £1653 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

23 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £496 /night

£3472 - £4629 / week

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Key info:

  • Swimming pool
  • Suitable 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 | 10 Bedrooms | sleeps 20

7 Nights min stay

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from £650 /night

£4546 - £6447 / week

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Key info:

  • Swimming pool
  • Suitable 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

18 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £142 /night

£992 - £3306 / week

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Key info:

  • Swimming pool
  • Suitable 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

18 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £74 /night

£517 - £1034 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
At only ten minutes' drive from Sinalunga town-centre and yet surrounded by peaceful, unspoilt countryside, this fully restored 17th century Tuscan farmhouse combines the best of both worlds.  …see more

19 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £272 /night

£1901 - £3058 / week

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Key info:

  • Swimming pool
  • Suitable 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

22 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £186 /night

£1302 - £2191 / week

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Key info:

  • Swimming pool
  • Suitable 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

21 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £414 /night

£2893 - £3926 / week

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Key info:

  • Swimming pool
  • Suitable 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

17 Photos

Villa | 6 Bedrooms | sleeps 12

Very Good 4/5 

7 Nights min stay

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from £224 /night

£1562 - £3430 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • 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

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

24 Photos

Villa | 8 Bedrooms | sleeps 16

7 Nights min stay

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from £402 /night

£2810 - £4389 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • 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

Villa | 7 Bedrooms | sleeps 14

7 Nights min stay

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from £296 /night

£2067 - £4959 / week

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Key info:

  • Swimming pool
  • Suitable 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 8

3 Nights min stay

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from £473 /night

£3306 - £4794 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Suitable 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

24 Photos

Farmhouse | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £179 /night

£1247 - £1986 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • No pets allowed
The old style restoerd flats can offer a perfect feeling of Tuscany. The large garen with view will grant you of unforgettable sunsets over the hills. A large garden with 6x12 mt swimming pool and a very nice barbeque area are at the guest's disposal. In summertime is absolutely nice to go by bike/walking/jogging, it's very easy to find people doing the same  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 9

7 Nights min stay

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from £113 /night

£789 - £2629 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Thanks to its centrality and good road connection (the Florence-Siena dual carriage-way runs at just 7 km from the property) this place is an excellent starting point for daily trips to the main cultural sites of Tuscany: Colle di Val D'Elsa town is approx. 5 km. far. Within walking distance (approx.500 metres) a small village is offering a market, two bars and a restaurant.  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

7 Nights min stay

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from £215 /night

£1500 - £2850 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable 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

24 Photos

Villa | 3 Bedrooms | sleeps 7

3 Nights min stay

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from £182 /night

£1271 - £1534 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Thanks to its superb location is the ideal starting point for visiting the Val d'Orcia and Chianti hills, with its medieval towns such as Cortona, Montepulciano, Pienza, Montalcino and from there up to and San Gimignano and the beautiful art cities of Florence and Siena  …see more

20 Photos

House | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £141 /night

£982 - £1840 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Self-catering holiday house in the heart of Tuscany, private swimming pool, quiet place with stunning panoramic view . Holiday house is ideal for families, groups seeking relaxation, romantic gateway. No smoking vacation house, near Siena. Pet friendly rentals. Dream holiday with private swimming pool and garden, quiet area with beutiful views of the Tuscan country  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 7

3 Nights min stay

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from £182 /night

£1271 - £1621 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
The villa 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 art cities of Siena and Florence.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 7

3 Nights min stay

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from £182 /night

£1271 - £1621 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Thanks to its superb location is the ideal starting point for visiting the Val d'Orcia and Chianti hills, with its medieval towns such as Cortona, Montepulciano, Pienza, Montalcino and from there up to and San Gimignano and the beautiful art cities of Florence and Siena On demand services: Tranfer and Taxi service Wine and Olive Oil Tastings Cooking Lessons Dinners  …see more

20 Photos

Farmhouse | 8 Bedrooms | sleeps 25

Very Good 4.5/5 

Short stays welcome

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from £564 /night

£3943 - £4600 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
"The Harvest Moon" holiday house, is a Tuscan country mansion with a spectacular pool overlooking the boundless valley. The whole property is available for more comfort and privacy. The whole property is available for more confort and privacy.  …see more

23 Photos

Villa | 7 Bedrooms | sleeps 23

7 Nights min stay

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from £564 /night

£3943 - £6133 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Casale, montepulciano, villa, piscina, vigneti, matrimonio in toscana, matrimonio in Italia, Italy, Tuscany Antico casale, completamente restaurato e suddiviso in 7 accoglienti appartamenti  …see more

12 Photos

Villa | 8 Bedrooms | sleeps 25

7 Nights min stay

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from £169 /night

£1183 - £4381 / week

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Key info:

  • Swimming pool
  • Suitable 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

4 Photos

Farmhouse | 3 Bedrooms | sleeps 6

Short stays welcome

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from £197 /night

£1378 - £2438 / week

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Key info:

  • Nearest beach 50 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Farm Holiday for rent in Siena Toscany 6 bedrooms Farm Holiday for rent in Siena Firenze Toscany Italy  …see more

8 Photos

Villa | 9 Bedrooms | sleeps 12

3 Nights min stay

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from £192 /night

£1343 - £2996 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • Pets welcome
Villa Hamby is a beautifully restored five bedroom four bathroom country house with a great deal of warmth and charm. The villa has a great views across the Valdarno valley that stretches from Florence to Rome with the Appenini mountains as a dramatic backdrop to the co  …see more

12 Photos

Villa | 5 Bedrooms | sleeps 10

3 Nights min stay

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from £192 /night

£1343 - £2996 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • Pets welcome
Villa Dan is located between the cities of Arezzo, Florence and Siena, at the quaint old town of Figline Valdarno with its ancient piazza and historical buildings. The Villa Dan has 5 bedrooms and 3bathrooms, situated in Figline Valdarno, with a magnicificient view. On  …see more

24 Photos

House | 1 Bedroom | sleeps 5

Very Good 4/5 

3 Nights min stay

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from £50 /night

£348 - £538 / week

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Key info:

  • Nearest beach 50 km
  • Swimming pool
  • Suitable 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

24 Photos

Villa | 5 Bedrooms | sleeps 12

Excellent 5/5 

3 Nights min stay

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from £189 /night

£1323 - £2439 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • 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

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

4 Nights min stay

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from £188 /night

£1315 - £2720 / week

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Late Deal: save up to €987 (approx. £816)

Key info:

  • Nearest beach 110 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Typical Tuscany stone house with private swimming pool, large fenced garden and tennis court. Easy day trips to Florence, Siena, San Gimignano and many Tuscan villages. Cooking lessons and dinners at home on request. Countryside villa in silent and strategic position. Very spacious rooms, sleeps up to 7/8 persons.  …see more

4 Photos

Apartment | 2 Bedrooms | sleeps 5

2 Nights min stay

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from £94 /night

£658 - £877 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
The villa Podernovo offers a nice apartment called Il Forno, with stunning view on the sunflowers fields, with all comforts such air conditioning.  …see more

22 Photos

Villa | 5 Bedrooms | sleeps 14

1 night min stay

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from £72 /night

£500 - £3000 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Suitable 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

5 Photos

Apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £94 /night

£658 - £877 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
The Il Pino apartmnet is located at the first floor of the Podere Podernovo at San fabiano farmestate  …see more

16 Photos

Farmhouse | 6 Bedrooms | sleeps 20

Excellent 5/5 

2 Nights min stay

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from £526 /night

£3680 - £5081 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
Climatized villa with swimming pool, wi-fi,and TV with Sky channels, offers relax and fun at only 7 miles from Siena. The Count Filippo Fiorentini, English speaking will welcome you with a good glass of wine, in his villa.  …see more

22 Photos

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

1 night min stay

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from £50 /night

£348 - £728 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
The apartment has been made from the rooms where the farm cellar was once located. It measures 70 square metres. 1 bedroom with bathroom, large kitchen/diner, lounge with FIREPLACE and SATELLITE TV; VERANDA overlooking the swimming pool  …see more

6 Photos

Villa | 2 Bedrooms | sleeps 6

2 Nights min stay

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from £163 /night

£1139 - £1577 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
Unique villa in the area of Siena, pefect climatized and furnished with all comforts,The villa le Tortore offers private parking , private garden, exclusivity, access to the swimming pool, air conditioning, satellite Tv with Sky channels, PC with free dsl and wi-fi.  …see more