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1,814 Results  |  
22 Photos

Tower | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £125 /night

£874 - £2171 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car essential
  • May take pets – please enquire
  • Private garden
Stunning medieval tower near San Gimignano for holiday rentals  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 4

4 Nights min stay

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from £54 /night

£374 - £806 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
holiday apartments in Montepulciano. Farm stay in a wine estate in Montepulciano  …see more

22 Photos

Apartment | 1 Bedroom | sleeps 5

7 Nights min stay

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from £44 /night

£306 - £577 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
Stunning apartments for holiday rental in Torrita di Siena, near Pienza and Montepulciano  …see more

Featured properties

19 Photos

Villa | 4 Bedrooms | sleeps 10

7 Nights min stay

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from £182 /night

£1272 - £1824 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Beautiful independent country house near Pienza. This villa is located few minutes driving from Pienza, in a quiet and beautiful location in the middle of the country side. Private swimming pool. The villa is elegantly furnished, in a perfect combination between comfort and tradition  …see more

13 Photos

Apartment | 2 Bedrooms | sleeps 5

3 Nights min stay

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from £38 /night

£263 - £501 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Nice and comfortable apartments in walking distance from the village  …see more

19 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £36 /night

£251 - £484 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
Stunning apartments for holiday rental in Torrita di Siena, near Pienza and Montepulciano  …see more

18 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £38 /night

£263 - £509 / week

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Key info:

  • Swimming pool
  • Suitable for over 5s only
  • Car essential
  • No pets allowed
Stunning apartments for holiday rental in Torrita di Siena, near Pienza and Montepulciano  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £39 /night

£272 - £509 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
Stunning apartments for holiday rental in Torrita di Siena, near Pienza and Montepulciano  …see more

21 Photos

Apartment | 2 Bedrooms | sleeps 4

4 Nights min stay

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from £59 /night

£408 - £738 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Why the Owner Chose Buonconvento: This area of Tuscany is intensely beautiful and within easy reach of many of the most significant cultural sites in Italy. In addition I love golfing and 30 min away there are marvelous golf courses such as La Bagnaia, Tuscany Golf. In Summer time, Prisca House guest can have a swim in Buonconvento huge communal pool (10 minutes aways)  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 7

Excellent 5/5 

2 Nights min stay

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from £49 /night

£340 - £382 / week

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Key info:

  • Suitable for children of all ages
  • 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

Farmhouse | 4 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

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from £152 /night

£1060 / week

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Key info:

  • Nearest beach 100 km
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
Spectacular Views! Well equipped apartment in great location.Great for families. Outside, is a very attractive pergola, with BBQ for drinks and meals, overlooking the beautiful Tuscan hills and valleys. Vouchers for the local spa are provided upon request. Logs for the fire are provided free of charge.  …see more

10 Photos

Apartment | 3 Bedrooms | sleeps 7

4 Nights min stay

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from £146 /night

£1018 - £1866 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • No pets allowed
  • Private garden
.This charming accommodation lies in the countryside enjoying the most marvellous views of the undulating landscape and the towers of the city of San Gimignano only 3km away. It is a lovely location for enjoying country walks and relaxingr The pool and the garden are not shared  …see more

12 Photos

Apartment | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £97 /night

£679 - £1018 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
The best place to enjoy the real tuscan life: nice food and wine, wonderful landscape,history, art and nice people!  …see more

10 Photos

Apartment | 3 Bedrooms | sleeps 4

2 Nights min stay

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from £103 /night

£721 - £806 / week

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Key info:

  • Suitable for children of all ages
  • Air conditioning
  • May take pets – please enquire
A luminous apartment (65sqm) in Siena that can accommodate up to 4 guests. The apartment commands a wonderful view over the Sienese hills and is located 1,5 km away from the pedestrian historical centre of Siena.  …see more

14 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £164 /night

£1145 - £1569 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • Pets welcome
In Podere Malabiccia all the rooms enjoy views of the surrounding landscape. Sunroom with west-facing arced windows. Kitchen with a large fireplace and antique wood burning oven. Living room and informal dining room with a fireplace. Antique Tuscan ceramics. Garden.  …see more

11 Photos

Farmhouse | 2 Bedrooms | sleeps 5

6 Nights min stay

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from £63 /night

£441 - £501 / week

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Key info:

  • Suitable for children of all ages
  • Air conditioning
  • May take pets – please enquire
Holiday Apartment is situated in the middle of Tuscany, 8km far from San Gimignano, 30km far from Siena and Volterra , 40km far from Florence, 70Km from Pisa and 100Km far from Lucca. This farm is close to an abbandoned old paper-mill built on an ancient mill erected by friars of San Galgano  …see more

7 Photos

Apartment | 2 Bedrooms | sleeps 4

Very Good 4.5/5 

2 Nights min stay

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from £97 /night

£679 - £806 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Valiano is not so far from Arezzo, Perugia and Siena, nearby you can find Spa or nice villages. In Summer there are festivals and others kind of music intertainements around here.  …see more

23 Photos

Apartment | 4 Bedrooms | sleeps 11

3 Nights min stay

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from £143 /night

£1001 - £1434 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Not suitable for children
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
If you are a big group (6-11 persons), you can spent your holidays together. We offer you two attached apartments, so if you want to have meals and to spend your time together, you can. But, at the same time, everybody has its own place.  …see more

11 Photos

Villa | 7 Bedrooms | sleeps 13

3 Nights min stay

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from £175 /night

£1225 - £2239 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Villa with swimming-pool just five kilometers from Siena in the middle of Tuscany. Originally a 17th century chapel, Villa del Cielo has been tastefully converted into a charming and unique villa rental in Tuscany.  …see more

24 Photos

Villa | 9 Bedrooms | sleeps 18

3 Nights min stay

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from £182 /night

£1272 - £2396 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
  • Private garden
"Villa Palazzone" is a charming country house set in the Siena province in the heart of a large estate of 153 hectares. It is very close to the beautiful little towns of Sarteano, Cetona and Città della Pieve and within 30 minutes from the lakes Trasimeno and Bolsena.  …see more

24 Photos

Farmhouse | 2 Bedrooms | sleeps 8

Excellent 5/5 

2 Nights min stay

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from £49 /night

£340 - £467 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Il casale è situato a Montallese, piccolo paese nel comune di Chiusi, che si sviluppa lungo la statale 326, strada di collegamento con Siena. La posizione è strategica per arrivare in poco tempo nei paesi vicini (Chiusi, Chianciano Terme, Montepulciano, ecc.) Da visitare i centri termali dei dintorni e i numerosi ristoranti dove gustare la prelibatezze toscane.  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 6

Short stays welcome

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from £181 /night

£1264 - £1773 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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

4 Photos

B&B | 1 Bedroom | sleeps 2

1 night min stay

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from £72 /night

£499 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
ROOM: Double Room FACILITIES: Plasma Tv, Satellite Decoder Hairdryer, Minibar, Air Conditioning, Heating BATHROOM: Private Bathroom with Shower ROOM SIZE: 21 square meters SHARED AREAS: Private Parking, Gazebo, Swimming Pool  …see more

17 Photos

B&B | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £61 /night

£424 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
Every morning the lady of the house makes amazing and always new breakfasts, created with the genuine products of the area and with a deep experience of cooking. Gluten intolerant breakfast. Please notify us in advance.  …see more

20 Photos

Farmhouse | 1 Bedroom | sleeps 3

3 Nights min stay

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from £119 /night

£832 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
Apartment located inside an Agriturismo in Montepulciano Tuscany. The apartment has a double room, a kitchen, a dining room with Fireplace and a private batrhoom with Jacuzzi. Available to clients: Private Parking, Gazebo and Swimming Pool.  …see more

18 Photos

Villa | 3 Bedrooms | sleeps 6

Short stays welcome

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from £145 /night

£1010 - £1773 / 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
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

10 Photos

Farmhouse | 2 Bedrooms | sleeps 5

Excellent 5/5 

2 Nights min stay

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from £44 /night

£302 - £509 / week

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Key info:

  • Suitable for children of all ages
  • No pets allowed
  • Private garden
This apartment would be a good base to visit Siena and the hilltop towns – you would particularly like Monteriggioni, San Gimignano, Montalcino, Pienza, Montepulciano, and Castellina in Chianti!  …see more

10 Photos

Apartment | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £128 /night

£891 - £1018 / week

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Key info:

  • Nearest beach 100 km
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
  • Private garden
We are situated in the historical heart of Tuscany and Chianti, half way between Siena and Firenze, on a hill overlooking a green and striking valley.The apartments are located in a picturesque hamlet that has been completely ristored- chianti full immersion, wine, food, striking landscape and culture  …see more

20 Photos

Farmhouse | 8 Bedrooms | sleeps 25

Very Good 4.5/5 

Short stays welcome

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from £546 /night

£3816 - £4452 / 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

22 Photos

Farmhouse | 2 Bedrooms | sleeps 4

4 Nights min stay

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from £72 /night

£501 - £751 / 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
The Tuscan countryside with its aligned vineyards, the olive trees that cover the hills, groves, the cypresses... It is a landscape that takes your breath away and gives you peace and quiet. The realization that the most beautiful things in life are the simplest!  …see more

24 Photos

Farmhouse | 2 Bedrooms | sleeps 4

Very Good 4.5/5 

4 Nights min stay

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from £63 /night

£437 - £666 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Farmhouse in the heart of Tuscany with pool and wonderful view Relax, peace, lots of space, playground for children, nature, wine and typical food  …see more

21 Photos

Apartment | 2 Bedrooms | sleeps 6

1 night min stay

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from £136 /night

£950 - £1425 / week

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Key info:

  • Nearest beach 84 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Charming holiday apartment in heart of Tuscany; excellent for families and couples seeking relaxation. Just few minutes to Siena, San Gimignano and Florence. Pool and fresco dining area.  …see more

23 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £101 /night

£704 - £1069 / week

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Key info:

  • Suitable for children of all ages
  • Pets welcome
Podere Staggia is a splendid farm house (18 th century) located on the top of a hill. The apartment of this farmhouse offers you the unique and rare possibility to enjoy an old, large (170 m2) and luminous house in the Siena area with a 360° open view. Ideal place for a family or a group of friends to enjoy quiet and restful holidays.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £1454 /night

£10176 / week

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Key info:

  • Nearest beach 20 km
  • Swimming pool
  • Suitable for over 5s only
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
The first floor of a Villa dating from around 1760, a commanding position within a protected area of outstanding natural beauty. Described as 'Manhattan in Tuscany' the compassionate treatment of the lovely old structure is supercharged by contemporary interior design. Bright, spacious and fully equipped for entertainment and comfort. A/C,Plasm TVs, WiFI, home theatre, stereo  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 11

Short stays welcome

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from £240 /night

£1680 - £3596 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • Pets welcome
  • Private garden
Splendid 18th century mansion with typical Sienese architecture. It is situated next to the historical village of Basciano. The house position is ideal because one reaches the Chianti region in a few minutes or can enjoy the culture and convenience of the city of Siena.  …see more

18 Photos

Apartment | 3 Bedrooms | sleeps 4

Short stays welcome

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from £136 /night

£950 - £1468 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
The Villa is situated in a splendid 18th century mansion, with typical Sienese architecture. The property position is ideal because one reaches the Chianti region in a few minutes or can enjoy the culture and convenience of the city of Siena (6 km away).  …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

21 Photos

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

1 night min stay

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from £28 /night

£196 - £416 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
The apartment "La Tognazzina" is 42 mq. and it's situated at the first floor of an ancient building from the beginning of '900. it is few minutes drive from Siena.  …see more

9 Photos

Farmhouse | 4 Bedrooms | sleeps 6

2 Nights min stay

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from £61 /night

£424 / week

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Key info:

  • Nearest beach 90 km
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
Podere Capannacce and Torricella are two ancient farms located in the Ombrone valley known since Middle Ages for its abundance of water and its fertility. Torricella is placed over the valley and is only 500 m. far from Capannacce. Torricella is composed by a ancient mill and a tower, dating 1200 according to one olivetano manuscript.  …see more

16 Photos

Barn | 1 Bedroom | sleeps 3

Short stays welcome

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from £72 /night

£501 - £839 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
The property location allows a pleasant vacation in the countryside, and is a good point of reference for visiting Siena (5 miles).  …see more

20 Photos

Apartment | 4 Bedrooms | sleeps 9

1 night min stay

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from £145 /night

£1010 - £1188 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
On the ground floor of a 1600 Villa ,completely renovated for the maximum comfort of guests. All windows facing the valley and the natural reserve below.50 square meter private terrace with incredible view on the countryside.15x4 meter swimming pool .  …see more

16 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

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from £73 /night

£509 - £764 / week

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Key info:

  • Swimming pool
  • Suitable 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 £275 /night

£1925 - £2892 / week

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Key info:

  • Swimming pool
  • Suitable 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

24 Photos

Villa | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £110 /night

£764 - £6106 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
Private Apartment in historic Villa with swimming pool, tennis court and 5 hectare garden. Near Siena, Montepulciano, Cortona etc. 4 bedrooms (or more if needed) with 2 bathrooms, 1 separate WC, 1 kitchen, 1 living room, private terrace and garden!  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

Very Good 4.5/5 

3 Nights min stay

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from £352 /night

£2460 - £2629 / 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 with 3 apartment Everyapartment has bedrooms,bathroom and livingroom with kitchen corner big saloon smimmingpool,big garden Caio Alto offers to guests a nice and lovely holiday Asking to Paola and Alessandro (owers ) the guests may have collaboration and help the guests may sell organic products of Factory:oil extravergine DOP Terre diSiena, ,organic Wine  …see more

10 Photos

Villa | 4 Bedrooms | sleeps 4

Short stays welcome

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from £73 /night

£509 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • 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

8 Photos

Apartment | 1 Bedroom | sleeps 5

1 night min stay

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from £10 /night

£67 - £508 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Situated in the heart of tuscany (hills, between volterra, famous etruscan and medieval city and san gimignano, famous all over the world for its characteristic towers. You can easily visit florence, siena and pisa, chianti region, thyrrenian sea, monteriggioni. Charac  …see more

21 Photos

Farmhouse | 1 Bedroom | sleeps 4

Short stays welcome

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from £58 /night

£400 - £650 / week

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Key info:

  • Nearest beach 45 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Self catering Farmhouse with 4 luxury apartments in rural Tuscany with swimming pool spectacular views ,nearby golf, walking, trekking, fishing, biking. San Gimignano, and Certaldo, 20 minutes drive, Florence, Siena and Pisa one hour from the house.  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 9

Excellent 5/5 

7 Nights min stay

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from £267 /night

£1866 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
A really charming and full of style apartment in a XVI th century stone villa near Montalcino, Pienza, Siena, Montichiello. An enchanted garden and an amazing swimming pool with view on Montalcino for an unforgettable holiday: good food and wine, art, sport and relax..  …see more

21 Photos

Apartment | 4 Bedrooms | sleeps 9

7 Nights min stay

Add to shortlist

from £206 /night

£1442 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
A really charming and cosy mansard in the ancient stone villa Pian dell'Asso near Montalcino, Pienza, Siena, Montichiello. An enchanted garden and an amazing swimming pool with view on Montalcino for a relaxing holiday: good food and wine, art and sport.  …see more