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1,110 Results  |  

from £311 / night

£2174 - £3116 / week

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Castle / 6 Bedrooms / sleeps 16

Short stays welcome

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from £311 / night

£2174 - £3116 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Castle, tuscany, italy, swimmingpool, bed and breakfast, gaiole in chianti, events, wedding, private castle, private villa, Yoga, wine  …see more

from £155 / night

£1080 - £2694 / week

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Farmhouse / 3 Bedrooms / sleeps 6

7 Nights min stay

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from £155 / night

£1080 - £2694 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
Beautiful stone-built farmhouse that has been perfectly restored and equipped with all of the modern conveniences, situated in the heart of the Chianti Classico close to the typical tuscan town of Radda.  …see more

from £352 / night

£2464 - £3479 / week

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Villa / 5 Bedrooms / sleeps 10

7 Nights min stay

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from £352 / night

£2464 - £3479 / 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
Cosoli is located in Chianti Classico, conveniently half way from Florence and Siena. The villa overlooks a massive olive grove but yet surrounded by a great view of surrounding vineyards and small cities in the distance. 3 hours weekly housekeeping is included as well as the complete house cleaning after leaving.  …see more

Featured properties

from £171 / night

£1196 - £1515 / week

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Apartment / 2 Bedrooms / sleeps 4

2 Nights min stay

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from £171 / night

£1196 - £1515 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
This charming old hamlet is located at 5 km from San Giovanni d'Asso, in the heart of the Crete Senesi  …see more

from £171 / night

£1196 - £2029 / week

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Villa / 4 Bedrooms / sleeps 8

7 Nights min stay

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from £171 / night

£1196 - £2029 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
From a tiny hamlet that dates back to 1047 ad, the views of Monte Maggio seem drawn on the horizon.  …see more

from £311 / night

£2174 - £2899 / week

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Farmhouse / 4 Bedrooms / sleeps 16

2 Nights min stay

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from £311 / night

£2174 - £2899 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
The Podere Podernovo offers accomodation up to 16 people,with all comforts,as heating, air condititioning, Internet,wi-fi, Tv with Sky.The Count Fiorentini will welcome you in his farmhouse just 12 km south of Siena in the Arbia valley.  …see more

from £83 / night

£580 - £1667 / week

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Villa / 4 Bedrooms / sleeps 8

3 Nights min stay

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from £83 / night

£580 - £1667 / week

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Key info:

  • Swimming pool
  • Suitable for children over 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Tuscany. Heart of Chiant.iExclusive use of private swimming pool. The Villa accommodates up to 8/9 people. Beautiful views of the country side. Only a few other farmhouses are visible in the distance. Outdoor dining area. Fontecaresino, located in the hills of Chianti, in the heart of Tuscany. Breathtaking views.  …see more

from £108 / night

£750 - £950 / week

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House / 2 Bedrooms / sleeps 6

7 Nights min stay

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from £108 / night

£750 - £950 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Italy, Tuscany, Chianti, Castellina in Chianti, Florence, swimming pool, tennis court, private garden, stunning views, Luxury interior designed, house, beautiful gardens, San Gimignano, Siena, Florence, Firenze.  …see more

from £174 / night

£1218 - £2537 / week

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24 Photos

Villa / 6 Bedrooms / sleeps 10

7 Nights min stay

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from £174 / night

£1218 - £2537 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Villa in Siena with SPA room and swimming pool at exclusive use.  …see more

from £156 / night

£1087 - £1414 / week

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Apartment / 2 Bedrooms / sleeps 4

2 Nights min stay

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from £156 / night

£1087 - £1414 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
This charming old hamlet is located at 5 km from San Giovanni d'Asso, in the heart of the Crete Senesi  …see more

from £182 / night

£1269 - £1975 / week

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Farmhouse / 4 Bedrooms / sleeps 8

7 Nights min stay

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from £182 / night

£1269 - £1975 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Magical Tuscan farmhouse with pool overlooking the stunning Siena countryside. Enjoying the most beautiful and tranquil of settings Le Contessine offers both a relaxing escape and a strategic location for touring the whole of Tuscany and Umbria with ease. 4 bedrooms.  …see more

from £208 / night

£1450 - £1740 / week

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Villa / 3 Bedrooms / sleeps 7

7 Nights min stay

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from £208 / night

£1450 - £1740 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
As the house is part of a company that produces Brunello di Montalcino is possible to follow the stages of production or do a tasting tour to discover one of the best wines in the world in our cave.  …see more

from £218 / night

£1522 / week

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Villa / 3 Bedrooms / sleeps 6

2 Nights min stay

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from £218 / night

£1522 / week

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Key info:

  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Vila is in Sarteano Italy which is a small Tuscan town rich in history and beautiful Tuscan Architecture. It has a Castle open to the public, a museum, and A Parc with Pools which consists of thermal spring waters. Town has a Fresh Pasta Store, Pasticceria, and a Market Need a Car  …see more

from £143 / night

£1000 - £1600 / week

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Villa / 3 Bedrooms / sleeps 8

7 Nights min stay

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from £143 / night

£1000 - £1600 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Private viila and swimming pool deeped in nature and quiet.We rent out the whole house,so you could enjoy your holiday without any disturb.  …see more

from £166 / night

£1160 - £1812 / week

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Villa / 5 Bedrooms / sleeps 10

7 Nights min stay

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from £166 / night

£1160 - £1812 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Not far from Siena, for 5 minutes along the road from San Gimignano goes towards Gambassi, we find the gates of Villa Panorama. It is an old building of more than 5 centuries and tastefully decorated and with quality furniture and style typical of the villas in Tuscany  …see more

from £164 / night

£1142 - £2138 / week

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Villa / 9 Bedrooms / sleeps 18

1 night min stay

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from £164 / night

£1142 - £2138 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
"Villa Palazzone" is a charming country house set in the heart of a large estate of 153 hectares. The property has been completely renovated and upgraded with all modern conveniences.  …see more

from £182 / night

£1269 - £1595 / week

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Villa / 3 Bedrooms / sleeps 7

3 Nights min stay

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from £182 / night

£1269 - £1595 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • 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

from £100 / night

£698 - £997 / week

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Apartment / 2 Bedrooms / sleeps 2

3 Nights min stay

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from £100 / night

£698 - £997 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Pets welcome
  • Private garden
Located in the elegantly renovated barn, Iris is particularly spacious and filled with natural light. Baby bed on request is free  …see more

from £373 / night

£2609 - £2790 / week

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Castle / 6 Bedrooms / sleeps 16

7 Nights min stay

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from £373 / night

£2609 - £2790 / 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

from £51 / night

£356 - £761 / week

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Barn / 1 Bedroom / sleeps 3

1 night min stay

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from £51 / night

£356 - £761 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great 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

from £161 / night

£1124 - £1341 / week

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Apartment / 4 Bedrooms / sleeps 9

7 Nights min stay

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from £161 / night

£1124 - £1341 / 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
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

from £200 / night

£1400 - £1950 / week

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Cottage / 3 Bedrooms / sleeps 6

7 Nights min stay

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from £200 / night

£1400 - £1950 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
  • Private garden
Podere Le Lame is an enchanting Tuscan Mill house, set in four hectares of olives - a house for complete peace and relaxation. All bedrooms have en suite bathrooms with power showers. There is a large hall/dining/kitchen with an open fire and French windows to a loggia.  …see more

from £52 / night

£363 - £1522 / week

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Farmhouse / 2 Bedrooms / sleeps 6

3 Nights min stay

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from £52 / night

£363 - £1522 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Pets welcome
www.ilcellese.it  …see more

from £363 / night

£2537 - £4305 / week

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21 Photos

Villa / 8 Bedrooms / sleeps 12

Short stays welcome

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from £363 / night

£2537 - £4305 / 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

from £137 / night

£957 - £1519 / week

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House / 2 Bedrooms / sleeps 6

2 Nights min stay

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from £137 / night

£957 - £1519 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
All the charm and comfort for an artistic stay in the heart of Tuscany. Montalcino has remained quite untouched and therefore has kept it's charming atmosphere. Moreover, if you love food and wine, especially Brunello, you cannot go wrong around here, come and enjoy!  …see more

from £109 / night

£761 - £914 / week

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Apartment / 2 Bedrooms / sleeps 4

3 Nights min stay

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from £109 / night

£761 - £914 / week

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Key info:

  • Suitable for children over 5
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Thanks to the “Self-catering Formula” our guests will feel like they're at home, the equipments of every flat are really complete. The position in the heart of Chianti makes Resort Olmo a privileged starting point to explore Tuscany.  …see more

from £63 / night

£435 - £653 / week

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Apartment / 2 Bedrooms / sleeps 4

2 Nights min stay

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from £63 / night

£435 - £653 / 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

from £42 / night

£290 - £392 / week

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Farmhouse / 2 Bedrooms / sleeps 8

2 Nights min stay

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from £42 / night

£290 - £392 / week

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Key info:

  • Nearest beach 80 km
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
The apartment is an excellent starting point for excursions on foot or mountain bike in the via Francigena or Montagnola senese.Siena is about 13 km, Monteriggioni approx. 8 km. you can do excursions also to s. Gimignano, Colle di Val D'elsa, Casole, s. Galgano  …see more

from £65 / night

£450 - £928 / week

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22 Photos

Farmhouse / 2 Bedrooms / sleeps 4

1 night min stay

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from £65 / night

£450 - £928 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
Created in the former barn and warehouse, this is a large 124 square metre apartment on two floors. Discover Tuscany from a privileged starting point: its heart.  …see more

from £151 / night

£1051 - £1805 / week

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Farmhouse / 5 Bedrooms / sleeps 10

3 Nights min stay

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from £151 / night

£1051 - £1805 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Podernovo is farmhouse, of the 19th century, surrounded by greenery with a breath-taking swimming pool. 5 Bedrooms, 5 Bathrooms, Panoramic Private Pool, Car Parking, Outdoor Facilities. Halfway between Rome and Florence. 5 km from the well-known SPA resort Fonteverde Come to relax and find out how to get lost in nature and rediscover yourself.  …see more

from £86 / night

£602 - £863 / week

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Cottage / 3 Bedrooms / sleeps 6

3 Nights min stay

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from £86 / night

£602 - £863 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
Once the pigsty of the Counts of Lucciana. The cottage is situated on the ground floor and composed as follows: › Spacious kitchen with dish washing machine › 3 bedrooms › 2 bathrooms with shower enfant bed  …see more

from £83 / night

£580 - £3551 / week

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Hotel apartment / 7 Bedrooms / sleeps 22

1 night min stay

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from £83 / night

£580 - £3551 / week

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Key info:

  • Great for children of all ages
  • Air conditioning
  • Pets welcome
  • Private garden
It is the second structure that we have opened. Half way up the main street of Montepulciano, a few meters from Piazza delle Erbe and the Tower of Pulcinella, “La Dimora” provides large space and is equipped with every comfort, air conditioning and Wi-Fi included. On t  …see more

from £85 / night

£594 - £660 / week

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Apartment / 2 Bedrooms / sleeps 4

3 Nights min stay

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from £85 / night

£594 - £660 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
Apartment totally renewed in 1999. It is composed by 2 bedrooms (one with a duoble bed and the other with two single beds), bathroom (with tub and shower), a spacious living and dining room with fireplace (and dishwasher too), attic with tv.  …see more

from £95 / night

£660 - £1160 / week

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Apartment / 3 Bedrooms / sleeps 4

4 Nights min stay

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from £95 / night

£660 - £1160 / 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
"Casa Serena" is located in a panoramic position, blessed with mesmerising views over the Chianti vineyards and enchanting hamlets. Quiet location but not isolated. Local assistant 24 H in case of need - english speaking  …see more

from £389 / night

£2723 - £3907 / week

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Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

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from £389 / night

£2723 - £3907 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa San Francesca is a prestigious and luxurious villa in the heart of south Siena countryside with breathtaking panoramic views that enjoy the surrounding, and only a few kilometers from the historic town of Cetona.  …see more

from £845 / night

£5914 - £7392 / week

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Villa / 7 Bedrooms / sleeps 14

7 Nights min stay

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from £845 / night

£5914 - £7392 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
A beautifully renovated Tuscan villa in the Orcia valley with stunning countryside views and ideal location for relaxing and exploring the Tuscan and Umbrian countryside.  …see more

from £373 / night

£2609 - £4174 / week

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Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

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from £373 / night

£2609 - £4174 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
If a villa holiday in Tuscany is calling to you, take a closer look at Villa Magna. This property provides ample room for twelve guests, offering six beautiful bedrooms and a variety of other features you'll fall in love with on first sight.  …see more

from £510 / night

£3566 - £5044 / week

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Villa / 7 Bedrooms / sleeps 14

7 Nights min stay

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from £510 / night

£3566 - £5044 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa Cecilia is an incredible rustic farmhouse villa in the heart of south Siena countryside with breathtaking panoramic views that enjoy the surrounding with beautiful gardens and swimming pool ideal for group holidays or larger families with children.  …see more

from £1005 / night

£7029 - £7754 / week

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Villa / 7 Bedrooms / sleeps 14

7 Nights min stay

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from £1005 / night

£7029 - £7754 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Located in the heart of the Brunello di Montalcino wine land, this super luxury villa for rent was an old customhouse, whose central tower dates back to 1400 AD. The property is surrounded by 4 hectares of gardens and woods, and offers glorious view of the Siena hills.  …see more

from £86 / night

£602 - £1087 / week

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Apartment / 2 Bedrooms / sleeps 6

7 Nights min stay

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from £86 / night

£602 - £1087 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
This 69sqm apartment is on one floor only and consists of a sitting room with double divan bed and stone fireplace, dining area and fully equipped kitchenette, a double bedroom with bathroom fitted with shower and built-in wardrobe, a twin bedroom and another bathroom  …see more

from £232 / night

£1624 - £2760 / week

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Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

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from £232 / night

£1624 - £2760 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Some pets are welcome - please contact the owner
  • Private garden
Siena villas - Swimming Pool - Tennis court. A detached villa with garden for exclusive guest use. The fountain adds a classic touch to the outdoors that can be admired from the wide windows of the villa and accessed from the large dining room.  …see more

from £751 / night

£5254 / week

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Villa / 5 Bedrooms / sleeps 10

7 Nights min stay

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from £751 / night

£5254 / week

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Key info:

  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
An independent farmhouse that sleeps 10 and is composed of a main building and a tower. The main house sleeps 6 people. Excellent furnishings and well appointed property.  …see more

from £415 / night

£2899 - £3298 / week

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Villa / 7 Bedrooms / sleeps 14

7 Nights min stay

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from £415 / night

£2899 - £3298 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
A delightful Villa in Siena overlooking a small lake between woods and rolling hills. A beautiful spot for a large family.  …see more

from £202 / night

£1414 - £3298 / week

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Villa / 5 Bedrooms / sleeps 10

7 Nights min stay

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from £202 / night

£1414 - £3298 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
This superb villa with pool in Tuscany is located at 8 km from the pretty medieval village of Asciano, 30 km east of Siena. Surrounded by a private garden full of olive trees, this holiday home has been renovated to an extremely high standard  …see more

from £57 / night

£399 - £906 / week

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Apartment / 2 Bedrooms / sleeps 6

2 Nights min stay

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from £57 / night

£399 - £906 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Beautiful farmhouse with wonderful swimming pool set close to Siena. Quiet location in strategic position to visit the famous Crete Senesi as well as the Val d'Orcia region and of course Siena and Florence. The sapcious garden allows to enjoy privacy and peace. The farmhouse is also suitable for families with children thanks to our children play ground and play room!  …see more

from £73 / night

£508 - £653 / week

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Apartment / 1 Bedroom / sleeps 4

2 Nights min stay

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from £73 / night

£508 - £653 / week

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Key info:

  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
A spacious and luminous two roomed unit (55sqm) 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. 500 metres away the apartment start a commercial area with 3 supermarkets, shops, coffee, bar, bakery, etc.  …see more

from £104 / night

£725 - £2319 / week

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Villa / 3 Bedrooms / sleeps 9

7 Nights min stay

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from £104 / night

£725 - £2319 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great 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

from £85 / night

£594 - £660 / week

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Apartment / 2 Bedrooms / sleeps 4

3 Nights min stay

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from £85 / night

£594 - £660 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
Apartment totally renewed in 1999.It is composed by 2 bedrooms (one with a duoble bed and the other with two single beds), bathroom (with the shower), a spacious kitchen and dining room with TV and an outside area with table and chairs.  …see more

from £57 / night

£399 - £1116 / week

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Apartment / 3 Bedrooms / sleeps 6

2 Nights min stay

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from £57 / night

£399 - £1116 / week

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Key info:

  • Nearest beach 40 km
  • Suitable for children over 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
La casa si trova in località Crevole di Murlo detto anche " Rocca di Crevole" sotto le rimanenze di una antica torre residuo di un forte castello fortificato, presidiato da una guarnigione di soldati sotto il comando dei Vescovi di Siena . il prezzo è comprensivo di biancheria bagno e camera , riscaldamento ,letto singolo a richiesta ,  …see more

from £131 / night

£914 - £1595 / week

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Farmhouse / 3 Bedrooms / sleeps 7

3 Nights min stay

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from £131 / night

£914 - £1595 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Silence, privancy  …see more

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