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from £263 / night

£1839 - £4339 / week

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(11) Excellent 5/5 

1 / 26

Holiday villa in Bettolle

Villa / 12 Bedrooms / sleeps 34

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Pets welcome

Excellent 5/5 

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from £263 / night

£1839 - £4339 / week

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Romantic and beautiful Villa in the most tipical tuscany countryside. Its location is in Foiano della Chiana, close to Cortona, Trasimeno Lake, Pienza, Arezzo, Siena, Perugia, Assisi and Florence. The breathtaking view joins a complete privacy in a luxury resort. We can organize cooking classes on request. Prices are calculated on occupacy up to 24 guests.  …see more

from £211 / night

£1471 - £3861 / week

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(8) Very Good 4.5/5 

1 / 23

Holiday farmhouse rental

Farmhouse / 8 Bedrooms / sleeps 25

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome

Very Good 4.5/5 

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from £211 / night

£1471 - £3861 / week

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"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

from £258 / night

£1802 - £2574 / week

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(1) Excellent 5/5 

1 / 24

Holiday villa with swimming pool in Montepulciano

Villa / 6 Bedrooms / sleeps 12

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Excellent 5/5 

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from £258 / night

£1802 - £2574 / week

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The place is peaceful, outside in the garden; you have the possibility to relax under the trees or to eat under the stars. Beautiful structure for a relaxing holiday in the tuscany area . ask for availability we have several solution for you. also self catering apartments with breakfast service.  …see more

Featured properties

from £452 / night

£3162 - £4265 / week

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(1) Excellent 5/5 

1 / 16

Holiday farmhouse with swimming pool in San Fabiano

Farmhouse / 6 Bedrooms / sleeps 20

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary

Excellent 5/5 

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from £452 / night

£3162 - £4265 / week

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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

from £185 / night

£1293 - £3328 / week

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(3) Excellent 5/5 

1 / 24

Holiday villa in San Giovanni d'Asso

Villa / 5 Bedrooms / sleeps 10

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Excellent 5/5 

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from £185 / night

£1293 - £3328 / week

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5 BDR beautiful indipendent house with pool,AC,WiFi in the Siena countryside, close to a village. Please,ALWAYS enquiry about prices.The house can be rented just in part (3BDR apt))  …see more

from £147 / night

£1023 - £2023 / week

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(3) Excellent 5/5 

1 / 24

Holiday guest house in Siena

Guest house / 2 Bedrooms / sleeps 4

  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner

Excellent 5/5 

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from £147 / night

£1023 - £2023 / week

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Villa di Geggiano - home and winery of the Bianchi Bandinelli family since 1527. Just 5 kilometres from Siena, in the hills of Chianti Classico. Originally built in 14th century, the the Villa has now been complemented by the recent addition of two luxury guest suites. The Villa and its gardens are a National Heritage property and there is a great deal to see and enjoy!  …see more

from £190 / night

£1324 - £1618 / week

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(2) Excellent 5/5 

1 / 24

Holiday villa in Costaltino

Villa / 3 Bedrooms / sleeps 6

  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden

Excellent 5/5 

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from £190 / night

£1324 - £1618 / week

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Traditional Farmhouse with stunning views at Siena's doorstep - Free WiFi A Liability Waiver is an essential part of the booking & a specific requirement from our Insurer.  …see more

from £206 / night

£1439 - £1947 / week

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(3) Excellent 5/5 

1 / 24

Holiday farmhouse rental

Farmhouse / 2 Bedrooms / sleeps 5

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

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from £206 / night

£1439 - £1947 / week

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A typical stone barn immersed in the Tuscan countryside of San Gimignano. A large garden overlooks the hills and surrounding countryside. Up to 7 people in a both modern and rustic atmosphere.  …see more

from £788 / night

£5515 - £5809 / week

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(1) Very Good 4/5 

1 / 20

Holiday villa in Monticiano

Villa / 9 Bedrooms / sleeps 18

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Very Good 4/5 

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from £788 / night

£5515 - £5809 / week

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Ideal family and wedding Tuscan villa with private salt water pool. Tucked away yet not isolated. All amenities in the nearby village, walking distance. Siena 25 minutes.All Tuscan art cities and seaside daily outings. Nature, art, peace and quiet.  …see more

from £106 / night

£736 - £1471 / week

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(1) Excellent 5/5 

1 / 10

San Gimignano holiday apartment rental

Apartment / 3 Bedrooms / sleeps 7

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Excellent 5/5 

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from £106 / night

£736 - £1471 / week

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.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 relaxing The pool and the garden are not shared  …see more

from £116 / night

£809 - £1030 / week

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(4) Very Good 4.5/5 

1 / 24

Holiday apartment rental

Apartment / 3 Bedrooms / sleeps 7

  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Great for children of all ages
  • Car advised

Very Good 4.5/5 

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from £116 / night

£809 - £1030 / week

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Warm and welcoming, ten kilometres away from Siena, this apt is set in an ancient, XVth century villa, recently restored by a sensitive and art historically conscious architect & designer. The very best of the Tuscan tradition can be enjoyed here. Ideal for every configuration, romantic getaway, to read and draw, perfect for family or a group of friends  …see more

from £211 / night

£1471 - £3420 / week

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(3) Excellent 5/5 

1 / 24

Villa rental in Siena with swimming pool

Villa / 9 Bedrooms / sleeps 18

  • Nearest beach 95 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Excellent 5/5 

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from £211 / night

£1471 - £3420 / week

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Beautiful Tuscan detached villa with swimming pool near Siena to rent for sleeps up to-10-16-20-It is an ideal place for families to spend a relaxing holiday far from town noises among the peace of the country. A heaven of peace in the heart of Montagnola Senese at a stone's throw from Siena.  …see more

from £205 / night

£1434 - £1581 / week

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(1) Excellent 5/5 

1 / 21

Buonconvento holiday farmhouse rental

Farmhouse / 4 Bedrooms / sleeps 8

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

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from £205 / night

£1434 - £1581 / week

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Spacious Tuscan farmhouse with 4 large bedrooms in a cozy hamlet immersed in Orcia valley countryside with shared pool. Al-fresco private garden dining and stunning views. Perfect for families with children! Wine tasting and cooking classes. Golf, horseback riding near The Pheasant farmhouse is the original house of this historical hamlet immersed in the rolling Tuscan hills.  …see more

from £179 / night

£1250 - £2519 / week

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(2) Very Good 4.5/5 

1 / 24

Holiday farmhouse with swimming pool in Montepulciano

Farmhouse / 5 Bedrooms / sleeps 10

  • Nearest beach 200 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Very Good 4.5/5 

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from £179 / night

£1250 - £2519 / week

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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

from £441 / night

£3085 - £3383 / week

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(1) Excellent 5/5 

1 / 24

Villa rental in Castellina In Chianti with shared pool

Villa / 7 Bedrooms / sleeps 14

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Excellent 5/5 

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from £441 / night

£3085 - £3383 / week

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Sleeps 14 with possibility to add adjacent apartments up to total of 33. A beautiful 15th-century villa in the heart of the Chianti countryside, with 360° uninterrupted views of olives, vines and forests, with amazing sunset views over San Gimignano and the Apennines  …see more

from £158 / night

£1103 - £2280 / week

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(4) Very Good 4.5/5 

1 / 24

Cetona holiday villa rental

Villa / 5 Bedrooms / sleeps 10

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

Very Good 4.5/5 

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from £158 / night

£1103 - £2280 / week

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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

from £106 / night

£736 - £1648 / week

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(2) Very Good 4.5/5 

1 / 27

Holiday farmhouse with shared pool in Buonconvento

Farmhouse / 4 Bedrooms / sleeps 8

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Very Good 4.5/5 

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from £106 / night

£736 - £1648 / week

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Spacious farmhouse with country antiques immersed in the unique Orcia valley hillside. 4 bedrooms with shared pool, horseback riding, tennis and golf nearby. Outdoor covered eating patio with a view of Montalcino. Wine tastings onsite. Ceiling fans and large bedrooms. This spacious apartment in its own farmhouse isrentable for f 4 or 8 persons, in a peaceful country setting  …see more

from £177 / night

£1236 - £1633 / week

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(1) Excellent 5/5 

1 / 21

Holiday villa with swimming pool in San Giovanni d'Asso

Villa / 3 Bedrooms / sleeps 5

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Excellent 5/5 

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from £177 / night

£1236 - £1633 / week

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3 BDR cosy house with patio,small pool,AC,Wifi, in the heart of Siena countryside, nestled in a village. Private parking. Please,ALWAYS enquiry about prices.  …see more

from £72 / night

£500 - £898 / week

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(3) Very Good 4.5/5 

1 / 19

Siena holiday villa rental

Villa / 4 Bedrooms / sleeps 7

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome

Very Good 4.5/5 

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from £72 / night

£500 - £898 / week

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Gorgeous holiday villa in Siena, just 5 minutes walking from the town. blloming garden, shared swimming pool, private car parking, internet (with flash drive), laundry room, chef for dinner or meal on request  …see more

from £358 / night

£2502 - £3661 / week

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(1) Excellent 5/5 

1 / 21

Radicondoli holiday farmhouse rental

Farmhouse / 9 Bedrooms / sleeps 20

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden

Excellent 5/5 

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from £358 / night

£2502 - £3661 / week

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Podere Costarella is a farmhouse in the heart of the Tuscan countryside , specifically in Radicondoli. Located in the area of Chianti , the farmhouse has four apartments surrounded by nature , a swimming pool and a restaurant serving traditional Tuscan dishes.  …see more

from £174 / night

£1214 - £1508 / week

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(3) Excellent 5/5 

1 / 21

Holiday apartment in Val d'Orcia

Apartment / 4 Bedrooms / sleeps 9

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden

Excellent 5/5 

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from £174 / night

£1214 - £1508 / week

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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

from £171 / night

£1192 - £2170 / week

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(3) Excellent 5/5 

1 / 31

Holiday lodge in Pienza

Lodge / 3 Bedrooms / sleeps 8

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

Excellent 5/5 

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from £171 / night

£1192 - £2170 / week

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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

from £127 / night

£883 / week

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(2) Excellent 5/5 

1 / 20

Holiday villa in Radicondoli

Villa / 3 Bedrooms / sleeps 6

  • Nearest beach 65 km
  • Great for children of all ages
  • Car essential
  • Pets welcome

Excellent 5/5 

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from £127 / night

£883 / week

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Completely restored old country villa surrounded by private garden with superb views on one of the most pristine parts of Tuscany.  …see more

from £85 / night

£589 - £1912 / week

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(1) Excellent 5/5 

1 / 19

Holiday farmhouse with swimming pool in San Casciano dei Bagni

Farmhouse / 6 Bedrooms / sleeps 12

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Excellent 5/5 

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from £85 / night

£589 - £1912 / week

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Beautiful Tuscan country house and cottage set on a natural terrace with commanding views of the Tuscan hills. Deep in the countryside with easy day trips to Florence, Sienna and Perugia. SLEEPS 8 PEOPLE IN THE MAIN HOUSE AND 4 PEOPLE IN THE GUEST COTTAGE.  …see more

from £103 / night

£721 - £927 / week

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(1) Excellent 5/5 

1 / 22

Radicondoli holiday home rental

House / 3 Bedrooms / sleeps 6

  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Great for children of all ages
  • Car advised

Excellent 5/5 

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from £103 / night

£721 - £927 / week

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Podere la Fonte is situated in a most spectacular position just below the ancient castellated village of Radicondoli. It has magnificent uninterrupted views over the Cecina valley and the surrounding hills.At night you can see the lights of Volterra.  …see more

from £375 / night

£2625 - £4203 / week

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(4) Excellent 5/5 

1 / 26

Holiday villa rental

Villa / 8 Bedrooms / sleeps 16

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Excellent 5/5 

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from £375 / night

£2625 - £4203 / week

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8 BDR luxury historical villa with garden and pool in the heart of Siena countryside nestled in a village.AC, WiFi,Private parking Please,ALWAYS,enquiry about prices.The house can be rented just in part (4BDR).  …see more

from £190 / night

£1324 - £2133 / week

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1 / 14

Farmhouse rental in Montepulciano with shared pool

Farmhouse / 7 Bedrooms / sleeps 18

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

Add to shortlist

from £190 / night

£1324 - £2133 / week

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Entire Farmhouse in Montepulciano with 5 independent apartments, a large garden, seasonal outdoor pool. Tuscany country estate surrounded with the wonderful Nobile-vineyards and Touscany country.  …see more

from £72 / night

£500 - £890 / week

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(6) Excellent 5/5 

1 / 23

Holiday farmhouse with shared pool in Montepulciano

Farmhouse / 2 Bedrooms / sleeps 6

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

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from £72 / night

£500 - £890 / week

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2 bedroom beautiful 500 year old restored farmhouse. 7km outside of Montepulciano. Pool, terrace, garden area, patio, and BBQ. 5 minute drive to nearest supermarket, shops, bars and restaurants.  …see more

from £91 / night

£631 - £700 / week

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(4) Excellent 5/5 

1 / 24

Montisi holiday fort rental

Fort / 1 Bedroom / sleeps 3

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed

Excellent 5/5 

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from £91 / night

£631 - £700 / week

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Romantic and charming 14th century fortress. Very authentic medieval atmosphere. Strategically located between Val d'Orcia and Crete Senesi, close to Montalcino, Montepulciano, Pienza and Siena. Shops at walking distance. Organic wine and extra virgin olive oil.  …see more

from £137 / night

£956 - £1030 / week

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(1) Very Good 4/5 

1 / 20

Holiday apartment with swimming pool in Monteroni d'Arbia

Apartment / 3 Bedrooms / sleeps 6

  • Nearest beach 60 km
  • Swimming pool
  • Not suitable for children
  • Car advised

Very Good 4/5 

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from £137 / night

£956 - £1030 / week

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Swimming pool only available during the summer. Garden is shared with the owners of the house. English-speaking representative on hand to answer any questions.  …see more

from £100 / night

£699 - £1177 / week

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(16) Excellent 5/5 

1 / 23

Holiday farmhouse rental

Farmhouse / 3 Bedrooms / sleeps 8

  • Nearest beach 99 km
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner

Excellent 5/5 

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from £100 / night

£699 - £1177 / week

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Gorgeous views from this spacious restored farmhouse on artisanal working farm . Priv. balcony and patios, huge kitchen, Wi-Fi, Sat TV. Help in finding cooking classes, baby-sitting, horseback riding, motorcycle, winery, bike & walking tours  …see more

from £137 / night

£956 - £1250 / week

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(2) Excellent 5/5 

1 / 17

Monteriggioni holiday villa rental

Villa / 2 Bedrooms / sleeps 6

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

Add to shortlist

from £137 / night

£956 - £1250 / week

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Wonderful Villa with private pool overlooking the castle of Monteriggioni  …see more
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