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Province of Siena

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  • Abbadia San Salvatore (2)
  • Asciano (22)
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To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

Filters applied: Pets allowed (701)

32 of 701 Results

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from £167 / night

£1166 - £2123 / week

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(3) Excellent 5/5 

1 / 31

Holiday lodge in Pienza

Province of Siena / 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 £167 / night

£1166 - £2123 / 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 £201 / night

£1403 - £1547 / week

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(1) Excellent 5/5 

1 / 21

Buonconvento holiday farmhouse rental

Province of Siena / Buonconvento

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 £201 / night

£1403 - £1547 / 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 £155 / night

£1080 - £2231 / week

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(4) Very Good 4.5/5 

1 / 24

Cetona holiday villa rental

Province of Siena / Cetona

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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Not on the map

from £155 / night

£1080 - £2231 / 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

Featured properties

from £206 / night

£1439 - £3346 / week

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(3) Excellent 5/5 

1 / 24

Villa rental in Siena with swimming pool

Province of Siena / Siena

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 £206 / night

£1439 - £3346 / 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 £367 / night

£2569 - £4112 / week

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(4) Excellent 5/5 

1 / 80

Holiday villa rental

Province of Siena / San Giovanni d'Asso

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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Not on the map

from £367 / night

£2569 - £4112 / 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 £101 / night

£706 - £907 / week

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(1) Excellent 5/5 

1 / 22

Radicondoli holiday home rental

Province of Siena / Radicondoli

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 £101 / night

£706 - £907 / 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 £143 / night

£1000 - £1979 / week

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(3) Excellent 5/5 

1 / 56

Holiday guest house in Siena

Province of Siena / 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 £143 / night

£1000 - £1979 / 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 £173 / night

£1209 - £1598 / week

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(1) Excellent 5/5 

1 / 50

Holiday villa with swimming pool in San Giovanni d'Asso

Province of Siena / 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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Not on the map

from £173 / night

£1209 - £1598 / 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 £103 / night

£720 - £1612 / week

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(2) Very Good 4.5/5 

1 / 27

Holiday farmhouse with shared pool in Buonconvento

Province of Siena / 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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Not on the map

from £103 / night

£720 - £1612 / 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 £160 / night

£1116 - £1799 / week

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(3) Excellent 5/5 

1 / 16

Radicondoli holiday villa rental

Province of Siena / Radicondoli

Villa / 5 Bedrooms / sleeps 12

  • Nearest beach 40 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

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from £160 / night

£1116 - £1799 / week

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Charming independent villa in the heart of Tuscany with panoramic pool, FREE WI FI, garden, parking, wonderful panorama, near Siena, San Gimignano, Florence. Enjoy the real tuscan experience: city tour,food & wine tasting, massage, cooking lesson,horse riding...  …see more

from £114 / night

£792 - £1008 / week

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(4) Very Good 4.5/5 

1 / 24

Holiday apartment rental

Siena / Val di Merse

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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Not on the map

from £114 / night

£792 - £1008 / 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 £181 / night

£1265 - £3256 / week

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(3) Excellent 5/5 

1 / 45

Holiday villa in San Giovanni d'Asso

Province of Siena / 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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Not on the map

from £181 / night

£1265 - £3256 / 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 £175 / night

£1224 - £1475 / week

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(3) Excellent 5/5 

1 / 21

Holiday apartment in Val d'Orcia

Montalcino / 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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Not on the map

from £175 / night

£1224 - £1475 / 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 £98 / night

£684 - £1152 / week

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(16) Excellent 5/5 

1 / 21

Holiday farmhouse rental

Province of Siena / Buonconvento

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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Not on the map

from £98 / night

£684 - £1152 / 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 £84 / night

£583 - £986 / week

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(2) Very Good 4/5 

1 / 20

Home rental in Castellina In Chianti with shared pool

Province of Siena / Castellina In Chianti

House / 4 Bedrooms / sleeps 5

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

Very Good 4/5 

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from £84 / night

£583 - £986 / week

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CASALTA di PESA: Beautiful stone Tuscan hamlet in the splendid Chianti Classico vineyards. This property still shows the blazon of the astronomer Galileo Galilei who stayed in this hamlet many years and drew inspiration from the beauties of the surrounding landscape. Casalta di Pesa is an Holiday Home surrounded by vineyards, just outside Castellina in Chianti  …see more

from £94 / night

£655 - £684 / week

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(6) Excellent 5/5 

1 / 19

Holiday apartment rental

Province of Siena / Monteroni d'Arbia

Apartment / 1 Bedroom / sleeps 4

  • 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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Not on the map

from £94 / night

£655 - £684 / week

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This holiday home comes with country-style decor, and an open-plan lounge and dining area. The kitchenette is equipped with a stove, kitchenware, and a refrigerator.  …see more

from £823 / night

£5756 / week

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(8) Very Good 4.5/5 

1 / 21

Holiday guest house with shared pool in Chiusi

Province of Siena / Chiusi

Guest house / 15 Bedrooms / sleeps 30

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

Very Good 4.5/5 

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Not on the map

from £823 / night

£5756 / week

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Tuscany hamlet, nature, relax, historical sigh, holiday, tours, walking, swimmingpool  …see more

from £141 / night

£983 - £1209 / week

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(5) Excellent 5/5 

1 / 20

Radicondoli holiday apartment rental

Province of Siena / Radicondoli

Apartment / 3 Bedrooms / sleeps 9

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

Excellent 5/5 

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from £141 / night

£983 - £1209 / week

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Enjoy the view, meanwhile swimming in the pool, dine in the outside garden watching the beautiful sunset vew,in front of the chimney during the winter in the comfort of the heated pavements.  …see more

from £71 / night

£497 - £673 / week

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(1) Excellent 5/5 

1 / 24

Holiday castle with shared pool in Monteroni d'Arbia

Province of Siena / Monteroni d'Arbia

Castle / 2 Bedrooms / sleeps 4

  • Beach / lakeside relaxation
  • Nearest beach 50 km
  • Swimming pool
  • Great for children of all ages

Excellent 5/5 

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Not on the map

from £71 / night

£497 - £673 / week

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A country hideaway with traditional comforts. Excellent equestrian, golfing and spa activities, hiking and biking. Kids Club. Excellent for touring art cities and Chianti and Brunello wine countries. For nature lovers, artists and photographers. Full concierge services. Please request for Formignano B&B, Horse Riding & Golf, Spa Days, Art City & Local Tours, Weddings & Events.  …see more

from £47 / night

£324 - £720 / week

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(2) Excellent 5/5 

1 / 19

Holiday guest house in Radicondoli

Province of Siena / Radicondoli

Guest house / 3 Bedrooms / sleeps 5

  • Nearest beach 60 km
  • Suitable for children over 5
  • Car advised
  • Some pets are welcome - please contact the owner

Excellent 5/5 

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from £47 / night

£324 - £720 / week

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Spacious thirteenth century town house built right on the walls of the historic centre of Radicondoli, perfect for family or couple. Stunning views at all three levels of this historic building.  …see more

from £134 / night

£936 - £1008 / week

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(1) Very Good 4/5 

1 / 20

Holiday apartment with swimming pool in Monteroni d'Arbia

Province of Siena / 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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Not on the map

from £134 / night

£936 - £1008 / 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 £185 / night

£1295 - £2087 / week

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(1) Excellent 5/5 

1 / 14

Farmhouse rental in Montepulciano with shared pool

Province of Siena / Montepulciano

Farmhouse / 7 Bedrooms / sleeps 18

  • 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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Not on the map

from £185 / night

£1295 - £2087 / 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 £47 / night

£324 - £576 / week

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(1) Excellent 5/5 

1 / 23

Holiday apartment in Radicondoli

Province of Siena / Radicondoli

Apartment / 2 Bedrooms / sleeps 4

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

Excellent 5/5 

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from £47 / night

£324 - £576 / week

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Immerse yourself into the authentic Tuscan countryside for a special holiday treat in the middle of olive groves and wineyards with your hosts only too willing to let you taste the produce of such wonders accompanied by their own home cooking.  …see more

from £101 / night

£706 - £972 / week

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(3) Very Good 4.5/5 

1 / 24

Farmhouse rental in Caprera

Siena / Caprera

Farmhouse / 3 Bedrooms / sleeps 6

  • Nearest beach 100 km
  • Great for children of all ages
  • Car advised
  • Air conditioning

Very Good 4.5/5 

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from £101 / night

£706 - £972 / week

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Elegant Liberty farmhouse on the hills, in a quite village just ten minutes from Siena city centre. Stunning view toward the city steeples across the countryside. Olive groves and fields for walking and horse riding. Garden and farm yard for outdoor dining.  …see more

from £47 / night

£324 - £540 / week

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(3) Very Good 4.5/5 

1 / 14

Radicondoli holiday farmhouse rental

Province of Siena / Radicondoli

Farmhouse / 1 Bedroom / sleeps 4

  • Nearest beach 40 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Very Good 4.5/5 

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from £47 / night

£324 - £540 / week

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Typical Apartment sleeping 2+2 persons with private patio, garden, pool, parking, panorama in charming Resindence in Old Mill in the heart of Tuscany between Siena, San Gimignano and Florence. city tour, typical food & wine tasting, massage, cooking lesson, horse riding, air ballon, biking, tennis ..  …see more

from £78 / night

£540 - £720 / week

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(1) Excellent 5/5 

1 / 23

Holiday apartment in Val di Merse

Siena / Val di Merse

Apartment / 2 Bedrooms / sleeps 5

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

Excellent 5/5 

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Not on the map

from £78 / night

£540 - £720 / week

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Apartment Raffaello is a warm and welcoming apartment set in a XVth century villa, recently restored by a sensitive and art historically conscious architect and designer.The very best of the Tuscan tradition where nature and culture have mingled for centuries. Virtual Visit Raffaello http://www.visitesvirtuelles-360.com/hebergement/raffaello/raffaello.html  …see more

from £54 / night

£378 - £569 / week

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(3) Very Good 4.5/5 

1 / 20

Apartment rental in Montepulciano with shared pool

Province of Siena / Montepulciano

Apartment / 2 Bedrooms / sleeps 6

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

Very Good 4.5/5 

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Not on the map

from £54 / night

£378 - £569 / week

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Located in a wonderful area, along the wine road that leads from Montepulciano to Pienza, sorrounded by vineyards, olive trees, fields, woods. we offer self catering apartments , and also B&B service . new airport at 30 Km distance http://www.airport.umbria.it/en ASK AVAILABILITY we have apartment 4 people located in rustic farmhouses  …see more

from £49 / night

£342 - £396 / week

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(2) Excellent 5/5 

1 / 17

Holiday home in Cetona

Province of Siena / Cetona

House / 2 Bedrooms / sleeps 4

  • Not suitable for children
  • Car advised
  • Some pets are welcome - please contact the owner

Excellent 5/5 

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Not on the map

from £49 / night

£342 - £396 / week

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Opportunity awaits you to experience your Italian holiday in this unique home. The history and character of the home, neighborhood and Cetona will make you feel immersed in the lifestyle and truly feel like a local. We specialize in bike tours,rental and itineraries A short stroll from the home will take you to the piazza where you find restaurants, cafes, and shops  …see more

from £75 / night

£522 / week

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(5) Excellent 5/5 

1 / 23

Apartment rental in San Gimignano

Province of Siena / San Gimignano

Apartment / 2 Bedrooms / sleeps 5

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

Excellent 5/5 

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from £75 / night

£522 / week

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Staying in the Old Town is the best you could want from a holiday, everything is at hand, quaint shops for shopping, restaurants, taverns, museums and art galleries. Remember that the center is a pedestrian zone, calm and quiet  …see more

from £324 / night

£2268 - £3442 / week

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1 / 53

Holiday villa in Cetona

Province of Siena / Cetona

Villa / 10 Bedrooms / sleeps 20

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

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Not on the map

from £324 / night

£2268 - £3442 / week

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The villa is the ideal starting point to visit many importants city and towns such as : Montepulciano, Pienza, Montalcino, Siena, Arezzo, Cortona, Assisi, Perugia, C.della Pieve, Orvieto, Trasimeno Lake etc. We are only 90 minutes far from Rome and Florence. SPA nearby. Included: WIFI, electricity, water, gas for cooking use, weekly linen change, initial and final cleaning  …see more

from £297 / night

£2073 - £4126 / week

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(1) Very Good 4/5 

1 / 12

Holiday villa letting

Province of Siena / Siena

Villa / 7 Bedrooms / sleeps 14

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning

Very Good 4/5 

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Not on the map

from £297 / night

£2073 - £4126 / week

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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

from £47 / night

£324 - £432 / week

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1 / 22

Holiday apartment in Val di Merse

Siena / Val di Merse

Apartment / 1 Bedroom / sleeps 2

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

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Not on the map

from £47 / night

£324 - £432 / week

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Giotto is a warm and welcoming two person apartment, ideal for a romantic stay just 10 kilometres away from Sienna. Set in an ancient, XVth century villa, recently restored by a sensitive and art historically conscious architect and designer. Virtual Visit Giotto http://www.visitesvirtuelles-360.com/hebergement/giotto/giotto.html  …see more
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