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Province of Siena

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32 of 2,777 Results

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from £352 / night

£2464 - £3551 / week

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(1) Excellent 5/5 

1 / 13

Holiday farmhouse rental

Province of Siena / Gaiole in Chianti

Farmhouse / 5 Bedrooms / sleeps 18

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

Excellent 5/5 

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from £352 / night

£2464 - £3551 / week

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This is a traditional 5 bedroom villa situated between the towns of Gaiole in Chianti and Radda in Chianti. Accommodating up to 18 guests in total as additional apartments are available within the grounds, it's an ideal base for a stay with family or friends. The wonderful gardens and exceptionally large private swimming pool will mean it's hard to drag yourself away to see the sights of Tuscany. However, for those that do want to enjoy some sightseeing during their stay, the property is perfectly placed for exploring the best that this region has to offer.  …see more

from £206 / night

£1439 - £1947 / week

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(3) Excellent 5/5 

1 / 24

Holiday farmhouse rental

San Gimignano / Montauto

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 £208 / night

£1450 - £3370 / 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 £208 / night

£1450 - £3370 / 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

Featured properties

from £144 / night

£1008 - £1993 / week

View

(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 £144 / night

£1008 - £1993 / 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 £94 / night

£656 - £1479 / week

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(9) Excellent 5/5 

1 / 15

Holiday apartment in Siena

Province of Siena / Siena

Apartment / 2 Bedrooms / sleeps 4

  • Great for children of all ages
  • Car not necessary
  • No pets allowed

Excellent 5/5 

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from £94 / night

£656 - £1479 / week

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In the very center of Siena, Historic Residence Palazzo Bichi Ruspoli is the best choice to visit the city. Just a few steps from the famous Piazza del Campo, you'll live in an ancient medieval building in a newly remodeled apartment.  …see more

from £102 / night

£711 - £914 / 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 £102 / night

£711 - £914 / 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 £161 / night

£1124 - £1812 / 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 £161 / night

£1124 - £1812 / 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 £88 / night

£616 - £1667 / week

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(2) Very Good 4.5/5 

1 / 19

Casaglia holiday tower rental

San Gimignano / Casaglia

Tower / 2 Bedrooms / sleeps 10

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

Very Good 4.5/5 

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from £88 / night

£616 - £1667 / week

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characterful and historic place with awesome view on the tuscan landscape; nice and quiet place; strategic spot to visit the whole Tuscany  …see more

from £249 / night

£1740 - £2609 / week

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(5) Excellent 5/5 

1 / 20

Holiday villa with swimming pool in Torrita di Siena

Province of Siena / Torrita di Siena

Villa / 4 Bedrooms / sleeps 10

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

Excellent 5/5 

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from £249 / night

£1740 - £2609 / week

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Villa Reggello is located amidst the gently rolling Tuscan hills, between Pienza and Montepulciano, complitely surrounded by organic plantations.The rooms have been decorated with colours that recall the typical plants of the area : Lavender, Rose hip, Strawberry tree. We can organize for you a typical Tuscan dinner with hand-made pasta,coupled with the excellent local wine.  …see more

from £51 / night

£356 - £381 / week

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(10) Excellent 5/5 

1 / 19

Holiday apartment with shared pool in Monteroni d'Arbia

Province of Siena / Monteroni d'Arbia

Apartment / 1 Bedroom / sleeps 2

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

Excellent 5/5 

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from £51 / night

£356 - £381 / week

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Casanova di Lucignano is an old farmhouse completely restored and set in the Crete Senesi. It is an ideal place to relax, admire the landscape and enjoy many outdoor activities or for a short romantic getaway. Experience the homely atmosphere of the Tuscan countryside.  …see more

from £73 / night

£508 - £1087 / week

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(4) Excellent 5/5 

1 / 20

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

Apartment / 2 Bedrooms / sleeps 4

  • Great for children of all ages
  • No pets allowed

Excellent 5/5 

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from £73 / night

£508 - £1087 / week

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At MOntorio is easy to arrive and difficult to live, will be your home in Tuscany. Montorio has a special and unique spot , and you will feel in love for it  …see more

from £72 / night

£500 - £678 / 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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from £72 / night

£500 - £678 / 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 £21 / night

£144 - £454 / week

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(5) Very Good 4.5/5 

1 / 22

Holiday apartment with shared pool in Radicondoli

Province of Siena / Radicondoli

Apartment / 3 Bedrooms / sleeps 7

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

Very Good 4.5/5 

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from £21 / night

£144 - £454 / week

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In the hills of Tuscany, 3 bedrooms, swimming pool, ideal for family or friends  …see more

from £66 / night

£457 - £761 / week

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(2) Very Good 4.5/5 

1 / 51

Holiday cottage in Siena

Province of Siena / Siena

Cottage / 3 Bedrooms / sleeps 8

  • Nearest beach 100 km
  • Great for children of all ages
  • Car essential
  • Pets welcome

Very Good 4.5/5 

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from £66 / night

£457 - £761 / week

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A beautiful farm where you can relax on the porch with a good book and a glass of Chianti or walking on the grass in the magnificent park of oak trees, it is also an excellent base for exploring the heart of Tuscany, between Siena and Florence. A caretaker lives on the first floor with his wife and two children.  …see more

from £47 / night

£327 - £725 / 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

£327 - £725 / 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 £435 / night

£3040 - £3334 / week

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(1) Excellent 5/5 

1 / 24

Villa rental in Castellina In Chianti with shared pool

Province of Siena / Castellina In Chianti

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 £435 / night

£3040 - £3334 / 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 £286 / night

£1996 - £2816 / week

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(1) Excellent 5/5 

1 / 62

Cetona holiday villa rental

Province of Siena / Cetona

Villa / 10 Bedrooms / sleeps 20

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

Excellent 5/5 

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from £286 / night

£1996 - £2816 / week

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We can organize typical lunchs or dinners, parties, weddings, cooking lessons, visit to wineries and olive mills taste, babysitting and we are at your disposal for any request you can have. Free WIFI, Satellite TV, DVD and CD player, dishwasher, washing machine, barbecue  …see more

from £68 / night

£472 - £580 / week

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(1) Excellent 5/5 

1 / 32

Holiday apartment in Siena

Province of Siena / Siena

Apartment / 2 Bedrooms / sleeps 5

  • Great for children of all ages
  • Car not necessary
  • No pets allowed

Excellent 5/5 

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from £68 / night

£472 - £580 / week

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Fully furnished country style apartment 5 minutes away from the historic Medieval city of Siena. Confortable and spacious living-room, private parking, WiF, shops close. 1 hour drive from main Tuscan attractions, Florence, S. Gimignano, Chianti Vineyard, Hill Towns. Siena Tuscany Chianti Wine Palio Country Art Museum architecture hills pizza gelato comfortable parking nice  …see more

from £47 / night

£327 - £544 / 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

£327 - £544 / 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 £102 / night

£711 - £979 / 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 £102 / night

£711 - £979 / 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 £72 / night

£500 - £890 / week

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(6) Excellent 5/5 

1 / 23

Holiday farmhouse with shared pool in Montepulciano

Province of Siena / 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 £47 / night

£327 - £580 / 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

£327 - £580 / 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 £34 / night

£232 - £356 / week

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(2) Excellent 5/5 

1 / 19

Farmhouse letting in Radda in Chianti

Province of Siena / Radda in Chianti

Farmhouse / 2 Bedrooms / sleeps 3

  • Not suitable for children
  • No pets allowed
  • Private garden

Excellent 5/5 

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from £34 / night

£232 - £356 / week

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A holiday in Tuscany at Podere Tegline Farmhouse to enjoy and get to know life in Chianti Classico wine territory.You can live in an ancient house of 1500 to offer the authenticity of the past with an old charm in a virgin natural Oasis where you are WELCOME. Our house is in a central position between art cities as Florence, Siena, S.Gimignano, Lucca, Pisa, Arezzo.  …see more

from £63 / night

£435 - £505 / week

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(3) Very Good 4.5/5 

1 / 16

Holiday farmhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

Farmhouse / 1 Bedroom / sleeps 4

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

Very Good 4.5/5 

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from £63 / night

£435 - £505 / week

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Romantic one bedroom apartment in a converted traditional Tuscan farmhouse between San Gimignano and Volterra. Beautifully renovated farm building, Terraces with fantastic views, pool, ideal for rest and relaxation! Easy access Siena , Pisa and Florence.  …see more

from £63 / night

£435 - £627 / week

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(2) Excellent 5/5 

1 / 18

Montalcino holiday studio rental

Province of Siena / Montalcino

Studio / sleeps 2

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

Excellent 5/5 

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from £63 / night

£435 - £627 / week

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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 £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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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 £44 / night

£305 - £522 / week

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(2) Excellent 5/5 

1 / 24

Holiday farmhouse in Radda in Chianti

Province of Siena / Radda in Chianti

Farmhouse / 2 Bedrooms / sleeps 4

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Pets welcome
  • Private garden

Excellent 5/5 

Add to shortlist

from £44 / night

£305 - £522 / week

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In our farm only  …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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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 £299 / night

£2087 - £4154 / 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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from £299 / night

£2087 - £4154 / 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 £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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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

from £252 / night

£1763 - £2518 / week

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(1) Excellent 5/5 

1 / 23

Holiday villa with swimming pool in Montepulciano

Province of Siena / Montepulciano

Villa / 6 Bedrooms / sleeps 8

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

Excellent 5/5 

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from £252 / night

£1763 - £2518 / 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

from £99 / night

£689 - £1160 / 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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from £99 / night

£689 - £1160 / 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
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