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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 £38 / night

£265 - £500 / week

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(7) Excellent 5/5 

1 / 16

Holiday apartment in Monticchiello

Pienza / Monticchiello

Apartment / 2 Bedrooms / sleeps 6

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

Excellent 5/5 

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from £38 / night

£265 - £500 / week

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Villa PoliFlora is a modern residence consists of two bedrooms and two bathrooms with a shared kitchen. The owners husband and wife Poli and Flora built the villa in 1988 and from there they guard with love the classic environment of the house surrounded by garden. Villa PoliFlora is a modern residence in Monticchiello in Val d'Orcia, a Unesco world heritage site.  …see more

from £156 / night

£1087 - £1740 / week

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(1) Excellent 5/5 

1 / 57

Pienza holiday villa rental

Province of Siena / Pienza

Villa / 3 Bedrooms / sleeps 6

  • 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 £156 / night

£1087 - £1740 / week

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I CIPRESSINI - Pienza - Val d'Orcia - casolare con piscina, con 3 camere 3 bagni, posti letto 6+2, a 500 mt da Pienza, in paese a piedi in 15 minuti. VRBO : 445398ha altre informazioni e reviews clienti.  …see more

Featured properties

from £339 / night

£2367 - £2785 / week

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1 / 17

Monticchiello holiday villa rental

Pienza / Monticchiello

Villa / 4 Bedrooms / sleeps 9

  • Swimming pool
  • Ask owner if suitable for children
  • Some pets are welcome - please contact the owner
  • Private garden

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from £339 / night

£2367 - £2785 / week

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Situated in a prominent position overlooking the Val d'Orcia, this villa for rent in Tuscany offers incredible views and is in a peaceful and natural setting. It's within walking distance of Monticchiello, which is home to many shops and restaurants as well as a castle.  …see more

from £287 / night

£2004 - £4677 / week

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1 / 24

Holiday villa with swimming pool in Pienza

Province of Siena / Pienza

Villa / 6 Bedrooms / sleeps 13

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

Add to shortlist

from £287 / night

£2004 - £4677 / week

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Luxury Villa near Pienza, ideal for large families or friend's group.  …see more

from £86 / night

£599 - £1103 / week

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(2) Excellent 5/5 

1 / 23

Holiday apartment in Pienza

Province of Siena / Pienza

Apartment / 4 Bedrooms / sleeps 8

  • Great for children of all ages
  • Air conditioning
  • No pets allowed

Excellent 5/5 

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from £86 / night

£599 - £1103 / week

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Terrace - pool - Wine - Brunello - spa - restaurants - shops - great standard - wine tours - cycling - walking - big jacuzzi on roof terrace - wifi - AC - Sky TV - SMEG Jacuzzi on the roof terrace with beautiful views over Montalcino - home of the famous Brunello wine. Truly a luxorius flat with stunning views from the roof terrace.  …see more

from £173 / night

£1209 - £1691 / week

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1 / 20

Villa rental in Montepulicano with swimming pool

Pienza / Montepulicano

Villa / 6 Bedrooms / sleeps 12

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

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from £173 / night

£1209 - £1691 / week

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Beautiful house with private pool in one of the most interesting area of Tuscany. It also perfect for trekking, jogging and mountain biking among the forests of Monte Amiata.  …see more

from £373 / night

£2609 - £4174 / week

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1 / 24

Monticchiello holiday villa rental

Pienza / Monticchiello

Villa / 6 Bedrooms / sleeps 12

  • Swimming pool
  • Ask owner if suitable for children
  • Some pets are welcome - please contact the owner
  • Private garden

Add to shortlist

from £373 / night

£2609 - £4174 / week

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Is a typical Tuscan “farm” from the 1800's located in the heart of Tuscany, in the municipality of Pienza in the province of Siena, and in the Val d'Orcia Natural Park nominated by UNESCO as a human patrimony. At 500mt above sea level it has a unique view  …see more

from £298 / night

£2085 - £2648 / week

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1 / 19

Holiday villa rental

Province of Siena / Pienza

Villa / 4 Bedrooms / sleeps 9

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

Add to shortlist

from £298 / night

£2085 - £2648 / week

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Situated in a prominent position overlooking the Val d'Orcia, this villa for rent in Tuscany offers incredible views and is in a peaceful and natural setting.  …see more

from £453 / night

£3166 - £5108 / week

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1 / 24

Holiday apartment with indoor pool in Pienza

Province of Siena / Pienza

Apartment / 8 Bedrooms / sleeps 15

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

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from £453 / night

£3166 - £5108 / week

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This lovely 18th century villa with swimming-pool in Val d'Orcia is located near Pienza, surrounded by the gently rolling hills of this magnificent countryside  …see more

from £160 / night

£1116 - £1929 / week

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1 / 24

Holiday villa rental

Province of Siena / Pienza

Villa / 6 Bedrooms / sleeps 14

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

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from £160 / night

£1116 - £1929 / week

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This enchanting holiday home is on a knoll overlooking the typical Tuscan countryside of the area around Pienza, San Quirico and Montalcino. In a very quiet position, only surrounded by a peaceful Tuscan countryside, this holiday accommodation consists of 4 apartments  …see more

from £129 / night

£900 - £1684 / week

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1 / 19

Holiday villa in Pienza

Province of Siena / Pienza

Villa / 4 Bedrooms / sleeps 10

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

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from £129 / night

£900 - £1684 / week

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Beautiful independent country house near Pienza. This villa is located few minutes driving from Pienza, in a quiet and beautiful location in the middle of the country side. Private swimming pool. The villa is elegantly furnished, in a perfect combination between comfort and tradition  …see more

from £336 / night

£2348 - £4174 / week

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1 / 16

Holiday villa rental

Province of Siena / Pienza

Villa / 6 Bedrooms / sleeps 12

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

Add to shortlist

from £336 / night

£2348 - £4174 / week

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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 £503 / night

£3515 - £4706 / week

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1 / 20

Villa rental in Montepulicano with swimming pool

Pienza / Montepulicano

Villa / 5 Bedrooms / sleeps 12

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

Add to shortlist

from £503 / night

£3515 - £4706 / week

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Charming Villa for rent in Tuscany is nice located on a farm of 150 hectares producing excellent extra virgin olive oil, the farmhouse is set on a kind of natural terrace with a breathtaking view over the valley below  …see more

from £858 / night

£6000 - £7500 / week

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1 / 22

Villa rental in Monticchiello with swimming pool

Pienza / Monticchiello

Villa / 7 Bedrooms / sleeps 14

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

Add to shortlist

from £858 / night

£6000 - £7500 / week

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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 £169 / night

£1180 - £1929 / week

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1 / 34

Holiday villa in Pienza

Province of Siena / Pienza

Villa / 7 Bedrooms / sleeps 13

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

Add to shortlist

from £169 / night

£1180 - £1929 / week

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it is the ideal place if you are looking to relax, private pool and beautiful view  …see more

from £599 / night

£4191 / week

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1 / 24

Holiday villa in Monticchiello

Pienza / Monticchiello

Villa / 6 Bedrooms / sleeps 12

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner

Add to shortlist

from £599 / night

£4191 / week

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This very well furnished farm is situated in one hundred and fifty hectares of farm land producing excellent extra virgin olive oil, the farmhouse is set on a natural terrace overlooking the beautiful valley below.  …see more

from £211 / night

£1471 - £2059 / week

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1 / 24

Holiday farmhouse with swimming pool in Pienza

Province of Siena / Pienza

Farmhouse / 4 Bedrooms / sleeps 11

  • Nearest beach 95 km
  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner

Add to shortlist

from £211 / night

£1471 - £2059 / week

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The farmholiday borders on a nature park in the Val d'Orcia, at Castelluccio di Pienza. Its location offers a panoramic view of two natural reserves: Pietraporciana and Lucciolabella. From the pool, nestled in an olive grove, guests enjoy a marvelous view.  …see more

from £72 / night

£500 / week

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1 / 14

Pienza holiday home rental

Province of Siena / Pienza

House / 2 Bedrooms / sleeps 4

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

Add to shortlist

from £72 / night

£500 / week

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L' appartamento LA CORTE ANTICA , da poco ristrutturato, è la casa ideale per trascorrere una vacanza rilassante nella bellissima val d'orcia  …see more

from £75 / night

£523 - £773 / week

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1 / 9

Holiday apartment with shared pool in Pienza

Province of Siena / Pienza

Apartment / 3 Bedrooms / sleeps 5

  • Nearest beach 98 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Add to shortlist

from £75 / night

£523 - £773 / week

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L'agriturismo Selvoli si trova nel Parco Artistico Naturale e Culturale della Val d'Orcia, dichiarato dall'UNESCO “Patrimonio dell'umanità  …see more

from £41 / night

£283 / week

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1 / 10

Pienza holiday apartment rental

Province of Siena / Pienza

Apartment / 1 Bedroom / sleeps 2

  • Ask owner if suitable for children
  • No pets allowed
  • Private garden

Add to shortlist

from £41 / night

£283 / week

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il monolocale LA CORTE ANTICA , da poco ristrutturato in stile toscano, è l'ideale per coppie in quanto dispone di un divano letto matrimoniale comodissimo , cucina completa di elettodomestici forno, frigo, lavastoviglie e tv, bagno con doccia e piccola corte esclusiv  …see more

from £87 / night

£603 - £868 / week

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1 / 15

Holiday apartment rental

Province of Siena / Pienza

Apartment / 3 Bedrooms / sleeps 6

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner

Add to shortlist

from £87 / night

£603 - £868 / week

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L'agriturismo Selvoli si trova nel Parco Artistico Naturale e Culturale della Val d'Orcia, dichiarato dall'UNESCO “Patrimonio dell'umanità  …see more

from £10 / night

£67 - £74 / week

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(1) Excellent 5/5 

1 / 10

Holiday apartment in Monticchiello

Pienza / Monticchiello

Apartment / 2 Bedrooms / sleeps 5

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

Excellent 5/5 

Add to shortlist

from £10 / night

£67 - £74 / week

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Enjoy Tuscany, in a unique village in a UNESCO world heritage site: access to art, good food and excellent wine.  …see more

from £129 / night

£900 - £1403 / week

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1 / 24

Holiday apartment with shared pool in Monticchiello

Pienza / Monticchiello

Apartment / 3 Bedrooms / sleeps 7

  • Nearest beach 110 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Add to shortlist

from £129 / night

£900 - £1403 / week

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Casa Oriolo is an elegant apartment with 3 bedrooms and it is part of a small complex with 3 apartments total sharing a pool. Here you can enjoy a sojourn in contact with nature in a protected and uncontaminated oasis.  …see more

from £286 / night

£2000 - £2754 / week

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1 / 20

Pienza holiday farmhouse rental

Province of Siena / Pienza

Farmhouse / 4 Bedrooms / sleeps 8

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

Add to shortlist

from £286 / night

£2000 - £2754 / week

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Farmhouse with swimming pool  …see more

from £173 / night

£1209 - £1738 / week

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1 / 23

Pienza holiday farmhouse rental

Province of Siena / Pienza

Farmhouse / 5 Bedrooms / sleeps 12

  • Not suitable for children
  • Car advised
  • No pets allowed

Add to shortlist

from £173 / night

£1209 - £1738 / week

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Farmhouse Casa Orcia - holiday accommodation in Tuscany with swimming pool is for discerning travelers wishing to spend their holidays in Tuscany. This rental farmhouse is wonderful for a family holiday and located between Pienza and S.Quirico.  …see more

from £448 / night

£3136 - £5750 / week

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1 / 24

Holiday villa with swimming pool in Pienza

Province of Siena / Pienza

Villa / 8 Bedrooms / sleeps 14

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed

Add to shortlist

from £448 / night

£3136 - £5750 / week

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stunning villa, located in Tuscany Italy, has a max. capacity of 14 people. This stunning villa is perfect for families and friends  …see more

from £124 / night

£864 - £1511 / week

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1 / 24

Pienza holiday villa rental

Province of Siena / Pienza

Villa / 3 Bedrooms / sleeps 6

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

Add to shortlist

from £124 / night

£864 - £1511 / week

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It is the most photographed house in the area, a symbol of the Tuscany countryside, featured on many postcards and calendars simply because it has maintained the charm of the old farmhouse and the surrounding fields, without any new buildings as far as the eye can see.  …see more

from £161 / night

£1124 - £1736 / week

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1 / 24

Montepulicano holiday farmhouse rental

Pienza / Montepulicano

Farmhouse / 6 Bedrooms / sleeps 14

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

Add to shortlist

from £161 / night

£1124 - £1736 / week

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Self-catering farmhouse for groups of 10 or 14 at different prices near Pienza, in Val d'Orcia. Swimming pool, children's playground, barbecue, table-tennis table, mountain bikes. Partly accessible to people with disabilities.  …see more

from £300 / night

£2097 - £2870 / week

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1 / 24

Holiday farmhouse with swimming pool in Pienza

Province of Siena / Pienza

Farmhouse / 5 Bedrooms / sleeps 10

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden

Add to shortlist

from £300 / night

£2097 - £2870 / week

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Villa / Farmhouse / Home in Montefollonico with 5 bedrooms sleeps 10  …see more

from £889 / night

£6218 - £12247 / week

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1 / 24

Holiday villa in Pienza

Province of Siena / Pienza

Villa / 9 Bedrooms / sleeps 19

  • Not suitable for children
  • Car not necessary
  • No pets allowed

Add to shortlist

from £889 / night

£6218 - £12247 / week

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Villa Esteandnbsp;is a beautiful villa situated on a dramatic hilltop, overlooking the rolling hills of the Val d`Orcia near Contignano in Tuscany. Theandnbsp;first floorandnbsp;may also be reached by an internal staircase. Two stone-paved patios flank the external  …see more

from £297 / night

£2077 - £5398 / week

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1 / 24

Farmhouse rental in Pienza with swimming pool

Province of Siena / Pienza

Farmhouse / 6 Bedrooms / sleeps 14

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

Add to shortlist

from £297 / night

£2077 - £5398 / week

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Villa / Farmhouse / Home in Pienza with 6 bedrooms sleeps 14  …see more
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