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36 Holiday homes

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Travellers going to Pienza are booking September dates now. Secure your holiday home today and have the perfect trip.

(1) Excellent 

1 / 24

Casa Oriolo - Monticchiello apartment sleeps 7

Pienza / Monticchiello

3 7 7 nights min stay

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min stay
Key info: Nearest beach 110 km; Swimming pool; Child friendly ;
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.The owners have carefully furnished the property wit  …see more

from £153 / night

£1069 - £1667 / week

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from £153 / night

1 / 23

10001 - Casa Orcia - Pienza farmhouse sleeps 12

Province of Siena / Pienza

5 12 3 nights min stay

  • 5 bedrooms
  • Sleeps 12
  • 3 nights min stay
Key info: Not suitable for children; Car advised; No pets allowed;
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 (where the english patient was filmed) a  …see more

from £300 / night

£1966 / week

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from £300 / night

(5) Excellent 

1 / 23

Pure 5 star Luxury in Tuscany-Jacuzzi-AC-wifi-S - Pienza apartment sleeps 8

Province of Siena / Pienza

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Child friendly ; Air conditioning; No pets allowed;
New lower price - one of the nicest flat in Tuscany 5 star standard !!The apartment has its own entrance and occupies the whole 1st and top floors of this classical building next to the ancient city wall. Private parking, large roof terrace (55m2) with great views over  …see more

from £120 / night

£838 / week

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from £120 / night

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Casa Marelli - Pienza townhouse sleeps 5

Province of Siena / Pienza

2 5 7 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Nearest beach 100 km; Child friendly ; Car not necessary;
In the very center of a lovely ancient medieval village stands Casa Marelli. Recently carefully restored preserving all the traditional Tuscan characteristics of the building such as wooden beamed ceilings and brick work arches. It was meant to become the owner's r  …see more

from £107 / night

£748 - £962 / week

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from £107 / night

(2) Excellent 

1 / 57

I CIPRESSINI : il Casale Toscano più fotografato - Pienza villa sleeps 6

Province of Siena / Pienza

3 6 1 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Swimming pool; Child friendly ; Ask about pets;
Villa I CIPRESSINI è la casa più fotografata della zona, raffigurata da anni su cartoline e calendari proprio perchè rappresenta intatto il fascino della antica casa colonica Toscana. In piena campagna ma a soli 500 mt.dal paese offre grandi spazi esterni; la pisc  …see more

from £257 / night

£1283 / week

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from £257 / night

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Villa Andrea - Pienza villa sleeps 6

Province of Siena / Pienza

3 6 7 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 95 km; Swimming pool; Child friendly ;
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 £165 / night

£1154 - £1710 / week

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from £165 / night

1 / 23

Fonte Senesi - Pienza villa sleeps 12

Province of Siena / Pienza

6 12 7 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
Villa la Fonte is situated in the marvellous Val d'Orcia, the valley of the Sienese Crete.An ancient farmhouse dating back to 1846 that lies in an agricultural farm that extends over a surface of 150 hectares. Every year our olive grove produces a tasty oil that ca  …see more

from £543 / night

£3800 - £5009 / week

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from £543 / night

1 / 24

Province of Siena / Pienza

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
Key info: Nearest beach 95 km; Swimming pool; Child friendly ;
 …see more

from £300 / night

£1795 - £3018 / week

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from £300 / night

1 / 20

Cypress Villa (v008) - Pienza farmhouse sleeps 13

Province of Siena / Pienza

6 13 7 nights min stay

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min stay
Key info: Nearest beach 44 km; Swimming pool; Child friendly ;
Ground floor: a large living room with fireplace, small kitchen, a double bedroom with a separate entrance from the outside with an en-suite bathroom with washing machine.First floor: a double bedroom with Jacuzzi inside the room and en-suite bathroom with shower, a dou  …see more

from £352 / night

£2462 - £4385 / week

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from £352 / night

1 / 24

Luxury villa near Pienza - Pienza villa sleeps 13

Province of Siena / Pienza

6 13 7 nights min stay

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
This magnificent holiday villa with swimming pool (18mx4, open Apr-Oct) sits on one of the knolls at the foot of Pienza (3km) with a breathtaking 360 degree view over the Val d'Orcia countryside. The villa is a tastefully restored stone farmhouse, beautifully furnished  …see more

from £312 / night

£2180 - £6069 / week

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from £312 / night

1 / 24

luxury villa few steps from Pienza - Pienza apartment sleeps 15

Province of Siena / Pienza

8 15 7 nights min stay

  • 8 bedrooms
  • Sleeps 15
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
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. This tastefully furnished villa can comfortably accommodate up to 15 people and consists of 2 large sitt  …see more

from £452 / night

£3163 - £6556 / week

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from £452 / night

1 / 20

Montefollonico - 65998001 - Pienza farmhouse sleeps 10

Province of Siena / Pienza

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Child friendly ; Pet friendly;
Large Tuscan farmhouse dating back to the 15trh century built on the ruins of an ancient convent of the year 1200. This property with a charming inner courtyard, is situated in quiet and panoramic location on a large 100-hectare estate producing olive oil and wine. Thi  …see more

from £424 / night

£2473 - £3385 / week

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from £424 / night

(7) Excellent 

1 / 57

Poggio ai Gelsi - Pienza lodge sleeps 8

Province of Siena / Pienza

3 8 7 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Nearest beach 100 km; Swimming pool; Child friendly ;
Poggio ai Gelsi is located in the south of Tuscany between the hills of Val d'Orcia, Siena and halfway between Montepulciano and Pienza. The property enjoys a magnificent view over Montichiello and Pienza. The colours of the nature in this corner of Tuscany are bea  …see more

from £169 / night

£1180 - £2522 / week

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from £169 / night

(1) Excellent 

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Lodge Ulivo wonderful view in Val D'Orcia - Pienza lodge sleeps 2

Province of Siena / Pienza

1 2 7 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 7 nights min stay
Key info: Nearest beach 100 km; Swimming pool; Child friendly ;
Poggio ai Gelsi is located in the south of Tuscany between the hills of Val d'Orcia, Siena and halfway between Montepulciano and Pienza. The property enjoys a magnificent view over Montichiello and Pienza. The colours of the nature in this corner of Tuscany are bea  …see more

from £61 / night

£424 - £821 / week

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from £61 / night

1 / 100

Montefollonico 65998 - Pienza villa sleeps 10

Province of Siena / Pienza

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Child friendly ; Air conditioning;
Large Tuscan farmhouse dating back to the 15trh century built on the ruins of an ancient convent of the year 1200. This property with a charming inner courtyard, is situated in quiet and panoramic location on a large 100-hectare estate producing olive oil and wine. This  …see more

from £424 / night

£2473 - £3385 / week

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from £424 / night

1 / 100

Pienza 44315 - Pienza villa sleeps 14

Province of Siena / Pienza

6 14 7 nights min stay

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
Beautiful stone farmhouse situated in peaceful and panoramic location near the charming medieval town of Pienza, in the heart of the Orcia Valley region. This villa which has been recently restored with all its original details preserved, comprises 3 separate units rent  …see more

from £353 / night

£2467 - £6734 / week

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from £353 / night

1 / 52

Villa Manafiore - Monticchiello villa sleeps 9

Pienza / Monticchiello

6 9 7 nights min stay

  • 6 bedrooms
  • Sleeps 9
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; No pets allowed;
This marvelous villa occupies a gently sloping site facing west across the fertile Orcia Valley towards the majestic Amiata Mountain. Sheltered to the east by a woodland and surrounded by well-tended gardens, the property includes several acres of vineyards and olive  …see more

from £825 / night

£5770 / week

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from £825 / night

1 / 23

Pienza - 44315001 - Pienza farmhouse sleeps 14

Province of Siena / Pienza

6 14 7 nights min stay

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Ask about pets;
Beautiful stone farmhouse situated in peaceful and panoramic location near the charming medieval town of Pienza, in the heart of the Orcia Valley region. This villa which has been recently restored with all its original details preserved, comprises 3 separate units rent  …see more

from £353 / night

£2467 - £6734 / week

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from £353 / night

1 / 13

Pienza / Monticchiello

2 2 7 nights min stay

  • 2 bedrooms
  • Sleeps 2
  • 7 nights min stay
Key info: Ask owner if suitable for children; Air conditioning; No pets allowed;
 …see more

from £86 / night

£599 / week

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from £86 / night

(2) Very Good 

1 / 26

Province of Siena / Pienza

3 6 7 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 153 km; Swimming pool; Child friendly ;
 …see more

from £165 / night

£1154 - £1710 / week

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from £165 / night

(1) Excellent 

1 / 29

Pienza / Monticchiello

4 8 7 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Ask about pets;
 …see more

from £392 / night

£2739 - £5344 / week

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from £392 / night

1 / 37

Pienza / Monticchiello

3 6 7 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Ask about pets;
 …see more

from £191 / night

£1337 - £1658 / week

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from £191 / night

1 / 25

Pienza / Monticchiello

6 12 2 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Ask owner if suitable for children;
 …see more

from £474 / night

£3318 - £4424 / week

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from £474 / night

1 / 36

Province of Siena / Pienza

6 16 1 night min stay

  • 6 bedrooms
  • Sleeps 16
  • 1 night min stay
Key info: Swimming pool; Ask owner if suitable for children; Pet friendly;
 …see more

from £805 / night

£5631 - £7742 / week

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from £805 / night

1 / 26

Province of Siena / Pienza

9 19 Min stay varies

  • 9 bedrooms
  • Sleeps 19
  • Min stay varies
Key info: Swimming pool; Ask owner if suitable for children; Air conditioning;
 …see more

from £1008 / night

£7052 - £13889 / week

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from £1008 / night

1 / 44

Pienza / Monticchiello

3 6 7 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Ask about pets;
 …see more

from £191 / night

£1337 - £1658 / week

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from £191 / night

1 / 48

Province of Siena / Pienza

6 11 7 nights min stay

  • 6 bedrooms
  • Sleeps 11
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
 …see more

from £275 / night

£1925 - £2851 / week

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from £275 / night

1 / 24

Province of Siena / Pienza

8 19 Min stay varies

  • 8 bedrooms
  • Sleeps 19
  • Min stay varies
Key info: Swimming pool; Ask owner if suitable for children; Air conditioning;
 …see more

from £1008 / night

£7052 - £13889 / week

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from £1008 / night

1 / 44

Province of Siena / Pienza

6 14 7 nights min stay

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Ask about pets;
 …see more

from £443 / night

£3101 - £8036 / week

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from £443 / night

1 / 41

Province of Siena / Pienza

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
Key info: Swimming pool; Ask owner if suitable for children; Air conditioning;
 …see more

from £360 / night

£2514 - £4485 / week

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from £360 / night

1 / 44

Province of Siena / Pienza

4 8 7 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
 …see more

from £242 / night

£1693 - £2398 / week

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from £242 / night

1 / 54

Pienza / Monticchiello

7 14 7 nights min stay

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Ask about pets;
 …see more

from £482 / night

£3368 - £4169 / week

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from £482 / night

1 / 39

Province of Siena / Pienza

8 14 Min stay varies

  • 8 bedrooms
  • Sleeps 14
  • Min stay varies
Key info: Swimming pool; Ask owner if suitable for children; Air conditioning;
 …see more

from £561 / night

£3922 - £5410 / week

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from £561 / night

1 / 31

Pienza / Monticchiello

6 12 7 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Ask about pets;
 …see more

from £611 / night

£4275 - £6413 / week

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from £611 / night

1 / 21

Province of Siena / Pienza

8 12 7 nights min stay

  • 8 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Ask owner if suitable for children; Ask about pets;
 …see more

from £1222 / night

£8548 - £11197 / week

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from £1222 / night

1 / 35

Province of Siena / Pienza

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Suitable for children age 5+; Air conditioning;
 …see more

from £480 / night

£3357 / week

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from £480 / night

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