Villas in Pienza and Apartments – Holiday Lettings - Holiday Rentals Pienza

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147 Holiday homes

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

1 / 24

Tuscany / Province of Siena / Pienza

1 bedroomSleeps 35 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 5 nights min stay
Key info: Nearest beach 120 km; Swimming pool; Great for children of all ages ;
 …see more

from £105 / night

£0 / week

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from £105 / night

1 / 20

Tuscany / Province of Siena / Pienza

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Ask owner if suitable for children; Pets welcome;
 …see more

from £300 / night

£2099 - £3360 / week

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from £300 / night

1 / 48

Tuscany / Province of Siena / Pienza

6 bedroomsSleeps 117 nights min stay

  • 6 bedrooms
  • Sleeps 11
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £269 / night

£1877 - £2780 / week

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from £269 / night

1 / 19

Stunning Villa near Pienza - Pienza villa sleeps 10

Tuscany / Province of Siena / Pienza

4 bedroomsSleeps 107 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
This lovely holiday home in the Middle Ages was probably a resting place for pilgrims travelling on the Via Francigena, that passes nearby. Furthermore, opposite the property is the 13th century Castello di Spedaletto, one of the most important monastic granges of the S  …see more

from £157 / night

£1093 - £2017 / week

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from £157 / night

(4) Excellent 

1 / 11

Tuscany / Province of Siena / Pienza

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Suitable for children age 5+; Some pets are welcome - please contact the owner;
 …see more

from £59 / night

£334 / week

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from £59 / night

(4) Excellent 

1 / 23

Pure 5 star Luxury in Tuscany-Jacuzzi-AC-wifi-S

Tuscany / Province of Siena / Pienza

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Great for children of all ages ; 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 £117 / night

£0 / week

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from £117 / night

1 / 20

Wisteria Farm (V036) - Pienza farmhouse sleeps 8

Tuscany / Province of Siena / Pienza

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
The farmhouse, set in one of the most fascinating areas of the south of Sienese territory, between Pienza and Montepulciano, shows sober, almost austere lines. Its placing, the group of cypresses, its position on a high ground which raise the whole valley, makes it the  …see more

from £343 / night

£2400 - £3359 / week

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from £343 / night

1 / 9

Tuscany / Province of Siena / Pienza

3 bedroomsSleeps 5Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 98 km; Swimming pool; Great for children of all ages ;
 …see more

from £34 / night

£592 - £892 / week

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from £34 / night

1 / 20

The Spring (v024) - Pienza villa sleeps 12

Tuscany / Province of Siena / Pienza

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
Situated on a farm of 150 hectares producing excellent extra virgin olive oil, the farmhouse is set on a kind of natural terrace overlooking the lovely valley below. The house, built in the first half of the eighteenth century, has been renovated carefully by the couple  …see more

from £472 / night

£3300 - £4375 / week

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from £472 / night

1 / 13

Tuscany / Province of Siena / Pienza / Monticchiello

2 bedroomsSleeps 27 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 £84 / night

£584 / week

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from £84 / night

(1) Excellent 

1 / 29

Tuscany / Province of Siena / Pienza / Monticchiello

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Some pets are welcome - please contact the owner;
 …see more

from £389 / night

£2719 - £5304 / week

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from £389 / night

1 / 37

Tuscany / Province of Siena / Pienza / Monticchiello

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Some pets are welcome - please contact the owner;
 …see more

from £190 / night

£1327 - £2069 / week

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from £190 / night

1 / 34

Villa Fonte all'Oppio Pienza - Pienza villa sleeps 13

Tuscany / Province of Siena / Pienza

7 bedroomsSleeps 137 nights min stay

  • 7 bedrooms
  • Sleeps 13
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
Ancient stone farmhouse, nowadays beautiful holiday villa, set in a very panoramic position inside the Parco Artistico Naturale of Val d'Orcia. Only 2 km far we find the well-known Renaissance village of Pienza. In a short drive there are renowned villages such as Monti  …see more

from £197 / night

£1379 - £2253 / week

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from £197 / night

1 / 20

Tuscany / Province of Siena / Pienza

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Ask owner if suitable for children; Air conditioning; No pets allowed;
 …see more

from £1256 / night

£8788 - £10985 / week

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from £1256 / night

1 / 20

Tuscany / Province of Siena / Pienza

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Ask owner if suitable for children; Air conditioning; No pets allowed;
 …see more

from £380 / night

£2660 - £6648 / week

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from £380 / night

1 / 9

Tuscany / Province of Siena / Pienza

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Some pets are welcome - please contact the owner;
 …see more

from £67 / night

£400 - £617 / week

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from £67 / night

1 / 23

10001 - Casa Orcia - Pienza farmhouse sleeps 12

Tuscany / Province of Siena / Pienza

5 bedroomsSleeps 123 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 £292 / night

£1917 / week

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from £292 / night

1 / 25

Lodge Melograno wonderful view in Val D'Orcia

Tuscany / Province of Siena / Pienza

1 bedroomSleeps 27 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 7 nights min stay
Key info: Nearest beach 100 km; Swimming pool; Not suitable for children;
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 £64 / night

£442 - £709 / week

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from £64 / night

1 / 20

Tuscany / Province of Siena / Pienza

8 bedroomsSleeps 147 nights min stay

  • 8 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Ask owner if suitable for children; Air conditioning; No pets allowed;
 …see more

from £760 / night

£5319 - £7311 / week

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from £760 / night

1 / 20

Tuscany / Province of Siena / Pienza

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Suitable for children age 5+; Pets welcome;
 …see more

from £155 / night

£1085 - £2001 / week

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from £155 / night

1 / 31

Tuscany / Province of Siena / Pienza

2 bedroomsSleeps 57 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Ask owner if suitable for children; No pets allowed;
 …see more

from £90 / night

£625 - £813 / week

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from £90 / night

1 / 36

Tuscany / Province of Siena / Pienza

3 bedroomsSleeps 87 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Not suitable for children; Pets welcome;
 …see more

from £197 / night

£1377 - £2124 / week

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from £197 / night

(2) Excellent 

1 / 22

Tuscany / Province of Siena / Pienza / Monticchiello

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Great for children of all ages ; Pets welcome; Private garden;
 …see more

from £42 / night

£284 - £365 / week

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from £42 / night

1 / 24

Tuscany / Province of Siena / Pienza / Monticchiello

1 bedroomSleeps 21 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Not suitable for children; Air conditioning; No pets allowed;
 …see more

from £61 / night

£325 / week

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from £61 / night

1 / 24

Tuscany / Province of Siena / Pienza

4 bedroomsSleeps 11Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
Key info: Nearest beach 95 km; Swimming pool; Great for children of all ages ;
 …see more

from £292 / night

£1750 - £2942 / week

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from £292 / night

(2) Very Good 

1 / 26

Tuscany / Province of Siena / Pienza

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 153 km; Swimming pool; Great for children of all ages ;
 …see more

from £161 / night

£1125 - £1667 / week

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from £161 / night

(2) Very Good 

1 / 13

Tuscany / Province of Siena / Pienza

2 bedroomsSleeps 41 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Great for children of all ages ; Pets welcome;
 …see more

from £67 / night

£459 / week

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from £67 / night

1 / 24

Tuscany / Province of Siena / Pienza / Monticchiello

4 bedroomsSleeps 81 night min stay

  • 4 bedrooms
  • Sleeps 8
  • 1 night min stay
Key info: Great for children of all ages ; Air conditioning; Some pets are welcome - please contact the owner;
 …see more

from £75 / night

£500 - £2075 / week

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from £75 / night

(1) Excellent 

1 / 14

Tuscany / Province of Siena / Pienza

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Suitable for children age 5+; Some pets are welcome - please contact the owner;
 …see more

from £155 / night

£1084 - £2002 / week

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from £155 / night

1 / 23

Fonte Senesi - Pienza villa sleeps 12

Tuscany / Province of Siena / Pienza

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; 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 £530 / night

£3705 - £4884 / week

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from £530 / night

1 / 15

Tuscany / Province of Siena / Pienza

3 bedroomsSleeps 62 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car not necessary;
 …see more

from £200 / night

£684 - £1000 / week

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from £200 / night

1 / 21

Villa Arpicella - Pienza villa sleeps 4

Tuscany / Province of Siena / Pienza

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Nearest beach 95 km; Great for children of all ages ; Car advised;
Villa Arpicella really does offer the best of both worlds! Despite its prime location at just 10 minutes’ walking distance from Pienza, it enjoys the peace and quiet of a beautiful countryside setting with spectacular panoramic views. It is a large, traditionally Tusc  …see more

from £83 / night

£580 - £832 / week

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from £83 / night

(1) Excellent 

1 / 24

Casa Oriolo - Monticchiello apartment sleeps 7

Tuscany / Province of Siena / Pienza / Monticchiello

3 bedroomsSleeps 77 nights min stay

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min stay
Key info: Nearest beach 110 km; Swimming pool; Great for children of all ages ;
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 £149 / night

£1042 - £1625 / week

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from £149 / night

(7) Excellent 

1 / 57

Poggio ai Gelsi - Pienza lodge sleeps 8

Tuscany / Province of Siena / Pienza

3 bedroomsSleeps 87 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Nearest beach 100 km; Swimming pool; Great for children of all ages ;
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 £193 / night

£1350 - £2459 / week

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from £193 / night

(1) Excellent 

1 / 22

Tuscany / Province of Siena / Pienza / Monticchiello

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Some pets are welcome - please contact the owner;
 …see more

from £525 / night

£3674 - £4243 / week

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from £525 / night

1 / 44

Tuscany / Province of Siena / Pienza / Monticchiello

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Some pets are welcome - please contact the owner;
 …see more

from £190 / night

£1327 - £2069 / week

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from £190 / night

(1) Very Good 

1 / 20

Tuscany / Province of Siena / Pienza

2 bedroomsSleeps 42 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Great for children of all ages ; No pets allowed; Private garden;
 …see more

from £109 / night

£584 / week

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from £109 / night

1 / 5

Tuscany / Province of Siena / Pienza

2 bedroomsSleeps 51 night min stay

  • 2 bedrooms
  • Sleeps 5
  • 1 night min stay
Key info: Great for children of all ages ; Car advised; Air conditioning;
 …see more

from £109 / night

£584 / week

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from £109 / night

(15) Excellent 

1 / 43

Villa PoliFlora - Monticchiello apartment sleeps 6

Tuscany / Province of Siena / Pienza / Monticchiello

2 bedroomsSleeps 61 night min stay

  • 2 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Great for children of all ages ; Some pets are welcome - please contact the owner; Private garden;
Villa PoliFlora is a modern residence in Monticchiello in Val d'Orcia, a Unesco world heritage site. The owners and creators invite you for a relaxing stay, in the triangle among Montalcino, Pienza and Montepulciano. A few kilometers away from Siena and Chianti Classico  …see more

from £63 / night

£309 - £752 / week

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from £63 / night

1 / 5

Tuscany / Province of Siena / Pienza

2 bedroomsSleeps 43 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
 …see more

from £134 / night

£559 - £817 / week

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from £134 / night

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