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110 Holiday homes

Filters applied: Internet access (110)

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

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

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 £476 / night

£3328 - £4412 / week

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from £476 / 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 £118 / night

£0 / week

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from £118 / 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

(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 £68 / night

£463 / week

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from £68 / 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 £346 / night

£2421 - £3387 / week

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from £346 / 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 £43 / night

£286 - £369 / week

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from £43 / 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 £110 / night

£589 / week

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from £110 / night

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 £106 / night

£0 / week

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from £106 / 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 / 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

£446 - £715 / week

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from £64 / night

1 / 41

Tuscany / Province of Siena / Pienza / Monticchiello

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £143 / night

£1000 - £1177 / week

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from £143 / 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 £195 / night

£1362 - £2479 / week

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from £195 / 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 £295 / night

£1765 - £2967 / week

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from £295 / night

1 / 20

Cypress Villa (v008) - Pienza farmhouse sleeps 13

Tuscany / Province of Siena / Pienza

6 bedroomsSleeps 137 nights min stay

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min stay
Key info: Nearest beach 44 km; Swimming pool; Great for children of all ages ;
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 £346 / night

£2421 - £5782 / week

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from £346 / night

1 / 12

Tuscany / Province of Siena / Pienza / Monticchiello

2 bedroomsSleeps 21 night min stay

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

from £83 / night

£362 / week

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from £83 / 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 £91 / night

£631 - £820 / week

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from £91 / night

1 / 18

Antica Locanda Pienza - Monticchiello b&b sleeps 12

Tuscany / Province of Siena / Pienza / Monticchiello

4 bedroomsSleeps 121 night min stay

  • 4 bedrooms
  • Sleeps 12
  • 1 night min stay
Key info: Not suitable for children; Air conditioning; No pets allowed;
Sul Corso Rossellino, proprio nel centro di Pienza, a meno di cento metri da Piazza Pio II con la sua magnifica cattedrale e lo splendido Palazzo Piccolomini, l'Antica Locanda offre ad ospiti esigenti una piacevole ed esclusiva sistemazione.L'Antica Locanda è  …see more

from £72 / night

£463 - £505 / week

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from £72 / 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 £76 / night

£505 - £2093 / week

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from £76 / 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 £534 / night

£3736 - £4925 / week

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from £534 / night

1 / 23

Villa Andrea - Pienza villa sleeps 6

Tuscany / Province of Siena / Pienza

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 95 km; Swimming pool; Great for children of all ages ;
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 £163 / night

£1135 - £1681 / week

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from £163 / night

1 / 4

Tuscany / Province of Siena / Pienza

1 bedroomSleeps 21 night min stay

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

from £59 / night

£328 / week

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from £59 / night

1 / 19

Tuscany / Province of Siena / Pienza / Monticchiello

2 bedroomsSleeps 55 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min stay
Key info: Great for children of all ages ; Some pets are welcome - please contact the owner; Private garden;
 …see more

from £106 / night

£631 - £715 / week

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from £106 / night

1 / 15

Casa Marelli - Pienza townhouse sleeps 5

Tuscany / Province of Siena / Pienza

2 bedroomsSleeps 57 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Nearest beach 100 km; Great for children of all ages ; 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 £106 / night

£736 - £946 / week

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from £106 / night

(6) Excellent 

1 / 10

Tuscany / Province of Siena / Pienza / Monticchiello

1 bedroomSleeps 31 night min stay

  • 1 bedroom
  • Sleeps 3
  • 1 night min stay
Key info: Nearest beach 80 km; Not suitable for children; Car advised;
 …see more

from £72 / night

£471 / week

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from £72 / 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 £64 / night

£311 - £758 / week

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from £64 / 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 £151 / night

£1051 - £1639 / week

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from £151 / night

1 / 4

Villa Bandida - Pienza villa sleeps 14

Tuscany / Province of Siena / Pienza

7 bedroomsSleeps 14Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
Key info: Great for children of all ages ; Car advised; Some pets are welcome - please contact the owner;
As a luxury villa, Villa Bandida really works best as a place where friends and family come to relax, share meals, explore the countryside and drink wine late into the night. If your looking for the perfect location for a group get together, relaxing break, birthday cel  …see more

from £2799 / night

£11196 / week

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from £2799 / night

1 / 21

Tuscany / Province of Siena / Pienza

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Ski; Great for children of all ages ; Car advised;
 …see more

from £101 / night

£463 - £547 / week

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from £101 / night

1 / 24

Luxury villa near Pienza - Pienza villa sleeps 13

Tuscany / Province of Siena / Pienza

6 bedroomsSleeps 137 nights min stay

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; 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 £313 / night

£2185 - £5967 / week

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from £313 / night

1 / 20

Azienda Agricola Barbi (Monticchiello - Pienza)

Tuscany / Province of Siena / Pienza / Monticchiello

3 bedroomsSleeps 22 nights min stay

  • 3 bedrooms
  • Sleeps 2
  • 2 nights min stay
Key info: Great for children of all ages ; Car essential; Some pets are welcome - please contact the owner;
The Azienda Agricola Barbi, is situated in quiet and panoramic location in the heart of the Val D'Orcia, on the road from Pienza to Montichiello with breathtaking views of the valley and Mount Amiata.It is not easy to describe the feelings that can reserve a period  …see more

from £85 / night

£530 / week

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from £85 / night

1 / 22

Tuscany / Province of Siena / Pienza

3 bedroomsSleeps 21 night min stay

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

from £89 / night

£530 / week

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from £89 / night

1 / 6

Tuscany / Province of Siena / Pienza

1 bedroomSleeps 21 night min stay

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

from £59 / night

£253 / week

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from £59 / night

1 / 6

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 ; Pets welcome;
 …see more

from £122 / night

£463 / week

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from £122 / night

(2) Excellent 

1 / 57

I CIPRESSINI : il Casale Toscano più fotografato

Tuscany / Province of Siena / Pienza

3 bedroomsSleeps 61 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Swimming pool; Great for children of all ages ; Some pets are welcome - please contact the owner;
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 £253 / night

£1261 / week

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from £253 / night

1 / 10

Tuscany / Province of Siena / Pienza / Monticchiello

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Not suitable for children; No pets allowed;
 …see more

from £68 / night

£471 / week

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from £68 / night

1 / 14

Tuscany / Province of Siena / Pienza

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Ski; Great for children of all ages ; Car advised;
 …see more

from £51 / night

£295 - £337 / week

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from £51 / night

(1) Very Good 

1 / 24

Tuscany / Province of Siena / Pienza / Monticchiello

3 bedroomsSleeps 63 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Ask owner if suitable for children; Car advised; No pets allowed;
 …see more

from £169 / night

£1009 / week

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from £169 / night

1 / 13

Tuscany / Province of Siena / Pienza / Monticchiello

2 bedroomsSleeps 51 night min stay

  • 2 bedrooms
  • Sleeps 5
  • 1 night min stay
Key info: Not suitable for children; Air conditioning; No pets allowed;
 …see more

from £127 / night

£715 / week

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from £127 / night

(1) Excellent 

1 / 12

Tuscany / Province of Siena / Pienza / Monticchiello

1 bedroomSleeps 22 nights min stay

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

from £76 / night

£421 / week

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from £76 / night

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