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37 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 / 12

Pienza / Monticchiello

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Child friendly ; Pet friendly; Private garden;
 …see more

from £171 / night

£855 / week

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from £171 / night

1 / 17

Pienza / Monticchiello

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Child friendly ; Pet friendly; Private garden;
 …see more

from £103 / night

£642 / week

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from £103 / night

1 / 21

Villa Arpicella - Pienza villa sleeps 4

Province of Siena / Pienza

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Nearest beach 95 km; Child friendly ; 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 £85 / night

£590 - £877 / week

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from £85 / night

1 / 14

Province of Siena / Pienza

1 2 2 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: Ask owner if suitable for children; No pets allowed; Private garden;
 …see more

from £60 / night

£300 / week

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from £60 / night

(1) Very Good 

1 / 20

Province of Siena / Pienza

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Child friendly ; No pets allowed; Private garden;
 …see more

from £112 / night

£599 / week

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from £112 / night

(15) Excellent 

1 / 43

Villa PoliFlora - Monticchiello apartment sleeps 6

Pienza / Monticchiello

2 6 1 night min stay

  • 2 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Child friendly ; Ask about pets; 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 £65 / night

£317 - £771 / week

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from £65 / night

1 / 15

Rosemary Villa (v007) - Pienza farmhouse sleeps 12

Province of Siena / Pienza

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Nearest beach 44 km; Swimming pool; Child friendly ;
Ground floor: a large dining/living room overlooking the garden, kitchen, breakfast room, small sitting room with fireplace, study, twin bedded room with en suite bathroom with tub and shower, double bedroom with en suite bathroom with shower. First floor: large lounge  …see more

from £666 / night

£4659 - £6265 / week

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from £666 / night

(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 / 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

(4) 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

1 / 19

Stunning Villa near Pienza - Pienza villa sleeps 10

Province of Siena / Pienza

4 10 7 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; 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

£1095 - £2052 / week

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from £157 / night

1 / 20

The Spring (v024) - 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 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 £484 / night

£3385 - £3932 / week

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from £484 / night

1 / 9

Province of Siena / Pienza

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 98 km; Swimming pool; Child friendly ;
 …see more

from £35 / night

£607 - £915 / week

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from £35 / 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

1 / 20

Wisteria Farm (V036) - Pienza farmhouse sleeps 8

Province of Siena / Pienza

4 8 7 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; 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 £352 / night

£2462 - £3035 / week

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from £352 / night

1 / 23

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) Excellent 

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Lodge Gelso wonderful view in Val D'Orcia - Pienza lodge sleeps 4

Province of Siena / Pienza

1 4 7 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 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 £89 / night

£620 - £1283 / week

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from £89 / 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

1 / 24

Villa near Pienza - Pienza villa sleeps 14

Province of Siena / Pienza

6 14 3 nights min stay

  • 6 bedrooms
  • Sleeps 14
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
This enchanting holiday home in Tuscany 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  …see more

from £428 / night

£1325 - £1599 / week

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from £428 / 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 / 15

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

1 / 36

Province of Siena / Pienza

2 7 3 nights min stay

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min stay
Key info: Nearest beach 100 km; Ask owner if suitable for children; Car advised;
 …see more

from £56 / night

£389 / week

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from £56 / night

1 / 15

Province of Siena / Pienza

3 6 2 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay
Key info: Swimming pool; Child friendly ; Car not necessary;
 …see more

from £206 / night

£701 - £1026 / week

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from £206 / 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 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 / 34

Villa Fonte all'Oppio Pienza - Pienza villa sleeps 13

Province of Siena / Pienza

7 13 7 nights min stay

  • 7 bedrooms
  • Sleeps 13
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; 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 £201 / night

£1402 - £2291 / week

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from £201 / night

1 / 100

Incanto - Pienza villa sleeps 16

Province of Siena / Pienza

8 16 7 nights min stay

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min stay
Key info: Nearest beach 150 km; Swimming pool; Child friendly ;
ExteriorsThis deluxe villa is situated in the centre of Val d'Orcia, very close to Pienza, province of Siena, where guests will find lots of shops and restaurants, among many other facilities. The villa is an ideal location to visit and discover all the famous cultural  …see more

from £733 / night

£5129 - £8548 / week

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from £733 / night

1 / 20

The Posting House (V040) - Pienza manor house sleeps 14

Province of Siena / Pienza

7 14 7 nights min stay

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
This large manor house was a well-known post-house for changing coaches and horses along the Via Francigena as far back as the tenth century and the architecture of the house shows its origin. A pleasant garden surrounds the elegant farmhouse, a lovely swimming pool loo  …see more

from £871 / night

£6095 - £7830 / week

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from £871 / 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) Excellent 

1 / 27

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 / 20

Tuscany 5 bedroom villa with private pool - Montepulicano villa sleeps 10

Pienza / Montepulicano

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Child friendly ; Air conditioning;
This is a fantastic 5 bedroom villa near the wonderful town of Montepulciano in Tuscany. Completely surrounded by olive grove and vineyards, it occupies an idyllic setting for guests to enjoy a peaceful and relaxing holiday. Recently restored, it offers a perfect mix o  …see more

from £257 / night

£1710 - £3206 / week

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from £257 / 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 / 20

Pienza - 65573001 - Pienza farmhouse sleeps 14

Province of Siena / Pienza

8 14 7 nights min stay

  • 8 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Pet friendly;
Imposing farmhouse dating back to the 18th century comprising 2 independent units (rentable only together as a private property). This beautiful 5–hectare estate is situated in quiet and panoramic location, in the heart of the Val d’Orcia region, a short distance a  …see more

from £529 / night

£3699 - £6906 / week

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from £529 / 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 / 12

Province of Siena / Pienza

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Nearest beach 100 km; Child friendly ; Car not necessary;
 …see more

from £62 / night

£428 / week

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from £62 / night

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