Pienza apartment or villa with a private pool area | Holiday Lettings

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  • Italy
  • Tuscany
  • Province of Siena
  • Pienza

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  • Montepulicano (1)
  • Monticchiello (5)

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44 Holiday homes

Filters applied: Private pool (44)

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

1 / 24

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 / 19

Stunning Villa near Pienza - Pienza villa sleeps 10

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 £155 / night

£1084 - £2000 / week

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from £155 / night

1 / 20

The Spring (v024) - Pienza villa sleeps 12

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 / 20

Cypress Villa (v008) - Pienza farmhouse sleeps 13

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 £343 / night

£2400 - £5734 / week

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from £343 / night

1 / 34

Villa Fonte all'Oppio Pienza - Pienza villa sleeps 13

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

Wisteria Farm (V036) - Pienza farmhouse sleeps 8

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 / 41

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 £142 / night

£992 - £1167 / week

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from £142 / night

1 / 15

Rosemary Villa (v007) - Pienza farmhouse sleeps 12

Province of Siena / Pienza

6 bedroomsSleeps 12Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Nearest beach 44 km; Swimming pool; Great for children of all ages ;
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 £649 / night

£4542 - £6109 / week

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from £649 / night

1 / 24

Luxury villa near Pienza - Pienza villa sleeps 13

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 £310 / night

£2167 - £5917 / week

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from £310 / night

1 / 24

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

(7) Excellent 

1 / 57

Poggio ai Gelsi - Pienza lodge sleeps 8

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 / 100

Pienza 44315 - Pienza villa sleeps 14

Province of Siena / Pienza

6 bedroomsSleeps 147 nights min stay

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; 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 £344 / night

£2405 - £6565 / week

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from £344 / night

1 / 24

Villa near Pienza - Pienza villa sleeps 14

Province of Siena / Pienza

6 bedroomsSleeps 14Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; 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 £417 / night

£1292 - £2234 / week

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from £417 / night

1 / 23

Fonte Senesi - Pienza villa sleeps 12

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 / 23

Villa Andrea - Pienza villa sleeps 6

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 £161 / night

£1125 - £1667 / week

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from £161 / night

1 / 24

luxury villa few steps from Pienza - Pienza apartment sleeps 15

Province of Siena / Pienza

8 bedroomsSleeps 157 nights min stay

  • 8 bedrooms
  • Sleeps 15
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; 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 £477 / night

£3334 - £6392 / week

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from £477 / night

1 / 48

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 / 100

Montefollonico 65998 - Pienza villa sleeps 10

Province of Siena / Pienza

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; 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 £413 / night

£2411 - £3300 / week

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from £413 / night

1 / 20

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

Province of Siena / Pienza

7 bedroomsSleeps 147 nights min stay

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; 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 £849 / night

£5942 - £7634 / week

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from £849 / night

1 / 48

Villa dell'Architetto - Pienza villa sleeps 14

Province of Siena / Pienza

8 bedroomsSleeps 147 nights min stay

  • 8 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Not suitable for children; No pets allowed;
<br>Villa dell'Architetto - Pienza - Tuscany<br>8 Bedrooms (6 double, 2 single) - Pool<br>Here we find ourselves in southern Tuscany, the Val D'Orcia, a UNESCO World Heritage site for several years now. Val D'Orcia is well know  …see more

from £810 / night

£5667 / week

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from £810 / night

(2) Excellent 

1 / 57

I CIPRESSINI : il Casale Toscano più fotografato

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 £250 / night

£1250 / week

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from £250 / night

1 / 100

Incanto - Pienza villa sleeps 16

Province of Siena / Pienza

8 bedroomsSleeps 167 nights min stay

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min stay
Key info: Nearest beach 150 km; Swimming pool; Great for children of all ages ;
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 cult  …see more

from £953 / night

£6667 - £8334 / week

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from £953 / night

1 / 20

Montefollonico - 65998001 - Pienza farmhouse sleeps 10

Province of Siena / Pienza

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Pets welcome;
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 £413 / night

£2411 - £3300 / week

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from £413 / night

1 / 39

Villa Afrodite - Pienza villa sleeps 10

Province of Siena / Pienza

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Not suitable for children; No pets allowed;
<br>Villa Afrodite – Pienza – Tuscany<br>5 Double Bedrooms – Pool<br>Villa Afrodite lays on top of a hill that leads to the Nobile vineyards of Montepulciano and on the other hand to the hills of the Val d'Orcia; from the villa Afrodite you  …see more

from £477 / night

£3334 - £4334 / week

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from £477 / night

1 / 20

Tuscany 5 bedroom villa with private pool

Pienza / Montepulicano

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; 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 £250 / night

£1667 - £3125 / week

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from £250 / night

1 / 23

Pienza - 44315001 - Pienza farmhouse sleeps 14

Province of Siena / Pienza

6 bedroomsSleeps 147 nights min stay

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Some pets are welcome - please contact the owner;
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 £344 / night

£2405 - £6565 / week

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from £344 / night

1 / 20

Pienza - 65573001 - Pienza farmhouse sleeps 14

Province of Siena / Pienza

8 bedroomsSleeps 147 nights min stay

  • 8 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Pets welcome;
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 £516 / night

£3606 - £6734 / week

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from £516 / night

1 / 52

Villa Manafiore - Monticchiello villa sleeps 9

Pienza / Monticchiello

6 bedroomsSleeps 97 nights min stay

  • 6 bedrooms
  • Sleeps 9
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; 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 £811 / night

£5673 / week

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from £811 / night

(1) Excellent 

1 / 14

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 / 36

Province of Siena / Pienza

3 bedroomsSleeps 87 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Pets welcome;
 …see more

from £197 / night

£1377 - £2124 / week

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from £197 / night

(2) Very Good 

1 / 26

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

1 / 44

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 ; Air conditioning;
 …see more

from £236 / night

£1650 - £2338 / week

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from £236 / night

1 / 44

Province of Siena / Pienza

6 bedroomsSleeps 147 nights min stay

  • 6 bedrooms
  • Sleeps 14
  • 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 £443 / night

£3101 - £8036 / week

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from £443 / night

(1) Very Good 

1 / 47

Province of Siena / Pienza

7 bedroomsSleeps 147 nights min stay

  • 7 bedrooms
  • Sleeps 14
  • 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 £1146 / night

£8016 - £9485 / week

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from £1146 / night

1 / 28

Province of Siena / Pienza

6 bedroomsSleeps 147 nights min stay

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Suitable for children age 5+; Air conditioning;
 …see more

from £404 / night

£2824 - £8004 / week

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from £404 / night

1 / 31

Pienza / Monticchiello

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 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 £611 / night

£4275 - £6413 / week

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from £611 / night

1 / 40

Province of Siena / Pienza

4 bedroomsSleeps 87 nights min stay

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

from £161 / night

£1125 - £2188 / week

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from £161 / night

1 / 24

Province of Siena / Pienza

8 bedroomsSleeps 19Min stay varies

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

from £983 / night

£6875 - £13542 / week

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from £983 / night

1 / 25

Pienza / Monticchiello

6 bedroomsSleeps 12Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Swimming pool; Ask owner if suitable for children; Pets welcome;
 …see more

from £463 / night

£3235 - £4804 / week

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from £463 / night

1 / 39

Province of Siena / Pienza

8 bedroomsSleeps 14Min stay varies

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

from £547 / night

£3824 - £6353 / week

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from £547 / night

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