50 Best Vacation Rentals in Pienza - Holiday Lettings - Cabins

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138 Vacation rentals

(4) Excellent 

11

Pienza Vacation apartment rental

Province of Siena / Pienza

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Suitable for children age 5+
  • Ask about pets
Characteristic apartment located in Nice recently restored Plaza of Spain, in the historical centre of Pienza. Fully equipped kitchen, double bedroom, bedroom with sofa bed and 1 1/2, living room with fireplace and single sofa bed. Bathroom with large shower, washing ma …see more

Pricing unknown

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Pricing unknown

(6) Excellent 

23

Vacation apartment in Pienza

Province of Siena / Pienza

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Child friendly
  • Air conditioning
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 g …see more

from $169 / night

$1179 / week

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Responds fast!
avg. 3 hours 5 minutes

from $169 / night

(21) Excellent 

Certificate of Excellence

43

Vacation apartment in Monticchiello

Pienza / Monticchiello

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Pet friendly
  • 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

Certificate of Excellence

from $85 / night

$416 - $1013 / week

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from $85 / night

16

Farmhouse rental in Pienza with shared pool

Province of Siena / Pienza

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Welcoming farmhouse situated in panoramic location in the beautiful area of Val D’Orcia. This property comprises 4 units (one is occupied by the owners) and offers a well-groomed garden, a private furnished area for all of the 3 apartments and a nice pool (with Jacuzzi …see more

from $131 / night

$768 - $1254 / week

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from $131 / night

24

Vacation farmhouse with swimming pool in Pienza

Province of Siena / Pienza

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • 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 $461 / night

$3216 - $4403 / week

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from $461 / night

23

Vacation villa with swimming pool in Pienza

Province of Siena / Pienza

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 can …see more

from $689 / night

$4817 - $6591 / week

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from $689 / night

(2) Excellent 

22

Vacation apartment in Monticchiello

Pienza / Monticchiello

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Lovely apartment in Monticchiello (Pienza) at the entrance of the Val d'Orcia in an ancient village ' of recent construction. New apartment has satellite tv, garden with deck chairs, table and chairs on the porch. Has the most-photographed view of Tuscany and is ideal f …see more

from $57 / night

$382 - $492 / week

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Responds fast!
avg. 3 hours 22 minutes

from $57 / night

25

Pienza Vacation lodge rental

Province of Siena / Pienza

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Nearest beach 100 mi
  • Swimming pool
  • Air conditioning
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 beautifu …see more

from $85 / night

$590 - $1062 / week

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Responds fast!
avg. 2 hours 59 minutes

from $85 / night

(3) Excellent 

21

Tower rental in Monticchiello

Pienza / Monticchiello

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Ask about children
  • Private garden
In Val d'Orcia, Monticchiello di Pienza is a small medieval town, surrounded by walls and protected by four towers; one of these is ' Charles ' Tower, which stands at the highest point of the village and has a panoramic view across the Valley. Sunsets and beautiful wil …see more

from $169 / night

$899 / week

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from $169 / night

22

B&b rental in Pienza

Province of Siena / Pienza

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
For travellers who want to get in touch with the true spirit of Pienza, the ideal city Suites is the perfect choice.The structure provides 3 charming suites equipped with every comfort: a four-poster bed, sofa bed, TV, a minibar, air conditioning, Wi-Fi, tea and coffee …see more

from $117 / night

$702 / week

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from $117 / night

(1) Excellent 

9

Vacation apartment with shared pool in Pienza

Province of Siena / Pienza

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 98 mi
  • Swimming pool
  • Child friendly
The farm Selvoli is situated in the Artistic natural and cultural Park of the Val d'Orcia, declared by the UNESCO "patrimony of humanity", the middle of a farm of 180 ha., on a hill from which you can enjoy the splendid landscape of the Val d'Orcia, just 5 km from Pienz …see more

from $236 / night

$798 - $1292 / week

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from $236 / night

(6) Excellent 

10

Vacation apartment in Monticchiello

Pienza / Monticchiello

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Nearest beach 80 mi
  • Private garden
The property is located in UNESCO's Heritage Valdorcia in Monticchiello one of most beatifull she village in Tuscany. Between Siena and Rome is a perfect location to enjoy an unforgettable holiday. Wine tour, good food, art and history the village can offer you 3 restau …see more

from $96 / night

$629 / week

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Responds fast!
avg. 2 hours 32 minutes

from $96 / night

20

Vacation manor house with swimming pool in Pienza

Province of Siena / Pienza

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 $841 / night

$5884 - $7355 / week

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from $841 / night

12

B&b rental in Monticchiello

Pienza / Monticchiello

2 2 1 night min

  • 2 bedrooms
  • Sleeps 2
  • 1 night min
  • Air conditioning
The B&B is located few meters away from the entrance door to the Castle in Monticchiello. Maria Gabriella can host you in her comfortable annexe legantly furnitured. The hotel has its private bathroom with shower, TV and free internet connection. There is a private par …see more

from $110 / night

$480 / week

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Responds fast!
avg. 2 hours 27 minutes

from $110 / night

(1) Excellent 

9

Apartment rental in Pienza with shared pool

Province of Siena / Pienza

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
The farm Selvoli is situated in the Artistic natural and cultural Park of the Val d'Orcia, declared by the UNESCO "patrimony of humanity", the middle of a farm of 180 ha., on a hill from which you can enjoy the splendid landscape of the Val d'Orcia, just 5 km from Pienz …see more

from $78 / night

$535 - $836 / week

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from $78 / night

20

Farmhouse rental in Pienza with shared pool

Province of Siena / Pienza

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Welcoming farmhouse situated in panoramic location in the beautiful area of Val D’Orcia. This property comprises 4 units (one is occupied by the owners) and offers a well-groomed garden, a private furnished area for all of the 3 apartments and a nice pool (with Jacuzzi …see more

from $103 / night

$602 - $1053 / week

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from $103 / night

34

Vacation villa in Pienza

Province of Siena / Pienza

7 13 7 nights min

  • 7 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
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 $264 / night

$1842 - $3010 / week

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from $264 / night

19

Vacation villa in Pienza

Province of Siena / Pienza

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
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 $206 / night

$1438 - $2695 / week

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Responds fast!
avg. 3 hours 14 minutes

from $206 / night

15

Vacation apartment rental

Province of Siena / Pienza

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
The farm Selvoli is situated in the Artistic natural and cultural Park of the Val d'Orcia, declared by the UNESCO "patrimony of humanity", the middle of a farm of 180 ha., on a hill from which you can enjoy the splendid landscape of the Val d'Orcia, just 5 km from Pienz …see more

from $248 / night

$921 - $1460 / week

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from $248 / night

6

Apartment rental in Monticchiello

Pienza / Monticchiello

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 100 mi
  • Child friendly
The residence "Il Torrino" is a panoramic apartment obtained from the restauration of an ancient tower belonging to the boundaries of the medieval suburb Monticchiello. The structure, in proximity of the principal access to the village, has been completely restructu …see more

from $142 / night

$914 / week

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from $142 / night

22

Vacation villa rental

Province of Siena / Pienza

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
Casale Reggello is located in the gently rolling Tuscan hills, between the wonderful towns of Pienza and Montepulciano, just a short distance from the thermal baths of Bagno Vignoni. Reggello is a single House with 8/10 beds and as its own swimming pool and surrounding …see more

from $385 / night

$2695 - $4379 / week

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from $385 / night

20

Villa rental in Pienza with swimming pool

Province of Siena / Pienza

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 $636 / night

$4447 - $5895 / week

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from $636 / night

41

Monticchiello Vacation townhouse rental

Pienza / Monticchiello

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
House with private pool,reserved to one booking so to guarantee privacy is in the pool, in home and in the garden.With views over Monticchiello, Pienza and Montepulciano. Also from here you can see the famous "Monticchiello" curves that were the backdrop to many intern …see more

from $197 / night

$1348 - $1572 / week

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from $197 / night

(2) Excellent 

36

Vacation apartment in Pienza

Province of Siena / Pienza

2 7 3 nights min

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 100 mi
  • Ask about children
  • Pet friendly
The apartment is on the ground floor, with private entrance, garden, small porch, living room with sofa bed, kitchen, bathroom and a double and a triple room. Its beams and its fixtures on walnut make the interior of the apartment warm, its decoration are a blend of ant …see more

from $73 / night

$507 / week

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from $73 / night

16

Farmhouse rental in Pienza with shared pool

Province of Siena / Pienza

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Welcoming farmhouse situated in panoramic location in the beautiful area of Val D’Orcia. This property comprises 4 units (one is occupied by the owners) and offers a well-groomed garden, a private furnished area for all of the 3 apartments and a nice pool (with Jacuzzi …see more

from $86 / night

$502 - $878 / week

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from $86 / night

5

Vacation apartment rental

Province of Siena / Pienza

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
Is a large and flat, like the solar plant that is inspired, located on the first floor of the structure. Its Windows overlook the garden on one side, the other on a characteristic internal courtyard. Has a living room and equipped kitchen (cooking point, fridge, TV), …see more

from $146 / night

$786 / week

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from $146 / night

(2) Very Good 

24

Vacation apartment rental

Pienza / Monticchiello

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Ask about children
  • Private garden
CAMPO ALLA PIANA è un podere in campagna ma a soli 500 metri dal borgo di Monticchiello di Pienza. Mettiamo a disposizione degli ospiti 3 camere spaziose, luminose e ben arredate; anche i bagni sono eleganti , spaziosi e con ampie finestre. Dalle camere si può ammirar …see more

from $225 / night

$1348 / week

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from $225 / night

4

Vacation villa rental

Province of Siena / Pienza

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Child friendly
  • Ask about pets
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

Pricing unknown

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Pricing unknown

(2) Excellent 

24

Vacation apartment with shared pool in Monticchiello

Pienza / Monticchiello

3 7 5 nights min

  • 3 bedrooms
  • Sleeps 7
  • 5 nights min
  • Nearest beach 110 mi
  • 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 prop …see more

from $201 / night

$1404 - $2190 / week

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from $201 / night

(1) Very Good 

24

Vacation b&b in Monticchiello

Pienza / Monticchiello

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Child friendly
  • Air conditioning
  • Ask about pets
The B&B is located few meters away from the entrance door to the Castle in Monticchiello. Maria Gabriella can host you in her 4 comfortable rooms elegantly furnitured. Each room has its private bathroom with shower, TV and free internet connection. There is a private p …see more

from $102 / night

$674 - $2796 / week

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Responds fast!
avg. 2 hours 27 minutes

from $102 / night

(1) Excellent 

15

Apartment rental in Monticchiello

Pienza / Monticchiello

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
The property is dated back XVIII century, has been completly restored saving the antique charme. In the centre of the village, distance by walk 3 resturants, cofee bar, grocery, bakery bank and tourist office. If you wish relax , good food good wine art and history you …see more

from $134 / night

$936 / week

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Responds fast!
avg. 2 hours 32 minutes

from $134 / night

5

Vacation apartment in Pienza

Province of Siena / Pienza

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
The farm Selvoli is situated in the Artistic natural and cultural Park of the Val d'Orcia, declared by the UNESCO "patrimony of humanity", the middle of a farm of 180 ha., on a hill from which you can enjoy the splendid landscape of the Val d'Orcia, just 5 km from Pienz …see more

from $158 / night

$753 - $1179 / week

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from $158 / night

40

Pienza Vacation farmhouse rental

Province of Siena / Pienza

9 17 7 nights min

  • 9 bedrooms
  • Sleeps 17
  • 7 nights min
  • Child friendly
  • Pet friendly
The farmhouse is situated within the ' Lucciola Bella ' Nature reserves, south west of Pienza in a small corner of the typical landscape of the crete senesi. In fact the striking feature of the nature reserve is this unusual landscape of the ' Badlands ' and ' biancane …see more

from $82 / night

$574 / week

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from $82 / night

5

Vacation farmhouse in Pienza

Province of Siena / Pienza

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Cacciamici farm is located in one of the most beautiful, but at the same time less note of Val d'Orcia. The same location is rather special as it is on the border between the municipalities of Sarteano and Pienza and at bella vista before him the rocca di Radicofani beh …see more

Pricing unknown

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Pricing unknown

(9) Excellent 

57

Vacation lodge in Pienza

Province of Siena / Pienza

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 100 mi
  • 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 beautifu …see more

from $287 / night

$2005 - $3655 / week

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Responds fast!
avg. 2 hours 59 minutes

from $287 / night

30

Vacation apartment with indoor pool in Pienza

Province of Siena / Pienza

8 15 7 nights min

  • 8 bedrooms
  • Sleeps 15
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 sitting r …see more

from $594 / night

$4155 - $7804 / week

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Responds fast!
avg. 3 hours 14 minutes

from $594 / night

24

Monticchiello Vacation b&b rental

Pienza / Monticchiello

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Air conditioning
Inside the medieval village of Monticchiello, Maria Gabriella is happy to welcome you in its comfortable beautifully furnished annexe. The dependence is equipped with:-Separate entrance-Private bathroom with shower, Television, Air Conditioner _-Free WI-FI. From Monti …see more

from $82 / night

$438 / week

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Responds fast!
avg. 2 hours 27 minutes

from $82 / night

21

Villa rental in Pienza

Province of Siena / Pienza

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 95 mi
  • Child friendly
  • Private garden
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 Tuscan …see more

from $114 / night

$792 - $1151 / week

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from $114 / night

(1) Excellent 

12

Monticchiello Vacation farmhouse rental

Pienza / Monticchiello

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden


The Podere Ada, a typical rural structure of the early ' 900, is in a unique position: surrounded by a large olive grove, a few hundred metres from the medieval walls of Monticchiello, is situated along the panoramic road that leads to Pienza. 
The farm consists of a …see more

from $225 / night

$1123 / week

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from $225 / night

(1) Excellent 

11

Ski apartment to rent in Pienza

Province of Siena / Pienza

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Ski
  • Child friendly
  • Pet friendly
Located on a beautiful hillside, overlooking farm in the Valley of Val d'Orcia. An estate of 800 served as accommodation of sick, before arriving at the old hospital of Siena. In 2006 it was restored and were obtained 4 apartments. Agriturismo Chiancianello consists o …see more

from $101 / night

$390 / week

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from $101 / night

1