50 Best Vacation Rentals in Pienza - Holiday Lettings - Cabins

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144 Vacation rentals

(1) Excellent 

15

Apartment rental in Monticchiello

Pienza / Monticchiello

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Nearest beach 80 mi
  • Child friendly
  • Air conditioning
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 $141 / night

$986 / week

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avg. 2 hours 14 minutes

from $141 / night

(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

(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 $60 / night

$403 - $519 / week

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avg. 3 hours 42 minutes

from $60 / night

12

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 $131 / night

$711 - $829 / week

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from $131 / night

(1) Excellent 

12

Monticchiello Vacation b&b rental

Pienza / Monticchiello

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Ask about pets
Rigopesci Farm Bed and Breakfast & nestled in the heart of the natural park of Val d'Orcia, halfway between Siena and Florence, territory rich in history, culture, food and fine wines. We welcome you to the best of our ability to offer you a relaxing stay, to give you u …see more

from $107 / night

$592 / week

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Responds fast!
avg. 3 hours 27 minutes

from $107 / night

(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 $212 / night

$1480 - $2308 / week

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from $212 / night

(7) 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 $178 / night

$1243 / week

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avg. 3 hours 52 minutes

from $178 / 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 $101 / night

$705 - $1119 / week

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avg. 3 hours 43 minutes

from $101 / night

32

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 $214 / night

$1421 - $1657 / week

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from $214 / 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 $249 / night

$841 - $1362 / week

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from $249 / night

(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 $302 / night

$2113 - $3853 / week

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avg. 3 hours 43 minutes

from $302 / night

(6) Excellent 

13

Vacation apartment in Monticchiello

Pienza / Monticchiello

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Nearest beach 80 mi
  • Child friendly
  • Pet friendly
The property is located in UNESCO's Heritage Valdorcia in Monticchiello one of most beatifull medioeval 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 …see more

from $101 / night

$663 / week

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Responds fast!
avg. 2 hours 14 minutes

from $101 / night

(1) Excellent 

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 $403 / night

$2815 - $4574 / week

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from $403 / 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 $215 / night

$1502 - $2815 / week

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avg. 3 hours 42 minutes

from $215 / 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 $87 / night

$605 / week

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from $87 / 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 $83 / night

$569 - $888 / week

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from $83 / night

(4) 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 $178 / night

$947 / week

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from $178 / 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 $86 / night

$458 / week

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Responds fast!
avg. 2 hours 44 minutes

from $86 / night

15

Vacation townhouse in Pienza

Province of Siena / Pienza

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 100 mi
  • 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 reside …see more

from $148 / night

$1036 - $1332 / week

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from $148 / 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 $115 / night

$505 / week

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avg. 2 hours 44 minutes

from $115 / night

(1) Excellent 

12

Vacation b&b in Monticchiello

Pienza / Monticchiello

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Ask about pets
Rigopesci Farm Bed and Breakfast & nestled in the heart of the natural park of Val d'Orcia, halfway between Siena and Florence, territory rich in history, culture, food and fine wines. We welcome you to the best of our ability to offer you a relaxing stay, to give you u …see more

from $107 / night

$592 / week

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Responds fast!
avg. 3 hours 27 minutes

from $107 / night

(1) Excellent 

20

Vacation home in Monticchiello

Pienza / Monticchiello

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Child friendly
  • Private garden
The "Noble" apartment (so called because it overlooks Montepulciano) Consists of: kitchen with large living room, three double bedrooms each with en suite shower. From the large windows you can admire Montepulciano, home of the noble wine, and the woods of oak and chest …see more

from $237 / night

$1421 / week

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from $237 / 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 $235 / night

$1408 / week

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from $235 / night

(23) 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 $89 / night

$438 - $1068 / week

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from $89 / 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 $116 / night

$816 - $1332 / week

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from $116 / night

(2) Excellent 

23

Pienza Vacation villa rental

Province of Siena / Pienza

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa I CIPRESSINI is the most photographed house in the area, for years depicted on postcards and calendars just because it is the charm of the old Tuscan farmhouse. In the countryside but only 500 mt.dal country offers great outdoor spaces; the pool open 15 / 6-15 / 9 …see more

from $575 / night

$4024 - $8048 / week

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Responds fast!
avg. 3 hours 32 minutes

from $575 / 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 $93 / night

$640 - $1119 / week

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from $93 / 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 $670 / night

$4687 - $6214 / week

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from $670 / night

7

Vacation b&b rental

Pienza / Monticchiello

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Ask about pets
Rigopesci Farm Bed and Breakfast & nestled in the heart of the natural park of Val d'Orcia, halfway between Siena and Florence, territory rich in history, culture, food and fine wines. We welcome you to the best of our ability to offer you a relaxing stay, to give you u …see more

from $107 / night

$592 / week

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Responds fast!
avg. 3 hours 27 minutes

from $107 / 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 $124 / night

$739 / week

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from $124 / night

(2) Very Good 

20

Pienza Vacation home rental

Province of Siena / Pienza

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Private garden
Just a few steps from the famous Piazza Pio II, in the historical centre of Pienza, the ANCIENT COURT apartment, recently renovated, has a double bedroom with bathroom, a bedroom with two beds, complete kitchen appliances oven, fridge and dishwasher, bathroom with showe …see more

from $119 / night

$711 - $1208 / week

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from $119 / 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 $151 / night

$971 / week

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from $151 / night

(3) Excellent 

19

Home rental in Monticchiello

Pienza / Monticchiello

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • Child friendly
  • Ask about pets
  • Private garden
The House, built on an ancient structure and recently restored, is located in the heart of Monticchiello, its highest position, next to the large medieval church. Enjoys an extensive garden on the ancient walls, with a wide and incomparable views over the Woods and Vall …see more

from $148 / night

$888 / week

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from $148 / night

9

Vacation guest house in Pienza

Province of Siena / Pienza

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
It is a nice and cozy apartment, as the plant that inspires, which opens directly onto the garden. Has a nice double bedroom, a bathroom with shower and a large living-kitchen fully equipped (kitchenette, fridge, point TV) characterized by a large old fireplace at gue …see more

from $89 / night

$533 - $651 / week

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from $89 / 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 $76 / night

$533 - $933 / week

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from $76 / night

(3) Excellent 

24

Vacation b&b in Monticchiello

Pienza / Monticchiello

4 7 1 night min

  • 4 bedrooms
  • Sleeps 7
  • 1 night min
A small village, the landscapes of the Val d'Orcia, an ancient historical residence dating back to the 13th century. These are just some of the features of ' La Casa di Adelina, a bed and breakfast in & montichiello, small village near Pienza. Monticchiello is little mo …see more

from $449 / night

$2971 / week

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from $449 / night

21

Vacation villa in Monticchiello

Pienza / Monticchiello

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
In the countryside and 5 km from Pienza, the villa on Lime Tree is a beautiful house located in the middle of the Natural and Artistic Park of Val d'Orcia. With breathtaking views and surrounded by hills, is a 10-minute drive from Pienza and Vignoni Bangna. Ideal for we …see more

from $214 / night

$1492 / week

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from $214 / night

10

Monticchiello Vacation townhouse rental

Pienza / Monticchiello

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
The hospitality and refinement of the Bed and Breakfast La Casa di Adelina continues in the quiet apartment situated in the center of Monticchiello. The nock will leave you speechless! This capability provides our guests to stay in a context of value, architectural st …see more

Pricing unknown

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Pricing unknown

18

Pienza Vacation villa rental

Province of Siena / Pienza

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 150 mi
  • Swimming pool
  • Child friendly
Careful restoration, ended in May 2015, using original period materials, has maintained the style of the farm and ensured an ancient atmosphere with modern technology. The 4 beautiful and spacious bedrooms have been decorated with elegant colours. Stylish and spacious …see more

from $711 / night

$3788 - $5445 / week

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from $711 / night

(4) 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 $77 / night

$539 / week

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from $77 / night