50 Best Vacation Rentals in Pienza - Holiday Lettings - Cabins

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2,848 Vacation rentals

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 $508 / night

$3,549 - $4,858 / week

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from $508 / night

32

Vacation home in Pienza

Province of Siena / Pienza

2 3 2 nights min

  • 2 bedrooms
  • Sleeps 3
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
"Nido d'amore" in the heart of Tuscany: great to spend the holidays in complete relaxation. Two minutes from the medieval village of Pienza and really a few kilometers from Montepulciano (15 km), Montalcino (20 km). Not far away are also the cities of art like Siena, Fl …see more

from $149 / night

$1,041 / week

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avg. 1 hour 5 minutes

from $149 / night

24

Vacation farmhouse with swimming pool in Pienza

Province of Siena / Pienza

4 11 2 nights min

  • 4 bedrooms
  • Sleeps 11
  • 2 nights min
  • Nearest beach 95 mi
  • Swimming pool
  • Child friendly
The farmholuiday borders on a nature park in the Val d'Orcia, at Castelluccio di Pienza. Its location offers a panoramic view of two natural reserves: Pietraporciana and Lucciolabella. From the pool, nestled in an olive grove, guests enjoy a marvelous view of the entire …see more

from $484 / night

$3,098 - $3,878 / week

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from $484 / 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
Villa Il Mandorlo is one the three Villas of Casali Cellini farm . The Villa 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. Villa Il Mandorlo is a Vi …see more

from $461 / night

$3,222 - $4,832 / week

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avg. 3 hours 37 minutes

from $461 / 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 $123 / night

$738 - $1,255 / week

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from $123 / night

16

Farmhouse rental in Pienza with shared pool

Province of Siena / Pienza

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • 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 $122 / night

$854 - $1,394 / week

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from $122 / night

(2) Excellent 

22

Vacation apartment in Monticchiello

Pienza / Monticchiello

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • 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 $62 / night

$422 - $595 / week

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avg. 1 hour 48 minutes

from $62 / night

(5) 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 $186 / night

$992 / week

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from $186 / night

16

Farmhouse rental in Pienza with shared pool

Province of Siena / Pienza

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • 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 $80 / night

$558 - $977 / week

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from $80 / night

20

Farmhouse rental in Pienza with shared pool

Province of Siena / Pienza

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • 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 $97 / night

$669 - $1,171 / week

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from $97 / 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 $273 / night

$1,718 / week

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from $273 / 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 $186 / night

$1,301 / week

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from $186 / night

34

Vacation villa in Pienza

Province of Siena / Pienza

7 15 7 nights min

  • 7 bedrooms
  • Sleeps 15
  • 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 $293 / night

$2,047 - $3,331 / week

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from $293 / night

(2) Very Good 

16

Vacation guest house in Pienza

Province of Siena / Pienza

7 14 1 night min

  • 7 bedrooms
  • Sleeps 14
  • 1 night min
  • Nearest beach 103 mi
  • Child friendly
  • Pet friendly
We are in the historical centre of Pienza, a stone's throw from the main piazza PIO II. Our House is a residence in the 700 with a large walled garden where our guests can spend their free time or eat. We have two bedrooms, an apartment with bedroom, kitchen with large …see more

from $100 / night

$744 / week

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from $100 / 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 $137 / night

$744 - $868 / week

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from $137 / night

18

Vacation apartment with shared pool in Pienza

Province of Siena / Pienza

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly
Apartment with three bedrooms, three bathrooms, a large living room and a kitchen equipped with everything you need. The swimming pool and the green garden are great places to relax while enjoying a glass of wine or reading a book. Also in the surroundings you can visit …see more

from $298 / night

$2,082 / week

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avg. 1 hour 5 minutes

from $298 / night

(7) Very Good 

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 $106 / night

$694 / week

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Responds fast!
avg. 1 hour 24 minutes

from $106 / night

(3) 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 $602 / night

$4,213 / week

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avg. 3 hours 46 minutes

from $602 / night

17

Vacation farmhouse in Monticchiello

Pienza / Monticchiello

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
The Ada is in a unique position: surrounded by a large olive grove, a few hundred metres from the medieval walls of Monticchiello, is located along the panoramic road that leads to Pienza. Recently restored respecting the ancient structure, our apartment has vaulted bea …see more

from $149 / night

$930 / week

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Responds fast!
avg. 1 hour 19 minutes

from $149 / 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 $91 / night

$484 / week

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from $91 / night

9

Pienza Vacation apartment rental

Province of Siena / Pienza

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The apartments at Agriturismo I Casali Osteria feature a double bed, living room with kitchenette sofa bed and bathroom. Air conditioning, WI-FI, veranda, garden and use of the shared pool. Furnished in Tuscan style and well-groomed. Guests can enjoy the garden and the …see more

from $85 / night

$521 / week

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from $85 / 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 $112 / night

$620 / week

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Responds fast!
avg. 3 hours 27 minutes

from $112 / night

(1) Excellent 

21

Ski apartment to rent in Pienza

Province of Siena / Pienza

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Ski
  • Child friendly
  • Pet friendly
Farmhouse situated in the hills, in the middle of the countryside in the Firefly Park Beautiful OASIS immersed in typical Crete Senesi. Very spacious apartment with 2 bedrooms, lounge and bathrooms .2 1 kitchen.For those who love tranquillity and a relaxing holiday.Pets …see more

from $174 / night

$806 / week

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from $174 / 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 $227 / night

$1,586 - $2,974 / week

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avg. 1 hour 47 minutes

from $227 / 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 $223 / night

$1,561 / week

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from $223 / night

20

Farmhouse rental in Pienza with swimming pool

Province of Siena / Pienza

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • 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 $1,239 / night

$8,673 - $13,009 / week

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from $1,239 / night

25

Pienza Vacation lodge rental

Province of Siena / Pienza

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • 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 $121 / night

$842 - $1,301 / week

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from $121 / 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 $122 / night

$533 / week

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from $122 / 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 $1,023 / night

$7,161 - $11,151 / week

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Responds fast!
avg. 1 hour 31 minutes

from $1,023 / 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 $112 / night

$434 / week

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from $112 / night

14

Ski apartment to rent in Pienza

Province of Siena / Pienza

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Ski
  • Child friendly
  • Pet friendly
overlooking the Val D'orcia situated in a beautiful Hill, lies the AGRITURISMO CHIANCIANELLO. an old farmhouse of 800 completely restructured with comfortable and to guarantee our clients maximum tranquillity. our farmhouse is situated within the Firefly Park Beautiful …see more

from $87 / night

$496 / week

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from $87 / night

(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 $149 / night

$1,041 / week

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Responds fast!
avg. 1 hour 24 minutes

from $149 / night

(3) Very Good 

51

Monticchiello Vacation villa accommodation

Pienza / Monticchiello

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 130 mi
  • Swimming pool
  • Child friendly
Between Pienza and Montepulciano fascinating Villa of three hundred. The real estate complex of 800 square meters. ca composed of the main house, two outbuildings, a loft, a studio, and various local wineries; They are connected by a beautiful courtyard covered with a v …see more

from $1,238 / night

$7,310 - $13,009 / week

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from $1,238 / night

7

B&b rental in Pienza

Province of Siena / Pienza

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
The room is located on the first floor and as the flower that is inspired by that search light, enjoys a bright and beautiful views of the garden. Is cool and comfortable with a large lobby where you can enjoy breakfast, reading quietly or to add a third bed. Has a b …see more

from $87 / night

$496 - $558 / week

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from $87 / 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 $347 / night

$2,416 / week

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from $347 / night

(3) Excellent 

19

Home rental in Monticchiello

Pienza / Monticchiello

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 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 $155 / night

$930 / week

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from $155 / night

(24) 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 $93 / night

$651 / week

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from $93 / night

35

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 take privacy is in the pool, in home and in the garden. From the windows you see Monticchiello, Pienza and Montepulciano. Also from here you can see the famous "Monticchiello" curves that were the backdrop to many …see more

from $223 / night

$1,487 - $1,735 / week

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from $223 / 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 $200 / night

$1,394 / week

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from $200 / night

23

Vacation villa with swimming pool in Monticchiello

Pienza / Monticchiello

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 $760 / night

$5,315 - $7,273 / week

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from $760 / night