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Holiday Rentals and Villas in Pienza, Italy

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    1 / 23
    5 of 5 stars (5) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    1 / 19
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    1 / 34
    7 Bedrooms, 5 Bathrooms, Sleeps 13 | Quick View
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    1 / 9
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Pienza, Province of Siena
    5 of 5 stars Reviewed 8 August 2016
    Excellent holiday, the reception was generous and warm; the location is superb. It was our third stay and it is still Paradise on earth!
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    1 / 57
    5 of 5 stars (7) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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 beautiful and change day after day,... View all property information
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    Pienza, Province of Siena
    5 of 5 stars Reviewed 15 August 2015
    This is excellent accommodation with a fantastic swimming pool. We travelled as a family with teenage children so having separate accommodation units worked well. The outdoor...
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    1 / 5
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Pienza, Province of Siena
    1 / 41
    5 Bedrooms, Sleeps 10 | Quick View
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    About this property
    Immersed between the winding hills of the Sienese Crete, rising between the oak tree woods and the branches of the olive trees lies the ancient cottage Villa Le Crete. Situated on a naturally formed terrace of the Val d'Orcia, which formerly was the home of many peasants and their families, has... View all property information
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    Pienza, Province of Siena
    1 / 55
    5 of 5 stars (2) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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 piscina aperta 15/6-15/9 offre relax... View all property information
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    Pienza, Province of Siena
    1 / 25
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    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 beautiful and change day after day,... View all property information
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    Pienza, Province of Siena
    1 / 37
    5 of 5 stars (1) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    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 beautiful and change day after day,... View all property information
    Location Information
    Pienza, Province of Siena
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    1 / 24
    6 Bedrooms, 6 Bathrooms, Sleeps 13 | Quick View
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    About this property
    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 in a fine country style, and... View all property information
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    Pienza, Province of Siena
    1 / 13
    4 of 5 stars (2) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
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    About this property
    This property has been restored with every confort,full equiped kitchen, large bedrooms each with bathrooms. This apartment however mantain the antique charme,because the original structure is still visible. The accomodation is suitable for couple wit baby or kid . Pets are welcome The village can... View all property information
    Location Information
    Pienza, Province of Siena
    3 of 5 stars Reviewed 4 September 2015
    We got off to a poor start as the friendly landlady had planned to put us in the next apartment (which was occupied!) and then showed us into a place which had been used but not...
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    1 / 21
    5 of 5 stars (1) Excellent
    2 Bedrooms, 6 Bathrooms, Sleeps 4 | Quick View
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    Pienza, Province of Siena
    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    Pienza, Province of Siena
    1 / 22
    5 of 5 stars (7) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Mountain Views
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    About this property
    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 park. It has an external wood... View all property information
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    Pienza, Province of Siena
    5 of 5 stars Reviewed 8 October 2014
    We stayed at Villa Maggio for a week and wanted to stay much longer. The villa is amazing and the setting is extraordinary. We were centrally located near all the wonderful...
    4 of 5 stars Reviewed 27 May 2014
    Our group of 8 stayed at this charming renovated farmhouse located between Pienza and Montepulciano. The location, villa and grounds were wonderful. The villa is decorated in an...
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    1 / 20
    4 of 5 stars (1) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
    Location Information
    Pienza, Province of Siena
    4 of 5 stars Reviewed 4 October 2015
    This apartment's location are what make it special. It's just steps out the door into charming and picturesque Pienza. Alice and Simone are very nice and helpful. The apartment...
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    1 / 5
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Shared Garden
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    Pienza, Province of Siena
    1 / 20
    6 Bedrooms, 6 Bathrooms, Sleeps 13 | Quick View
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    • Internet Access
    • Balcony
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    • Terrace
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    • Hot Tub
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    • Pet-friendly
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    • x
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    • x
    About this property
    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.<BR><BR>First floor: a double bedroom with Jacuzzi inside the room and en-suite bathroom with shower, a double bedroom with... View all property information
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    Pienza, Province of Siena
    1 / 6
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Mountain Views
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    • Pet-friendly
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    Location Information
    Pienza, Province of Siena
    1 / 43
    5 of 5 stars (17) Excellent
    Monticchiello
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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, best destinations in... View all property information
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    Monticchiello, Pienza
    5 of 5 stars Reviewed 2 weeks ago
    Previous reviews nearly all comment on the friendliness and hospitality of the hosts , without doubt the praise is fully justified . They are a lovely couple who do everything...
    5 of 5 stars Reviewed 3 August 2016
    Poli and Flora are a delightful couple who welcome you with open arms. Nothing is too much trouble and they will advise you on where to go and how to get there. The apartment is...
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    1 / 20
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
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    • Pet-friendly
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    • ?
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    • x
    About this property
    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 who own it and who have... View all property information
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    Pienza, Province of Siena
    1 / 16
    5 of 5 stars (1) Excellent
    7 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    • Outdoor Dining Area
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    • Central Heating
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    • Pet-friendly
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    • x
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    Pienza, Province of Siena
    1 / 20
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Private Outdoor...
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    • Pet-friendly
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    • x
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    • x
    About this property
    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 ideal residence for a high... View all property information
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    Pienza, Province of Siena
    1 / 11
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Wi-Fi
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    Pienza, Province of Siena
    1 / 9
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    Pienza, Province of Siena
    5 of 5 stars Reviewed 2 weeks ago
    We have spent a few holidays in the Val d'Orcia over the last 20+ years and Selvoli has proved the most perfect accommodation for us - an idyllic Tuscan farmhouse in an idyllic...
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    1 / 12
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    Pienza, Province of Siena
    1 / 24
    5 of 5 stars (1) Excellent
    Monticchiello
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • ?
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    About this property
    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.<BR><BR>The owners have carefully furnished the property with wrought iron lamps,... View all property information
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    Monticchiello, Pienza
    5 of 5 stars Reviewed 5 July 2016
    Probably like you, I searched plenty of spots online trying to find the ideal Tuscan rental at a reasonable weekly rate... Sure is nice when a place actually exceeds expectations...
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    1 / 20
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Air Conditioning
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    • x
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    About this property
    20% discount for the period of August 27, 2016 to September 17, 2016 (Minimum of one week rental required) Villa Rosina is an old, Tuscan country-style residence at the foot of Pienza that was recently restored into a beautiful six bedroom villa with ensuite bathrooms. The villa is arranged into... View all property information
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    Pienza, Province of Siena
    1 / 23
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Central Heating
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    About this property
    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) and San Quirico (a lovely... View all property information
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    Pienza, Province of Siena
    1 / 6
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Pienza, Province of Siena
    1 / 14
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Wi-Fi
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    Pienza, Province of Siena
    1 / 24
    4 Bedrooms, 4 Bathrooms, Sleeps 11 | Quick View
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    • Washer
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    • Children's Pool
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    • ?
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    Pienza, Province of Siena
    1 / 36
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • Patio
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    • ?
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    • x
    Location Information
    Pienza, Province of Siena
    1 / 20
    6 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    • Shared Garden
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    • Pet-friendly
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    • x
    • ?
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    • x
    About this property
    (Minimum of one week rental required) Minimum rental one week rental Saturday to Saturday except for urban apartments. Recently restored to the highest standard, this deluxe country house is in the beautiful Val D'Orcia in the South-Eastern part of the Siena province in Tuscany. This is a region of... View all property information
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    Pienza, Province of Siena
    1 / 20
    8 Bedrooms, 8 Bathrooms, Sleeps 14 | Quick View
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    • x
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    • x
    About this property
    (Minimum of one week rental required) Villa Chiara is a very exclusive villa in the Val D'orcia countryside, just three kilometers from Pienza. The villa sleeps up to 14 guests and is perfect for a large group or families traveling together. It boasts two living rooms (one elegant and the other... View all property information
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    Pienza, Province of Siena
    1 / 22
    Private Room, 3 Bathrooms, Sleeps 2 | Quick View
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    • Terrace
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    Pienza, Province of Siena
    1 / 18
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Grill
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    • Pet-friendly
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    • Smoking allowed
    • x
    About this property
    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 bathrooms, equipped with... View all property information
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    Pienza, Province of Siena
    1 / 24
    8 Bedrooms, 10 Bathrooms, Sleeps 15 | Quick View
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    • Air Conditioning
    • Patio
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    • Hot Tub
    • DVD Player
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    • Private Indoor Pool
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    • Pet-friendly
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    • Smoking allowed
    About this property
    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 rooms, 2 fully equipped... View all property information
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    Pienza, Province of Siena
    1 / 15
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Private Garden
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    • Pet-friendly
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    • x
    • Smoking allowed
    • x
    About this property
    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. <BR><BR>First floor: large lounge with imposing... View all property information
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    Pienza, Province of Siena
    1 / 36
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    Having a holiday in this countryhouse is like having a holiday in a postcard. Photographed from all angles, it represents Tuscany, used by a large number of advertising agencies who want to render the image of the Tuscan countryside. It is very close to Pienza, the city built by will of Pope Pius... View all property information
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    Pienza, Province of Siena
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    • Satellite TV
    • Grill
    • Air Conditioning
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • ?
    About this property
    Highlights This large farmhouse was famous as far back as the 10th century as a post-house for changing coaches and horses along the Via Francigena and the architecture of the house shows this origin. A beautiful garden surrounds the elegant farmhouse and a lovely swimming pool looks over the Val... View all property information
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    Pienza, Province of Siena
    1 / 21
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Secure Parking
    • Grill
    • Wi-Fi
    • Terrace
    • Washer
    • Outdoor Dining Area
    • Balcony
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    About this property
    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 17th century farmhouse, now... View all property information
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    Pienza, Province of Siena
    1 / 16
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Parking
    • Satellite TV
    • Grill
    • Central Heating
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    'Podere Osteria” is a country house which was originally one of the first examples of European hospitals. The building, completely refurbished in 2012, is in the heart of the Val d’Orcia valley, an area marked by enchanting landscapes and the most varied Medieval towns. From its central location,... View all property information
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    Pienza, Province of Siena
    1 / 4
    Private Room, 2 Bathrooms, Sleeps 2 | Quick View
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    • Wi-Fi
    • Private Garden
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    Location Information
    Pienza, Province of Siena
    1 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
    • Private Garden
    • Balcony
    • Grill
    • Satellite TV
    • Parking
    • Central Heating
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Our Agriturismo is situated on top of Souhern-Tuscany's hills, in the sunny Val d'Orcia and within a short distance from Pienza. <BR><BR>Our farmhouse is made up of two independent apartments with private garden. They can be rented by either families or small groups of friends. <BR><BR>The... View all property information
    Location Information
    Pienza, Province of Siena
    1 / 24
    6 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    • Private Outdoor...
    • Private Garden
    • Washer
    • Parking
    • Terrace
    • Balcony
    • Central Heating
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    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 comfortable apartments (2 on... View all property information
    Location Information
    Pienza, Province of Siena
    1 / 23
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Balcony
    • Central Heating
    • Wi-Fi
    • Washer
    • Private Outdoor...
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    About this property
    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. Villa Andrea is located only... View all property information
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    Pienza, Province of Siena
    1 / 24
    5 of 5 stars (2) Excellent
    Monticchiello
    Private Room, 10 Bathrooms, Sleeps 7 | Quick View
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    • Hot Tub
    • Wi-Fi
    • Parking
    • Washer
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    Location Information
    Monticchiello, Pienza
    5 of 5 stars Reviewed 12 January 2015
    This place was wonderful, Francesco couldn't do enough for you. Its located in a gorgeous little town in Val d'Orcia area. There are three restaurants in the town and a...
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    1 / 23
    4 of 5 stars (1) Very good
    Private Room, 9 Bathrooms, Sleeps 20 | Quick View
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    • Satellite TV
    • Washer
    • Grill
    • Shared Garden
    • Air Conditioning
    • Shared Outdoor Pool...
    • Parking
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    Location Information
    Pienza, Province of Siena
    1 / 6
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Parking
    • Mountain Views
    • Shared Garden
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    Location Information
    Pienza, Province of Siena