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    Travellers to Pienza are booking January dates now. Secure your vacation rental today, and have the perfect trip.
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    3 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    CAMPO ALLA PIANA agriturismo in Val D'Orcia1 / 24
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Valdorcia1 / 15
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
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    About this property
    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 will enjoy a perfect...
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    53026, Monticchiello, Pienza
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    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...
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    53049, Pienza, Province of Siena
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Studio, 6 Bathrooms, Sleeps 14 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
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    • Central Heating
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    Pet friendly
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    About this property
    This large home in the heart of the Orcia Valley region is perfect for those looking for incredible views as well as privacy. Set amidst a large estate, this vacation rental in Tuscany is comprised of three independent units making it perfect for three families. It also features a private swimming...
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    Pienza, Province of Siena
    Holiday Rental House - 6 Bathrooms, Sleeps 14
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    Podere Rigopesci relax in Val d'Orcia.1 / 12
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Shared Garden
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    53026, Monticchiello, Pienza
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Garden
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    53026, Pienza, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Secure Parking
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    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...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Affittacamere Maria Gabriella (B&B)1 / 24
    (1)Very good
    4 Bedrooms, 10 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Housekeeping Included
    • Porch
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    • Mountain Views
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    Pet friendly
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    53026, Monticchiello, Pienza
    Private Room - 4 Bedrooms, 10 Bathrooms, Sleeps 8
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    Podere Rigopesci nel cuore della Val d'Orcia.1 / 12
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    53026, Monticchiello, Pienza
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Central Heating
    • Private Outdoor Pool (Unheated)
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    • Hot Tub
    • Cable/satellite TV
    • Mountain Views
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    Pet friendly
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    Smoking allowed
    About this property
    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 internationally renowned film...
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    53026, Monticchiello, Pienza
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    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,...
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    53026, Pienza, Province of Siena
    Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Central Heating
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    Pet friendly
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    About this property
    Luxurious and scenic two-bedroom, two-bathroom apartment full of rich details, in the beautiful town of Pienza, in the heart of Val d'Orcia. This 111sqm apartment stretches over two floors and is comfortably furnished with antique, valuable furniture. It is located on a quiet street in the historic...
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    53026, Pienza, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Private Garden
    • Balcony
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    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. Our farmhouse is made up of two independent apartments with private garden. They can be rented by either families or small groups of friends. The Agriturismo is...
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    53020, Pienza, Province of Siena
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
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    Pet friendly
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    About this property
    (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 three independent apartments. Great care was taken by the owners and...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Washer
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    • Housekeeping Included
    • Central Heating
    • Cable/satellite TV
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
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    53026, Monticchiello, Pienza
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    7 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 Monticchiello 2 km, Montepulciano...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 15
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    Villa Four Seasons1 / 15
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
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    Four Bedroom Semi-Detached Villa Val d'Orcia Villa Four Seasons is situated in a beautiful position in the heart of Tuscany with stunning views of the surrounding hills. It is one half of a Tuscan Stone built Farmhouse and was recently renovated in traditional Tuscan style. It boasts a private...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 Bedrooms, 6 Bathrooms, Sleeps 13 Quick View
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    • Internet Access
    • Balcony
    • DVD Player
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    • Air Conditioning
    • Terrace
    • Private Outdoor Pool (Unheated)
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    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. First floor: a double bedroom with Jacuzzi inside the room and en-suite bathroom with shower, a double bedroom with en-suite...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 13
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    Tuscany Villa with Pool within Walking Distance of Town - Villa Monticchiello1 / 22
    (1)Excellent
    Studio, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    Situated in a prominent position overlooking the Val d’Orcia, this villa for rent in Tuscany offers incredible views and is in a peaceful and natural setting. It’s within walking distance of Monticchiello, which is home to many shops and restaurants as well as a castle. You’ll be able to enjoy the...
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    53020, Monticchiello, Pienza
    Holiday Rental House - 3 Bathrooms, Sleeps 8
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    53026, Monticchiello, Pienza
    Private Room - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Central Heating
    • Private Garden
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    Pet friendly
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    53026, Monticchiello, Pienza
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Podere Ada1 / 12
    (1)Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 4 Quick View
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    • Central Heating
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    53026, Monticchiello, Pienza
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 4
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    Agriturismo Chiancianello IL FORNO1 / 21
    (1)Excellent
    2 Bedrooms, 6 Bathrooms, Sleeps 4 Quick View
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    • Porch
    • Outdoor Dining Area
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    • Skiing: Property Is In A Ski Resort
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    53026, Pienza, Province of Siena
    Condo/Apartment - 2 Bedrooms, 6 Bathrooms, Sleeps 4
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    6 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    About this property
    The Val d'Orcia stretches to the south of Siena in a landscape at once harmonious and poetic that strikes the imagination: this is a landscape full of light, characterised by gentle hills rolling as far as the eye can reach and crisp clear colours, distinctly different and enthralling in every...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 10
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    2 Bedrooms, 6 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    • Mountain Views
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    Pet friendly
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    53026, Monticchiello, Pienza
    Holiday Rental House - 2 Bedrooms, 6 Bathrooms, Sleeps 4
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    1 Bedroom, 2 Bathrooms, Sleeps 3 Quick View
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    • Wi-Fi
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    53026, Pienza, Province of Siena
    Private Room - 1 Bedroom, 2 Bathrooms, Sleeps 3
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    Agriturismo Chiancianello App. Il Lago1 / 11
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Wi-Fi
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    • Skiing: Property Is In A Ski Resort
    • Mountain Views
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    53026, Pienza, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Studio, 5 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Central Heating
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
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    About this property
    Tuscany’s beautiful Val d’Orcia is the setting for this family-friendly farmhouse and annex, which feature local artisanal furnishings. Admire panoramic views from the property’s lovely garden, enjoy alfresco meals, go for a swim, or explore nearby Monticchiello and Pienza. The property is also...
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    53026, Monticchiello, Pienza
    Holiday Rental House - 5 Bathrooms, Sleeps 12
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    53026, Pienza, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 2 Bathrooms, Sleeps 2 Quick View
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    • Shared Garden
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    53026, Monticchiello, Pienza
    Private Room - 2 Bedrooms, 2 Bathrooms, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Shared Garden
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    53026, Monticchiello, Pienza
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Washer
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    53026, Pienza, Province of Siena
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    IL GIARDINO SEGRETO1 / 16
    (2)Very good
    7 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Outdoor Dining Area
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    53026, Pienza, Province of Siena
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 14
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    Poggio ai Gelsi, Lodge Ulivo1 / 27
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
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    Pet friendly
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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,...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Terrace
    • Private Outdoor Pool (Unheated)
    • Balcony
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    • Private Garden
    • Central Heating
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    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. First floor: large lounge with imposing fireplace,...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Patio
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    • Washer
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa is in the heart of the Val D'Orcia countryside offering luxurious accomodation with a fabulous HEATED swimming pool. The entire country chic house has 6 bedrooms, 6 bathrooms, living rooms with 3 kitchens, dining room, big patio with a stunning view and a special vegetable garden. Spoil...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Garden
    • Washer
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
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    53026, Monticchiello, Pienza
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    7 Bedrooms, 8 Bathrooms, Sleeps 13 Quick View
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    • Private Garden
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    About this property
    This 800 sq.mts.Villa has been recently restored combining traditional materials as old cotto for the floors and oak beams for the ceilings with vintage furniture and contemporary art works. The insulated large walls and the ventilated roof keep the house naturally cool during hot summer months....
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    Location Information
    53045, Monticchiello, Pienza
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 13
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One-bedroom, 58 m2 apartment located on the first floor of a historic building dating back to the Renaissance, in the scenic historic center of Pienza, a beautiful town in the province of Siena. After climbing an imposing staircase to access apartment Lucrezia, a historic one-bedroom property...
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    Location Information
    53026, Pienza, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
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    The building includes four brand new completely independent flats, structured on two floors; they are very new and furnished in a modern manner, equipped with all comforts like a kitchen supplied with all of the tools and household appliances, colour TV-Set, autonomous heating, bed linen and...
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    Location Information
    53026, Pienza, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 5
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    8 Bedrooms, 11 Bathrooms, Sleeps 16 Quick View
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    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Parking
    • Balcony
    • Washer
    • Terrace
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casanova Relais is a wonderful podere dating back to the 1600s, that has painstakingly been restored with a perfect taste. The owners have tastefully created an extremely elegant and comfortable home for modern living with spacious bedrooms, a well equipped kitchen and a beautiful swimming pool....
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    Location Information
    53026, Monticchiello, Pienza
    Holiday Rental House - 8 Bedrooms, 11 Bathrooms, Sleeps 16
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Wi-Fi
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Casale Tranquillo in Siena-Val d'Orcia, Tuscany is an authentic farmhouse dating back to the 19th century that has been transformed into a delightful six-bedroom villa with modern conveniences. From the moment you see the traditional stone structure tucked away in the Tuscan hills, you will...
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    Location Information
    53026, Pienza, Province of Siena
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Grill
    • Private Garden
    • Secure Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    the villa is dated back XI century is semidetached 3 levels tipical medioeval house. Compleltly restored maintened all storical signs: stone walls.stairs as a castle,tipicalTuscany beems in wood . You will be in Unesco's heritage and you will enjoy the quiet , the art the special atmosphere and...
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    Location Information
    53020, Monticchiello, Pienza
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Agriturismo Chiancianello App. Il Forno1 / 6
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Mountain Views
    • Parking
    • Air Conditioning
    • Grill
    • Shared Garden
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    53026, Pienza, Province of Siena
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    53026, Monticchiello, Pienza
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Central Heating
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    53026, Pienza, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Patio
    • Private Garden
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    53026, Monticchiello, Pienza
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    After climbing an imposing staircase to access the apartment, guests are welcomed to the large living room, furnished with comfortable furniture and TV stand, as well as extendable table with 4 chairs and cozy Queen-size sleeper sofa. The kitchen adjoins the living room and features an additional...
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    Location Information
    53026, Pienza, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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