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Pienza Holiday Homes

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    Travellers to Pienza are booking July dates now. Secure your holiday rental today, and have the perfect trip.
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    7 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    Agriturismo Chiancianello IL FORNO1 / 21
    (1)Excellent
    2 Bedrooms, 6 Bathrooms, Sleeps 4 Quick View
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    Studio, 6 Bathrooms, Sleeps 14 Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    Villa Fiordaliso is perfect for those looking to spend their holiday in a home away from home with stunning views of the Tuscan landscape. Perfect for families and large groups of friends. Villa Fiordaliso is perfect for those looking to spend their holiday in a home away from home with stunning...
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    53020, Pienza, Province of Siena
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Air Conditioning
    • Housekeeping Included
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    • Balcony
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    Pet friendly
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    53026, Pienza, Province of Siena
    Private Room - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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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    • Private Garden
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    Pet friendly
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    53026, Monticchiello, Pienza
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Central Heating
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    About this property
    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. <BR>The structure, in proximity of the principal access to the village, has been completely restructured from the owner with taste...
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    53026, Monticchiello, Pienza
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Shared Garden
    • Mountain Views
    • Grill
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    Pet friendly
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    53026, Pienza, Province of Siena
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • Washer
    • Private Garden
    • Grill
    • Satellite TV
    • Air Conditioning
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    6 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    This exclusive villa works as the perfect starting point to explore the countryside and all the art cities in Tuscany and their surroundings. It is spacious, airy, welcoming and fully equipped and accommodates up to 16 people. This exclusive villa works as the perfect starting point to explore the...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 14
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    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
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    53026, Pienza, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    9 Bedrooms, 8 Bathrooms, Sleeps 17 Quick View
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    • Washer
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    53026, Pienza, Province of Siena
    Holiday Rental House - 9 Bedrooms, 8 Bathrooms, Sleeps 17
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    Studio, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On a large estate surrounded by olive groves and flower fields, this Italian villa is just the place if you and your family are looking for beauty and tranquility. Whether its sunrises in the morning, sunsets in the evening, or midday gazing, you’ll have views that will take your breath away while...
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    53026, Monticchiello, Pienza
    Condo/Apartment - 2 Bathrooms, Sleeps 6
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    Studio, 5 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On a large estate surrounded by olive groves and flower fields, this Italian villa is just the place if you and your group are looking for beauty and tranquility. Whether its sunrises in the morning, sunsets in the evening, or midday gazing, you’ll have views that will take your breath away while...
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    53026, Monticchiello, Pienza
    Holiday Rental House - 5 Bathrooms, Sleeps 14
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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
    • Patio
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    • Skiing: Property Is In A Ski Resort
    • Mountain Views
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    Pet friendly
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    Smoking allowed
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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 4 Quick View
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    • Shared Garden
    • Private Garden
    • Grill
    • Washer
    • Parking
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
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    53026, Pienza, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Washer
    • Satellite TV
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa la Fonte is situated in the marvellous Val d'Orcia, the valley of the Sienese Crete.<BR>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 be tasted and purchased...
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    53027, Pienza, Province of Siena
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    Studio, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On a large estate surrounded by olive groves and flower fields, this Italian villa is just the place if you and your family are looking for beauty and tranquility. Whether its sunrises in the morning, sunsets in the evening, or midday gazing, you’ll have views that will take your breath away while...
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    53026, Monticchiello, Pienza
    Condo/Apartment - 2 Bathrooms, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Central Heating
    • Private Garden
    • Grill
    • Parking
    • Washer
    • Outdoor Dining Area
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    Pet friendly
    Kid friendly
    Smoking allowed
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    53026, Monticchiello, Pienza
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    7 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
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    Pet friendly
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    About this property
    As a luxury villa, Villa Bandida really works best as a place where friends and family come to relax, share meals, explore the countryside and drink wine late into the night. If your looking for the perfect location for a group get together, relaxing break, birthday celebration or wedding - Villa...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 14
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    6 Bedrooms, 6 Bathrooms, Sleeps 13 Quick View
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    • Internet Access
    • Balcony
    • DVD Player
    • Washer
    • 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.<BR><BR>First floor: a double bedroom with Jacuzzi inside the room and en-suite bathroom with shower, a double bedroom with...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 13
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Central Heating
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    • Private Garden
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    Pet friendly
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    Smoking allowed
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    53026, Pienza, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Villa in Southern Tuscany with Privacy and Views - Villa Altare1 / 47
    (1)Very good
    Studio, 7 Bathrooms, Sleeps 14 Quick View
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    • Washer
    • Central Heating
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Isn't it about time you organize that family reunion you've all been meaning to do, but can't seem to figure out where to go or where to stay? This farmhouse for rent in Tuscany is a perfect destination for families coming together once again! Large, spacious, and well equipped with enough room and...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 7 Bathrooms, Sleeps 14
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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
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Washer
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    Pet friendly
    Kid friendly
    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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    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Washer
    • Central Heating
    • Children's Pool
    • Grill
    • DVD Player
    • Wi-Fi
    • Parking
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
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    53026, Pienza, Province of Siena
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 11
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Grill
    • Private Garden
    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    the villa is dated back XI century is semidetached 3 levels tipical medioeval house.<BR>Compleltly restored maintened all storical signs: stone walls.stairs as a castle,tipicalTuscany beems in wood .<BR>You will be in Unesco's heritage and you will enjoy the quiet , the art the special atmosphere...
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    53020, Monticchiello, Pienza
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Central Heating
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    Pet friendly
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    Smoking allowed
    About this property
    Sophisticated one-bedroom, 66 m2 apartment located on the second 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. The Isabella apartment is located on the second floor of the historic building which also...
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    53026, Pienza, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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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
    • Wi-Fi
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    • Private Garden
    • Central Heating
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    Pet friendly
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    Smoking allowed
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    53026, Pienza, Province of Siena
    Holiday Rental House - 7 Bedrooms, 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
    • Patio
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    Pet friendly
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    53026, Monticchiello, Pienza
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • Satellite TV
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
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    53026, Pienza, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • Central Heating
    • Shared Garden
    • Terrace
    • Internet Access
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    La Quercia is the largest apartment of our recently-renovated farmhouse. Ideal for 6 people, this apartment can also be rented on request to a lower number of people or even to couples. The kitchen and bedrooms are decorated with the farmhouse's original furnishings. Also the large fireplace, the...
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    53026, Pienza, Province of Siena
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    AGRITURISMO PIANOIA1 / 20
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Private Garden
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    53026, Monticchiello, Pienza
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    8 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Grill
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Pienza from Renate Villas is a large and elegant villa composed of a main house, small annex and large garden with private pool and lots of outdoor living spaces. The main house has three floors with the living spaces all on the main floor. Here there is a large kitchen with all the...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 14
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Garden
    • Washer
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Grill
    • Parking
    • Air Conditioning
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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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    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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    53026, Monticchiello, Pienza
    Holiday Rental House - 8 Bedrooms, 11 Bathrooms, Sleeps 16
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Grill
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    • Shared Garden
    • Skiing: Property Is In A Ski Resort
    • Central Heating
    • Parking
    • Porch
    Suitability
    Pet friendly
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    Smoking allowed
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    53026, Pienza, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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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
    About this property
    Four Bedroom Semi-Detached Villa Val d'Orcia<br /><br />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...
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    Pienza, Province of Siena
    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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    Questo mini-appartamento offre un'unica ed incredibile vista della valle che circonda Pienza sia dalla finestra di camera che dal soggiorno. E' possibile ammirare per chilometri, fin dove arriva lo sguardo, uno dei più bei panorami della campagna toscana.<BR><BR>L'appartamento si compone di una...
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    53026, Monticchiello, Pienza
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
    • Air Conditioning
    • Sauna
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    • Satellite TV
    • Hot Tub
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ABOUT - Within the UNESCO World Heritage Natural Park of Valdorcia, an entire organically conducted Tuscan hill to yourself. At its very top, a genuine farmhouse with high-grade specs and 360-degree views of medieval towers, vineyards and olive groves. A unique opportunity to observe wild life...
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    53026, Pienza, Province of Siena
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 8
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    Studio, 5 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Central Heating
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • Washer
    • Grill
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
    • Washer
    • Grill
    • Wi-Fi
    • Patio
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just South of Siena, The Val d’Orcia is UNESCO World Heritage. Its enchanting towns and villages like Montalcino and Pienza are surrounded by a sea of vines and olives whose slopes intermittently give way to deep forest of pines, chestnuts and oaks, cool and refreshing. And amongst these strikingly...
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    Location Information
    53026, Monticchiello, Pienza
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Balcony
    • Grill
    • Private Outdoor Pool (Unheated)
    • Terrace
    • Parking
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a fantastic 5 bedroom villa near the wonderful town of Montepulciano in Tuscany. Completely surrounded by olive grove and vineyards, it occupies an idyllic setting for guests to enjoy a peaceful and relaxing holiday. Recently restored, it offers a perfect mix of traditional Tuscan...
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    Location Information
    Pienza, Province of Siena
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    53026, Pienza, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The property is located in a beatifull medioeval village between Pienza and Montepulciano in UNESCO'S Heritage The house is dates back XI century , you will feel the history in the meantime you will have every confort. The building is on 3 levels like a little tower as the medioeval architecture...
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    Location Information
    53026, Monticchiello, Pienza
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    4 Bedrooms, 8 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sul Corso Rossellino, proprio nel centro di Pienza, a meno di cento metri da Piazza Pio II con la sua magnifica cattedrale e lo splendido Palazzo Piccolomini, l'Antica Locanda offre ad ospiti esigenti una piacevole ed esclusiva sistemazione.<BR><BR><BR>L'Antica Locanda è ubicata in un palazzo del...
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    Location Information
    53026, Monticchiello, Pienza
    Private Room - 4 Bedrooms, 8 Bathrooms, Sleeps 12
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Shared Garden
    • Patio
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    53026, Monticchiello, Pienza
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this 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 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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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Wi-Fi
    • Satellite TV
    • Parking
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    53026, Pienza, Province of Siena
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    53026, Pienza, Province of Siena
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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