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Pienza Smoking Friendly Vacation Rentals

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    Travelers to Pienza are booking August dates now. Secure your vacation rental today, and have the perfect trip.
    36 Matching Rentals in PienzaView all 157 rentals
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    Valdorcia1 / 15
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 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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    7 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    • Wi-Fi
    • Parking
    • Grill
    • Outdoor Dining Area
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Central Heating
    • Washer
    Suitability
    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
    Rental Home - 7 Bedrooms, 5 Bathrooms, Sleeps 15
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    Secret Tuscany property1 / 8
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Pet friendly
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    Reviewed September 17, 2015
    I booked this apartment for my parents and sister prior to my wedding at Terre di Nano. By all accounts they were very happy with the property, the host was very welcoming and...
    Reviewed January 2, 2015
    Many times we have stayed in Barbara's lovely Maribelle apartments - the smaller, Maribelle 2 is our favourite, fine for a couple and with doors from the bedroom opening onto a...
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    About this property
    Located in UNESCO's heritage out of normal touristics tour Monticchiello is a special place where the the time is stop on Reinassance.The apartment is completly restored, and has every falicilities to enjoy the pleasure to have storical Tuscany house dated back XVII century joint to good food ,...
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    53026, Monticchiello, Pienza
    Condo/Apartment - 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 Yard
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    53026, Pienza, Province of Siena
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Mountain Views
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
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    53026, Monticchiello, Pienza
    Condo/Apartment - 3 Bedrooms, 6 Bathrooms, Sleeps 12
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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
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 11
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    Apartment in B&B close to Pienza1 / 15
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Yard
    • Wi-Fi
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This agritourism is settled at about 15 km from Pienza, in Val d’Orcia Valley. There are about 100 ha cultivated fields. The owners also breeds the famous Chianina cows and produces wine. Clients will be welcome to taste both of them!. Sabrina, the owner, will be glad under request to prepare for...
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    53026, Pienza, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedroom Vacation Apartment with Antique Charm1 / 13
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Outdoor Dining Area
    • Cable/satellite TV
    • Shared Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 4, 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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    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...
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    Location Information
    53026, Pienza, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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
    • Shared Yard
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    • Skiing: Property Is In A Ski Resort
    • Mountain Views
    • Parking
    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 3
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Shared Yard
    • Mountain Views
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    Pet friendly
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    Smoking allowed
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    Location Information
    53026, Pienza, Province of Siena
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Shared Yard
    • Skiing: Property Is In A Ski Resort
    • Central Heating
    • Parking
    • Porch
    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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    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
    • Washer
    • Wi-Fi
    • Parking
    • Patio
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 1, 2016
    Very spacious home with a one bed separate villa. Nice country decor. Walking distance to the local village of Montichiello. However, a bit far from Florence and sienna. So you...
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    Location Information
    53026, Monticchiello, Pienza
    Private Room - 4 Bedrooms, 10 Bathrooms, Sleeps 8
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    8 Bedrooms, 10 Bathrooms, Sleeps 15 Quick View
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    • Air Conditioning
    • Patio
    • Washer
    • Hot Tub
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Private Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    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...
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    53026, Pienza, Province of Siena
    Condo/Apartment - 8 Bedrooms, 10 Bathrooms, Sleeps 15
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    Casa Oriolo1 / 24
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Secure Parking
    • Cable/satellite TV
    • DVD Player
    • Central Heating
    • Balcony
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 18, 2016
    Absolutely stunning views in the middle of Tuscany, completely tranquil in the middle of a nature reserve with lots of wildlife. Lovely house with lots of space and all the...
    Reviewed July 5, 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...
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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. The owners have carefully furnished the property with wrought iron lamps, linen...
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    53026, Monticchiello, Pienza
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    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
    Kid friendly
    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...
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    53026, Pienza, Province of Siena
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Yard
    • 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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    53026, Monticchiello, Pienza
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Air Conditioning
    • Housekeeping Included
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    53026, Pienza, Province of Siena
    Private Room - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Central Heating
    • Private Outdoor Pool (Unheated)
    • Washer
    • Hot Tub
    • Cable/satellite TV
    • Mountain Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    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
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
    • Central Heating
    • Private Yard
    • DVD Player
    • Grill
    • Balcony
    • Terrace
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 residence therefore everything is...
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    53020, Pienza, Province of Siena
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    8 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Casale Campagna in Siena-Val d\'Orcia, Tuscany is a classic country retreat in the heart of the Tuscan hills. This little gem of a home retains its traditional charm with all the modern conveniences, making it the perfect choice for those seeking an authentic Italian experience. Enter a...
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    Location Information
    Pienza, Province of Siena
    Rental Home - 8 Bedrooms, 8 Bathrooms, Sleeps 14
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Wi-Fi
    • DVD Player
    • Hot Tub
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    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...
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    53026, Pienza, Province of Siena
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Central Heating
    • Shared Yard
    • Terrace
    • Internet Access
    • Balcony
    Suitability
    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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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Housekeeping Included
    • Central Heating
    • 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 - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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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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    53026, Pienza, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Cable/satellite TV
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    53026, Monticchiello, Pienza
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    3 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Parking
    • Grill
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    • Housekeeping Included
    • Central Heating
    • Cable/satellite TV
    • Washer
    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
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    53026, Monticchiello, Pienza
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 9
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Yard
    • Washer
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
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    • 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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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Patio
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    Pet friendly
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    Smoking allowed
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    53026, Monticchiello, Pienza
    Rental Home - 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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    53026, Pienza, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    9 Bedrooms, 9 Bathrooms, Sleeps 23 Quick View
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    • Grill
    • Private Yard
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    • Housekeeping Included
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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
    Rental Home - 9 Bedrooms, 9 Bathrooms, Sleeps 23
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    9 Bedrooms, 8 Bathrooms, Sleeps 17 Quick View
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    53026, Pienza, Province of Siena
    Rental Home - 9 Bedrooms, 8 Bathrooms, Sleeps 17
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    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Washer
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Location Information
    53026, Monticchiello, Pienza
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    casa vacanze pienza1 / 10
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    53026, Pienza, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Porch
    • Grill
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    • Central Heating
    • Private Yard
    • Outdoor Dining Area
    • Housekeeping Included
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    Pet friendly
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    Smoking allowed
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    Location Information
    53026, Pienza, Province of Siena
    Private Room - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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