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Vacation Rentals in Pienza, Italy

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    Travelers to Pienza are booking August dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 43
    5 of 5 stars (15) Excellent
    Monticchiello
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 57
    5 of 5 stars (7) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    1 / 55
    5 of 5 stars (2) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Monticchiello
    Private Room, 10 Bathrooms, Sleeps 8 | Quick View
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    53026, Monticchiello, Pienza
    8 Bedrooms, 10 Bathrooms, Sleeps 15 | Quick View
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    • Private Indoor Pool
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    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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    53026, 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
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    Location Information
    53026, Monticchiello, Pienza
    5 of 5 stars Reviewed January 12, 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
    5 of 5 stars (4) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    New lower price - one of the nicest flat in Tuscany 5 star standard !!<BR><BR>The apartment has its own entrance and occupies the whole 1st and top floors of this classical building next to the ancient city wall. <BR><BR>Private parking, large roof terrace (55m2) with great views over the valley... View all property information
    Location Information
    53027, Pienza, Province of Siena
    5 of 5 stars Reviewed April 13, 2015
    Casa Travertino is a wonderful restoration project. It strikes the perfect balance of having a classic style on the outside, and containing all mod-cons on the inside. The flat...
    5 of 5 stars Reviewed October 21, 2013
    Excellent location in delightful hillside village. Comfortable, well-equipped apartment with lovely rooftop terrace - great for drinking prosecco in the afternoon. Brilliant...
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    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
    53026, Pienza, Province of Siena
    4 Bedrooms, 4 Bathrooms, Sleeps 11 | Quick View
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    • Washer
    • Central Heating
    • Children's Pool
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    • Balcony
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    • ?
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    Location Information
    53026, Pienza, Province of Siena
    1 / 8
    5 of 5 stars (2) Excellent
    Monticchiello
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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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 ,... View all property information
    Location Information
    53026, Monticchiello, Pienza
    5 of 5 stars 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...
    5 of 5 stars 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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    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
    Location Information
    53026, Pienza, Province of Siena
    7 Bedrooms, 5 Bathrooms, Sleeps 13 | Quick View
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    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... View all property information
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    53026, Pienza, Province of Siena
    1 / 35
    Monticchiello
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Parking
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    Location Information
    53026, Monticchiello, Pienza
    Monticchiello
    2 Bedrooms, 4 Bathrooms, Sleeps 4 | Quick View
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    • Patio
    • Central Heating
    • Private Outdoor...
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    • Mountain Views
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    • x
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    Location Information
    53026, Monticchiello, Pienza
    1 / 10
    5 of 5 stars (6) Excellent
    Monticchiello
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Wi-Fi
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    53026, Monticchiello, Pienza
    5 of 5 stars Reviewed July 16, 2014
    By the time we arrived to the house and found Barbara waiting for us as we had planned,we where already fascinated by the surrounding landscape.Monticchiello is a little charming...
    4 of 5 stars Reviewed October 22, 2013
    Just returned from a week in Mirabelle 2. A lovely relaxing apartment in a very beautiful town called Monticchiello. Peace and solitude dominate. The views of the scenery are...
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    1 / 37
    Monticchiello
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    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... View all property information
    Location Information
    53026, Monticchiello, Pienza
    Monticchiello
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Grill
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    • Secure Parking
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    • x
    • x
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    • x
    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... View all property information
    Location Information
    53020, Monticchiello, Pienza
    Monticchiello
    2 Bedrooms, 4 Bathrooms, Sleeps 4 | Quick View
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    • Central Heating
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    • Private Yard
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    • Pet-friendly
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    53026, Monticchiello, Pienza
    1 / 24
    4 of 5 stars (1) Very good
    Monticchiello
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Central Heating
    • Private Yard
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    • Shared Yard
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    • x
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    • x
    Location Information
    53026, Monticchiello, Pienza
    1 / 22
    5 of 5 stars (1) Excellent
    Monticchiello
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
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    • Pet-friendly
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    • ?
    • ?
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    • ?
    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... View all property information
    Location Information
    53020, Monticchiello, Pienza
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    1 / 21
    5 of 5 stars (2) Excellent
    Monticchiello
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Satellite TV
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    • x
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    • x
    Location Information
    53026, Monticchiello, Pienza
    1 / 13
    4 of 5 stars (2) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
    • Outdoor Dining Area
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    • Pet-friendly
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    • Smoking allowed
    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
    53026, Pienza, Province of Siena
    3 of 5 stars 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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    1 / 24
    5 of 5 stars (1) Excellent
    Monticchiello
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    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
    Location Information
    53026, Monticchiello, Pienza
    5 of 5 stars Reviewed 2 weeks ago
    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 / 23
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Central Heating
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    • x
    • x
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    • x
    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
    Location Information
    Pienza, Province of Siena
    1 / 54
    Monticchiello
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
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    • x
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    About this property
    Highlights This very well furnished farm is situated in one hundred and fifty hectares of farm land producing excellent extra virgin olive oil, the farmhouse is set on a natural terrace overlooking the beautiful valley below. The house was built in the first half of the 18th century and has been... View all property information
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    Monticchiello, Pienza
    1 / 20
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
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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
    Location Information
    53026, Pienza, Province of Siena
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
    • x
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    • x
    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
    53026, Pienza, Province of Siena
    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Washer
    • Central Heating
    • Private Yard
    • DVD Player
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    • Balcony
    • Terrace
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    • Pet-friendly
    • Child-friendly
    • x
    • 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... View all property information
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    53020, Pienza, Province of Siena
    1 / 21
    Monticchiello
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Private Yard
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    53026, Monticchiello, Pienza
    1 / 25
    Monticchiello
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Private Outdoor...
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    • Waterfront
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    • Pet-friendly
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    • ?
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    • ?
    About this property
    Monticchiello is a magical place. A village enclosed by medieval walls but connected to the world through the vibrant culture that has characterized it for years, this villa is very near Monticchello and overlooks the most beautiful section of Val D'Orcia.L'Apparita is situated under a kilometer... View all property information
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    Monticchiello, Pienza
    1 / 47
    4 of 5 stars (1) Very good
    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    • Washer
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    • Hot Tub
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    • Pet-friendly
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    • ?
    • ?
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    • ?
    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... View all property information
    Location Information
    53026, Pienza, Province of Siena
    1 / 14
    5 of 5 stars (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • 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... View all property information
    Location Information
    Pienza, Province of Siena
    1 / 42
    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    • Satellite TV
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    • Pet-friendly
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    • x
    • x
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    • ?
    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 / 20
    6 Bedrooms, 6 Bathrooms, Sleeps 13 | Quick View
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    • Internet Access
    • Balcony
    • DVD Player
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    • Terrace
    • Private Outdoor...
    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    53026, Pienza, Province of Siena
    6 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    • Private Outdoor...
    • Private Yard
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    • Pet-friendly
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    • 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
    53026, Pienza, Province of Siena
    1 / 30
    8 Bedrooms, 8 Bathrooms, Sleeps 14 | Quick View
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    • Shared Outdoor Pool...
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    • ?
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    • ?
    About this property
    Imposing farmhouse dating back to the 18th century comprising 2 independent units (rentable only together as a private property). This beautiful 5–hectare estate is situated in quiet and panoramic location, in the heart of the Val d’Orcia region, a short distance away from the charming medieval... View all property information
    Location Information
    53026, Pienza, Province of Siena
    1 / 19
    8 Bedrooms, 8 Bathrooms, Sleeps 14 | Quick View
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Imposing farmhouse dating back to the 18th century comprising 2 independent units (rentable only together as a private property). This beautiful 5hectare estate is situated in quiet and panoramic location, in the heart of the Val d’Orcia region, a short distance away from the charming medieval town... View all property information
    Location Information
    53026, Pienza, Province of Siena
    1 / 30
    Monticchiello
    8 Bedrooms, 7 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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    • ?
    About this property
    Description: Notes for this villa All prices are per week for the villa only. Villas are booked from 2:30pm on your arrival day (Saturday) to 10:00am on your departure day (the following Saturday). Please note that availability shown is subject to confirmation - please call our reservations team.... View all property information
    Location Information
    53026, Monticchiello, Pienza
    1 / 30
    6 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    • Shared Outdoor Pool...
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    • ?
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    • ?
    About this property
    Beautiful stone farmhouse situated in peaceful and panoramic location near the charming medieval town of Pienza, in the heart of the Orcia Valley region. This villa which has been recently restored with all its original details preserved, comprises 3 separate units rented together to have a large... View all property information
    Location Information
    53026, Pienza, Province of Siena
    1 / 28
    6 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    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... View all property information
    Location Information
    Pienza, Province of Siena
    1 / 28
    6 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    Amenities & Details
    • Private Outdoor...
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Beautiful stone farmhouse situated in peaceful and panoramic location near the charming medieval town of Pienza, in the heart of the Orcia Valley region. This villa which has been recently restored with all its original details preserved, comprises 3 separate units rented together to have a large... View all property information
    Location Information
    53026, Pienza, Province of Siena
    1 / 31
    6 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Beautiful stone farmhouse situated in peaceful and panoramic location near the charming medieval town of Pienza, in the heart of the Orcia Valley region. This villa which has been recently restored with all its original details preserved, comprises 3 separate units rented together to have a large... View all property information
    Location Information
    53026, Pienza, Province of Siena
    1 / 25
    1 Bedroom, 1 Bathroom, Sleeps 10 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    In the heart of the Natural Park of the Val d 'Orcia, Pienza, Rent In Tuscany offers a unique experience that will immerse you in the real, magical Tuscany, where rolling hills, vineyards, olive groves and truffle fields, frame Villa Poggio Di Toscana, an estate of 38 hectares of organic management... View all property information
    Location Information
    Pienza, Province of Siena
    1 / 31
    8 Bedrooms, 8 Bathrooms, Sleeps 14 | Quick View
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    • Internet Access
    • Shared Outdoor Pool...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Imposing farmhouse dating back to the 18th century comprising 2 independent units (rentable only together as a private property). This beautiful 5–hectare estate is situated in quiet and panoramic location, in the heart of the Val d’Orcia region, a short distance away from the charming medieval... View all property information
    Location Information
    53026, Pienza, Province of Siena
    5 Bedrooms, Sleeps 10 | Quick View
    other traveler has booked this property
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    • Patio
    • Secure Parking
    • Private Outdoor...
    • Grill
    • Internet Access
    • Washer
    • Outdoor Dining Area
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    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
    Location Information
    53026, Pienza, Province of Siena
    Monticchiello
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • Central Heating
    • Private Yard
    • Grill
    • Parking
    • Washer
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    Location Information
    53026, Monticchiello, Pienza
    Monticchiello
    Private Room, 2 Bathrooms, Sleeps 2 | Quick View
    other traveler has booked this property
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    • Shared Yard
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    Location Information
    53026, Monticchiello, Pienza
    1 / 20
    4 of 5 stars (1) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other traveler has booked this property
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    • Private Yard
    • Central Heating
    • Washer
    • Parking
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    Location Information
    53026, Pienza, Province of Siena
    4 of 5 stars Reviewed October 4, 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 / 22
    5 of 5 stars (2) Excellent
    Monticchiello
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travelers have booked this property
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    • Satellite TV
    • Parking
    • Washer
    • Wi-Fi
    • Private Yard
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    Location Information
    53026, Monticchiello, Pienza
    7 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Outdoor Dining Area
    • Wi-Fi
    • Grill
    • Private Yard
    • Central Heating
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    Location Information
    53026, Pienza, Province of Siena