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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 / 23
    5 of 5 stars (4) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    5 Bedrooms, Sleeps 10 | 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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    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
    5 of 5 stars Reviewed August 14, 2015
    This is excellent accommodation with a fantastic swimming pool. We travelled as a family with teenage children so having separate accommodation units worked well. The outdoor...
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    1 / 48
    6 Bedrooms, 4 Bathrooms, Sleeps 11 | Quick View
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    About this property
    RECEPTIVE STRUCTURE. In the unique landscape of the Val d'Orcia, lulled by the embrace of gentle hills that surround the countryside of Pienza, stands Casa Andrei, on a discreet panoramic hilltop. A rural house completely restored with salvaged materials in the typical local tradition, the exterior... View all property information
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    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
    Monticchiello
    Private Room, 10 Bathrooms, Sleeps 8 | Quick View
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    53026, Monticchiello, Pienza
    1 / 43
    5 of 5 stars (15) Excellent
    Monticchiello
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Villa PoliFlora is a modern residence in Monticchiello in Val d'Orcia, a Unesco world heritage site. The owners and creators invite you for a relaxing stay, in the triangle among Montalcino, Pienza and Montepulciano. A few kilometers away from Siena and Chianti Classico, best destinations in... View all property information
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    53026, Monticchiello, Pienza
    5 of 5 stars Reviewed July 18, 2015
    A beautifully appointed apartment. A short walk into Montichiello. We were joyfully greeted by Flora - who supplied breakfast fruit and pastries which we enjoyed in the garden...
    5 of 5 stars Reviewed June 22, 2015
    Villa poliflora is a perfect place to stay for a week in val d,orca.the apartment has two bedrooms each with en suite and a lovely small garden. It is beautifully frrnished.the...
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    4 Bedrooms, 4 Bathrooms, Sleeps 11 | Quick View
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    53026, Pienza, Province of Siena
    1 / 23
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Farmhouse Casa Orcia - holiday accommodation in Tuscany with swimming pool is for discerning travelers wishing to spend their holidays in Tuscany. This rental farmhouse is wonderful for a family holiday and located between Pienza (where the english patient was filmed) and San Quirico (a lovely... View all property information
    Location Information
    Pienza, Province of Siena
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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
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    53026, Pienza, Province of Siena
    1 / 21
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Villa Arpicella really does offer the best of both worlds! Despite its prime location at just 10 minutes’ walking distance from Pienza, it enjoys the peace and quiet of a beautiful countryside setting with spectacular panoramic views. It is a large, traditionally Tuscan 17th century farmhouse, now... View all property information
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    53026, Pienza, Province of Siena
    1 / 20
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    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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    About this property
    Poggio ai Gelsi is located in the south of Tuscany between the hills of Val d'Orcia, Siena and halfway between Montepulciano and Pienza. The property enjoys a magnificent view over Montichiello and Pienza. The colours of the nature in this corner of Tuscany are beautiful and change day after day,... View all property information
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    53026, Pienza, Province of Siena
    1 / 16
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    "Podere Osteria” is a country house which was originally one of the first examples of European hospitals. The building, completely refurbished in 2012, is in the heart of the Val d’Orcia valley, an area marked by enchanting landscapes and the most varied Medieval towns. From its central location,... View all property information
    Location Information
    53026, Pienza, Province of Siena
    Monticchiello
    2 Bedrooms, 4 Bathrooms, Sleeps 4 | Quick View
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    53026, Monticchiello, Pienza
    1 / 20
    6 Bedrooms, 6 Bathrooms, Sleeps 13 | Quick View
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    • x
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    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
    1 / 20
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    The farmhouse, set in one of the most fascinating areas of the south of Sienese territory, between Pienza and Montepulciano, shows sober, almost austere lines. Its placing, the group of cypresses, its position on a high ground which raise the whole valley, makes it the ideal residence for a high... View all property information
    Location Information
    53100, Pienza, Province of Siena
    1 / 26
    9 Bedrooms, 9 Bathrooms, Sleeps 19 | Quick View
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    • ?
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    About this property
    Villa Rombi is a beautiful Tuscan property located in Contignano. The spacious villa sleeps up to 19 guests in the main house and annexe. It is surrounded by breathtaking views over the Italian countryside.Villa Rombi has been beautiful decorated with a relaxed, modern Tuscan style. There is a... View all property information
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    Pienza, Province of Siena
    1 / 25
    Monticchiello
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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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
    Location Information
    Monticchiello, Pienza
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    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    53026, Pienza, Province of Siena
    1 / 40
    Monticchiello
    10 Bedrooms, 9 Bathrooms, Sleeps 16 | Quick View
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    About this property
    As a luxury villa, Villa Bandida works best as a place where friends and family come to relax, share meals, explore the countryside and drink wine late into the evening. For guests looking for the perfect location for a group get-together, relaxing break, birthday celebration or wedding, Villa... View all property information
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    Monticchiello, Pienza
    1 / 13
    4 of 5 stars (2) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This property has been restored with every confort,full equiped kitchen, large bedrooms each with bathrooms. This apartment however mantain the antique charme,because the original structure is still visible. The accomodation is suitable for couple wit baby or kid . Pets are welcome The village can... View all property information
    Location Information
    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 / 22
    5 of 5 stars (2) Excellent
    Monticchiello
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    53026, Monticchiello, Pienza
    1 / 36
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Having a holiday in this countryhouse is like having a holiday in a postcard. Photographed from all angles, it represents Tuscany, used by a large number of advertising agencies who want to render the image of the Tuscan countryside. It is very close to Pienza, the city built by will of Pope Pius... View all property information
    Location Information
    53026, Pienza, Province of Siena
    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 / 10
    5 of 5 stars (6) Excellent
    Monticchiello
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    Location Information
    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 / 44
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Mountain Views
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    • x
    About this property
    RECEPTIVE STRUCTURE. In the unique landscape of the Val d'Orcia, lulled by the embrace of gentle hills that surround the countryside of Pienza, stands Casa Andrei, on a discreet panoramic hilltop. A rural house completely restored with salvaged materials in the typical local tradition, the exterior... View all property information
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    53026, Pienza, Province of Siena
    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • x
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    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 / 24
    8 Bedrooms, 9 Bathrooms, Sleeps 19 | Quick View
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    About this property
    For visitors in search of an exceptional and luxurious Italian retreat, Villa Casella is the perfect choice. The exquisite villa is located in Contignano and surrounded by spectacular views of rolling clay hills and countryside. The villa sleeps up to 19 in 8 very spacious bedrooms: 2 twin, 5... View all property information
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    Pienza, Province of Siena
    1 / 24
    5 of 5 stars (1) Excellent
    Monticchiello
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    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 3 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 / 8
    5 of 5 stars (2) Excellent
    Monticchiello
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    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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    1 / 15
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Ground floor: a large dining/living room overlooking the garden, kitchen, breakfast room, small sitting room with fireplace, study, twin bedded room with en suite bathroom with tub and shower, double bedroom with en suite bathroom with shower. <BR><BR>First floor: large lounge with imposing... View all property information
    Location Information
    53026, Pienza, Province of Siena
    1 / 29
    5 of 5 stars (1) Excellent
    Monticchiello
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    When you look out the windows of this restored farmhouse in Tuscany, you’ll be gazing out on the landscape that has inspired everyone from Renaissance painters to modern-day UNESCO – the green, rolling hills of the Val d’Orcia. With views from the windows of the modern kitchen, the private pool,... View all property information
    Location Information
    Monticchiello, Pienza
    5 of 5 stars Reviewed December 18, 2014
    Two families travelling together, this property was perfect, seperate units for each family but big enough to share meals using the local produce and wines. You will need a car...
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    1 / 26
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    It is the most photographed house in the area, a symbol of the Tuscany countryside, featured on many postcards and calendars simply because it has maintained the charm of the old farmhouse and the surrounding fields, without any new buildings as far as the eye can see. Villa Andrea is located only... View all property information
    Location Information
    53026, Pienza, Province of Siena
    4 of 5 stars Reviewed September 4, 2012
    Our group of 5 adults spent an enjoyable week in early May at I Cipressini, a lovely 3-bedroom Tuscan farmhouse located in the middle of fluorescent fields of yellow rapeseed and...
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    1 / 14
    5 of 5 stars (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    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
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    Pienza, Province of Siena
    6 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    • Balcony
    • Central Heating
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    This enchanting holiday home in Tuscany is on a knoll overlooking the typical Tuscan countryside of the area around Pienza, San Quirico and Montalcino. In a very quiet position, only surrounded by a peaceful Tuscan countryside, this holiday accommodation consists of 4 comfortable apartments (2 on... View all property information
    Location Information
    53026, Pienza, Province of Siena
    1 / 22
    5 of 5 stars (1) Excellent
    Monticchiello
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
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    • Pet-friendly
    • Child-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... View all property information
    Location Information
    53020, Monticchiello, Pienza
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Parking
    • Private Yard
    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    Location Information
    Pienza, Province of Siena
    Monticchiello
    Private Room, 2 Bathrooms, Sleeps 2 | Quick View
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    • Air Conditioning
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    • Pet-friendly
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    • x
    • x
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    • x
    Location Information
    53026, Monticchiello, Pienza
    3 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • Grill
    • Shared Yard
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    • Shared Outdoor Pool...
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    • Private Yard
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    Location Information
    53026, Pienza, Province of Siena
    1 / 44
    6 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    • Satellite TV
    • Private Outdoor...
    • Grill
    • DVD Player
    • Internet Access
    • Central Heating
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    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... View all property information
    Location Information
    Pienza, Province of Siena
    Monticchiello
    2 Bedrooms, 1 Bathroom, Sleeps 2 | Quick View
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    • Patio
    • Washer
    • DVD Player
    • Balcony
    • Mountain Views
    • Satellite TV
    • Air Conditioning
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Half way between Rome and Florence in monticchiello among the verdant hills of an ancient land where the sound of nature pervades over silence and privacy stands our vacation home .Here it is possible to experience the country life of times gone by.At the foot steps of medieval Montichiello village... View all property information
    Location Information
    53026, Monticchiello, Pienza
    1 / 37
    Monticchiello
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Internet Access
    • Shared Outdoor Pool...
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Child-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... View all property information
    Location Information
    53026, Monticchiello, Pienza
    1 / 23
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Balcony
    • Central Heating
    • Wi-Fi
    • Washer
    • Private Outdoor...
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    About this property
    It is the most photographed house in the area, a symbol of the Tuscany countryside, featured on many postcards and calendars simply because it has maintained the charm of the old farmhouse and the surrounding fields, without any new buildings as far as the eye can see. Villa Andrea is located only... View all property information
    Location Information
    53026, Pienza, Province of Siena
    1 / 4
    7 Bedrooms, 8 Bathrooms, Sleeps 14 | Quick View
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    Amenities & Details
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    53026, Pienza, Province of Siena
    1 / 47
    4 of 5 stars (1) Very good
    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    • Washer
    • Central Heating
    • Private Outdoor...
    • Hot Tub
    • Grill
    Suitability
    • Pet-friendly
    • Child-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... View all property information
    Location Information
    53026, Pienza, Province of Siena
    1 / 72
    6 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    Amenities & Details
    • Grill
    • Hot Tub
    • Washer
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Monticchiello
    Private Room, 2 Bathrooms, Sleeps 2 | Quick View
    other traveler has booked this property
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    Amenities & Details
    • Shared Yard
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    Location Information
    53026, Monticchiello, Pienza
    1 / 37
    5 of 5 stars (1) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Wi-Fi
    • Porch
    • Washer
    • Grill
    • Satellite TV
    • Shared Outdoor Pool...
    • Patio
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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