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Holiday Rentals in Pienza, Italy

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    ₹ 24,271 Average
    ₹ 67,000+
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    Travellers to Pienza are booking September dates now. Secure your holiday home today, and have the perfect trip.
    1 / 43
    5 of 5 stars (16) Excellent
    Monticchiello
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 23
    5 of 5 stars (5) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    1 / 19
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    1 / 37
    5 of 5 stars (1) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | 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 / 20
    4 of 5 stars (1) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Location Information
    53026, Pienza, Province of Siena
    4 of 5 stars Reviewed 4 October 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 / 55
    5 of 5 stars (2) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    About this property
    Villa I CIPRESSINI è la casa più fotografata della zona, raffigurata da anni su cartoline e calendari proprio perchè rappresenta intatto il fascino della antica casa colonica Toscana. In piena campagna ma a soli 500 mt.dal paese offre grandi spazi esterni; la piscina aperta 15/6-15/9 offre relax... View all property information
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    53026, Pienza, Province of Siena
    1 / 64
    6 Bedrooms, 6 Bathrooms, Sleeps 13 | Quick View
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    About this property
    Highlights Independent farmhouse that sleeps 13 people. The main house sleeps 6. On the ground floor there are a large living room with fireplace, library, hi-fi, TV, DVD, small kitchen, a double bedroom with a separate entrance from the outside with an en-suite bathroom with washing machine.... View all property information
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    Pienza, Province of Siena
    1 / 42
    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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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 / 24
    6 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    • Private Outdoor...
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    • 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
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    53026, Pienza, Province of Siena
    1 / 21
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Secure Parking
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    • Pet-friendly
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    • x
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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
    Location Information
    53026, Pienza, Province of Siena
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    1 / 5
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Location Information
    53026, Pienza, Province of Siena
    1 / 4
    7 Bedrooms, 8 Bathrooms, Sleeps 14 | Quick View
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    • ?
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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... 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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    • Shared Outdoor Pool...
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    • Pet-friendly
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    • ?
    • ?
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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 18 December 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 / 14
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Wi-Fi
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    • Central Heating
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    Location Information
    53026, Pienza, Province of Siena
    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 Garden
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    • Pet-friendly
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    • x
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    Location Information
    53026, Monticchiello, Pienza
    1 / 21
    5 of 5 stars (2) Excellent
    Monticchiello
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    53026, Monticchiello, Pienza
    1 / 22
    5 of 5 stars (6) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    Casale Reggello is located in the gently rolling Tuscan hills, between the wonderful towns of Pienza and Montepulciano, just a short distance from the thermal baths of Bagno Vignoni. Reggello is a single House with 8/10 beds and as its own swimming pool and surrounding park. It has an external wood... View all property information
    Location Information
    53049, Pienza, Province of Siena
    5 of 5 stars Reviewed 8 October 2014
    We stayed at Villa Maggio for a week and wanted to stay much longer. The villa is amazing and the setting is extraordinary. We were centrally located near all the wonderful...
    4 of 5 stars Reviewed 28 May 2014
    Our group of 8 stayed at this charming renovated farmhouse located between Pienza and Montepulciano. The location, villa and grounds were wonderful. The villa is decorated in an...
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    1 / 25
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Pet-friendly
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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 / 9
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • ?
    • Smoking allowed
    Location Information
    Pienza, Province of Siena
    5 of 5 stars Reviewed 3 weeks ago
    Excellent holiday, the reception was generous and warm; the location is superb. It was our third stay and it is still Paradise on earth!
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    1 / 12
    Monticchiello
    2 Bedrooms, 4 Bathrooms, Sleeps 4 | Quick View
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    • Central Heating
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    • Pet-friendly
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    • x
    Location Information
    53026, Monticchiello, Pienza
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    1 / 5
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Shared Garden
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    • ?
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    53026, Pienza, Province of Siena
    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • Shared Garden
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    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
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    • Shared Outdoor Pool...
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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 / 24
    Monticchiello
    Private Room, 10 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Porch
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    • Mountain Views
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    • Pet-friendly
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    • ?
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    Location Information
    53026, Monticchiello, Pienza
    1 / 14
    5 of 5 stars (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • ?
    • ?
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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
    Location Information
    Pienza, Province of Siena
    1 / 15
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Balcony
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    • Pet-friendly
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    • x
    • Smoking allowed
    • x
    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 / 37
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    • Private Outdoor...
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    • Pet-friendly
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    • ?
    • ?
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    • ?
    About this property
    This marvelous villa is located in the heart of Tuscany, near the enchanting town of Pienza, and is the ideal villa for anyone looking for a relaxing and peaceful getaway in Tuscany. This marvelous villa is located in the heart of Tuscany, near the enchanting town of Pienza, and is the ideal villa... View all property information
    Location Information
    53020, Pienza, Province of Siena
    1 / 12
    5 of 5 stars (1) Excellent
    Monticchiello
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Parking
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    • Pet-friendly
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    • ?
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    • x
    Location Information
    53026, Monticchiello, Pienza
    1 / 26
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    • Patio
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    • 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
    4 of 5 stars Reviewed 5 September 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 / 24
    6 Bedrooms, 6 Bathrooms, Sleeps 13 | Quick View
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    • Washer
    • Satellite TV
    • DVD Player
    • Hot Tub
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    • Pet-friendly
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    • ?
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    • x
    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 / 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 5 July 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 expectations...
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    1 / 54
    Monticchiello
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
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    • Pet-friendly
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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 / 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 / 14
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    • x
    Location Information
    53026, Pienza, Province of Siena
    1 / 18
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    • Hot Tub
    • Satellite TV
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    • Terrace
    • Balcony
    • Shared Garden
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    (Minimum of one week rental required) On the ground floor there is the living room with fireplace and a fully-equipped corner kitchen (fridge with freezer, oven, 4 ring stove, microwave, toaster, kettle, washing machine, dishwasher, American coffee maker, and Italian "moka"), Satellite TV, DVD... View all property information
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    Pienza, Province of Siena
    1 / 21
    2 Bedrooms, 6 Bathrooms, Sleeps 4 | Quick View
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    • Porch
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    53026, Pienza, Province of Siena
    1 / 16
    7 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    • Outdoor Dining Area
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    • Smoking allowed
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    Location Information
    53026, Pienza, Province of Siena
    1 / 41
    Monticchiello
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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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
    1 / 23
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Central Heating
    • Satellite TV
    • DVD Player
    • Washer
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    • Shared Garden
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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 / 20
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
    • Washer
    • Private Garden
    • Grill
    • Satellite TV
    • Air Conditioning
    • Parking
    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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 / 23
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Balcony
    • Central Heating
    • Wi-Fi
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    • DVD Player
    • Satellite TV
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    • 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 / 41
    Monticchiello
    2 Bedrooms, 4 Bathrooms, Sleeps 4 | Quick View
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    • Patio
    • Central Heating
    • Private Outdoor...
    • Washer
    • Hot Tub
    • Satellite TV
    • Mountain Views
    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    Location Information
    53026, Monticchiello, Pienza
    1 / 45
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Air Conditioning
    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Hidden at the end of a long drive through never ending fields of wheat, guests will find this enchanting farmhouse surrounded by a typical Mediterranean garden with rosemary, lavender, sage and flowers in every season. The colours of the countryside surrounding Pienza Villa inspire the interior... View all property information
    Location Information
    Pienza, Province of Siena
    1 / 22
    5 of 5 stars (2) Excellent
    Monticchiello
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
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    • Satellite TV
    • Parking
    • Washer
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    • Private Garden
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    Location Information
    53026, Monticchiello, Pienza
    1 / 9
    5 of 5 stars (3) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 3 | Quick View
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    • Central Heating
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Abbiamo ricavato il 'country loft' dalle antiche stalle al piano terra del nostro podere. Lo spazio è rimasto praticamente invariato e ha due porte che si aprono direttamente sul giardino e sul panorama magnifico della Val d'Orcia. Lo spazio principale di ca 100 mq è composto da: - una cucina open... View all property information
    Location Information
    53042, Pienza, Province of Siena
    1 / 12
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • Washer
    • Wi-Fi
    • Grill
    • Private Garden
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    Location Information
    53026, Pienza, Province of Siena
    1 / 20
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Private Outdoor...
    • Wi-Fi
    • Parking
    • Satellite TV
    • Private Garden
    • Washer
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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 / 4
    Private Room, 2 Bathrooms, Sleeps 2 | Quick View
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    • Wi-Fi
    • Private Garden
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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
    1 / 24
    8 Bedrooms, 9 Bathrooms, Sleeps 19 | Quick View
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    • Private Outdoor...
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    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
    Location Information
    Pienza, Province of Siena