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Vacation Rentals in Pienza, Italy

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    1 / 64
    5 of 5 stars (6) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    1 / 43
    5 of 5 stars (14) Excellent
    Monticchiello
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | 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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    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 / 23
    5 of 5 stars (3) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Mountain Views
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    About this property
    New lower price - one of the nicest flat in Tuscany 5 star standard !! The apartment has its own entrance and occupies the whole 1st and top floors of this classical building next to the ancient city wall. Private parking, large roof terrace (55m2) with great views over the valley and... View all property information
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    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 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
    8 Bedrooms, 8 Bathrooms, Sleeps 15 | Quick View
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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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    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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    Monticchiello
    4 Bedrooms, 9 Bathrooms, Sleeps 8 | Quick View
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    53026, Monticchiello, Pienza
    6 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    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
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    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Pienza, Province of Siena
    1 / 24
    5 of 5 stars (2) Excellent
    Monticchiello
    4 Bedrooms, 10 Bathrooms, Sleeps 7 | Quick View
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    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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    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... View all property information
    Location Information
    53026, Pienza, Province of Siena
    1 / 37
    Monticchiello
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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
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    53026, Monticchiello, Pienza
    1 / 35
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
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    • x
    • x
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    About this property
    Arriving at Villa Leccetino, down a short tree covered road is like entering a very secret location. Tucked into the hillside surrounded by olive trees, this is a spectacular masonry villa, made with stones dug up from the ground on this terraced property. It has been masterly reconstructed just a... View all property information
    Location Information
    53020, Pienza, Province of Siena
    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 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 private... View all property information
    Location Information
    Pienza, Province of Siena
    5 of 5 stars Reviewed August 9, 2011
    My husband and I stayed at La Terrazza for 5 days in June 2011, along with our children aged 11 and 15. We loved the apartment - especially al fresco dining on the balcony...
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    1 / 21
    6 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    • Grill
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    About this property
    Casavecchia is situated in the heart of Val D'Orcia, close to Pienza. This property consists of a main villa and of a guesthouse. The villa is surrounded by a 360 degrees view on the valley close to Pienza. From the main entrance there is the direct access to the kitchen which combines the... View all property information
    Location Information
    Pienza, Province of Siena
    1 / 23
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Central Heating
    • Satellite TV
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    • Shared Yard
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    • Pet-friendly
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    • Child-friendly
    • x
    • x
    • x
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    • Elder access
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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
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • x
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    • x
    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
    • Grill
    • DVD Player
    • Wi-Fi
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    • Balcony
    Suitability
    • Pet-friendly
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    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    Location Information
    53026, Pienza, Province of Siena
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    1 / 24
    Monticchiello
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • x
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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... View all property information
    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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    • Elder access
    • ?
    • ?
    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
    5 of 5 stars Reviewed August 11, 2012
    My family of six loved every minute of our time at this villa. We had never used this site before, but everything was exactly as described. The villa is literally a 5-10 minute...
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    1 / 27
    6 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    • ?
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    About this property
    Situated in the heart of Val d'Orcia, an ancient corner of Tuscany, where the architecture is more essential and humble than in the rest part of it, the villa represents a stone-built house decorated with a rustic yet aristocratic style and is provided with every comfort. In the 18th century when... View all property information
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    Pienza, Province of Siena
    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Washer
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    • Private Yard
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    • Pet-friendly
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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
    Location Information
    53020, Pienza, Province of Siena
    1 / 41
    6 Bedrooms, 6 Bathrooms, Sleeps 13 | Quick View
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    • Private Outdoor...
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    About this property
    Villa Prugnolo is located in the heart of the wine country and surrounded by probably the most spectacular views. Rolling hills, vineyards and cupressus trees surround the villa and it offers views of Montepulciano, Mount Amiata and, of course Pienza.This fabulous six bedroom air conditioned 19th... 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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    • Internet Access
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    • Pet-friendly
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    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • 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
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    53026, Pienza, Province of Siena
    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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    • ?
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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 / 37
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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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
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    53020, Pienza, Province of Siena
    1 / 18
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Private Outdoor...
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    • ?
    • ?
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    • x
    • ?
    About this property
    Set between rolling vineyards and distant medieval towers, and the ageless beauty of the UNESCO-acclaimed Val d'Orcia, Podere Enea has the look of a farmstead undisturbed by time. Yet like its famed neighbouring city Pienza, it has undergone transformation. In the same spirit with which the 15th... View all property information
    Location Information
    53026, Pienza, Province of Siena
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • Central Heating
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    • Balcony
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    • Mountain Views
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • ?
    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
    NK, Pienza, Province of Siena
    Monticchiello
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    53026, Monticchiello, Pienza
    1 / 20
    6 Bedrooms, 6 Bathrooms, Sleeps 13 | Quick View
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    • Terrace
    • Private Outdoor...
    • Hot Tub
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
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    • Elder access
    • 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. First floor: a double bedroom with Jacuzzi inside the room and en-suite bathroom with shower, a double bedroom with en-suite... View all property information
    Location Information
    53026, Pienza, Province of Siena
    1 / 39
    8 Bedrooms, 8 Bathrooms, Sleeps 14 | Quick View
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    • Private Indoor Pool
    • Internet Access
    • Air Conditioning
    • Hot Tub
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    • Pet-friendly
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    • Child-friendly
    • ?
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    • Smoking allowed
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    About this property
    Villa Orcias is a sublime country residence and estate in an outstanding position completely surrounded by Val d’Orcia’s fairytale-like rolling hills. The property is strategically located just a few minutes drive from Pienza, one of Tuscany’s most beautiful towns, and comprises a lovely period... 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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    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
    4 of 5 stars Reviewed October 13, 2012
    Very good. Spacious and private. We had several chefs come to prepare meals. We walked into the town of Monticchiello. Other local towns were also great.
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    Monticchiello
    4 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
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    • x
    About this property
    Sul Corso Rossellino, proprio nel centro di Pienza, a meno di cento metri da Piazza Pio II con la sua magnifica cattedrale e lo splendido Palazzo Piccolomini, l'Antica Locanda offre ad ospiti esigenti una piacevole ed esclusiva sistemazione. L'Antica Locanda è ubicata in un palazzo del XV secolo... View all property information
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    53026, Monticchiello, Pienza
    1 / 22
    Monticchiello
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Secure Parking
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    • Satellite TV
    • Wi-Fi
    • Terrace
    • Balcony
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Villa Daria is a spacious former family home, lovingly remodeled to create a cozy and comfortable environment for you to relax after a long day of adventures in the Val d’Orcia, a Unesco World Heritage site. Location: The residence was built around 1890 at a superb position within the walled... View all property information
    Location Information
    53026, Monticchiello, Pienza
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
    • Balcony
    • Grill
    • Private Outdoor...
    • Terrace
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    • Wi-Fi
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This is a fantastic 5 bedroom villa near the wonderful town of Montepulciano in Tuscany. Completely surrounded by olive grove and vineyards, it occupies an idyllic setting for guests to enjoy a peaceful and relaxing holiday. Recently restored, it offers a perfect mix of traditional Tuscan... View all property information
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    Pienza, Province of Siena
    1 / 14
    4 of 5 stars (1) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Private Yard
    • Central Heating
    • Washer
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • 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 / 10
    5 of 5 stars (1) Excellent
    Monticchiello
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Wi-Fi
    • Private Yard
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    About this property
    The apartment dates back to the XVII (17th) Century and has been restored respecting the original architecture. The apartment has a large living room with a fully equipped kitchen as is beautifully furnished including original antiques. The property has 2 bedrooms, each with private bathroom,... View all property information
    Location Information
    53026, Monticchiello, Pienza
    5 of 5 stars Reviewed May 24, 2012
    Beautiful apartment in the heart of the ancient village of Monticchiello. The village though small has two exceptional restaurants, a fun bar and a shop that sells everything you...
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    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Washer
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    • Wi-Fi
    • Private Outdoor...
    • Grill
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    Location Information
    53026, Pienza, Province of Siena
    1 / 11
    4 of 5 stars (2) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
    • Outdoor Dining Area
    • Satellite TV
    • Shared Yard
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    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...
    5 of 5 stars Reviewed October 5, 2011
    This apartment has all the conveniences and is situated in the beautiful small village of Monticchiello overlooking the Val d'Orcia. Comfortable beds, nicely equipped kitchen...
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    1 / 46
    Monticchiello
    6 Bedrooms, 6 Bathrooms, Sleeps 9 | Quick View
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    • Balcony
    • Patio
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    • Terrace
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    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    This marvelous villa occupies a gently sloping site facing west across the fertile Orcia Valley towards the majestic Amiata Mountain. Sheltered to the east by a woodland and surrounded by well-tended gardens, the property includes several acres of vineyards and olive groves on this warm and private... View all property information
    Location Information
    53026, Monticchiello, Pienza
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • Private Yard
    • Shared Yard
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    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    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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    • Pet-friendly
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    • ?
    • ?
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    • Elder access
    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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    Monticchiello
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • Central Heating
    • Private Yard
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    • Outdoor Dining Area
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    Location Information
    53026, Monticchiello, Pienza
    Monticchiello
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Central Heating
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    • Grill
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    • Shared Yard
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    Location Information
    53026, Monticchiello, Pienza
    Monticchiello
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • Patio
    • Central Heating
    • Private Outdoor...
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    • Hot Tub
    • Satellite TV
    • Mountain Views
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • ?
    Location Information
    53026, Monticchiello, Pienza
    9 Bedrooms, 8 Bathrooms, Sleeps 17 | Quick View
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    • Pet-friendly
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    Location Information
    53026, Pienza, Province of Siena
    Monticchiello
    2 Bedrooms, 4 Bathrooms, Sleeps 4 | Quick View
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    • Central Heating
    • Parking
    • Private Yard
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    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    Location Information
    53026, Monticchiello, Pienza
    1 / 12
    5 of 5 stars (1) Excellent
    Monticchiello
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Parking
    • Outdoor Dining Area
    • Wi-Fi
    • Central Heating
    • Shared Yard
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    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    Location Information
    53026, Monticchiello, Pienza