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Vacation Rentals in Montalcino, Italy

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    Travelers to Montalcino are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Amiata is a carefully and tastefully renovated country villa set in the most desirable location in the beautiful Val d’Orcia.  Guests are accommodated in four queen bedded rooms. There are four bathrooms.  The villa has been recently updated with every possible modern convenience.  Amiata is part... View all property information
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    53024, Montalcino, Province of Siena
    1 / 23
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This villa provides guests with a panoramic pool, a living room, a fully equipped kitchen, a study room, four double bedrooms and three bathrooms. This villa provides guests with a panoramic pool, a living room, a fully equipped kitchen, a study room, four double bedrooms and three bathrooms.... View all property information
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    53024, Montalcino, Province of Siena
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    A large (70 m²) and bright apartment set on the first floor, in the historical centre of Montalcino. There's a living room with sofa and TV at the entrance, a fully equipped kitchen that opens up into a small internal courtyard with barbecue, table and chairs. Up a few steps and there's a bathroom... View all property information
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    53024, Montalcino, Province of Siena
    1 / 16
    3 Bedrooms, 4 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Massimo and Chiara Ferragamo, a name of excellence representing elegance “made in Italy” worldwide; a location, the Val D'Orcia, UNESCO Natural Park; a private estate of 5000 acres. This combination makes this place an idyllic retreat. Castiglion del Bosco is one of the largest private estates in... View all property information
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    Montalcino, Province of Siena
    1 / 27
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Exteriors The fragrant smell of 10 hectares of vineyards and olive groves envelope this villa for rent in Tuscany, Italy, which at present shows its best face, thanks to the devoted restoration it underwent.From the panoramic pool guests will envisage before leaving on a walking tour the beauty... View all property information
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    53024, Montalcino, Province of Siena
    1 / 20
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    'Vivo d'Orcia is not a place, it is a way of life...' The Castle of Vivo d'Orcia lies in the widespread Orcia valley in southern Tuscany, 2 hours from Florence, 1 hour from Siena, close to such cultural jewels as Pienza, Montalcino and Montepulciano, to name but a few. The hamlet lies at an... View all property information
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    53023, Montalcino, Province of Siena
    1 / 43
    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    About this property
    This completely independent property with private pool is a classic stone farmhouse situated on the edge of the historic town of Montalcino, home of the famous 'Brunello' wine. The house is in a splendid and peaceful spot with a beautiful view of Montalcino and the surrounding countryside. It has... View all property information
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    53024, Montalcino, Province of Siena
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    5 of 5 stars (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    La Giocosa is located in the most desirable region south of Siena, in the Val d'Orcia, an enchanting and miraculously unspoilt valley in southern Tuscany, listed as UNESCO world heritage in 2004. This beautiful country house is located just 10 km from the historical centre of Montalcino. Set on a... View all property information
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    Montalcino, Province of Siena
    5 of 5 stars Reviewed August 1, 2012
    We were two families and rented this house for one week. The house is beautiful, decorated with taste and well maintained. The floors are stone-paved, the kitchen is made in...
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    2 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    Location Information
    53024, Montalcino, Province of Siena
    1 / 18
    6 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Villa San Giovese is a spacious luxury farmhouse, set among sweet rolling hills, extensive greens and wine producing vineyards in the Montalcino area, swimming pool and air conditioning Villa San Giovese is a spacious luxury farmhouse, set among sweet rolling hills, extensive greens and wine... View all property information
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    53024, Montalcino, Province of Siena
    1 / 50
    Poggio alle Mura
    8 Bedrooms, 8 Bathrooms, Sleeps 16 | Quick View
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    About this property
    Chic interior design, a private guest house and covered al fresco dining with stunning views are sure to please any group of friends or a large family looking for a one-of-a-kind Tuscan villa experience. Located south of Siena near the coveted Brunello vineyards of Montalcino, this villa was... View all property information
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    53024, Poggio alle Mura, Montalcino
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    2-room apartment 70 m2, on the ground floor. Spacious, renovated, beautiful and tasteful furnishings: living/dining room with 1 double sofabed and satellite TV. 1 double bedroom. Kitchenette (oven, X ceramic glass hob hotplates). Shower/bidet/WC. Air-conditioning (extra). Facilities: Internet... View all property information
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    53024, Montalcino, Province of Siena
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • Elder access
    • x
    About this property
    A few kilometers from Montalcino on the way to Castelnuovo Abate, in a finely renovated ancient stone farmhouse, five spacious apartments await you for your Tuscan vacation. All the apartments feature authentic period furnishings and modern amenities. Ville di Castelnuovo is situated at the top of... View all property information
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    53024, Montalcino, Province of Siena
    1 / 81
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Hot Tub
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    About this property
    Our one-bedroom “suite” is an excellent choice for a couple on a romantic getaway or even a honeymoon. It is particularly elegant with a large bedroom including a 4-poster bed, a sleek bathroom with a bathtub, spacious living room with large sofa, dining area and your own little kitchen for cozy... View all property information
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    53024, Montalcino, Province of Siena
    1 / 17
    4 Bedrooms, 7 Bathrooms, Sleeps 8 | Quick View
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    • ?
    • ?
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    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Massimo and Chiara Ferragamo, a name of excellence representing elegance “made in Italy” worldwide; a location, the Val D'Orcia, UNESCO Natural Park; a private estate of 5000 acres. This combination makes this place an idyllic retreat. Castiglion del Bosco is one of the largest private estates in... View all property information
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    Montalcino, Province of Siena
    1 / 9
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
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    • Private Yard
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    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    Location Information
    53024, Montalcino, Province of Siena
    5 of 5 stars Reviewed April 28, 2015
    The Caprili family made our stay in there vineyard amazing. Very friendly and helpful. While secluded it's not far from all the tourist destinations. Also you really can't beat...
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    1 / 18
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    This property is professionally managed by Vacasa. While we are headquartered in Portland, Oregon - our 900 employees all over the world ensure the same professional standards and ease of booking at our international properties that we do at our 2500 properties in the USA. This wine country... View all property information
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    53024, Montalcino, Province of Siena
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    9 Bedrooms, 9 Bathrooms, Sleeps 19 | Quick View
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    • Balcony
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    • Pet-friendly
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    About this property
    Perched atop a hill in one of the most picturesque areas of Italy, Villa Ranuncolo is a magnificent country house located in the Val d’Orcia area of Tuscany. The setting is ripe with astonishing rolling hills and the lush wine country that has made Tuscany so famous. Set on a private piece of land,... View all property information
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    Montalcino, Province of Siena
    1 / 25
    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    Sitting on a spectacular 25-acre estate and boasting stunning views of the hills of Montalcino, Villa Leopolda is a true gem of Tuscany's countryside. This remarkable 7-bedroom 7-bathroom property has been recently restored and tastefully furnished with a fine selection of antiques and exquisite... View all property information
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    Montalcino, Province of Siena
    1 / 73
    2 Bedrooms, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    This stylishly decorated ground floor apartment opens up to a spacious living room with a charming kitchenette located towards the rear of the apartment. From here you can access the mezzanine above the kitchen, where a single bed is found. Through the corridor you will find a beautiful double... View all property information
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    53024, Montalcino, Province of Siena
    1 / 19
    5 Bedrooms, 5 Bathrooms, Sleeps 9 | Quick View
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    About this property
    Set on the estate of Castiglion del Bosco in Tuscany’s Val d’Orcia region, Villa Stabbi pairs the charm of a traditional Tuscan country house with resort-worthy amenities and a stunning setting amid vineyards and a golf course. The property’s five bedrooms are divided between the main villa and a... View all property information
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    Montalcino, Province of Siena
    1 / 20
    3.5 of 5 stars (3) Average
    7 Bedrooms, 1 Bathroom, Sleeps 2 | Quick View
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    Location Information
    53024, Montalcino, Province of Siena
    4 of 5 stars Reviewed August 18, 2015
    The position of Piombaia a few km from Montalcino is perfect for exploring southern Tuscany. The site itself is beautiful with an outdoor pool which came in handy after a hot...
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    1 / 22
    5 of 5 stars (2) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Private Yard
    • Outdoor Dining Area
    • Terrace
    • Balcony
    • Mountain Views
    • Wi-Fi
    • Secure Parking
    • Central Heating
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    • Pet-friendly
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    • Child-friendly
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    About this property
    We are in Sant'Angelo in Colle, a suburb of Montalcino, surrounded by the most beautiful Brunello vineyards. We offer a cosy 2-floor terrace house in typical Tuscan style, with wooden beam ceilings and a colourful, warm ambiance, offering every comfort for up to five guests. Minnie's Cottage was... View all property information
    Location Information
    53024, Montalcino, Province of Siena
    5 of 5 stars Reviewed October 16, 2015
    My husband and I spent a week at Minnie's cottage in October. We had a wonderful time and Minnie is a wonderful host, very friendly and will do anything to help make your stay a...
    5 of 5 stars Reviewed October 16, 2015
    As someone that doesn't get to vacation much, I very much looked forward to having a peaceful, quiet time in Tuscany. I'm happy to say that I was not disappointed in my stay at...
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    1 / 20
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    Villa Bandini is located only 300 meters from the hamlet of Lucignano d’Asso on top of a hill on the border between the Val d’Orcia and the Sienese clay hills. Lucignano d’Asso is a medieval ancient hamlet which, since the XV century, has belonged to the Piccolomini family, one of the most... View all property information
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    53020, Montalcino, Province of Siena
    1 Bedroom, Sleeps 2 | Quick View
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    53027, Montalcino, Province of Siena
    1 / 55
    Poggio alle Mura
    5 Bedrooms, 5 Bathrooms, Sleeps 16 | Quick View
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    • Pet-friendly
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    • Child-friendly
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    About this property
    Fontanelle is without doubt one of our loveliest Tuscan properties. It is located to the west of Montalcino, an area renowned for its beauty and for its wines, especially the famous Brunello di Montalcino. The property is in a spectacular position, surrounded by vineyards, olive trees, cypresses... View all property information
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    53024, Poggio alle Mura, Montalcino
    1 / 36
    12 Bedrooms, 11 Bathrooms, Sleeps 24 | Quick View
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    About this property
    Pian Dell'asso is a beautiful, rustic Italian villa with a wide open lawn and spectacular interior furnishing. The furniture is elegant and comfortable, perfect for lounging about, reading, chatting, napping and setting the stresses of modern life aside.  The pool is particularly unique in its... View all property information
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    Montalcino, Province of Siena
    1 / 21
    5 of 5 stars (4) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 9 | Quick View
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    • Pet-friendly
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    • ?
    • x
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    • Elder access
    About this property
    One of three unique and charming apartments in a XVI century villa situated in the wonderful Siena countryside a few kms from Montalcino, in the natural park of the Val d'Orcia, a precious architectural and natural context. Here you will feel embraced by the fascinating old architecture of the... View all property information
    Location Information
    53024, Montalcino, Province of Siena
    5 of 5 stars Reviewed August 30, 2015
    Simona and Michele were perfect hosts for our family week in Toscany. The Villa is magnificent offering a beautiful setting for a relaxing stay. It is ideally located for...
    5 of 5 stars Reviewed September 4, 2013
    We have just returned from a truly memorable stay in Siena. The villa is perfect! Beautifully decorated, light and airy and a huge living space - perfect for families or large...
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
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    • Balcony
    • Children's Pool
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
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    • x
    About this property
    Suite d'Artista is a perfect place to enjoy a relaxing holiday, combining the atmosphere of typical Tuscan countryside with Montalcino's amenities. Nestled just below Montalcino's historical centre, a peaceful spot with a large panoramic garden, swimming pool, Jacuzzi, Turkish bath, gazebo,... View all property information
    Location Information
    53024, Montalcino, Province of Siena
    4 Bedrooms, 6 Bathrooms, Sleeps 9 | Quick View
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    • Grill
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    • Private Yard
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    One of three unique and charming apartments in a XVI century villa situated in the wonderful senese countryside a few km's from Montalcino, in the natural park of the Val d' Orcia, a precious architectural and natural context. Here you will feel embraced by the fascinating old architecture of the... View all property information
    Location Information
    53024, Montalcino, Province of Siena
    1 / 24
    5 of 5 stars (7) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 9 | Quick View
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    • Central Heating
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    About this property
    One of three unique and charming apartments in a XVI century villa situated in the wonderful senese countryside a few km's from Montalcino, in the natural park of the Val d' Orcia, a precious architectural and natural context. Here you will feel embraced by the fascinating old architecture of the... View all property information
    Location Information
    53024, Montalcino, Province of Siena
    5 of 5 stars Reviewed July 21, 2015
    The villa was everything we imagined a villa in Tuscany would be like. It was charming and spacious; the grounds beautiful - cypresses, lavender and of course the inviting pool...
    5 of 5 stars Reviewed July 19, 2015
    We just got back from a week at Simona and Michael's fabulous villa and I'm already planning another trip! The house itself is absolutely beautiful, exactly what you imagine when...
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Patio
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
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    • x
    Location Information
    53024, Montalcino, Province of Siena
    1 Bedroom, Sleeps 1 | Quick View
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    • Pet-friendly
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    • x
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    Location Information
    53027, Montalcino, Province of Siena
    1 Bedroom, Sleeps 2 | Quick View
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    • Pet-friendly
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    • x
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    • x
    Location Information
    53027, Montalcino, Province of Siena
    1 Bedroom, Sleeps 3 | Quick View
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    • Pet-friendly
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    • Child-friendly
    • x
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    • x
    Location Information
    53027, Montalcino, Province of Siena
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Satellite TV
    • Terrace
    • Private Yard
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Balcony
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    Location Information
    53024, Montalcino, Province of Siena
    1 / 74
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
    • Shared Outdoor Pool...
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    The second of the two 3 bedroom apartments, it is just as lovely and light and bright. It is laid out over two floors so the ground floor bedrooms have direct access onto the estate´s stunning grounds. Also on the lower level is the very large living space consisting of a fully-equipped kitchen... View all property information
    Location Information
    53024, Montalcino, Province of Siena
    1 / 38
    6 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    • Washer
    • Private Outdoor...
    • Satellite TV
    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    EXTERIORVilla San Giovese is a spacious luxury farmhouse, set among sweet rolling hills, extensive greens and wine producing vineyards. The hilltop privileged position of the property has turned the villa into a relaxation stand view point from where tranquility can be savored. This elegant villa... View all property information
    Location Information
    53024, Montalcino, Province of Siena
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Shared Yard
    • Parking
    • Central Heating
    • Wi-Fi
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
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    • Elder access
    • x
    • x
    Location Information
    53027, Montalcino, Province of Siena
    1 / 30
    14 Bedrooms, 14 Bathrooms, Sleeps 30 | Quick View
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    • Private Outdoor...
    • Shared Yard
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Perfect for weddings, business meetings or a quiet getaway, Villa Tolomei is on top of a hill with a spectacular view of the verdant Tuscan landscape. Exercise as well as relax while being transported to forgotten places of exquisite taste. Perfect for weddings, business meetings or a quiet... View all property information
    Location Information
    53015, Montalcino, Province of Siena
    12 Bedrooms, 12 Bathrooms, Sleeps 24 | Quick View
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    • Patio
    • Sauna
    • Housekeeping...
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Located within the wineries of the Brunello region and accesses through a gravel and dirt road with great views overlooking the vineyards, this secluded country house is only 15 minutes from Montalcino. Recently restored with special attention to the search of exclusive comfort for guests, this... View all property information
    Location Information
    53024, Montalcino, Province of Siena
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • DVD Player
    • Parking
    • Wi-Fi
    • Private Outdoor...
    • Mountain Views
    • Air Conditioning
    • Satellite TV
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    Location Information
    53027, Montalcino, Province of Siena
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Terrace
    • Internet Access
    • Grill
    • Parking
    • Shared Outdoor Pool...
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    2-room apartment 60 m2, on the upper ground floor, spacious, renovated, beautiful and tasteful furnishings: living/dining room with satellite TV. 1 double bedroom. Kitchenette (oven, X ceramic glass hob hotplates). Shower/bidet/WC. Air-conditioning (extra). Small terrace. Terrace furniture.... View all property information
    Location Information
    53024, Montalcino, Province of Siena
    1 / 73
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Private Outdoor...
    • Internet Access
    • Satellite TV
    • Grill
    • DVD Player
    • Central Heating
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    This villa is set on a hill and overlooks the beautiful countryside as well as the nearby town of Montalcino. If you and your friends are looking for a quiet holiday in Tuscany, this vacation rental is certainly for you. Here you will be able to swim in a private swimming pool, enjoy homemade meals... View all property information
    Location Information
    Montalcino, Province of Siena
    1 / 13
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Air Conditioning
    • Internet Access
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Set on a hilltop next to the ruins of a medieval castle, Villa Castello offers a private, romantic retreat with panoramic views, intimate interiors and resort-worthy amenities. Three bedrooms make this restored farmhouse the perfect size for a family or a few couples, and its location on the... View all property information
    Location Information
    53024, Montalcino, Province of Siena
    1 / 26
    5 of 5 stars (27) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
    other travelers have booked this property
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    • Private Outdoor...
    • Wi-Fi
    • Parking
    • Central Heating
    • Outdoor Dining Area
    • Shared Yard
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Fonte Aulente is a Tuscan farmhouse from the 12th century recently restored and surrounded by beautiful garden-park, 2 km from Montalcino, in a panoramic position with amazing views over the Tuscan hills. The apartment is a part of the old farmhouse, with its own entrance. The apartment can... View all property information
    Location Information
    53024, Montalcino, Province of Siena
    5 of 5 stars Reviewed November 14, 2015
    Everything about our stay at Fonte Aulente exceeded our expectations. Lovely apartment, very comfortable bedroom, and an amazing property. Relaxing on the patio, sipping a glass...
    3 of 5 stars Reviewed November 7, 2015
    Next time we book accommodations other than with a hotel, we will make sure to confirm our arrival time with the owner. We did not hear from Alexandra and assumed that because...
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    1 / 33
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Private Outdoor...
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    This large villa, characterized by its elegant country décor, has airy and spacious rooms. A beautiful, private swimming pool and green, sprawling lawns are ideal for taking in valley views. With both a main house and guest house, this property offers privacy, beauty, and modern conveniences.... View all property information
    Location Information
    Montalcino, Province of Siena