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Holiday Homes and Apartments Montalcino, Italy

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    Travellers to Montalcino are booking September dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 21
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    1 / 20
    5 of 5 stars (1) Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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
    1 / 20
    3.5 of 5 stars (3) Average
    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    53024, Montalcino, Province of Siena
    1 / 82
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    A charming 2 bedroom apartment at Borgo Brunello, like all the apartments it has been very recently decorated and boasts a lovely décor and excellent modern facilities. The 2 bedrooms are spacious doubles and there are also 2 bathrooms with a shower. The living room is a very pleasant place to... View all property information
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    53024, Montalcino, Province of Siena
    1 / 12
    4 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
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    About this property
    Charming and comfortable, villa Manfredi is an ideal spot for a relaxed getaway in the Val d’Orcia area of southern Tuscany. The quiet outdoor spaces and casual interiors of this four-bedroom stone villa invite you to spend lazy days at this home-away-from-home, but if you’d like to explore, it’s... View all property information
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    Montalcino, Province of Siena
    1 / 60
    5 of 5 stars (7) Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    • DVD Player
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    • Mountain Views
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    About this property
    PRIVATE STRUCTURE. The villa is situated on an isolated hill, surrounded by the green Tuscan countryside, in the heart of the Val d'Orcia between San Quirico and Montalcino. Il Giardiniello is an old Leopoldino villa of unique architectural style, with the original structure dating to the 16th... 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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    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 / 13
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    53024, Montalcino, Province of Siena
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    1 / 18
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Shared Garden
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    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 / 15
    5 Bedrooms, Sleeps 12 | Quick View
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    • Terrace
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    • Balcony
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    About this property
    The 300 m2 farmhouse has been beautifully restored. Split into 2 levels, the farmhouse has a huge open living room that has access to the terrace with outdoor furnishings for dining and relaxing. The farmhouse is adorned with fine Tuscan country furnishings.<BR><BR>The farmhouse has beautiful views... View all property information
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    53023, Montalcino, Province of Siena
    1 / 13
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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
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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 / 24
    2 Bedrooms, 25 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Whether you’re gathering to celebrate, reunite, or plan for the future, Borgo Finocchieto offers ample space, luxurious amenities and a beautiful historic setting near Siena. Finocchieto was abandoned in the 1960s after nearly 800 years as a farming village, but it’s been restored to offer 22... View all property information
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    53022, Montalcino, Province of Siena
    1 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Parking
    • Porch
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    • Outdoor Dining Area
    • Private Garden
    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    About this property
    Montosoli is a sixteenth-century villa built on a design by famous Sienese architect Baldassare Peruzzi and is located near the town of Montalcino, in the countryside, among olive groves and vineyards. The place is steeped in history and art, architecture and even already present owners are... View all property information
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    53024, Montalcino, Province of Siena
    1 / 14
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Montebello is located at an altitude of 400 metres above sea level. It stands on its own and benefits of complete privacy. The house is reached by a 4 km country gravel road. This beautiful valley is a nature preserve located in the southernmost part of Tuscany with magnificent views 360 degrees... 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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    • x
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    • x
    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 / 18
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    Location Information
    53024, Montalcino, Province of Siena
    1 / 24
    22 Bedrooms, 25 Bathrooms, Sleeps 44 | Quick View
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    • ?
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    • ?
    About this property
    Whether you’re gathering to celebrate, reunite, or plan for the future, Borgo Finocchieto offers ample space, luxurious amenities and a beautiful historic setting near Siena. Finocchieto was abandoned in the 1960s after nearly 800 years as a farming village, but it’s been restored to offer 22... View all property information
    Location Information
    53022, Montalcino, Province of Siena
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    1 / 23
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | 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 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
    1 / 17
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Once an olive-oil press for the estate of Castiglion del Bosco, Villa Oliviera has been converted to a charming three-bedroom escape for a family or a few couples. With stunning views of the area around Montalcino, breezy living spaces and quiet, private bedroom suites, the villa offers all the... View all property information
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    Montalcino, Province of Siena
    1 / 16
    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    • Satellite TV
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    • Pet-friendly
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    About this property
    Highlights Excellent furnished property set In a dominant position and close to the wonderful Castle of Velona, this property is on the top of a high hill overlooking the vineyards of Brunello. Historians will appreciate that its only 1 km from the magnificent abbey of Sant’Antimo. Independent... View all property information
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    Montalcino, Province of Siena
    1 / 25
    9 Bedrooms, 9 Bathrooms, Sleeps 19 | Quick View
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    • Balcony
    • Internet Access
    • Terrace
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    • Pet-friendly
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    • ?
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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 / 10
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Terrace
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    About this property
    Villa Oddi, featuring 6 bedrooms, is one of the largest Villas of the estate. Its renovation has accentuated the beauty and charm of the residence with a personal touch of its owner, bringing it into the 21st century with state-of-the-art technology, home automation and a private screening theater... View all property information
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    53024, Montalcino, Province of Siena
    1 / 14
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Perched on a hilltop and surrounded by gardens, Villa Alba is a quiet retreat in the heart of Tuscany’s Val d’Orcia region. Located on the Castiglion del Bosco estate, the three-bedroom villa is the perfect size for a family vacation, offering a private, luxurious space, resort-worthy amenities and... 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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    • ?
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    About this property
    Sitting on a spectacular estate of twenty-five acres and boasting stunning views of the hills, Villa Leopolda is a true gem of Tuscany’s beloved countryside. Villa Leopolda is situated in an unspoiled area south of Siena, between the fascinating wine region of Montalcino and the beautiful coast of... View all property information
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    Montalcino, Province of Siena
    1 / 44
    12 Bedrooms, 10 Bathrooms, Sleeps 26 | Quick View
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    About this property
    Up to 27 guests! An enchanted place… FATTORIA PIAN DELL’ASSO is a beautiful 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... View all property information
    Location Information
    20240, Montalcino, Province of Siena
    1 / 76
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
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    • Pet-friendly
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    • x
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    • x
    About this property
    One of the larger apartments at 84sqm, it can comfortably accommodate up to 6 in 3 double bedrooms. It is very attractive in style with elegant neutrals, wooden beams and a pretty pastel blue as a contrasting colour. Everything down to the finest details has been taken care of to make you feel... View all property information
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    53024, Montalcino, Province of Siena
    1 / 40
    Poggio alle Mura
    5 Bedrooms, 5 Bathrooms, Sleeps 16 | Quick View
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    • Internet Access
    • Shared Garden
    • Washer
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    • Pet-friendly
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    • x
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    About this property
    [L A Y O U T] Ground Floor: Entrance hall; large beautifully furnished living room with fireplace and french windows opening onto the terrace and garden; covered dining terrace; dining room also opening to terrace; kitchen. In a separate wing, sitting room and, accessible through a staircase,... View all property information
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    53024, Poggio alle Mura, Montalcino
    1 / 38
    3 of 5 stars (1) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    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
    1 / 14
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    • Smoking allowed
    • x
    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. Does wine tasting in the... View all property information
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    53024, Montalcino, Province of Siena
    1 / 30
    9 Bedrooms, 9 Bathrooms, Sleeps 18 | Quick View
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    • ?
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    About this property
    Once upon a time, Borgo Finocchieto was the center of a medieval Tuscan village. Today, the nine-bedroom manor house near Buonconvento is an up-to-date gathering place, its 14th-century foundations supporting an event space for fifty, teaching kitchen, media room, gym and Jacuzzi. Book the villa... View all property information
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    53022, Montalcino, Province of Siena
    1 / 11
    Private Room, Sleeps 2 | Quick View
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    53027, Montalcino, Province of Siena
    1 / 6
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Central Heating
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    • Pet-friendly
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    • x
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    Location Information
    53024, Montalcino, Province of Siena
    1 / 31
    Private Room, 1 Bathroom, Sleeps 6 | Quick View
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    • Private Garden
    • Washer
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    • Mountain Views
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    • Balcony
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    • Pet-friendly
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    • Smoking allowed
    Location Information
    53024, Montalcino, Province of Siena
    1 / 16
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Located in the Val d'Orcia region south of Siena. This area has been declared a world heritage site by UNESCO. The house is located on a hill with panoramic views over the countryside and only 2 mins from the village of Montisi. Sitting out on your terrazza overlooking your swimming pool soaking up... View all property information
    Location Information
    SIENNA, Montalcino, Province of Siena
    1 / 21
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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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, steam bath, gazebo, barbeque,... View all property information
    Location Information
    53024, Montalcino, Province of Siena
    1 / 6
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    About this property
    Per chi ama trascorrere il proprio tempo libero o le vacanze a Montalcino e godersi lo stupendo paesaggio della Val D'orcia, il Bed and Breakfat Il Sogno del Musicista è il luogo ideale dove fermarsi. Il b&b ha tre ampie camere,con bagno privato, tv e connessione wi fi gratuita. Si trova nel... 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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    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 / 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
    Location Information
    Montalcino, Province of Siena
    1 / 14
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Monteverde is situated on top of the highest hill of a vineyard of 130 acres, this villa is a pleasant house whose owner wanted to maintain the rustic and authentic structure, which dates back to 800?, when the house was used by farmers. Located in the heart of Val d Orcia, the villa and pool... View all property information
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    Montalcino, Province of Siena
    1 / 39
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Patio
    • Washer
    • Private Outdoor...
    • Parking
    • Central Heating
    • Satellite TV
    • Shared Garden
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    A holiday at Poggio di Sopra means good wine, spectacular landscapes and peace. Located on top of a hill, it enjoys a unique 360-degree view. Take in kilometres of vineyards, woods, secular houses, churches and castles. Cypress trees, the very emblem of the Tuscan countryside, stand out amidst the... View all property information
    Location Information
    53024, Montalcino, Province of Siena
    1 / 12
    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Air Conditioning
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Charming and comfortable, villa Manfredi is an ideal spot for a relaxed getaway in the Val d’Orcia area of southern Tuscany. The quiet outdoor spaces and casual interiors of this four-bedroom stone villa invite you to spend lazy days at this home-away-from-home, but if you’d like to explore, it’s... View all property information
    Location Information
    Montalcino, Province of Siena
    1 / 17
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Secure Parking
    • Wi-Fi
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Located inside the medieval walls of Montalcino, this apartment offers ultimate convenience. You are able to walk to the bakery, the grocery store or one of Montalcino's wonderful restaurants to enjoy a delicious meal with some great wine. Private parking is a 2 minute walk for easy access. The... View all property information
    Location Information
    53024, Montalcino, Province of Siena
    1 / 33
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Private Outdoor...
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    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
    1 / 21
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Satellite TV
    • Washer
    • DVD Player
    • Grill
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Anyone with an appreciation for beautiful countryside, wine, and historic sites will love this rustic farmhouse in Southern Tuscany. Formerly a mill, this holiday rental near Montalcino provides privacy and seclusion, yet is very close to one of the jewels of Tuscany, the Abbey of San Antimo.... View all property information
    Location Information
    53024, Montalcino, Province of Siena
    1 / 14
    4 of 5 stars (2) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Internet Access
    • Private Outdoor...
    • Grill
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Friends and family alike will appreciate the seamless combination of this contemporary style with rustic Italian beauty. Renting this farmhouse accommodation also means having panoramic views of the countryside and surrounding vineyards, and a variety of options for lovers of nature, architecture,... 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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    Amenities & Details
    • Washer
    • Private Outdoor...
    • Internet Access
    • Satellite TV
    • Grill
    • DVD Player
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    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 / 27
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Discover a lesser-known side of Tuscany at villa Pieve A Pava. Located in the Crete Senesi area just south of Siena, the six-bedroom property was once its own small borgo, but was recently converted to a luxury villa. Original stone walls, a small chapel and old ruins create a charming atmosphere... View all property information
    Location Information
    Montalcino, Province of Siena