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Vacation Rentals in Montalcino, Italy

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    1 / 19
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    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 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Balcony
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    53024, Montalcino, Province of Siena
    1 / 30
    Poggio alle Mura
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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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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    Poggio alle Mura, Montalcino
    1 / 21
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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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 / 21
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    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
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    53024, Montalcino, Province of Siena
    1 / 50
    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 / 28
    Poggio alle Mura
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    [L A Y O U T] Ground Floor: Large living/dining room with fireplace; kitchen; small kitchen; dining room; sitting room; all the above rooms open onto courtyard; double bedroom bathroom. First Floor: Living room; two sitting rooms; four double bedrooms with en-suite bathroom (one of which with... View all property information
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    53024, Poggio alle Mura, Montalcino
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    1 / 21
    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • DVD Player
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    53024, Montalcino, Province of Siena
    1 / 73
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
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    Montalcino, Province of Siena
    1 / 21
    4 Bedrooms, 6 Bathrooms, Sleeps 9 | Quick View
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    • Grill
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    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.<BR>Here you will feel embraced by the fascinating old architecture of... View all property information
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    53024, Montalcino, Province of Siena
    1 / 34
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Villa with private swimming pool in the town of Montalcino, just opposite the famous fortress dating back to the year 1300, in the heart of Orcia Valley. The property is located just a few steps away from the traditional shops of the village, known all over the world for its excellent “Brunello'... View all property information
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    53024, Montalcino, Province of Siena
    1 / 31
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Beautiful, stone, independent villa with private pool situated on the hills surrounding the charming town of Montalcino renowned for Brunello wine. This villa is part of a farming estate and it is surrounded by beautiful vineyards producing excellent wines. The interiors are welcoming and... View all property information
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    Montalcino, Province of Siena
    1 / 11
    Private Room, Sleeps 3 | Quick View
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    53027, Montalcino, Province of Siena
    1 / 29
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Villa with private swimming pool in the town of Montalcino, just opposite the famous fortress dating back to the year 1300, in the heart of Orcia Valley. The property is located just a few steps away from the traditional shops of the village, known all over the world for its excellent “Brunello... View all property information
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    Montalcino, Province of Siena
    1 / 25
    4 Bedrooms, 7 Bathrooms, Sleeps 8 | Quick View
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    • Grill
    • Porch
    • DVD Player
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    • Pet-friendly
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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 / 52
    4.5 of 5 bubbles (34) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • DVD Player
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    • Central Heating
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    • Pet-friendly
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    • ?
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    • Smoking allowed
    • ?
    About this property
    This beautiful villa for rent in Tuscany is in a great location - within walking distance of the town of Montalcino and is an ideal starting point for excursions around southern Tuscany. You'll love exploring Siena and the other surrounding towns, but you'll also want to spend plenty of time at... View all property information
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    53024, Montalcino, Province of Siena
    1 / 16
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • Smoking allowed
    • x
    About this property
    Archi is a splendid independent apartment of about 130m2 which can host 4+2 persons. It's composed of 2 bedrooms (1 double + 1 twin), 2 bathrooms (1 with bathtub and shower + 1 with shower) and a huge open plan that serves as living room with 2 large couches (1 of the which can be turned into a... View all property information
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    53024, Montalcino, Province of Siena
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    1 / 24
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Satellite TV
    • Terrace
    • Private Garden
    • Wi-Fi
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    • Air Conditioning
    • Balcony
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    • Pet-friendly
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    • x
    • Smoking allowed
    • x
    Location Information
    53024, Montalcino, Province of Siena
    1 / 29
    7 Bedrooms, 7 Bathrooms, Sleeps 18 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Villa Cerretalta is in a wonderful position on a small hill surrounded by Brunello vineyards, within the national park of Val D Orcia. The property is set between the cities of Montalcino and San Quirico D Orcia (both are about 10 km away), yet in few minutes you can reach the little town of... View all property information
    Location Information
    53024, Montalcino, Province of Siena
    1 / 30
    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    This completely independent property with 4 bedrooms, 3 baths, and 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... View all property information
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    Montalcino, Province of Siena
    1 / 30
    Poggio alle Mura
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
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    • Pet-friendly
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    • Smoking allowed
    • ?
    About this property
    This exceptionally beautiful property is located in a very quiet and spectacular position, just a few kilometres away from the lovely village of Montalcino. The views from the house are outstanding taking in the Val d’Orcia and Crete Senesi, considered by many as the most beautiful areas of... View all property information
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    Poggio alle Mura, Montalcino
    1 / 41
    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Pet-friendly
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    • x
    • Smoking allowed
    About this property
    This completely independent property with 4 bedrooms, 3 baths, and 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... View all property information
    Location Information
    53024, Montalcino, Province of Siena
    1 / 14
    4 of 5 bubbles (2) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Washer
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    • 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
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    53024, Montalcino, Province of Siena
    1 / 24
    2 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Balcony
    • Terrace
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    • Private Garden
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    Location Information
    53024, Montalcino, Province of Siena
    1 / 30
    Poggio alle Mura
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • ?
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    • ?
    About this property
    Villa Lorian is a grand property located amidst mature cypresses, rolling hills and the vineyards of Montalcino from which Brunello di Montalcino wine, renowned as one of the best ones in the world, is produced. Built in the 1700s as one of the manors of the neighbouring Argiano Castle, the... View all property information
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    Poggio alle Mura, Montalcino
    1 / 21
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • DVD Player
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    • 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
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    53024, Montalcino, Province of Siena
    1 / 42
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Beautiful, stone, independent villa with private pool situated on the hills surrounding the charming town of Montalcino renowned for Brunello wine. This villa is part of a farming estate and it is surrounded by beautiful vineyards producing excellent wines. The interiors are welcoming and... View all property information
    Location Information
    53024, Montalcino, Province of Siena
    1 / 30
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Beautiful and characteristic villa with a swimming pool located on the slopes of the well-known town of Montalcino. The hills where the rental is situated are home to the vines that produce the famous wine “Brunello di Montalcino”. The fantastic panoramic views from the villa stretch across... 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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    • DVD Player
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    • Hot Tub
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    • Pet-friendly
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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
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    53022, Montalcino, Province of Siena
    1 / 15
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Outdoor Dining Area
    • Central Heating
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    • Pet-friendly
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    • x
    About this property
    Pozzo is an elegant and bright apartment of about 80m2 that can accommodate 4 persons. There are 2 bedrooms, a large bathroom with a shower cabinet and a nice living room with a fully equipped kitchen. The apartment is situated on the ground floor and suitable for handicapped people. Both bedrooms... View all property information
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    53024, Montalcino, Province of Siena
    1 / 20
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • ?
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    • ?
    About this property
    Bibbianello is a classic stone farmhouse on the edge of the historic town of Montalcino, home of the famous 'Brunello' wine. The house stands in a splendid and tranquil spot with a view of Montalcino and of the surrounding countryside. It has been perfectly renovated and furnished with taste,... 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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    • x
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    • x
    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 / 31
    Private Room, 1 Bathroom, Sleeps 6 | Quick View
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    • Private Garden
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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 / 13
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Washer
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    • Satellite TV
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    • Secure Parking
    • Private Garden
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    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
    1 / 10
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • DVD Player
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    • Pet-friendly
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    • ?
    • Smoking allowed
    • x
    About this property
    Situated within the UNESCO-listed Val d’Orcia Natural Park, Villa Oddi is one of the 10 Villas of Rosewood Castiglion del Bosco. . It is a recently and lovingly renovated property that features all of the traditional elements of villa design - terra cotta floors, tile walls, and high ceilings with... View all property information
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    Montalcino, Province of Siena
    1 / 38
    3 of 5 bubbles (1) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | 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. This wine country... View all property information
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    53024, Montalcino, Province of Siena
    1 / 31
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    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
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    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 (approx. 2023 hecatres). This combination makes this place an idyllic retreat. Castiglion del Bosco is one of the... View all property information
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    Montalcino, Province of Siena
    1 / 22
    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Beautiful stone built villa rental accommodation (230 m2) situated approx. 500 m from the historical centre of Montalcino, ideal starting point for excursions to the spa resorts at Bagno Vignoni, the Orcia valley, Monte Amiata, the Maremma, Siena and the nearby wine producing estates for the... View all property information
    Location Information
    53024, Montalcino, Province of Siena
    1 / 24
    4 Bedrooms, 25 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • ?
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    • Smoking allowed
    • ?
    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
    1 / 30
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Beautiful, stone, independent villa with private pool situated on the hills surrounding the charming town of Montalcino renowned for Brunello wine. This villa is part of a farming estate and it is surrounded by beautiful vineyards producing excellent wines. The interiors are welcoming and... View all property information
    Location Information
    Montalcino, Province of Siena
    1 / 21
    4 of 5 bubbles (1) Very good
    Private Room, 4 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Central Heating
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    Location Information
    53024, Montalcino, Province of Siena
    1 / 23
    Poggio alle Mura
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    This delightful farmhouse is located inside the Villa Torrigiani estate, one of the most luxurious and spectacular villas of the Lucca area, which dates back to the second half of the XVI century. The structures of the villas in this area are true works of art: large spaces, gardens, porticos,... View all property information
    Location Information
    Poggio alle Mura, Montalcino
    1 / 71
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Parking
    • Private Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    Location Information
    53024, Montalcino, Province of Siena
    1 / 31
    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    This completely independent property with 4 bedrooms, 3 baths, and 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... View all property information
    Location Information
    Montalcino, Province of Siena
    1 / 24
    5 Bedrooms, 25 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • DVD Player
    • Hot Tub
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    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
    1 / 11
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Parking
    • Wi-Fi
    • Private Outdoor...
    • Mountain Views
    • Air Conditioning
    • Satellite TV
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    Location Information
    53027, Montalcino, Province of Siena