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Montalcino Luxury Holiday Homes

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    AU$1,672 Average
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    Travellers to Montalcino are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    21 Matching Rentals in MontalcinoView all 142 rentals
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    14 Bedrooms, 14 Bathrooms, Sleeps 30 Quick View
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    FONTANELLE1 / 26
    (4)Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Studio, 8 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Washer
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    53024, Poggio alle Mura, Montalcino
    Holiday Rental House - 8 Bathrooms, Sleeps 16
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    Villa Brunello1 / 29
    (1)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Washer
    • Grill
    • Central Heating
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 September 2017
    Rented this villa in 2004. Off the beaten track, located in a vineyard it was a truly idyllic setting. The villla itself was roomy and comfortable. There were only 2 of us but...
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    About this property
    This comfortable, cosy villa nestles on a sheltered incline among gently rolling hills. These are covered in Brunello wine-producing vineyards, which border the lower pool-terrace. The San Giuseppe winery, from which the house takes its name, is situated nearby. Wonderful countryside views can be...
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    53024, Castelnuovo dell'Abate, Montalcino
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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    Villa San Giuseppe1 / 29
    (1)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Central Heating
    • Grill
    • Balcony
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 July 2017
    We stayed a week in this gorgeous Villa. This Villa is surrounded by its own vineyard. It meant lovely walking after dinner.It was beautifully appointed, cosy & luxurious...
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    About this property
    This comfortable, cosy villa nestles on a sheltered incline among gently rolling hills. These are covered in Brunello wine-producing vineyards, which border the lower pool-terrace. The San Giuseppe winery, from which the house takes its name, is situated nearby. Wonderful countryside views can be...
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    53024, Castelnuovo dell'Abate, Montalcino
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning property with outdoor private pool can host up to 12 people and is in the lovely Val D'Orcia area, in Tuscany. It boasts 6 elegant bedrooms and all the necessary amenities to provide the best of comfort to its guests.
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    53026, Montalcino, Province of Siena
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    8 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Washer
    • Parking
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    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...
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    Location Information
    53024, Poggio alle Mura, Montalcino
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 16
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    Studio, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Washer
    • Grill
    • Wi-Fi
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    53024, Poggio alle Mura, Montalcino
    Holiday Rental House - 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Central Heating
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: Located in a place that almost seems unchanged and untouched by time, villa oozed Montalcino charm, having been built on a travertine stone in Sienese style and given its first lease of life as a farm owned by Rossini Martelli that’s still standing and has been for over 70...
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    53024, Castelnuovo dell'Abate, Montalcino
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: Villathis property-Val D'Orcia Located in the beautiful area of Val D'Orcia, Villathis property is a private renovated house with swimming pool for 8 people set on a 15 hectare wine estate. From the villa you will have a panoramic view of the Val D'Orcia, historical Montalcino...
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    53024, Castelnuovo dell'Abate, Montalcino
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    8 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    • Internet Access
    • Air Conditioning
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: Description: Overlooking the spectacular Tuscan countryside Villathis property is a splendid home inside the charming Tuscan hilltown ofthis property d'Asso. Located near a medieval castle, the villa was built in the 16th century. The property has been carefully renovated,...
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    Location Information
    53020, San Giovanni d'Asso, Montalcino
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 16
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    8BDR Historic villa in the  Crete Senesi walking to a village : view,pool,garden1 / 40
    (11)Excellent
    8 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Grill
    • Air Conditioning
    • Washer
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2017
    For our annual family meeting, I chose villa " La Consuma" . It has been a great success. Villa La Consuma is beautiful, convivial, located in a superb spot. It is...
    Reviewed 5 November 2015
    I recently stayed here with 11 of my friends for our 50th birthdays. When we walked into the home all I could say was, "Wow!" The location was amazing among the hills...
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    About this property
    An old historic family house with a large hanging garden and fenced swimming pool (6x12) nestled in the middle of a tiny village, San Giovanni d'Asso (Community of Montalcino), in the Siennese countryside: the comfort to be in a village and the privacy of a place hidden at the sight. The extensive...
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    Location Information
    53020, San Giovanni d'Asso, Montalcino
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 16
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Internet Access
    • DVD Player
    • Grill
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: Main Description : this property 10 is located 9 km (6 mi) from Montalcino, Italy and only 10 km (6 mi) from Montalcino in the tourist area 'Grosseto - Maremma'. Holiday rental this property 10 is a beautiful stone building that includes private pool and WiFi internet. The...
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    53024, Poggio alle Mura, Montalcino
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Internet Access
    • Grill
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: Description: A cheerful house this property 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...
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    Location Information
    53024, Montalcino, Province of Siena
    Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Villa Giardinello, your dream villa in Tuscany1 / 59
    (2)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 11 Quick View
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    • Private Outdoor Pool (Unheated)
    • Patio
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Hot Tub
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Il Giardinello offers simplicity, wellness and every comfort from a pleasant holiday retreat in the heart of Val d’Orcia, UNESCO world heritage. A typical Italian Cypress tree-lined dirt road welcomes you to the villa, set in the municipality of Montalcino. Whether you are a wine connoisseur...
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    Location Information
    53024, San Giovanni d'Asso, Montalcino
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 11
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    Studio, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid 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....
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    Location Information
    Montalcino, Province of Siena
    Holiday Rental House - 5 Bathrooms, Sleeps 12
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    Villa Lorian1 / 53
    (1)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Grill
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 November 2018
    We have spent here two marvellous weeks and Meri, the house maid, has been always available to support us : especially with breakfast. We had a great time. Salogi (our agency...
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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...
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    Location Information
    53024, Poggio alle Mura, Montalcino
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Lavacchio 12 - Lavacchio1 / 41
    (2)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 July 2015
    Lavacchio is synonymous with paradise in the minds of my family. Extraordinarily beautiful, in the middle of a vineyard, perfectly located, each room stunningly designed and...
    Reviewed 20 August 2014
    The Villa is roomy and nicely furnished, and the swimming pool,accessed through the vineyard, was a great feature--especially for the grandkids.My only suggestion is that the...
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    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
    Location Information
    53024, Poggio alle Mura, Montalcino
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    Le Vigne1 / 12
    (2)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Housekeeping Included
    • Wi-Fi
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you’re an oenophile who dreams of a Tuscan vacation, villa Le Vigne is for you. Located on a working wine estate near Montalcino, the renovated 18th-century stone farmhouse is surrounded by vineyards, and guests can arrange to tour the on-site wine cellar and have a private tasting. If you’re...
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    Location Information
    53024, Montalcino, Province of Siena
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • DVD Player
    • Internet Access
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: Main Description : Conveniently located 8 km (5 mi) from Montalcino, Italy in the tourist area 'Grosseto - Maremma' and only 12 km (7 mi) from Montalcino. Vacation rental this property 12 is a lovely stone building that includes air conditioning, private pool and WiFi...
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    Location Information
    58045, Poggio alle Mura, Montalcino
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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