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Vacation Rentals in Montalcino, Italy

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    Travelers to Montalcino are booking September dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 25
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    1 / 26
    5 of 5 stars (28) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    1 / 24
    5 of 5 stars (7) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 9 | Quick View
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    1 / 21
    5 of 5 stars (4) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 9 | Quick View
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    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.<BR><BR>Here you will feel embraced by the fascinating old architecture of... 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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    1 / 15
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    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 / 16
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
    1 / 67
    5 of 5 stars (4) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Private Yard
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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. <BR>Minnie's Cottage... View all property information
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    53024, Montalcino, Province of Siena
    5 of 5 stars Reviewed 1 week ago
    Delicious hosting, fantastic Place, Nice Village vith two delicious Restaurant walking distant. Strategic location colse to The main attraction of The area
    5 of 5 stars Reviewed June 13, 2016
    Minnie's Cottage is clean and very homely. My friend and I stayed there for three nights as we were to attend a wedding at the Castel Banfi about 10 minutes drive away. The...
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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 / 19
    5 of 5 stars (1) Excellent
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Wi-Fi
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    • Children's Pool
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    • x
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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
    Location Information
    53024, Montalcino, Province of Siena
    5 of 5 stars Reviewed May 15, 2016
    Very nice studio apartment in a pretty garden. Everything we needed for our five day stay. Comfortable bed , great shower and kitchen facilities. Property has a pool but too cool...
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    1 / 20
    5 of 5 stars (13) Excellent
    Sant'Angelo in Colle
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    Location Information
    53024, Sant'Angelo in Colle, Montalcino
    5 of 5 stars Reviewed August 10, 2015
    I bumped into this lovely cottage few months ago while I was searching for a relaxing comfy place right in the heart of Montalcino to spend few days away from everything but...
    5 of 5 stars Reviewed June 21, 2015
    A charming cottage straight out of a Frederico Fellini movie, in an idyllic setting. It was like having our own Tuscan summer house, complete with the rustic kitchen table, the...
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    1 / 19
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
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    • Pet-friendly
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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
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    53024, Montalcino, Province of Siena
    1 / 24
    5 of 5 stars (1) Excellent
    12 Bedrooms, 12 Bathrooms, Sleeps 24 | Quick View
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    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
    5 of 5 stars Reviewed May 30, 2016
    We stayed at Brizio for 5 nights and loved every moment thoroughly. It was our first visit to Italy and the experience of staying at a wonderfully modern, comfortable farm stay...
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    1 / 17
    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    53024, Montalcino, Province of Siena
    1 / 41
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Private Yard
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    53024, Montalcino, Province of Siena
    1 / 71
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    53024, Montalcino, Province of Siena
    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    53024, Montalcino, Province of Siena
    1 / 11
    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 / 15
    5 of 5 stars (48) Excellent
    14 Bedrooms, 14 Bathrooms, Sleeps 26 | Quick View
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    • Balcony
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    • Mountain Views
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    About this property
    PLEASE NOTE: THE PROPERTY IS DIVIDED INTO EIGHT SELF CONTAINED APARTMENTS, EACH SLEEPING 2-4 PEOPLE. THIS LISTING IS FOR A SINGLE APARTMENT. IF YOU CANNOT FIND YOUR DESIRED AVAILABILITY, PLEASE CONTACT US AND WE WILL TRY TO FIND A SUITABLE ARRANGEMENT. RATES VARY ACCORDING TO APARTMENT SIZE AND... View all property information
    Location Information
    53024, Montalcino, Province of Siena
    5 of 5 stars Reviewed July 13, 2015
    A perfect place to recover from the excitement and craziness of the big cities amidst stunning scenery, food and wine. Matteo went out of his way to make sure we had a wonderful...
    5 of 5 stars Reviewed September 20, 2014
    This place is amazing and Matteo made our experience unforgettable. His recommendations where perfect and he was really helpful. We were lucky to visit in September so Matteo...
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    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 3 | Quick View
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    53024, Montalcino, Province of Siena
    1 / 19
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Private Yard
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    • Shared Yard
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    • Pet-friendly
    • Child-friendly
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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
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    1 / 10
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
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    • DVD Player
    • Hot Tub
    • Balcony
    • Air Conditioning
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    • Pet-friendly
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    • x
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    53024, 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 / 50
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Mountain Views
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    • x
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    • x
    About this property
    Enjoy winelovers' paradise in Montalcino from the beautifully renovated and spacious apartment - Casa Brunello di Montalcino - in the 17th century building with some nice original pieces, combining the traditional Tuscan countryside look with modern high-quality furniture and design. From the 30... View all property information
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    53024, Montalcino, Province of Siena
    1 / 21
    4 Bedrooms, 6 Bathrooms, Sleeps 9 | Quick View
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    • Grill
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    • Pet-friendly
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    • ?
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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 / 47
    Castelnuovo dell'Abate
    5 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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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... View all property information
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    53024, Castelnuovo dell'Abate, Montalcino
    1 / 39
    5 of 5 stars (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • x
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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
    1 / 52
    4.5 of 5 stars (34) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • DVD Player
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    • Pet-friendly
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    • ?
    • ?
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    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
    Location Information
    53024, Montalcino, Province of Siena
    4 of 5 stars Reviewed August 18, 2014
    Outstanding location and home. It was great having a pool (even though it was above ground, fabric, four feet deep and had a manual cover you had to put back every time you used...
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    1 / 19
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    With a winery in the estate this property is the perfect place for anyone who loves wine and nature. Country house 'Montalcino sunset', surrounded by vineyards. 3 km from the centre of Montalcino, in a sunny, elevated position, in the countryside. For shared use: terraced garden (fenced), swimming... View all property information
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    53024, Montalcino, Province of Siena
    1 / 24
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Satellite TV
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    • x
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    53024, Montalcino, Province of Siena
    1 / 15
    Private Room, 1 Bathroom, Sleeps 4 | Quick View
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    • Shared Yard
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    Location Information
    53027, Montalcino, Province of Siena
    1 / 23
    Poggio alle Mura
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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
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    Poggio alle Mura, Montalcino
    1 / 30
    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • ?
    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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    53024, Montalcino, Province of Siena
    1 / 30
    7 Bedrooms, 6 Bathrooms, Sleeps 18 | Quick View
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    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 7 bedroom, 6 bath 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... View all property information
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    Montalcino, Province of Siena
    1 / 30
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Description: A cheerful house 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... View all property information
    Location Information
    53024, Montalcino, Province of Siena
    1 / 30
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Description: A farmhouse with stunning views 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... View all property information
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    53024, Montalcino, Province of Siena
    1 / 29
    7 Bedrooms, 7 Bathrooms, Sleeps 18 | Quick View
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    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 / 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
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    53024, Montalcino, Province of Siena
    1 / 30
    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
    Location Information
    53024, Montalcino, Province of Siena
    1 / 11
    Castelnuovo dell'Abate
    6 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Description: Notes for this villa Security Deposit is 500 euro to be paid locally in cash upon arrival, unless different arrangements have been made at time of booking. The Security Deposit will be returned upon departure, minus any breakages. All prices are per week for the villa only. Villas are... View all property information
    Location Information
    53024, Castelnuovo dell'Abate, Montalcino
    1 / 22
    Poggio alle Mura
    7 Bedrooms, 6 Bathrooms, Sleeps 16 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    This striking medieval farmhouse is located in the Grosseto Maremma area in a commanding position overlooking the vineyards of Montecucco with views of Montalcino and Mount Amiata. The farmhouse is divided into 5 independent apartments which have recently been renovated and tastefully furnished.... View all property information
    Location Information
    Poggio alle Mura, Montalcino
    1 / 20
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Shared Outdoor Pool...
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    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
    Location Information
    Montalcino, Province of Siena
    1 / 30
    Poggio alle Mura
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    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
    Location Information
    53024, Poggio alle Mura, Montalcino
    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
    53024, Montalcino, Province of Siena
    1 / 30
    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    Amenities & Details
    • Shared Outdoor Pool...
    • Air Conditioning
    • Internet Access
    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
    53024, Montalcino, Province of Siena
    1 / 30
    Poggio alle Mura
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    Amenities & Details
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-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... View all property information
    Location Information
    Poggio alle Mura, Montalcino
    1 / 30
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    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
    53024, Montalcino, Province of Siena
    1 / 26
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • 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
    Location Information
    53024, Montalcino, Province of Siena
    1 / 21
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Secure Parking
    • Central Heating
    • Outdoor Dining Area
    • Terrace
    • Wi-Fi
    • Washer
    • Shared Outdoor Pool...
    • Balcony
    Suitability
    • 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
    5 of 5 stars Reviewed July 11, 2016
    Very cofortable!! Very good hospitality!! We stayed 3 couple and every couple has own bathroom and room, since it is a big hose , it felt like private rooms in a hotel!! It was...
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    1 / 20
    5 of 5 stars (1) Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    Amenities & Details
    • Washer
    • Internet Access
    • Grill
    • Shared Outdoor Pool...
    • Air Conditioning
    • Balcony
    • Satellite TV
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    (Minimum of one week rental required) Minimum rental one week rental Saturday to Saturday except for urban apartments. Villa Brunello 1 is as close to the universal dream of a perfect Tuscan country retreat as can be found! Set amongst a haven of natural tranquility and beauty, surrounded by twenty... View all property information
    Location Information
    53024, Montalcino, Province of Siena
    5 of 5 stars Reviewed October 4, 2015
    We stayed a group of 3 couples. It was the most wonderdful experience you can imagine. The villa is beautiful, well appointed , with the most beautiful views. There is a working...
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    1 / 12
    Castelnuovo dell'Abate
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Amenities & Details
    • Parking
    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool...
    • Wi-Fi
    • Private Yard
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    On the hill with view on the S.Antimo Church, 100 meters from the medieval village of Castelnuovo dell'Abate, is the country house La Palazzetta with 3 separate apartments; everyone has room, kitchen and bathroom. Outside the property have large open spaces: a garden with barbecue area and gazebo,... View all property information
    Location Information
    53024, Castelnuovo dell'Abate, Montalcino