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Holiday Rentals with Pools in Montalcino

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    Travellers to Montalcino are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    71 Matching Rentals in MontalcinoView all 139 rentals
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    Casa Lorenzo: Charming Tuscan house,pool, AC,WiFi1 / 40
    (12)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Podere Ferranino Townhouses- Alberti1 / 49
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Podere Ferranino Townhouses- Cimabue1 / 37
    (5)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Podere Ferranino Townhouses-Fra Angelico1 / 31
    (14)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Mountain Views
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 August 2017
    We had a great time at this property. Clean and light and very good quality facilities in the townhouse. We would all had a relaxing stay and would love to go back some time.
    Reviewed 10 June 2017
    We have just returned from a lovely week at Villa Ferranino, staying in Fra Angelico. The townhouses are beautifully restored and furnished, each with its own peaceful terrace...
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    About this property
    5 Townhouses Ferranino, the original carriage house for the Villa Ferrano, is now transformed into five duplex townhouse apartments. The apartments vary in size from two bedrooms with one bath to four bedrooms with three baths. Each apartment has the original carriage house doorway enclosed with a...
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    Location Information
    53020, San Giovanni d'Asso, Montalcino
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    La Palazzetta di Luca e Flavio Fanti1 / 12
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 July 2018
    Our first time to Italy. Being a Certified Sommelier and WSET advanced diploma I was dying to go to Montalcino and Montepulciano. La Palazzetta is 5 miles from Montalcino city...
    Reviewed 21 May 2017
    We don't know where to start. This was a wonderful location, a small and very quiet town, very accessible (we are traveling by car). This family will welcome you and treat you...
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    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,...
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    53024, Castelnuovo dell'Abate, Montalcino
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    I MELOGRANI II: 3BDR Tuscan villa,view,pool,WiFi1 / 41
    (2)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Grill
    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Private Garden
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 August 2017
    The small village location was a perfect for our visit to the Tuscany area. We were able to use this central location to visit many beautiful villages like Montepulciano, Siena...
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    About this property
    I MELOGRANI II is a section of a villa settled in the heart of Siena countryside :I MELOGRANI I. WHEN THIS PART OF THE HOUSE IS RENTED THE OTHER PART REMAINS CLOSED AND VACANT. This beautiful house is surrounded by a fenced olive grove with private pool (12x5), lawn, stunning view on rolling...
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    53020, San Giovanni d'Asso, Montalcino
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Podere Ferranino Townhouses -Brunelleschi1 / 37
    (11)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    • Washer
    • Cable/satellite TV
    • Mountain Views
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 July 2018
    We stayed in the Duccio townhouse, which Patricia was very transparent in explaining was the smallest but most economical of the townhouses-it was amazing! We are a family of...
    Reviewed 18 July 2017
    We had a wonderful stay. Patricia was so helpful and gracious, and their villas are beautiful, and off the beaten path. It is a very special spot - we hope to come again soon!
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    About this property
    5 Townhouses Ferranino, the original carriage house for the Villa Ferrano, is now transformed into five duplex townhouse apartments. The apartments vary in size from two bedrooms with one bath to four bedrooms with three baths. Each apartment has the original carriage house doorway enclosed with a...
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    53020, San Giovanni d'Asso, Montalcino
    Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 7
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    Fonte Aulente Montalcino1 / 26
    (31)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Parking
    • Central Heating
    • Outdoor Dining Area
    • Shared Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 August 2017
    This is a really gorgeous place to stay. The views could not be better, the garden is eclectic and the pool is warm and inviting. We were slightly unsure whether to book based...
    Reviewed 9 November 2016
    Our family thoroughly enjoyed this stay in Tuscany. My husband and I have been to Italy many times, but this is the first time we brought the kids with us. (Ages 3 and 6...
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    About this property
    Fonte Aulente is a Tuscan farmhouse from the 12th century recently restored and surrounded by beautiful garden-park, 2 km from the center of Montalcino, in a panoramic position with amazing views over the Tuscan hills. The apartment is a part of the old farmhouse, with its own entrance. The...
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    Location Information
    53024, Montalcino, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Country house,Montalcino, Tuscany, TENUTA CANINA1 / 45
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Central Heating
    • Housekeeping Included
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 June 2016
    A lovely comfortable well cared for villa set in a glorious location with a great pool. We went as a family (all adults) and really enjoyed the place. Stunning views of the area...
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    53024, Montalcino, Province of Siena
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    I MELOGRANI I:5 BDR Tuscan villa,view,pool ,WiFi1 / 45
    (14)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Grill
    • Porch
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 August 2018
    Well we always wanted to have a week in a Tuscan Villa in Tuscany and we can finally say we can tick this one off the bucket list. We had a group of 10, 5 couples visit the...
    Reviewed 3 August 2018
    We were a group of 10 adults looking to experience Tuscany. This beautiful villa provided us just that. Located close to the gorgeous little village of San Giovanni d'Asso, the...
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    About this property
    You could not ask for a more special place in which to celebrate an important anniversary or simply spend a vacation with your family and friends ! I Melograni is a beautiful antique,indipendent, 'casale' with a large fenced swimming pool (5x12 mt), 1km away (walking distance!) from the village...
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    Location Information
    53020, San Giovanni d'Asso, Montalcino
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    Piombaia1 / 20
    (5)Very good
    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Parking
    • Wi-Fi
    • Hot Tub
    • Central Heating
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 November 2017
    Piombaia is a dream. Located in the hills of Montalcino in Tuscany it is beautiful, surrounded by a garden and greenery everywhere. The staff is absolutely wonderful and...
    Reviewed 12 July 2017
    This is a really nice place to relax and it is perfect for a couple of days. The place is very well maintained.The rooms/apartments are big and well equipped. The location is...
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    Location Information
    53024, Montalcino, Province of Siena
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    4 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Washer
    • Patio
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Grill
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Le Due Sorelle is a charming farmhouse nested in the tranquillity of the Tuscan countryside. It is located near Montalcino (41 km from Siena) in the land of Brunello, one of Italy’s most famous wine producing areas. The rural surroundings make it a very quiet and peaceful dwelling, the only noises...
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    53024, Poggio alle Mura, Montalcino
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Garden
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    SIENNA, Montalcino, Province of Siena
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lavacchio 12 - Lavacchio1 / 41
    (2)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • 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 19 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...
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    53024, Poggio alle Mura, Montalcino
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    Glorious historic 8BDR Tuscan villa , pool,WIFI,AC1 / 77
    (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
    A beautiful 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, in the Siennese countryside: the comfort to be in a village and the privacy of a place hidden at the sight. Becoming somewhat familiar...
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    53020, San Giovanni d'Asso, Montalcino
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 16
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    Charming Tuscan villa with pool, Montalcino, Siena1 / 24
    (7)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Parking
    • Grill
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 July 2015
    The villa was everything we imagined a villa in Tuscany would be like. It was charming and spacious; the grounds beautiful - cypresses, lavender and of course the inviting pool...
    Reviewed 20 July 2015
    We just got back from a week at Simona and Michael's fabulous villa and I'm already planning another trip! The house itself is absolutely beautiful, exactly what you imagine...
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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. Here you will feel embraced by the fascinating old architecture of the...
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    Location Information
    53024, Montalcino, Province of Siena
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 9
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Private Garden
    • Parking
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The barn is part of a 19th century farm complex. It has been sympathetically renovated to its original beauty by focusing on the conservation of its impressive stone walls, Tuscan-style roofline, and rustic ceiling with beams. The main part of the barn is an open-space loft. The two bedrooms have...
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    58033, Montalcino, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Cozy Collection of Villas in Tuscany1 / 30
    (52)Excellent
    14 Bedrooms, 14 Bathrooms, Sleeps 26 Quick View
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    • Balcony
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Mountain Views
    • Shared Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 July 2018
    We couldn’t be happier with our stay. Matteo was so helpful with every request we had. He arranged for our cooking lesson in our apt that was amazing. The pool was very nice...
    Reviewed 26 October 2017
    We loved our villa, the property, our host and the region. The property was amazing. Wine, olives, lavender and lots of property. Located about 10-15 kilometers from...
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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...
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    53024, Montalcino, Province of Siena
    Holiday Rental House - 14 Bedrooms, 14 Bathrooms, Sleeps 26
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    4 Bedrooms, 5 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Parking
    • Private Outdoor Pool (Unheated)
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casale d’Asso is an ancient 18th-century holiday house, recently restored, on the edge of small Medieval hamlet which has been the property of the Piccolomini family for six hundred years, an ancient family whose name is strongly tied to the Italian Renaissance. Situated in the whereabouts of San...
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    53020, San Giovanni d'Asso, Montalcino
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 7
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    Fornello di Sopra, luxury villa with private pool1 / 57
    (4)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    We went there with my family and another family of friends last July. We all loved the place! It is super comfortable amazingly so for two families with 4 children aged between...
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    About this property
    Set within its own olive grove and surrounded by Brunello vineyards, our villa enjoys one of the best locations in Montalcino, with stunning views of the Val d'Orcia valley (UNESCO World Heritage Site) and within walking distance of the village. Fornello di Sopra is a an ancient stonehouse...
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    Location Information
    53024, Montalcino, Province of Siena
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 11
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    EXTENSIVE VILLA WITH PANORAMIC VIEWS1 / 47
    (7)Excellent
    9 Bedrooms, 9 Bathrooms, Sleeps 18 Quick View
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    • Patio
    • Secure Parking
    • Washer
    • Cable/satellite TV
    • Balcony
    • Central Heating
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 October 2017
    Montelandi is just the most magical tuscan retreat. We stayed here for our honeymoon back in 2000 and have returned many times since so suffice to stays Montelandi holds a...
    Reviewed 9 August 2017
    Our stay at Montelandi was incredible in every way! I so miss the pace of life we experienced in Tuscany, from waking to the sound of the bells as the sheep crossed the fields...
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    About this property
    The living room of Montelandi is large; it has a marble floor, a beamed ceiling and a hooded Tuscan fireplace. The room is comfortably furnished with English upholstery and antiques. Doors from the living room lead onto a covered loggia with arches framing the view across the valley. For...
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    53022, Montalcino, Province of Siena
    Holiday Rental House - 9 Bedrooms, 9 Bathrooms, Sleeps 18
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    Comfort and style in the Siena counrtyside,1 / 21
    (4)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
    • Parking
    • Grill
    • Wi-Fi
    • Central Heating
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 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...
    Reviewed 4 September 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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    About this property
    One of three unique and charming apartments in a XVI century villa situated in the wonderful Siena countryside a few kms from Montalcino, in the natural park of the Val d'Orcia, a precious architectural and natural context. Here you will feel embraced by the fascinating old architecture of the...
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    Location Information
    53024, Montalcino, Province of Siena
    Condo/Apartment - 4 Bedrooms, 5 Bathrooms, Sleeps 9
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • DVD Player
    • Wi-Fi
    • Parking
    • Private Outdoor Pool (Unheated)
    • Outdoor Dining Area
    • Private Garden
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    53020, San Giovanni d'Asso, Montalcino
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Parking
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Mountain Views
    • Air Conditioning
    • Cable/satellite TV
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    53027, Montalcino, Province of Siena
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Villa Spuntone1 / 22
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Grill
    • Washer
    • Parking
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 June 2018
    We’ve been to Tuscany before so looked long and hard to find a villa in Tuscany with a pool and in walking distance of a pretty town and Villa Spuntone exceeded our...
    Reviewed 24 June 2018
    The pictures of Villa Sputone are very accurate and we were most pleased with our one week stay (albeit time passed too quickly)! Sputone is everything you image when thinking...
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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...
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    Location Information
    53024, Montalcino, Province of Siena
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Shared Garden
    • Washer
    • Central Heating
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Outdoor Dining Area
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    53024, Montalcino, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    FONTANELLE1 / 26
    (2)Average
    5 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Terrace
    • Balcony
    • Washer
    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    I checked out a couple of days ago and I am now travelling in Tuscany before flying back to NY... I wish I was still there, the setting of the villa are one of a kind! When...
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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,...
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    53024, Poggio alle Mura, Montalcino
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 16
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    14 Bedrooms, 14 Bathrooms, Sleeps 30 Quick View
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    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect for weddings, business meetings or a quiet getaway, Villa Tolomei is on top of a hill with a spectacular view of the verdant Tuscan landscape. Exercise as well as relax while being transported to forgotten places of exquisite taste.
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    53015, Montalcino, Province of Siena
    Holiday Rental House - 14 Bedrooms, 14 Bathrooms, Sleeps 30
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Internet Access
    • Parking
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    53020, San Giovanni d'Asso, Montalcino
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Patio
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Balcony
    • Cable/satellite TV
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PRIVATE STRUCTURE. Alborata is an old Tuscan farmhouse entirely built in stone, dating to the beginning of the last century and situated not far from the village of San Giovanni d’Asso, in the unmistakable and characteristic countryside of the Crete Senesi. During the recent, careful renovation...
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    Location Information
    53100, San Giovanni d'Asso, Montalcino
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Central Heating
    • Parking
    • Washer
    • Outdoor Dining Area
    • Wi-Fi
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    53024, Montalcino, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Villa Brunello1 / 47
    (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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    Location Information
    53024, Castelnuovo dell'Abate, Montalcino
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Balcony
    • Cable/satellite TV
    • Mountain Views
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    RECEPTIVE STRUCTURE. Le Macine is a farmhouse which the owners finished renovating with great skill in 2011. It dates to the beginning of the 20th century and its name derives from the fact that along the entrance drive are present two antique millstones of an old oil mill. The renovation was...
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    Location Information
    53024, Montalcino, Province of Siena
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Shared Garden
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Outdoor Dining Area
    • Washer
    • Central Heating
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    53024, Montalcino, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 6 Bathrooms, Sleeps 9 Quick View
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    • Grill
    • Cable/satellite TV
    • Central Heating
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Washer
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One of three unique and charming apartments in a XVI century villa situated in the wonderful senese countryside a few km's from Montalcino, in the natural park of the Val d' Orcia, a precious architectural and natural context. Here you will feel embraced by the fascinating old architecture of the...
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    Location Information
    53024, Montalcino, Province of Siena
    Condo/Apartment - 4 Bedrooms, 6 Bathrooms, Sleeps 9
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    ART-HANGAR BY TUSCAN-EXPERIENCE1 / 25
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Housekeeping Included
    • Air Conditioning
    • Wi-Fi
    • Sauna
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 May 2018
    In a perfect location, surrounded by the hills of Tuscany you only imagined exististed in films, our family had a very pleasant stay in the modern, fresh, tastfully decorated...
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    About this property
    TUSCAN-EXPERIENCE is our new brand in which we have different locations from which Art-Hangar probably is the most special one. It is a place for artists, for dreamers, for people with an open mind, in a word: for people daring to leave the beaten path…If design and art makes part of your life,...
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    Location Information
    53024, Montalcino, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Parking
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Farmhouse Rental in Tuscany, Montalcino - Villa Montalcino1 / 46
    (34)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 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...
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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...
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    Location Information
    53024, Montalcino, Province of Siena
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Outdoor Dining Area
    • Central Heating
    • Grill
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    53024, Montalcino, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Villa Giardinello, your dream villa in Tuscany1 / 59
    (1)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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    7 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Terrace
    • Balcony
    • Patio
    • Air Conditioning
    • Parking
    • Grill
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    San Giovanni d'Asso is a small village located in the heart of the Crete Senesi , the unique landscape and spectacular in the south of Siena. Villa Asso offers visitors the perfect blend of classic Tuscan style , fabulous views and contact with nature and the Italian luxury. Located in the heart of...
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    Location Information
    53020, San Giovanni d'Asso, Montalcino
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 16
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    Villa San Giuseppe1 / 47
    (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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    Location Information
    53024, Castelnuovo dell'Abate, Montalcino
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Parking
    • Grill
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ground floor: 1 living kitchen with French windows onto front of house and the garden with pergola 1 family room with TV, comfortable sofas, table for games 1 double bedroom with en suite bathroom (bathtub) First floor: Loggia 1 large living room with fireplace 1 double bedroom with en suite...
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    Location Information
    53024, Montalcino, Province of Siena
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Central Heating
    • Wi-Fi
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Outdoor Dining Area
    • Private Garden
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    53024, Montalcino, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • DVD Player
    • Secure Parking
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    RECEPTIVE STRUCTURE. Casale Montebendico is a gracious, recently restored property. The property is located on the border of Val d’Orcia, area renown for the “Crete Cenesi” and the “Maremma”, a land which extends from the splendid countryside to the Tyrrhenian sea. Situated only a few kilometres...
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    Location Information
    53024, Montalcino, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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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    8 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful property can host up to 16 people with 8 bedrooms and it has an incredible covered/outdoor pool and an enormous garden.
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    Location Information
    53026, Montalcino, Province of Siena
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 16
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Central Heating
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Grill
    • Balcony
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    53024, Montalcino, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Villa with 2 bedroom , private garden and share pool1 / 15
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Grill
    • Parking
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    53020, San Giovanni d'Asso, Montalcino
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Grill
    • Parking
    • Central Heating
    • Cable/satellite TV
    • Waterfront
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The apartment is composed of: ground floor kitchen with dishwasher, oven, refrigerator, living room with double sofa bed, satellite TV and a little room.At upstairs bedroom with the addition of single bed and bathroom with shower and phon.Outside the apartment there is a garden with table, chairs...
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    Location Information
    50051, Montalcino, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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