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Smoking Allowed Holiday Rentals in Cortona

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    Travellers to Cortona are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    125 Matching Rentals in CortonaView all 739 rentals
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    Borgo di Vagli1 / 14
    (7)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Charming top floor Historic Cortona1 / 43
    (9)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Cottage Roccaio Cortona1 / 27
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Charming Cortona villa with private pool (Dardano)1 / 11
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Private Garden
    • Central Heating
    • Washer
    • Parking
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 October 2013
    The pictures do not do Dardano justice. Thoroughly enjoyed our stay, Carla and Paolo amazing hosts . Great spot to explore Siena and Umbria. Fantastic local food market 2...
    Reviewed 20 August 2012
    We stayed at Dardano in July of 2012 and enjoyed a wonderful vacation!. Dardano is beautiful, and very comfortable for an extended family (there were 7 of us). It was a warm...
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    About this property
    Dardano is a deceptively large house, full of atmosphere. It is a simple country home, basic even, but with an elemental charm. You drive up to the house with its ancient stone well and to one side there's a little vine-covered area for shady outdoor eating. The garden is a neatly mown meadow...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    Il Villino di Cortona (private property, private pool, wi-fi, air conditioning)1 / 23
    (44)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Private Outdoor Pool (Unheated)
    • Washer
    • Satellite TV
    • Patio
    • Housekeeping Included
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 June 2017
    This was our second stay at Il Villino di Cortona and we had a wonderful time once again! The villa is rustically comfortable and the little touches made by Michele (the owner...
    Reviewed 1 October 2016
    Just completed s wonderful week's stay at the villa! Michele looked after us very well and his enthusiasm and generosity have no boundaries!A great pool and all amenities on...
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    About this property
    "Il Villino di Cortona", cosy holiday home nestled in the green heart of the Chiana Valley in Cortona (Tuscany), an oasis of peace, tranquility and relaxation. Your holiday in contact with nature ... "Il Villino di Cortona”, is a small holiday home, nestled in the Val di Chiana, in the heart of...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    villa ai cedri1 / 35
    (24)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Wi-Fi
    • Mountain Views
    • Grill
    • Satellite TV
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Seriously. The beautiful views from the porch, the pool and the rooftop deck were beyond beautiful. Exploring the details of the olive trees, picking vegetables and fruit...
    Reviewed 12 September 2017
    The propert was breathtaking! Everything you need is available. The owners are extremely gracious as well.
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    About this property
    "The agriturismo can accommodate 8 - 10 guests. The villa (250sqm) is set on the hillside and, from both the house and the gardens, one can enjoy the spectacular 180 degree views over the Valdichiana valley to the hills of Montepulciano beyond. The colours change throughout the seasons; from the...
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Tuscan Dream Home in Cortona: Pool, WIFI, Magical1 / 27
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Parking
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Grill
    • Wi-Fi
    • DVD Player
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 days ago
    I have been renting homes (holiday villas, houses, apartments, etc) in Italy, Spain, and Greece for over 25 years; sometimes 2-3x/year. I have never experienced a so enjoyable...
    Reviewed 2 November 2016
    A return visit to this perfect location. The villa has everything you need for a relaxing stay. Quiet with beautiful views of the country with Cortona just down the road...
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    About this property
    A dream home just for you - with all the essential mod cons. Pool, lawn, easy indoor/outdoor living, fully equipped kitchen, comfy beds, and essential (free) Wi-Fi. Villa Rosa is nestled into the hillside and within walking distance to Cortona. Couples love it, families love it. A two...
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Private Outdoor Pool (Unheated)
    • Grill
    • Private Garden
    • Shared Garden
    • Wi-Fi
    • Secure Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stone-built farmhouse that has recently been restored with great care and is situated in the hills approximately three kilometres from Cortona. It is divided into two units that they can be rented separately or all. <BR>Encircled by a park of 5000 mq all surrounded with trees of olive. Panoramic...
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Fantastic 5 bedroom Tuscan farmhouse with panoramic views and swimming pool1 / 30
    (8)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Parking
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Balcony
    • Grill
    • Washer
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casa Contea was created from an old farmhouse dating back to 1800, completely renovated. With its stone walls, the courtyard, the wooden beams, you can recreate the atmosphere of the ancient past, combined with the comfort of our days. Its elevated position, surrounded by forest, dominates the...
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 16
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    VillaStefania Old Farmhouse Great View on Cortona1 / 20
    (4)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Grill
    • Wi-Fi
    • Secure Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 June 2016
    We recently returned from a one week stay at Villa Stefania. We had 11 people in our party and rented both apartments. The views of the surrounding area were fabulous and we...
    Reviewed 11 January 2016
    We were 3 Family with several Kids spending three days, including the new year´s eve in the Cortona area. Stefania and her husband was very kind, available and flexible to...
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    About this property
    Stone-built farmhouse that has recently been restored with great care and is situated in the hills approximately three kiliometers from Cortona. The property is situated in a well reserved country place but not remote, very near to all necessity. The Villa is divided into two indipendent units...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casa Contea was created from an old farmhouse dating back to 1800, completely renovated. With its stone walls, the courtyard, the wooden beams, you can recreate the atmosphere of the ancient past, combined with the comfort of our days. Its elevated position, surrounded by forest, dominates the...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 16
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    Casa Maria Laura1 / 30
    (5)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Satellite TV
    • Grill
    • Washer
    • Patio
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 August 2017
    We have been back to to this Villa year after year as it's so perfect. Too be honest it's so good I have delayed writing a review as wanted to keep it secret.The villa is tucked...
    Reviewed 8 May 2017
    The house and the location was wonderful! We spent four days here and only left the house once to go to a vineyard, otherwise we just stayed at the house enjoying the sun...
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Satellite TV
    • Private Garden
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    52044, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Washer
    • Wi-Fi
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    52040, Cortona, Province of Arezzo
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Casa Contea apt La Quercia with views and pool1 / 23
    (5)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Grill
    • Parking
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2017
    Valentina and Ivano were very kind, offering everything we needed including their lovely olive oil. We enjoyed alfresco dinners with incredible sunset views, swimming daily in...
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    About this property
    Casa Contea was created from an old farmhouse dating back to 1800, completely renovated. With its stone walls, the courtyard, the wooden beams, you can recreate the atmosphere of the ancient past, combined with the comfort of our days. Its elevated position, surrounded by forest, dominates the...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Set in the majestic Tuscan hills, six bedroom farmhouse with outdoor pool, private garden and gorgeous views1 / 46
    (16)Excellent
    6 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
    • Parking
    • Satellite TV
    • Wi-Fi
    • Grill
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 June 2015
    I Mandorli is the quintessential Tuscany experience. Rooms are simple and well appointed, one find all he needs in the kitchen, wi fi works well (does not happen all the...
    Reviewed 23 July 2013
    Beautiful location in a silent area with outstanding view. The house and garden is comfortable and well maintained. Well equipped with different amenities and equipment making...
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    About this property
    I Mandorli is an original Tuscan farmhouse. It has been refurbished using traditional materials and techniques to maintain it's rustic character and help stay cool through the long summer days. In autumn and winter you can relax in the spacious living room, in front of the fireplace.<BR>From the...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 10
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    Il Cipresso apt in CASA CONTEA view swimming pool1 / 24
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Garden
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Grill
    • Satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 August 2016
    We stayed there with another couple and had the downstairs apartment with two bedrooms and bathrooms either side of the apartment and then a living area and kitchen in between...
    Reviewed 10 August 2016
    This is a lovely place to stay, once you get there! The access road is long and narrow, dusty when it's dry and muddy when wet, so if you're a bit precious about your vehicle...
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    About this property
    Casa Contea was created from an old farmhouse dating back to 1800, completely renovated. With its stone walls, the courtyard, the wooden beams, you can recreate the atmosphere of the ancient past, combined with the comfort of our days. Its elevated position, surrounded by forest, dominates the...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Central Heating
    • Washer
    • Satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Grill
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Podere Cantalena is an ancient, stone farmhouse recently and wisely restored placed just outside the small hamlet of Cantalena. The old village is set around 15 km far from Cortona and Castiglion Fiorentino, prosperous towns in the lower Valdichiana rich in art and history. Cantalena, placed 600 mt...
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    Location Information
    52043, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tuscan holiday farmhouse villa features stunning grounds and pool, sleeps 41 / 23
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Grill
    • Shared Garden
    • Air Conditioning
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 June 2017
    We were so impressed with the beauty and charm of this little farmhouse. The view was incredible, the grounds gorgeous and the hosts just wonderful! We would stay here again in...
    Reviewed 7 August 2016
    Stunning service and personal treatment .the facility was up to dat and well orgnized .great view and area good for hiking location between all the great cities of tuscny...
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    About this property
    Casa Contea was created from an old farmhouse dating back to 1800, completely renovated. With its stone walls, the courtyard, the wooden beams, you can recreate the atmosphere of the ancient past, combined with the comfort of our days. Its elevated position, surrounded by forest, dominates the...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Water Mill and Millers House Rental in Cortona1 / 13
    (5)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    • Patio
    • Central Heating
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Washer
    • Mountain Views
    • Satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 August 2014
    just got back from the Millers house. I want to go straight back it was amazing !!The owners sister Marianne was fabulous she allowed us to access the property several hours...
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    About this property
    Ideal for a couple wanting a peaceful holiday, the mill was restored last year by local builders and craftsmen using traditional materials. It is set by a stream in 2 acres of grounds and has lovely views from the huge arched windows in the bedroom and kitchen. The private pool with optional...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 7
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    Il Cipresso apt in farmhouse Casa Contea with pool1 / 24
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 August 2016
    we went for 6 days with our extended familiy all tougheter 11 persons include 4 children 2-5 years old .it was emazing the villa was well orgenized clean and the host was very...
    Reviewed 9 June 2016
    This is a lovely location in terms of views and peace and quiet, although if you had a noisy family upstairs, it might not be so blissful. We were lucky to have the whole...
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    About this property
    Casa Contea was created from an old farmhouse dating back to 1800, completely renovated. With its stone walls, the courtyard, the wooden beams, you can recreate the atmosphere of the ancient past, combined with the comfort of our days. Its elevated position, surrounded by forest, dominates the...
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    52044, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedroom Vacation Rental at Appartamento del Borgo1 / 12
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Washer
    • Wi-Fi
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 July 2015
    My teenage children and I were traveling through Italy and Switzerland. Apartmento del Borgo was a dream apartment in the beautiful town of Cortona. Even my kids felt like we...
    Reviewed 31 October 2014
    Apartmento del Borgo has it all. It's convenient to town and parking. It's comfortable and spacious. Enough said? Not quite because the Italian hostess (Lilliana) and her...
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    About this property
    Appartamento del Borgo is situated in the centre of the Etruscan hilltop town of Cortona, near Piazza Garibaldi which is one of the main points of entry to the town. Public parking is just 50 meters away but guests can stop right outside the front door for loading and unloading luggage. The...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casa Il Pergolato is the perfect place to escape from daily life stress and enjoy a moment of relax in the green and in quiet of the Tuscan hills, away from the hustle and bustle of the city. The house (200 square meters) is made out of stone and is full of classic rustic Tuscan style. Outside it...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Fattoria Le Chianacce - La Mucchia. Cortona1 / 37
    (1)Average
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Mountain Views
    • Parking
    • Grill
    • Central Heating
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 July 2016
    This is a beautiful property in the Tuscan countryside about 15 mins from Cortona. Easy to reach local areas BUT the kitchen is ill equipped, there is no microwave or oven...
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    About this property
    Set in the verdant hills of the Valdichiana on the border between the Provinces of Arezzo and Siena the Fattoria delle Chianacce is a typical farmhouse built in the last century. These farms produced some of the very best beef and pork in the area and many continue to do so to the present day. The...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Casa per vacanze-Casa le Celle-1 / 27
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Balcony
    • Wi-Fi
    • Central Heating
    • Satellite TV
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 October 2016
    Beautiful house,lovely location,very peaceful.great hosts,very helpful.Mauro very obliging when we had car trouble,would highly recommend you visit for not only the house and...
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    About this property
    Casa le Celle Le Celle stands next to a small church which dates back to the 1500’s. Part of the house also dates back to that period. It is in a hillside position with various places for sitting and eating outside and the pool area with a lovely view. The property is just 2kms from Terontola, 4kms...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    AGRITURISMO DOMINUS DOMENICO1 / 7
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    52044, Pietraia, Cortona
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Wi-Fi
    • Secure Parking
    • Private Outdoor Pool (Unheated)
    • Private Garden
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    -Completely Renovated Multi-Level Stone Farmhouse -Located Above the Niccone Valley near Cortona, Tuscany with 360 degree views -Three Bedrooms, Three Bathrooms, Gourmet Kitchen -Fifteen Acres of Ancient Olive Groves -Private Swimming Pool, Outdoor Dining, 180 Degree Views Casa Montisole is a...
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    Location Information
    52044, Mercatale, Cortona
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Villa Giarradea - Appartamento Frantoio1 / 19
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • Grill
    • Wi-Fi
    • Mountain Views
    • Private Garden
    • Washer
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Giarradea è una magnifica residenza signorile della fine del 600. Completamente ristrutturata mantenendo l'aspetto esterno originale (la villa è protetta dalle 'belle arti'), la struttura è immersa nel verde della campagna Cortonese. Villa Giarradea è dotata di un ampio parco, spaziosi...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Agriturismo Henni pool sauna jacuzzi panoramicview1 / 34
    (4)Excellent
    6 Bedrooms, 8 Bathrooms, Sleeps 15 Quick View
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    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • Grill
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Old Farmhouse 'Agriturismo Henni' of 1800th totally renovated with antiseismic criteria in 2016, with swimming pool 6mt x 12mt, hydromassage and sauna with panoramic view. The building is situated upper the hill, around the house there is and olive grove, vineyard and wood. The ideal place for...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 6 Bedrooms, 8 Bathrooms, Sleeps 15
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    A residence out of a building of the year 500 sits in front of the towers, the domes the green and the sky of Cortona, a city of ancient origins, often visited by the ex French president Mitterand, and today by the University of Georgia (UGA). During august it is the chosen location for the...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Rustic Tuscan farmhouse in the town of Cortona with gorgeous views, swimming pool, private garden and barbecue1 / 41
    (13)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Washer
    • Grill
    • Wi-Fi
    • Balcony
    • Terrace
    • Private Outdoor Pool (Unheated)
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 January 2017
    I stayed at this beautiful house in Montanare (near Cortona) with my girlfriend and friends, and we had the most amazing holiday ever. The house is authentic, very spacious...
    Reviewed 15 August 2014
    We absolutely enjoyed our stay at casa al campo. The property was perfectly maintained and clean. The pool was spacious which our 4 children loved the most. The proximity of...
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    About this property
    This charming Tuscan Farmhouse is set in a lovely, unspoilt region near the Etruscan hill town of Cortona, amongst olive groves and sunflower fields. Casa Al Campo has 2 acres of unfenced land including its own private vineyard, two terraces and plenty of shaded seating areas and a 12m x 6m...
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    Location Information
    52040, Cortona, Province of Arezzo
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Secure Parking
    • Private Garden
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stone-built farmhouse that has recently been restored with great care and is situated in the hills approximately three kilometres from Cortona. It is divided into two independent units that they can be rented separately or all. <BR>Encircled by a park of 5000 mq all surrounded with trees of olive....
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Stunning Tuscan villa with five bedrooms, private1 / 27
    (1)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Patio
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Satellite TV
    • Wi-Fi
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This imposing two-storey villa is set in stunning grounds, which have the quality of a park. Here you can feel sheltered and secluded in each separate area, including that of the pool. The spaciousness of both the exterior and interior easily accommodates a large group. Modern comforts have been...
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Agriturismo Poggio del Fabbro1 / 19
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Parking
    • Outdoor Dining Area
    • Private Outdoor Pool (Unheated)
    • Grill
    • Private Garden
    • Wi-Fi
    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    L'agriturismo Poggio del Fabbro è situato in località San Pietro a Dame, frazione del comune di Cortona nella montagna cortonese, a 20km dalla città, in una posizione tranquilla e isolata tra le verdi montagne ad un'altezza di 700m slm al confine tra Toscana e Umbria. Si trova al centro di...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    VILLA FRANCESCA Cortona1 / 36
    (1)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Parking
    • Grill
    • Air Conditioning
    • Porch
    • Outdoor Dining Area
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Property DescriptionVilla Francesca is a beautiful villa located in the countryside in the green hills on the border between Tuscany and Umbria, a few kilometers from Cortona, a quaint town rich in history and offers shops and services of all kinds. At about 1 km you will find a restaurant and a...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Agriturismo Villa Giarradea1 / 23
    (5)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Mountain Views
    • Washer
    • Shared Garden
    • Secure Parking
    • Private Garden
    • Wi-Fi
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 16
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    15 Bedrooms, 10 Bathrooms, Sleeps 30 Quick View
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    • Shared Indoor Pool
    • Hot Tub
    • Washer
    • Ocean Views
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 15 Bedrooms, 10 Bathrooms, Sleeps 30
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    5 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Private Garden
    • Satellite TV
    • DVD Player
    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cortona Tuscan Villa with pool – this property consists of three aristocratic 19th century villas, occupying a large estate abundant with chestnut woods and olive groves, within walking distance of the medieval walled town of Cortona, jewel of Valdichiana. The main villa and the independent annex...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Secure Parking
    • Washer
    • Private Outdoor Pool (Unheated)
    • Grill
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In the verdant countryside in the heart of Tuscany close to Cortona, is located Villa Capezzine, which is a cosy retreat for your holidays in complete quiet and relaxation. The villa is bright and luminous furnished in keeping with the typical Tuscan style but with modern touches such as the fully...
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    Location Information
    52044, Pietraia, Cortona
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Secure Parking
    • Grill
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Balcony
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Barbara is situated on the top of a hill kissed by the sun and caressed by the stars. Skilfully restored to keep its ancient charm untouched, it attracts with its solemn dignity and with its remarkable environmental landscaping. Completely furnished following the original Tuscan style, with...
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    Location Information
    52040, Cortona, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Casa Contea was created from an old farmhouse dating back to 1800, completely renovated. With its stone walls, the courtyard, the wooden beams, you can recreate the atmosphere of the ancient past, combined with the comfort of our days. Its elevated position, surrounded by forest, dominates the...
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    52044, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Casa colonica Leopoldina1 / 29
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    ANTICO PALLAIO1 / 31
    (1)Excellent
    3 Bedrooms, 8 Bathrooms, Sleeps 9 Quick View
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    • Wi-Fi
    • Satellite TV
    • Sauna
    • DVD Player
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 October 2015
    The photos on Trip Advisor DO NOT give this place justice. Things got off to a great start with the warm and friendly welcome from Sergio and his family.Fabulous / extensive...
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    tipical old house, swimming pool, wifi, tv satelite,bbq, volley ball field, pétanque field, mini tennis field. <BR>beatiful wiew over the chiana valley. all the old charme of tuscany. <BR>4bedroom, 4 bathroom<BR>Located in the village of Ossaia ( 3 km from Cortona), the property can be used for...
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 8 Bathrooms, Sleeps 9
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    Casa Anna,  cosy holiday apartment Cortona1 / 20
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Outdoor Dining Area
    • Washer
    • Private Garden
    • Mountain Views
    • Shared Garden
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 August 2017
    We went to Casa Anna for ten days. We are a family of four members. Everything was fantastic: the owners are very friendly, nice and gentle; the house is a very nice country...
    Reviewed 21 July 2016
    I live very near Casa Anna and our friends have stayed there now on 2 occasions during Christmas last year and a festa for our sons birthday party this year.Those who stayed...
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    About this property
    Casa Anna is just a few km from the Etruscan-Medieval town of Cortona and offers a genuine and healthy holiday. It is situated in the hills area around Cortona (only 5 km from SR71 and 10 km from Cortona), in the heart of a small rural hamlet, and ensures guests real quiet ( 750 mt over the sea...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Casina via Iannelli1 / 22
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    Pet friendly
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    About this property
    Casina via Iannelli è una piccola abitazione medioevale (quattordicesimo secolo) dotata di tutti i confort moderni.Si trova nel centro storico di Cortona in una delle strade più caratteristiche della città che si presenta ancora pressoché immutata dal medioevo. Il vicolo è sicuramente uno dei più...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Washer
    • Parking
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    52044, Montecchio, Cortona
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Internet Access
    • Washer
    • Balcony
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Ginestra is the ideal place for nature lovers and those who want to relax. The villa is located on the hills surrounding the beautiful Etruscan town of Cortona, one of the most beautiful hamlets in Italy and famous throughout for its beauty and quality of life. The villa is elegant and...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Il Coniglio Bianco1 / 14
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Villa Maesta del Sasso1 / 35
    (1)Excellent
    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    • Mountain Views
    • Washer
    • Air Conditioning
    • Grill
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2017
    Ever since seeing 'Under the Tuscan Sun, I've dreamt of visiting Tuscany with family and friends and staying in a villa. This was the first time I've rented a vacation home...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 14
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
    • Mountain Views
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled in the rolling Tuscan hills on the border between Tuscany and Umbria, in a very peaceful location full of meadows, farmland and forests, stands Villa Fiordaliso, an old farmhouse built in the late 1800s and now completely renovated by the owners who have tried to keep the characteristics of...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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