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Holiday Rentals in Cortona

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    Travellers to Cortona are booking December dates now. Secure your holiday home today, and have the perfect trip.
    All 923 Rentals in Cortona
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    Villa Magnolia1 / 66
    (3)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Newly renovated Villa in Tuscany, spacious suites, Salty pool, outstanding views1 / 31
    (43)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Villa Borgo delle Spighe- A nice country estate set in a wonderful scenario1 / 35
    (4)Excellent
    7 Bedrooms, 7 Bathrooms, Sleeps 19 Quick View
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    • Private Outdoor Pool (Heated)
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 June 2017
    The whole picture of the house and landscape was perhaps best. We the family - parents, grandparents and children enjoyed this entirety. The pool - little extra fee for heating...
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    About this property
    Located at the foot of Cortona, Borgo delle Spighe lays in the heart of Valdichiana, one of the most evocative scenery in Tuscany. This large red-brick farmhouse, typical of the rural tradition of these valleys, has been completely remodeled and now it can easily accommodate groups up to 14...
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    52044, Cignano, Cortona
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 19
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    Villa Della Valle1 / 33
    (1)Average
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    • Central Heating
    • Private Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Della Valle is a charming villa in stone, in true Tuscan style, situated in an elevated position (500 m asl) on the high hills of Cortona, on the border between Tuscany and Umbria. At Villa Della Valle you will experience a holiday in close contact with nature, giving you a break from the...
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    Location Information
    52044, Teverina, Cortona
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    Cortona - 780011 / 30
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 May 2017
    We stayed for 3 nights to allow us time in Cortona before moving on through Tuscany, the apartment was all that we expected and more. The pictures do show what's on offer but...
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    About this property
    Casa Zeni Signorelli is a little gem located in the heart of the ancient Etruscan town of Cortona, a short walk from all the services and the beauty of the town but at the same time in a peaceful and quiet place. You will be immersed in an elegant and charming atmosphere, in a tasteful environment...
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    52044, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Agriturismo Henni pool sauna jacuzzi panoramicview1 / 34
    (5)Excellent
    6 Bedrooms, 8 Bathrooms, Sleeps 15 Quick View
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    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Grill
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 August 2018
    We are on our final night here and just don't want to leave. None of the photos do justice to the area, or the property. The problem is that every view of and from the property...
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    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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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 6 Bedrooms, 8 Bathrooms, Sleeps 15
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    Villa di Max1 / 29
    (1)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 11 Quick View
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    • Washer
    • Parking
    • Grill
    • Cable/satellite TV
    • Central Heating
    • Private Garden
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 July 2017
    Villa Max is a tastefully decorated home with high quality furnishings, that shows care and pride, not the typical furnishing vacation rental. The access road at first daunting...
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    About this property
    Max Weinberg, the long-time drummer for Bruce Springsteen's E Street Band, opens the doors of his marvellous holiday house situated in the gentle verdant hills between Tuscany and Umbria. Max and his wife bought their Tuscan home in 2000, succumbing to an infatuation with Italy after a family...
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    52044, Mercatale, Cortona
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 11
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    Il Bocciolo at La Lombarda1 / 57
    (11)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Central Heating
    • Grill
    • Parking
    • Washer
    • Balcony
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 August 2018
    We had a brilliant holiday at Il Bocciolo and enjoyed everything Tuscany had to offer. Nina and Peter were excellent hosts who were attentive prior to and during our stay...
    Reviewed 5 October 2017
    This was the first time we have stayed away from a city and absolutely loved our experience. Peter and Nina were fabulous hosts and La Lombarda is beautiful. The apartment was...
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    About this property
    La Lombarda, our beautifully restored traditional 18th century Tuscan farmhouse is ideally placed within easy reach of Tuscany and Umbria's wealth of art and cultural centres. Cortona, nestling in its hillside just 20 minutes away, with its medieval cobbled lanes is a delightful and atmospheric...
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    52044, Cortona, Province of Arezzo
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    La Mimosa at La Lombarda1 / 46
    (11)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Balcony
    • DVD Player
    • Parking
    • Grill
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Central Heating
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 September 2018
    We were looking for a romantic getaway in a part of Tuscany we hadn't yet explored. Not only did we find that, but we became friends with our hosts who couldn't have been nicer...
    Reviewed 10 September 2018
    Absolutely amazing stay at la mimosa. Couldn’t have asked for better hosts than Nina and peter, they were extremely welcoming and very knowledgable about the area. Apartment is...
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    About this property
    La Lombarda, our beautifully restored traditional 18th century Tuscan farmhouse is ideally placed within easy reach of Tuscany and Umbria's wealth of art and cultural centres. Cortona, nestling in its hillside just 20 minutes away, with its medieval cobbled lanes is a delightful and atmospheric...
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    Location Information
    52040, Cortona, Province of Arezzo
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Washer
    • Central Heating
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Balcony
    • Grill
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Due to its scenic location Villa Oleandro offers an unrivaled view over the town of Cortona and the whole Valdichiana. The villa has been carefully restored by the owners who have managed to keep the uniqueness of this beautiful stone farmhouse alive, which, with its rustic Tuscan style, will make...
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    52044, Montalla, Cortona
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Villa La Pergola1 / 31
    (7)Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Mountain Views
    • Washer
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 May 2015
    Wonderful charming old mill house converted to a guest home. Comfortable beds, spacious accomodations. Great hosts. Kitchen is first class. After a full day of touring we...
    Reviewed 16 September 2014
    the house, the people, the owners, the swimming pool, Cortona, the food, the wine all was so beautiful and good , but i have to say, that we had a lot of horse flies and we...
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    About this property
    Villa La Pergola is an authentic private villa in Tuscany, very close to the Etruscan town of Cortona. La Pergola is situated in a cosy village consisting of two other villas each with private swimming pool. The patio, decorated with elegant garden furniture, has a scenic view over the...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Casa del Balestriere In Centro Storico1 / 13
    (9)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 June 2018
    The apartment is very spacious, quiet, comfortable, clean, and, as others have pointed out, recently and very nicely renovated. The price for the apartment is extremely...
    Reviewed 27 January 2017
    I spent four weeks at Luca's rental in May and June last year. It was perfect. It was close enough to town to be able to easily walk to every restaurant, the grocery store...
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    52044, Cortona, Province of Arezzo
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Appartamento Luna1 / 31
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • DVD Player
    • Wi-Fi
    • Central Heating
    • Grill
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 October 2017
    The view can't be beat and the location was perfect for us. This apartment will make you feel like you're an Italian. The Italian family who owns the apartment live on sight and...
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    About this property
    Appartamento Luna is a beautiful ground floor studio with 2 bedrooms and two bathrooms in a panoramic position in Cortona; situated on the cone hill of Cortona, an Etruscan town of rare charm and beauty, it will give you an unrivaled view over the Valdichiana which stretches right in front of you...
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    52044, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Grill
    • Private Outdoor Pool (Unheated)
    • Central Heating
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Eleonora will give you a unique stay in a location characterized by quiet and privacy and incomparable views over the beautiful city of Cortona, whose views will accompany you while relaxing in the garden, enjoying the air of the Tuscan countryside in the morning or when you lean out the...
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    52044, Montalla, Cortona
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Villa Alma: the pool is a dream1 / 81
    (4)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Hot Tub
    • Sauna
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you are looking for an exclusive location where time seems to stand still, welcome to Villa Alma. Situated on the Cortona hill, with a breathtaking view on the valley, this villa will ensure you an unforgattable vacation. A charming cherry tree-lined drive takes you to the newly restored...
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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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)
    • Cable/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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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Casa dell'Ermanna1 / 53
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Balcony
    • Wi-Fi
    • Terrace
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 January 2016
    This well-located apartment in the center of Cortona offers Old World charm with modern comfort and convenience. The interior is imaginatively and artistically decorated. Of...
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    52044, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Splendid Villa by Olive Groves and Vinyards at Fontocchio on Cortona1 / 58
    (6)Excellent
    8 Bedrooms, 7 Bathrooms, Sleeps 17 Quick View
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    • DVD Player
    • Central Heating
    • Private Outdoor Pool (Unheated)
    • Grill
    • Washer
    • Patio
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 August 2015
    We’ve rented Villa Fontocchio through terretrusche.com, and right from the very beginning, they did a wonderful job. By the accident we were cheated before and they really tried...
    Reviewed 29 July 2014
    I made arrangements to lease Villa Fontocchio through terretrusche.com, and right from the very beginning, they did a wonderul job. I want to especially thank Michela from...
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    About this property
    Villa Fontocchio is situated at the foot of the Etruscan town of Cortona, in an enchanting location among vineyards and olive trees. Thanks to the careful restoration works, the charm of this typical Tuscan farmhouse, with its wooden beams and terracotta floors, has been preserved. A big gate leads...
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 17
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    Villa Conca D'oro1 / 41
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Private Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • DVD Player
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 June 2018
    This was the perfect week in Tuscany. A beautiful farmhouse renovated to ensure complete comfort. Nice bedrooms, bathrooms, a well stocked kitchen, and comfortable living room...
    Reviewed 5 June 2018
    The location is both remote yet so close to Cortona and the other wonderful hill top towns of Tuscany. It was so easy to visit Assisi, Arezzo, Perugia, Siena and other...
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    About this property
    Superb independent property perfectly nestled among the rolling hills surrounding the ancient Etruscan town of Cortona, Villa Conca D'oro is the ideal place to spend a holiday in the spirit of of nature, beauty and relaxation. Only 5 km from the historic center of Cortona and 1.5 km from the small...
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    52044, Cortona, Province of Arezzo
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Views Views Views!  Incredible Property. Incredible Price.1 / 14
    (14)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Mountain Views
    • Parking
    • Cable/satellite TV
    • Washer
    • Central Heating
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 June 2018
    Easy to find this apartment, nearby the Duomo Place. We arrived by car, so parking outside was free and easy access to the apartment on foot.Well equipped, renovated, great...
    Reviewed 6 October 2017
    What a wonderful location in the heart of Cortona. This apartment had everything we needed - comfort, clean, and beautiful! We couldn't have enjoyed the location any more...
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    About this property
    The Perfect Tuscany VacationThis beautiful penthouse apartment of approximately 55 m2 (600 sq.ft.) has classic Italian beamed ceilings, a wood burning fireplace for cozy winter nights, and unforgettable Tuscan views that everyone dreams of. The completely renovated and decorated separate living...
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    52044, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Tuscan Dream|Private|Pool|Walk to Cortona|FreeWiFi1 / 57
    (14)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Balcony
    • Wi-Fi
    • Grill
    • Mountain Views
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 October 2017
    Wow! We were very impressed with finding this gem in Cortona. The views are spectacular from this property only drawback is that we were only there for a few days and were out...
    Reviewed 29 March 2017
    The remodelled historic house is the perfect spot to relax and unwind. Open plan living areas with an amazing outlook over the Tuscan countryside. The close proximity to town...
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    About this property
    A dream home just for you. We created our home in Cortona with all the essential mod cons. Music, kitchen, comfy beds, and of course with the essential pool and (Free) Wi-Fi. Villa Rosa is nestled into the Cortona (Tuscan) hillside with only a few minutes drive to the historic hill top town or...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Washer
    • Balcony
    • Central Heating
    • Patio
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Secure Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa La Rugantina, a typical Tuscan stone farmhouse finely restored, lies in the open countryside surrounded by wheat and sunflowers fields. The property boasts extended gardens and 6 large bedrooms: 5 doubles and a family room that sleeps 4. The whole house then can comfortably accommodate up...
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    Location Information
    52044, Creti, Cortona
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Appartamento Maccari is located in the heart of the historic center of the ancient Etruscan town of Cortona, a place rich in history and charm, and one of the oldest medieval towns of Italy. Located just a few steps away from the squares and main streets of the town, yet in a secluded and quiet...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    7 Bedrooms, 6 Bathrooms, Sleeps 13 Quick View
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    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Sauna
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Del Sole is the perfect place for an unforgettable experience! This magnificent property is situated in the heart of the hills of Cortona, in an extremely panoramic position that will offer your eyes all the spectacular splendor of the lush Tuscan countryside. The villa has spacious and...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 13
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    Casa Contea apt La Quercia with views and pool1 / 23
    (6)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Parking
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 July 2018
    We really fell for this place when we were exploring Tuscany vacation rentals via Tripadvisor and it was everything we hoped for and more! The view was amazing and the house and...
    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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    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
    • Cable/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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    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
    • Cable/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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    CHARMING COTTAGE NEAR CORTONA, GARDEN, DINING PATIO, OLIVE GROVE, AC,WiFI1 / 57
    (23)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Mountain Views
    • Housekeeping Included
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 June 2018
    We so enjoyed our week here in 2016, it was always somewhere we had to return to. We managed it this year and our stay more than lived up to expectations. It is a truly charming...
    Reviewed 7 November 2017
    This beautiful and spotlessly clean cottage was perfect for 4 people. David was most helpful and had lots of information to share with us. It is in a charming village called...
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    About this property
    Charming small villa in pretty medieval village about 25 minutes from Cortona. The house is set in large gardens and olive grove with views of the surrounding hills. A/C and Wi-Fi throughout. Very comfortable and really fully equipped. Mint condition. Lovely Garden setting with dining patio...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Charming top floor Historic Cortona1 / 43
    (9)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Private Garden
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 August 2017
    Myself and 3 other ladies came to Italy to celebrate two birthdays. We stayed at Paulo and Daniella's charming villa in Cortona; it was beautiful!The bedrooms were spacious with...
    Reviewed 1 August 2017
    The accommodations were outstanding. And Daniela and Pablo were a pleasure to deal with. They provided excellent recommendations for places to visit and restaurants. Truly...
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    About this property
    Three double rooms each with private bathrooms and showers, dining room, kitchen. In the garden a cabin with a wood oven, barbecue, table and chairs and deckchairs. From june 15 to august 31 the price per night includes air conditioning. In the kitchen ceiling fan. The spacious apartment 'La...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Central Heating
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You wont believe the quality in this beautifully restored 2 bedroom apartment situated in the very heart of the Historical Center of Cortona. As soon as you walk through the ancient restored doors you will be immediately struck by the undeniable elegance. Enter into a large living room with high...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Charming 2 bedroom apartment in restored Tuscan farmhouse with pool located in historic Cortona1 / 60
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Wi-Fi
    • Patio
    • Washer
    • Grill
    • Central Heating
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 January 2017
    La Lombarda is an ideal spot for total peace, tranquillity and relaxation; it is exactly as described.With just 3 rented out guest accommodations and another for hosts Nina and...
    Reviewed 3 December 2014
    Nina and Peter were great. We went to see how olives are pressed and made into oil and it was a good learning experience.
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    About this property
    La Lombarda is our charmingly restored traditional 18th century Tuscan farmhouse in the comune of Cortona. La Stufa is a charming two bedroom apartment with wood-beamed ceilings and terracotta floors. There is a comfortable sofa and two armchairs in the lounge, TV, DVD, books, games and videos for...
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    Location Information
    52040, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Imola is located in the countryside at the foot of the beautiful Etruscan city of Cortona, which is only a few minutes away. The property has recently been renovated, creating a rich environment of comfort, with a strong modern character at the same time conservative since we can find many...
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    Location Information
    52044, Montecchio, Cortona
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Central Heating
    • Washer
    • Grill
    • Private Outdoor Pool (Unheated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The villa is the perfect place to spend a holiday immersed in the sweet Tuscan landscape. The villa is located just 500 meters (15 minute walk) from the heart of the historical center of the famous Etruscan town of Cortona, now one of the most beautiful and famous in Italy, and is located in one of...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    6 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Parking
    • Grill
    • Washer
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New, large, comfortable house with 2 apartments 'Casa Imola', built in 1956, renovated in 2015, surrounded by fields. House Equipment: central heating system, air conditioning, washing machine (private use). Access & Parking: parking by the house. All-season motor access to the house....
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    Location Information
    52044, Montecchio, Cortona
    Condo/Apartment - 6 Bedrooms, 3 Bathrooms, Sleeps 10
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    Beautiful Villa with Pool 10 Minutes from Cortona1 / 24
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Wi-Fi
    • Grill
    • Mountain Views
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 September 2017
    We stayed at Casaletto for one week on our first trip to Italy and we wish we stayed longer. Casaletto's stone and tile architecture is stunning, the spacious rooms are...
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    About this property
    There is nothing like Tuscany in the morning. Imagine waking up to the sound of birds chirping, the smell of freshly brewed coffee and the golden Tuscan sun warming your face as you sit outside in your Villa beside your private pool. Your biggest decision for the day….do you swim before...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Cortona, Tuscan Retreat, Serene, WiFi, Pool, Bliss1 / 50
    (15)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Mountain Views
    • Balcony
    • Washer
    • Air Conditioning
    • Patio
    • Private Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 September 2018
    I cannot tell you how often I close my eyes and wish I was back 'Under the Tuscan Sun' in Cortona.As we drove down the Cyprus lined lane and pulled into Villa Rosa, all our...
    Reviewed 17 April 2017
    The house at Cortona is so beautiful, well appointed and welcoming, we felt we'd become part of the wonderful Tuscan landscape and way of life.
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    About this property
    Your holiday to Tuscany is special. You want a home that will provide you with the essential pool and of course the internet. You want to be close to the amenities but far enough away for privacy, seclusion and relaxation. We would love to welcome you to Villa Rosa which has all these features...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Parking
    • Mountain Views
    • Private Outdoor Pool (Unheated)
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you are looking for an exclusive location where time seems to stand still, welcome to Villa Alma. Situated on the Cortona hill, with a breathtaking view on the valley, this villa will ensure you an unforgattable vacation. A charming cherry tree-lined drive, which flanks the swimming pool and the...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A splendid country residence immersed in the green hills of Val di Chiana, a few kilometers from Montepulciano and from Cortona. The brick house, built at the end of the 17th century, was constructed on the antique ruins of a brickyard and the traces of the centuries are still evident. Set into the...
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    Location Information
    53045, Pietraia, Cortona
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    8 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Private Garden
    • Sauna
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    tipical old house, swimming pool, wifi, tv satelite,bbq, volley ball field, pétanque field, mini tennis field. beatiful wiew over the chiana valley. all the old charme of tuscany. 4bedroom, 4 bathroom Located in the village of Ossaia ( 3 km from Cortona), the property can be used for different...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 16
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Grill
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very beautiful, cosy villa 'Toppicchio', surrounded by trees. In a hamlet 17 km from the centre of Cortona, 40 km from the centre of Arezzo, 115 km from the centre of Firenze, in a quiet, elevated position, 100 m from the edge of the forest, in the countryside. Private: property (fenced), terraced...
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    Location Information
    52044, Teverina, Cortona
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Parking
    • Private Outdoor Pool (Unheated)
    • Washer
    • Internet Access
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Centoia is an ideal home with swimming pool for your holidays in Tuscany. The Villa has just been renovated, situated in a quiet and panoramic position overlooking the city of Cortona. The house has 1 hectare of fully fenced garden and private and exclusive private pool. Internally it is well...
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    Location Information
    52044, Pietraia, Cortona
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Casa Zeni - Berrettini1 / 19
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Washer
    • Wi-Fi
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 September 2017
    We usually back to Casa Zeni to spent our holidays . Charming, clean and beautiful hotel. The gentleness of the owners and the centric place in Toscana always help our holidays...
    Reviewed 10 April 2017
    Amazing greeting out of hours and great coms prior.We were delayed with a collision but this did not cause a problem at all.What an amazing quality conversion.I wish we had...
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    About this property
    In the heart of the old town of Cortona, a step away from all services and beauties of this hill town, but at the same time in a peaceful and quiet place, you will be immersed in an elegant and charming atmosphere, tastefully set and equipped with all amenities: Appartamento Berrettini. The...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    CASA MIA A CORTONA  a real tuscan emotion in the heart of the town1 / 22
    (34)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Mountain Views
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 May 2018
    We stayed 5 days at Casa Mia a Cortona and really enjoyed it. After a hair raising journey through the winding Chianti hills .... getting used to driving a stick shift ... we...
    Reviewed 29 December 2017
    If you want to close your front door, and walk out into your wonderful neighborhood feeling like you live in Cortona, this is the place for you! Your grocery market is around...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A splendid country residence immersed in the green hills of Val di Chiana, a few kilometers from Montepulciano and from Cortona. The brick house, built at the end of the 17th century, was constructed on the antique ruins of a brickyard and the traces of the centuries are still evident. Set into the...
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    Location Information
    53045, Pietraia, Cortona
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Washer
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A few kilometers from the ancient Etruscan town of Cortona, in a flat and easily accessible location, Casa I Pini is the perfect location for those who want to spend a holiday in Tuscany close to all amenities. The structure is a portion of an old Leopoldina, a typical building of this area, the...
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    Location Information
    52044, Montecchio, Cortona
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Grill
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A few steps from the ancient Etruscan town of Cortona, only 1 Km from the center, Villa Vittoria sits surrounded by orchards and cultivated fields in a strategic position from which you can enjoy breathtaking views of Val di Chiana. This beautiful villa is immersed in the stunning Tuscan...
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    Location Information
    52044, Montalla, Cortona
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A splendid country residence immersed in the green hills of Val di Chiana, a few kilometers from Montepulciano and from Cortona. The brick house, built at the end of the 17th century, was constructed on the antique ruins of a brickyard and the traces of the centuries are still evident. Set into the...
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    Location Information
    53045, Pietraia, Cortona
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Imagine waking up in the heart of historical Cortona in this beautiful apartment overlooking romantic Piazza Signorelli. For those “Under the Tuscan Sun” fans, you will recognize the Teatro immediately. Every turn is magical and it is hard to believe that it has managed to retain its charm and...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you are looking for the best views in Cortona, look no further! Perched on the hillside, only a few minutes’ stroll to the historical centre sits Torreone House. From every window, you will be mesmerized by views of the most beautiful vineyards, olive groves and sunsets that are almost...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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