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Holiday Rentals with Pools in Cortona

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    Travellers to Cortona are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    540 Matching Rentals in CortonaView all 754 rentals
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    Tuscan villa with private pool and garden and breathtaking countryside views1 / 20
    (10)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Borgo Valecchie, Renaissance Villa set in the medieval Hamlet, Cortona Tuscany1 / 35
    (51)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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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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    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 12 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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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 6 Bedrooms, 8 Bathrooms, Sleeps 15
    Il Bocciolo at La Lombarda1 / 57
    (11)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • 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
    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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    52044, Teverina, Cortona
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Mountain Views
    • Grill
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Private Garden
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Teresa is a pretty villa with a wonderful view on Cortona valley, completely renovated and equipped with every comfort. Very near to the nice town of Cortona, this wonderful structure overlooks on a breathtaking landscape and it is situated short distance from a small village, which you can...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    ANTICO PALLAIO1 / 31
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Wi-Fi
    • Cable/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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    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 - 3 Bedrooms, 4 Bathrooms, Sleeps 11
    Villa Del Sole1 / 64
    (1)Very good
    7 Bedrooms, 5 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
    Reviewed 13 August 2019
    We had a lovely stay at Villa Del Sole. The location, just a stone's throw away from Cortona, is great and the views absolutely breathtaking.The communal areas were...
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    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, 5 Bathrooms, Sleeps 13
    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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    Amenities & Details
    • 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 beautifully 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...
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    Location Information
    52040, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Beautiful Renovated Tuscan Private Home|Pool|Walk to Cortona|WiFi|Magical1 / 71
    (14)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Washer
    • Balcony
    • Wi-Fi
    • Grill
    • Mountain Views
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 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 30 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
    8 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • 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
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Wi-Fi
    • Central Heating
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Grill
    • Washer
    • Cable/satellite TV
    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, Teverina, Cortona
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    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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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    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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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    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
    6 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Washer
    • Mountain Views
    • Air Conditioning
    • Private Garden
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Il Giardino di Silvana is a typical Tuscan stone house located on an evocative hilly position, a few steps away from the prestigious Santa Maria Nuova church and walk to town. The property preserves its rustic style with cotto flooring, wood beamed ceilings and Pietra Serena stone walls along...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 11
    Stunning Villa Rosa - Heaven in Tuscany |Relax|Pool|WiFi|Walk to Cortona|Private1 / 53
    (15)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Mountain Views
    • Patio
    • Grill
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 October 2018
    Villa Rosa sits comfortably nestled above the high Tuscan hillside town of Cortona.The views, to say the least, are spectacular. The bright and warm mid-September week my wife...
    Reviewed 20 September 2018
    Perfect if you want to relax, unpack, read books, self cater and enjoy the village life and surrounds. Excellent for day trips to Florence, Sienna, Montepulchiano, Arezzo...
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    About this property
    With essential private pool and (Free) Wi-Fi, Villa Rosa is nestled into the Tuscan hillside within a few minutes drive or leisurely walk into vibrant Cortona. Couples love it, families love it. It is heaven. A two bedroom, two bathrooms, fully furnished beautiful private house for your Tuscan...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    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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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 16
    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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    Location Information
    52044, Montalla, Cortona
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    2 Bedrooms, 4 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Grill
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    It 'a beautiful cottage completely restored, was once a barn and a tobacco warehouse. now has 2 bedrooms, a lounge, a kitchen, 2 bathrooms and a dining room that can become an extraordinary study. It has a swimming pool, a large garden, a bocce court, private parking. about 3 km from Cortona, and...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 4
    Villa Il Giardino di Diana1 / 26
    (10)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Grill
    • Mountain Views
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 January 2019
    We stayed at Villa IL Giardino do Diane in July 2018 and held our wedding reception there after getting married in Cortona. The villa, grounds and local surroundings are all...
    Reviewed 15 July 2018
    The villa was in pristine condition very clean and bedrooms very spacious. It was very comfortable with plenty of room in all areas and beautiful outdoor areas with stunning...
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    About this property
    Located in a beautiful hilly position, Il Giardino di Diana is a genuine stone and brick farmhouse surrounded by the characteristic Tuscan hills with olive groves and vineyards. Both the pool and the attic, boast spectacular panoramic views of the countryside with Cortona's hill in the distance....
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    Location Information
    52044, Montecchio, Cortona
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    Dream Location Private House  -Pool WIFI Walk to Cortona -Bliss in Tuscany1 / 72
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
    • Mountain Views
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Patio
    • Grill
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 March 2017
    We have visited Villa Rosa twice, and have had a wonderful time on both occasions. Set in olive groves under the walls of a Medici fortress, and a 20 minutes walk from the...
    Reviewed 29 March 2017
    Villa Rosa is a favourite destination where I have stayed a number of times and will keep going back. It is an ideal combination of rural idyll and urban convenience, being...
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    About this property
    A two bedroom, two bathrooms, fully furnished beautiful private house for your Tuscan holiday. Complete with the essential private sparkling pool and Wi-Fi connection, Villa Rosa is nestled into the Tuscan hillside within a few minutes drive or leisurely walk into vibrant and bustling Cortona....
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Villa Magnolia1 / 72
    (3)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Grill
    • Washer
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 June 2018
    It is tricky to find a property with enough beds and baths to accomodate 2 families - but Villa Magnolia did just that and more! This farmhouse has been beautifully remodeled...
    Reviewed 2 November 2016
    We were a group of 8 staying at Villa Magnolia. The property is up in the surrounding mountains of the city of Cortona with a beautiful view of the valley below. The...
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    About this property
    Immersed in the green hills surrounding the ancient Etruscan town of Cortona, which has always been considered one of the most beautiful hamlets in Italy, the country house Villa Magnolia will offer you an unforgettable experience. The facility can accommodate up to 12 people, the interior and...
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    Location Information
    52044, Teverina, Cortona
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Il Cipresso apt in CASA CONTEA view swimming pool1 / 24
    (4)Excellent
    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 23 January 2019
    Have stayed here on three occasions - it's a superb setting. Be warned it's a steep old drive up to the house(s) but it's worth it for the view, privacy, pool and the place...
    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...
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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
    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
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
    • Washer
    • Central Heating
    • Private Outdoor Pool (Unheated)
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    • Grill
    • Cable/satellite TV
    • Mountain Views
    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 - 6 Bedrooms, 5 Bathrooms, Sleeps 14
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
    • Mountain Views
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Teresa is a pretty villa with a wonderful view on Cortona valley, completely renovated and equipped with every comfort. Very near to the nice town of Cortona, this wonderful structure overlooks on a breathtaking landscape and it is situated short distance from a small village, which you can...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    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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    Location Information
    52044, Montalla, Cortona
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Villa Vittoria1 / 58
    (1)Excellent
    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
    Casa Gorgacce1 / 25
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Wi-Fi
    • Central Heating
    • Mountain Views
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 September 2019
    Lovely rustic house,ample space for 6 people.everything you could need in a house is there.fab outside space with a lovely pool. Surrounding area is beautiful with a small...
    Reviewed 6 February 2016
    this is a great place. lots for children to do around the pool and the BBQ and the table tennis. We preferred exploring perugia and cortona, wine tours and olive oil tasting. At...
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    About this property
    Casa Gorgacce is an old stone farmhouse with lots of character beautifully converted with all modern comforts. It has a private garden and pool, complete privacy yet with great access and only a few kilometres from 2 lively villages; Meratale di Cortona and Lisciano Niccone where there are shops,...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Cottage Roccaio Cortona1 / 27
    (7)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Central Heating
    • Mountain Views
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 September 2019
    The grounds of the house are ideal. The outdoor table is in a perfect spot for dining even in the rain. The view is wonderful. However, know that the road leading to this home...
    Reviewed 8 September 2018
    We came in a heat wave and enjoyed having the pool. We were able to do day trips all around Tuscany. We met the owner in town and traveled along to a dirt road up to the cottage...
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    About this property
    The search for a warm and welcoming Tuscan abode is over. Cottage Cortona Roccaio is a stone-clad home adjoined to another occupied house on a small family estate encircled by olive groves. From here, the alluring hill towns of Tuscany and Umbria are within easy reach. The vibrant, medieval hill...
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    Location Information
    52043, Cortona, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Charming Cortona villa with private pool (Dardano)1 / 21
    (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 14 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
    Set in the majestic Tuscan hills, six bedroom farmhouse with outdoor pool, private garden and gorgeous views1 / 46
    (17)Excellent
    6 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
    • Parking
    • Cable/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. From the...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 10
    Cortona villa in beautiful Tuscan countryside1 / 20
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Central Heating
    • Wi-Fi
    • Parking
    • Grill
    • Washer
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 June 2017
    Our time is coming to an end at the wonderful San Silvestro!Cortona and Camucia has provided an excellent base in order to explore the surrounding Tuscan and Umbrian...
    Reviewed 5 September 2014
    We have had a wonderful time at San Silvestro. The villa is a beautiful farmhouse set in a vineyard and a place of tranquility. On our arrival we were greeted with fresh...
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    About this property
    The sitting room has an old open fireplace and impressive, ancient wooden beams. Two comfy sofas are a nice modern addition! The dining room is authentic Italian 1950s decor under more seriously ancient ceiling beams. The atmosphere at San Silvestro is one of homely country simplicity. There's an...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Private Outdoor Pool (Unheated)
    • Parking
    • Washer
    • Patio
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Central Heating
    Suitability
    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, Teverina, Cortona
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Camilla is located in the hills near the Etruscan city of Cortona. It is a charming holiday home. Long ago it was an old farmhouse. The holiday home has been tastefully restored by the owners. The interior of the villa is a combination of modern and rustic Tuscan furnishings and atmosphere....
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    Location Information
    52044, Montalla, Cortona
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Washer
    • Air Conditioning
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Cignano is a former farmhouse in the Tuscan countryside between Cortona and Montepulciano. The villa is surrounded by sunflower fields and vineyards. The country-style villa consists of 2 apartments with a separate entrance and is therefore an ideal place for 2 families. The decor is rural...
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    Location Information
    52044, Cignano, Cortona
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    6 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Terrace
    • Wi-Fi
    • Central Heating
    • Grill
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just 1 km away from the historic center of Cortona, a beautiful town of Etruscan origin situated in the heart of the Tuscan countryside, stands Villa I Cocciai, a splendid independent villa set in a panoramic position, where you can spend an unforgettable holiday discovering Tuscany. The villa can...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 8
    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
    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Washer
    • Cable/satellite TV
    • Balcony
    • Grill
    • Private Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Lorenza is located at the foot of the beautiful Etruscan town of Cortona, in a convenient and strategic position that will allow you to easily reach the most beautiful cities of Tuscany and Umbria during beautiful day trips. The villa dates back to the 15th century and has been the subject...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Balcony
    • Grill
    • Terrace
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casale dell'Ombrello is an old farmhouse close to the beautiful city of Cortona. The house has been completely renovated. The atmosphere is rural because of the wooden beams on the ceiling and the cotto tiles on the floors and the rural interior. There is a path that goes through the olive grove...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Balcony
    • Terrace
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Nerium has a breathtaking view over the city of Cortona and the Valdichiana valley because of the particular location. The villa has been carefully restored and the uniqueness of this beautiful stone farmhouse is perfectly preserved. The style is rustic Tuscan. The villa is tastefully...
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    Location Information
    52044, Montalla, Cortona
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Private Outdoor Pool (Unheated)
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful rural farmhouse of 250 m2 composed by two independent apartments, located just below the town of Cortona, well exposed to the sun and surrounded by lush vegetation. The farmhouse has been recently renovated and the owner of the house has tried to keep the original features intact wherever...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Terrace
    • Central Heating
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Cielo is located in a splendid panoramic position about 550 meters above sea level. The villa is a charming stone house and was once used as a barn to dry chestnuts. The villa is surrounded by a hilly area and is ideal for those seeking peace and privacy. Here you can enjoy a wonderful view...
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    Location Information
    52044, Teverina, Cortona
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    12 Bedrooms, 13 Bathrooms, Sleeps 28 Quick View
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    • Wi-Fi
    • Terrace
    • Balcony
    • Grill
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Borgo del Falco is composed of 5 different small stone buildings that house 11 rooms of different types and sizes, all with private facilities and in some cases also with two bathrooms. Each rooms has its own access by a private small space with garden furniture. A delightful and spacious...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 12 Bedrooms, 13 Bathrooms, Sleeps 28
    1 Bedroom, 4 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Shared Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Bianca lies on the border of Tuscany and Umbria, near the ancient Etruscan city of Cortona. The villa is located in a hilly area with forests, olive trees and vineyards interspersed with small medieval villages. From the hills, you'll overlook the Valdichiana. You are close to the important...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 1 Bedroom, 4 Bathrooms, Sleeps 8
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Genny 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 characterized by a...
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    Location Information
    52044, Teverina, Cortona
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Grill
    • Air Conditioning
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In the heart of Tuscany's most authentic Tuscan countryside, Villa Isolina is an ancient farmhouse completely restored in colonial stone, keeping the traditional rural style intact. The interiors are rustic Tuscan style, the ceiling with exposed wooden beams, terracotta floors, wrought iron...
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    Location Information
    52044, Creti, Cortona
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    3 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Hot Tub
    • Washer
    • Grill
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Mara is immersed in the green hills near the ancient Etruscan city of Cortona. Cortona is considered one of the most beautiful villages in Italy in a rolling landscape. The villa can accommodate up to 12 people. The interior and the garden are spacious and comfortable, ideal for families and...
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    Location Information
    52044, Teverina, Cortona
    Holiday Rental House - 3 Bedrooms, 5 Bathrooms, Sleeps 12
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