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Holiday Rentals in Cortona, Italy

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    Travellers to Cortona are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 20
    5 of 5 bubbles (4) Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 16 | Quick View
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    1 / 14
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    5 of 5 bubbles (4) Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    The barn was the enchanted place of my youth rushes, when I grew up I realized the dream which was of my grandfather before and after of my dad.<BR><BR>Welcome to “Casale il Granaio”<BR>A magic place in the heart of Valdichiana...<BR>In the heart of Valdichana, bordering on Umbria, a few km from... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 45
    4.5 of 5 bubbles (2) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    About this property
    This beautiful tuscan Villa with annexed hayloft has been completely restored and transformed into a cosy holiday home set on a hill full of olive groves that dominate Cortona. From the property you will enjoy a fantastic panoramic view over the green valley, in almost absolute peace and quiet. The... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 37
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
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    About this property
    The house, made by stones, consists of living room with a converteble sofa-bed and a breath taking view of the Val di Chiana Valley, full kitchen with breakfast cristal table and the same view of the living room plus pantry with washer machine. Bathroom with shower, bidet, sink and toilette,... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 21
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    00100, Cortona, Province of Arezzo
    1 / 20
    5 of 5 bubbles (4) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Stone-built farmhouse that has recently been restored with great care and is situated in the hills approximately three kiliometers from Cortona. The property is situated in a well reserved country place but not remote, very near to all necessity. The Villa is divided into two indipendent units... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 37
    5 of 5 bubbles (6) Excellent
    8 Bedrooms, 7 Bathrooms, Sleeps 17 | Quick View
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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... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 23
    Montalla
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This is an idyllic 400 year old, 3 bedroom, semi detached farmhouse located near the beautiful town of Cortona in Tuscany. The property has a warm, welcoming feel and is furnished in keeping with the age of the property. Guests enjoy use of a private swimming pool (open 26 May to 21 September... View all property information
    Location Information
    52044, Montalla, Cortona
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    1 / 81
    4.5 of 5 bubbles (4) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Mountain Views
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    About this property
    If you are looking for an exclusive location where time seems to stand still, welcome to Villa dei Ciliegi. Situated on the Cortona hill, with a breathtaking view on the valley, this villa will ensure you an unforgattable vacation. The house takes its name from the charming cherry tree-lined drive... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 65
    5 of 5 bubbles (12) Excellent
    10 Bedrooms, 6 Bathrooms, Sleeps 20 | Quick View
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    About this property
    Cortona, Tuscany, Italy, Europe (Firenze 100 Km, Siena 60 Km, Rome 200 Km, Chianti Area 20) View Map Accommodations: Villa, 10 Bedrooms, 8 Baths (Sleeps 20-22) Villa Le Contesse is a beautiful independent villa lying on a hillside, a few minutes from the Etruscan town of Cortona. A large park... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 32
    Studio, 3 Bathrooms, Sleeps 9 | Quick View
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    About this property
    PRIVATE STRUCTURE. La Giurata is a typical country farmhouse immersed in the green with an exceptional view over the hills of Umbria and Tuscany, famous for their beauty and charm. This house is recommended for those who love direct contact with nature and the tranquillity of the countryside but... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 23
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    We restored this house 25 years ago. Is a lovely and peaceful house to stay in contact with the nature. You also have at close distance so many places to visit, the Trasimeno lake, Florence, Perugia, Pienza, Montefiascone, Città della Pieve, Gubbio, Assisi, Siena (one day visits). You may rent... View all property information
    Location Information
    52040, Cortona, Province of Arezzo
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
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    • Porch
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    About this property
    "Il Villino di Cortona", cosy holiday home nestled in the green heart of the Chiana Valley in Cortona (Tuscany), an oasis of peace, tranquility and relaxation. Your holiday in contact with nature ... "Il Villino di Cortona”, is a small holiday home, nestled in the Val di Chiana, in the heart of... View all property information
    Location Information
    52044, Cortona, Province of Arezzo
    1 / 24
    5 of 5 bubbles (5) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    The Cortonese hillside, La Fortezza and the ancient wall which encloses the town, dominate the view of the surrounding hillside. Guests have exclusive use of the delightful 12x6 swimming pool, with Roman steps, which lies in an extremely panoramic position and from where you can enjoy the view in... View all property information
    Location Information
    52044, Cortona, Province of Arezzo
    1 / 17
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    A luxury villa with private pool, Villa San Martino is set on a hill, high above the beautiful Niccone Valley on a quiet road, just 3 minutes from local village shops, restaurants and cafes. The position is a typically Tuscan, offering spectacular views from the house, garden, terrace and infinity... View all property information
    Location Information
    06060, Cortona, Province of Arezzo
    1 / 13
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    THE CHARM OF THE MIDDLE AGES-Etruscan walls, a wonderful and relaxing view over the Chiana Valley from the beautiful terrace, above the Etruscan walls.<BR><BR>A building of 1200 decorated with love between ancient and modern, a garden that is based on the Etruscan walls, after which is the name of... View all property information
    Location Information
    52044, Cortona, Province of Arezzo
    1 / 67
    4.5 of 5 bubbles (2) Very good
    5 Bedrooms, 7 Bathrooms, Sleeps 9 | Quick View
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    • Patio
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    • x
    About this property
    Surrounded by the gentle hills which frame the medieval town of Cortona, Villa Eugenio will assure you a peaceful vacation in the heart of Tuscany. This beautiful 17th century Tuscan farmhouse has been painstakingly restored and turned into a warm and welcoming country house that can accommodate up... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 36
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • ?
    • Smoking allowed
    • x
    About this property
    This magnificent villa is located at 400 m from the lovely town of Cortona, one of the most beautiful and renowned towns of Tuscany. An important Etruscan settlement, Cortona today is a medieval jewel on the side of a hill dominating the Val di Chiana. This elegant villa is situated in a wonderful... View all property information
    Location Information
    52044, Cortona, Province of Arezzo
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    1 / 11
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Private Outdoor...
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    • Outdoor Dining Area
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    • Pet-friendly
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    • x
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    • x
    About this property
    Located in a beautiful and very peaceful valley of the Cortonese countryside, but only 10 mins drive from the lively hilltown, this quaint and atmospheric farmhouse has been lovingly restored and tastefully furnished by its Italian-American owners. The property is cradled in 15 acres of its own... View all property information
    Location Information
    52044, Cortona, Province of Arezzo
    1 / 38
    5 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Pet-friendly
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    About this property
    Cortona Tuscan Villa with pool – this property consists of three aristocratic 19th century villas, occupying a large estate abundant with chestnut woods and olive groves, within walking distance of the medieval walled town of Cortona, jewel of Valdichiana. The main villa and the independent annex... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 61
    5 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    • Wi-Fi
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    • x
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    • x
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    52042, Cortona, Province of Arezzo
    1 / 40
    4.5 of 5 bubbles (3) Very good
    Studio, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    PRIVATE STRUCTURE. A stone parlour, where art and nature unite to form a perfect partnership: Cortona is a magical place with a timeless charm that envelops the visitor with its vibrant atmosphere, suspended between the history and legend of its origins, surprising him each time, with the reddish... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 11
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Private Garden
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    • Pet-friendly
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    About this property
    Uliveto is a marvelous and charming stone farmhouse, recently restored from an old barn which served an ancient manor dating back to the 18th century. It's located in one of the most idyllic areas of the mountains surrounding Cortona, 700mts above sea level, immersed in forests of oak and... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 22
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Central Heating
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    • Pet-friendly
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    • ?
    • x
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    • ?
    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... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 14
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • Wi-Fi
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    • Pet-friendly
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    • x
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    Location Information
    52044, Cortona, Province of Arezzo
    1 / 36
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Lovingly restored in 2004 Villa Orlando sleeps 8 people comfortably with four bedrooms, all with en-suite bathrooms with showers. This villa is perfect for families or groups that like to spend time enjoying the outdoors.<BR>You will enjoy a spacious , fully equipped kitchen, a dining room, and two... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 82
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
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    • Pet-friendly
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    • ?
    • ?
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    • ?
    About this property
    Villa di Costantino is a typical Tuscan stone built manor, surrounded by a large garden and located in a beautiful spot at the bottom of the hill of the Etruscan old town of Cortona that offers outstanding views over the Valdichiana. The house is spacious and welcoming, nestled in a very private... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 47
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Wi-Fi
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    • Pet-friendly
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    • x
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    • x
    About this property
    ExteriorsThis restored two-storey villa near Cortona in Tuscany is perfectly situated to enjoy the spectacular views of the valley. It can accommodate up to 10 people; and it has an 8x13m swimming pool, which once was the antique water reservoir for the property. There is also a lovely wide veranda... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 31
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Shared Garden
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    • ?
    • ?
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    • ?
    About this property
    The Casa della Seta apartment is set in a wonderful village complex with swimming pool, restaurant and plenty of recreational activities. The apartment has two bedrooms, two bathrooms, large living-dining room and fully-equipped kitchen as well as its own private outdoor space. It can accommodate... View all property information
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    52042, Cortona, Province of Arezzo
    1 / 19
    Montalla
    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    • ?
    • ?
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    • ?
    About this property
    Villa Fastia B is a welcoming apartment. It sleeps three people. It is appoximately 50 square meters (540 square feet). It features a shared swimming pool, a shared garden, air conditioning (please read description below to check in which rooms the units are installed) and winter heating. You will... View all property information
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    Montalla, Cortona
    1 / 28
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    Location Information
    52044, Cortona, Province of Arezzo
    1 / 59
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Washer
    • Waterfront
    • Internet Access
    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    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... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 34
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    52044, Cortona, Province of Arezzo
    1 / 19
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    About this property
    Situated in Cortona this charming holiday home is the ideal place for the perfect getaway in Italy. The house comprises of 3 double beds , so it can comfortably host a group of 6 people. There are also 3 bathrooms to allow for individual comfort and privacy. There is a swimming pool for guests... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 30
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    • Patio
    • Mountain Views
    • DVD Player
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    • Pet-friendly
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    • x
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    • x
    About this property
    A five double bedroomed villa with private pool offering its guests complete luxury. Villa Cortona is a beautifully restored villa retaining much of its original character and tastefully furnished with antiques and original paintings to a very high standard, with no expense spared. Only a... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 27
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The house is located on the lower slopes of the hills overlooking the Chiana Valley and where, higher up, stands the Etruscan city of Cortona. The property is immersed in the countryside covered with olive groves, forests and vineyards. This area is located on the border between Tuscany and Umbria... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 18
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
    • Balcony
    • Waterfront
    • Shared Outdoor Pool...
    • Parking
    • Washer
    • Grill
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Acero is a cosy apartment that belongs to a beautiful hillside property, Col di Leccio, an authentic farmhouse where nature and silence dominate. Acero is made up of a double bedroom, a bedroom with twin beds, a bathroom with a shower, a kitchen and a living room. There is a large terrace in front... View all property information
    Location Information
    52044, Cortona, Province of Arezzo
    1 / 36
    4.5 of 5 bubbles (4) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Private Outdoor...
    • Wi-Fi
    • Central Heating
    • DVD Player
    • Mountain Views
    • Satellite TV
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Villa Leccio is a beautiful stone farmhouse only 2 km away from Cortona belonging to a spectacular 10.000 square metre hilly property. Tucked in a huge olive grove, chestnut and holm oak wood, the villa offers its guests a breathtaking view over the Valdichiana and the Cortona hills and is the... View all property information
    Location Information
    52044, Cortona, Province of Arezzo
    1 / 56
    5 of 5 bubbles (1) Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Grill
    • Air Conditioning
    • Private Outdoor...
    • Satellite TV
    • Internet Access
    • Washer
    • DVD Player
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Tucked under the ancient Etruscan walls of Cortona, the recently restored old stone Villa Topazio lies up on the hill and is part of a beatiful Renaissance Villa. From Villa Topazio one can admire the splendid view of the Valdichiana completely surrounded by olive groves which produce some of our... View all property information
    Location Information
    52044, Cortona, Province of Arezzo
    1 / 40
    5 of 5 bubbles (4) Excellent
    Studio, 4 Bathrooms, Sleeps 8 | Quick View
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    • Private Outdoor...
    • Mountain Views
    • Patio
    • Washer
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    RECEPTIVE STRUCTURE. Casale Cinque Valli is immersed in the beautiful Tuscany landscape near Cortona, delightful medieval town at the Tuscan- Umbria border. Thanks to its breathtaking landscape this house is the ideal place for those who want to enjoy the silence and nature. Internally the house... View all property information
    Location Information
    52044, Cortona, Province of Arezzo
    1 / 40
    4.5 of 5 bubbles (7) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    Amenities & Details
    • Central Heating
    • DVD Player
    • Wi-Fi
    • Mountain Views
    • Washer
    • Satellite TV
    • Private Outdoor...
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Villa i Fontoni, a perfect shelter for those who look for a totally relaxing holiday, is shrouded by verdant greenery and set in a small corner of paradise. In a short range from the town of Cortona, the villa is named after the old tubs once used as common sources. Today a fascinating stone... View all property information
    Location Information
    52044, Cortona, Province of Arezzo
    1 / 49
    Studio, 7 Bathrooms, Sleeps 8 | Quick View
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    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Villa Panorama is a 17th century farmhouse immersed in an oasis of peace and silence, yet near important and lively cultural centres such as Cortona, Arezzo, Siena and Perugia. The main villa can host up to 6 guests, while two annexes increase the c Villa Panorama is a 17th century farmhouse... View all property information
    Location Information
    52044, Cortona, Province of Arezzo
    1 / 24
    4 of 5 bubbles (1) Very good
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
    • Internet Access
    • Satellite TV
    • Washer
    • Mountain Views
    • Air Conditioning
    • Private Outdoor...
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    RICEPTIVE STRUCTURE. Vinciluna, a little jewel of a house, is situated in the magnificent scenery of the hilly countryside of Cortona, one of the most picturesque and charming towns in Tuscany less than 10 minutes away, surrounded by the beautiful Val d'Esse, an area east of Cortona rich in... View all property information
    Location Information
    52044, Cortona, Province of Arezzo
    1 / 24
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
    • Parking
    • Private Garden
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    It is now possible to rent Casa Bellavista for the exclusive use of your family and friends this is the perfect location to discover and explore Tuscany and Umbria. The property with its 330 sq. meter can accommodate up to 10 people maximum, divided as follow: 3 bed rooms with en suite bathroom... View all property information
    Location Information
    52044, Cortona, Province of Arezzo
    1 / 36
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Amenities & Details
    • DVD Player
    • Washer
    • Grill
    • Hot Tub
    • Central Heating
    • Balcony
    • Waterfront
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • ?
    About this property
    Set in beautiful hilly position, the farmhouse is named after the 800 olive trees that surround the property and from which the owners obtain great olive oil. San Martino agli Ulivi is the result of a long and accurate renovation of the family estate. On one of the stones of the old barn you can... View all property information
    Location Information
    52044, Cortona, Province of Arezzo
    1 / 22
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Washer
    • DVD Player
    • Balcony
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Villa Santa Maria 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... View all property information
    Location Information
    52044, Cortona, Province of Arezzo
    1 / 46
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Secure Parking
    • Shared Outdoor Pool...
    • Grill
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    Location Information
    52044, Cortona, Province of Arezzo
    1 / 34
    5 of 5 bubbles (3) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
    • Wi-Fi
    • DVD Player
    • Sauna
    • Satellite TV
    • Private Outdoor...
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This magnificent villa is located at 400 m from the lovely town of Cortona, one of the most beautiful and renowned towns of Tuscany. An important Etruscan settlement, Cortona today is a medieval jewel on the side of a hill dominating the Val di Chiana. This elegant villa, 270 sq. m, can comfortably... View all property information
    Location Information
    52044, Cortona, Province of Arezzo