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Cortona Holiday Homes

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    Travellers to Cortona are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 30
    7 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    4 of 5 bubbles (1) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    52044, Cortona, Province of Arezzo
    1 / 35
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Casa indipendente, con uno stupefacente panorama. Potrete mangiare all'aperto gustando la bellezza della Valdichiana e di Cortona, sfondo su cui si staglia la figura del Palazzone, villa principesca del 1500 con la sua torre ed il suo muro merlato.In assoluta privacy, nel silenzio ma... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 13
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Central Heating
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    52044, Cortona, Province of Arezzo
    1 / 28
    5 of 5 bubbles (1) Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Private Garden
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    About this property
    main House<BR><BR>A charming Tuscan villa designed, decorated and furnished by 'Giusi', the Italian cook who often helps friend Frances Mayes prepare splendid luncheons and dinner parties at Villa Bramasole, near Cortona. Giusi is mentioned and photographed in Frances Mayes' books “Under The Tuscan... View all property information
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    52044, Cortona, Province of Arezzo
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Villa Capezzine has been restored in May 2014. It has been declared “Historical Monument”. Villa Capezzine is situated in the famous community of Cortona (“Under the Tuscan Sun”: have you seen this funny movie?), on the “scenic road” that takes you from Cortona to Montepulciano. It is one of the... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Porch
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    About this property
    Il Bozzino is a large apartment at the ground floor of Casa la Bozza. The house is in a quiet and relaxing location, close enough to a grocery for daily shopping, close to Cortona and the main roads. The garden, the parking and the entrance are independent and has access to the shared swimming... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 23
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Outdoor Dining Area
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    • ?
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    About this property
    'Vecchio Frantoio' is a bright and spacious air-conditioned two-bedroom apartment reconstructed from an ancient olive mill. Chestnut beams, terracotta tiles and antique stone all in the Tuscan manner add to the character of this comfortable and beautiful apartment. The apartment comprises a master... View all property information
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    52044, Cortona, Province of Arezzo
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    1 / 61
    5 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    52042, Cortona, Province of Arezzo
    1 / 29
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    52044, Cortona, Province of Arezzo
    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    About this property
    This beautiful holiday home near Cortona, is located at a 15 min drive (15km) from this famed Etruscan and medieval town, main cultural and artistic centre of the Val di Chiana after Arezzo. The cottage is the outbuilding of an old farmhouse, dating back to the 18th century, where the owners live.... View all property information
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    52040, Cortona, Province of Arezzo
    1 / 27
    8 Bedrooms, 9 Bathrooms, Sleeps 16 | Quick View
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    About this property
    Nestled in lush park surroundings, Villa Panphilii is a stunning 18th century villa located in Cortona, an ancient Etruscan city. The villa is set in breath-taking natural scenery, changing in colour and shades throughout the year, creating a unique atmosphere. There is hardly a better place to... 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
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    52040, Cortona, Province of Arezzo
    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Porch
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    About this property
    Set in the countryside surrounding Cortona, Villa La Camelia is a charming property obtained from an old farmhouse and lovingly restored by the owners in order to give their guests a place that evokes the history of the ancient Tuscan peasant families but at the same time offering all the comforts... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 34
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Villa Il Roseto is located in a beautiful panoramic position, where it dominates both Tuscany and Umbria, a few kilometers from the ancient Etruscan town of Cortona. Villa Il Roseto will allow you to easily reach the most beautiful cities of Tuscany and Umbria, but at the same time you'll enjoy a... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 14
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Wi-Fi
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    52044, Cortona, Province of Arezzo
    1 / 11
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Private Outdoor...
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    • x
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    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
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    52044, Cortona, Province of Arezzo
    1 / 31
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Grill
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    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... View all property information
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    52044, Cortona, Province of Arezzo
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    1 / 57
    5 of 5 bubbles (20) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • Mountain Views
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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... View all property information
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    52044, 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 / 18
    Private Room, 33 Bathrooms, Sleeps 20 | Quick View
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    • ?
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    • x
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    52044, Cortona, Province of Arezzo
    1 / 34
    5 of 5 bubbles (17) Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • Satellite TV
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    • Waterfront
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    • Pet-friendly
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    • x
    About this property
    Celle del Farinaio is a beautiful house, recently restored and situated only 6 km from the Etruscan town of Cortona, just 8 km from Lake Trasimeno. The property, completely fenced, is' situated on a hill (350 meters), near a small church dating originally back to Roman times and is surrounded by... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 121
    5 of 5 bubbles (58) Excellent
    13 Bedrooms, 12 Bathrooms, Sleeps 30 | Quick View
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    • x
    About this property
    Our luxury suites hotel can accommodate 9 suites, some for couples and some for families, if you are a group you can have the entire farmhouse for yourself. Price range from euro 70 a night for a couple in studio suite,(in low season), to euro 236 a night for a family in the biggest suite (in high... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Balcony
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    About this property
    Villa Capezzine has been restored in May 2014. It has been declared “Historical Monument”. Villa Capezzine is situated in the famous community of Cortona (“Under the Tuscan Sun”: have you seen this funny movie?), on the “scenic road” that takes you from Cortona to Montepulciano. It is one of the... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 14
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
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    • Mountain Views
    • Central Heating
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    • Pet-friendly
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    • x
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    • x
    About this property
    For the lovers of Beauty, History, Nature and Natural produce Antica Quercia Verde is the place where you can enjoy an authentic and inspiring experience in Cortona, Tuscany.<BR>Antica Quercia Verde is situated at an enjoyable walking distance (25 minutes uphill) from the town centre, in the most... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 31
    Montecchio
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Private Garden
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    52044, Montecchio, Cortona
    1 / 24
    5 of 5 bubbles (1) Excellent
    Montalla
    1 Bedroom, 2 Bathrooms, Sleeps 3 | Quick View
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    About this property
    Equipped with chairs, shades, and beach beds.<BR>It has been restored with respect for the original stile and all the furniture are antique, you will have a warm and relaxing feeling when you enter Il Moro Novo.<BR>The house is located just outside a small country village, so it is not easy to... View all property information
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    52044, Montalla, Cortona
    1 / 42
    5 of 5 bubbles (1) Excellent
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • Mountain Views
    • Grill
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    • Pet-friendly
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    • x
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    About this property
    This is a very characteristic "Tuscan Studio" with kitchen, bathroom, queen canopy bed and sofa bed, all in a very large and charming room with fireplace.<BR>Cheap but still with a lot of character and warmth, walking distance to the town center.<BR>I have many memories here: once it was my... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 29
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Mountain Views
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    • x
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    About this property
    This ground floor suite 77sq. Meters ) for your accommodation in Tuscany, comprises of a comfortable living area leading to the fully equipped kitchen with views over the countryside. There are 2 bedrooms and 1 bathroom. 1 bedroom has a double bed and the other, 2 single beds. This suite also... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 21
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Central Heating
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    52044, Cortona, Province of Arezzo
    1 / 14
    4.5 of 5 bubbles (2) Very good
    6 Bedrooms, 8 Bathrooms, Sleeps 16 | Quick View
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    52044, Cortona, Province of Arezzo
    1 / 38
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Patio
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    • Pet-friendly
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    • x
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    • x
    About this property
    72sq. Meters (775 sq. Ft) This charming 1 bedroom ground floor apartment rentals in Tuscany, has an open living area leading to a covered private terrace with great views of Chiana Valley and Cortona. It has a fully equipped kitchen leading to a double bedroom and a bath room. The suite is fully... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 13
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Lovely and intimate two-room apartment, La Finestra sulla Piazza is a welcoming property located in the heart of the characteristic town of Cortona. The living area is composed of a dining area and a pretty and simple kitchenette, which is characterised by two large windows overlooking the main... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 18
    Pietraia
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This house, located in Cortona, is ideal for 8 vacationers. It offers 3 bedrooms and an enclosed garden. The lounge is perfect for unwinding after a day of exploration. Curl up on the comfortable sofa and enjoy a good book. The kitchen is well-equipped for cooking up your favorite meals. Enjoy... View all property information
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    52044, Pietraia, Cortona
    1 / 20
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Casa Anna is just a few km from the Etruscan-Medieval town of Cortona and offers a genuine and healthy holiday. It is situated in the hills area around Cortona (only 5 km from SR71 and 10 km from Cortona), in the heart of a small rural hamlet, and ensures guests real quiet ( 750 mt over the sea... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 16
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Villa Capezzine at Palazzuolo Due is the last restoration we started and will be ready to welcome our Guests next May 2013. It has been declared "Historical Monument" Villa Capezzine is situated in the famous community of Cortona (“Under the Tuscan Sun”: have you seen this funny movie?), on the... 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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    • x
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    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 / 78
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    Location Information
    52044, Cortona, Province of Arezzo
    1 / 23
    Montalla
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Central Heating
    • Balcony
    • Grill
    • Parking
    • Private Outdoor...
    • Terrace
    • Washer
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    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
    1 / 9
    3 of 5 bubbles (2) Average
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Amenities & Details
    • Central Heating
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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: Casa Zeni - Berrettini. The property... View all property information
    Location Information
    52044, Cortona, Province of Arezzo
    1 / 20
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 3 | Quick View
    other traveller has booked this property
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    Amenities & Details
    • Grill
    • Shared Outdoor Pool...
    • Shared Garden
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    This recently renovated country villa is situated in a beautiful rural setting, nestled in a village in the valley below the Etruscan town of Cortona. <BR>It has been converted, in traditional Tuscan style, into seven fully-self-contained, apartments which sleep between 2 to 4 visitors each.... View all property information
    Location Information
    101 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 / 26
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    Amenities & Details
    • Private Garden
    • Secure Parking
    • Central Heating
    • Washer
    • Grill
    • Wi-Fi
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    Location Information
    52044, Cortona, Province of Arezzo
    1 / 25
    5 of 5 bubbles (3) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Outdoor Dining Area
    • Washer
    • Private Outdoor...
    • Private Garden
    • Wi-Fi
    • Parking
    • Mountain Views
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    Location Information
    52044, Cortona, Province of Arezzo
    1 / 19
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Grill
    • Balcony
    • Air Conditioning
    • Terrace
    • Wi-Fi
    • Shared Garden
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    This recently renovated country villa is situated in a beautiful rural setting, nestled in a village in the valley below the Etruscan town of Cortona. <BR>It has been converted, in traditional Tuscan style, into seven fully-self-contained, apartments which sleep between 2 to 4 visitors each.... View all property information
    Location Information
    101 52044, Cortona, Province of Arezzo
    1 / 14
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Washer
    • Private Garden
    • Grill
    • Terrace
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    Location Information
    52044, Cortona, Province of Arezzo
    1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    Payment Protection
    Amenities & Details
    • Private Outdoor...
    • Grill
    • Private Garden
    • Shared Garden
    • Wi-Fi
    • Secure Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    About this property
    Stone-built farmhouse that has recently been restored with great care and is situated in the hills approximately three kilometres from Cortona. It is divided into two units that they can be rented separately or all. <BR>Encircled by a park of 5000 mq all surrounded with trees of olive. Panoramic... View all property information
    Location Information
    52044, Cortona, Province of Arezzo
    1 / 20
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Satellite TV
    • Washer
    • Private Garden
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    Location Information
    52044, Cortona, Province of Arezzo