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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 Bedroom, Sleeps 2Quick View
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    3 Bedrooms, Sleeps 6Quick View
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    • Terrace
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    • Private Outdoor Pool (Unheated)
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    Smoking allowed
    About this property
    Villa Sonia is for sure, a really special property tucked away on the sleepy hillside of Cortona and, just a short distance form the enchanting franciscan monastery of Le Celle. Villa Sonia is perfect for four to 12 guests.<BR><BR>This ancient stone farmhouse dates back to the 17th century....
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    Cortona, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    1 Bedroom, Sleeps 4Quick View
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    • Wi-Fi
    • Balcony
    • Mountain Views
    • Shared Outdoor Pool (Unheated)
    • Central Heating
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    • Washer
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A lovely vacation home for 2 people or a family of 4. A charming and spacious sitting room converted from the Old Flour Mill with the original millstone. All the comforts of home in the fully fitted kitchen. Try out your Tuscan cooking skills or plan an evening barbecue celebration. The large...
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, Sleeps 10Quick View
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    • Private Garden
    • Outdoor Dining Area
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Parking
    • Wi-Fi
    • Mountain Views
    • Grill
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    Pet friendly
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    Smoking allowed
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 10
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    2 Bedrooms, Sleeps 4Quick View
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    Nice indipendent stone villa which have been recently restored. This property is situated in panoramic location on the hills surrounding the beautiful medieval town of Cortona which is only 10 km away. The villa offers comfortable interiors furnished in a rustic style and provide a private...
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, Sleeps 9Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Balcony
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 2 storey villa is located 600m above sea level, is surrounded by woods and has panoramic views of the Val Di Chiana. Casa Santí Egidio is only 7 km from the ancient Etruscan city of Cortona, making excursions to surrounding towns easy. The private garden has a gated entrance and has 2...
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    3 Bedrooms, Sleeps 7Quick View
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    Due to its scenic location Villa Oleandro offers an unrivaled view over the town of Cortona and the whole Valdichiana. The villa has been carefully restored by the owners who have managed to keep the uniqueness of this beautiful stone farmhouse alive, which, with its rustic Tuscan style, will make...
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    52044, Montalla, Cortona
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming share of an independent Tuscan villa rental affording extensive views over the surrounding landscape. The villa rental, offering tastefully furnished interiors, is quietly situated in a short distance from the lovely Tuscan town of Cortona (15 km). Distances: food shops 3 km, Foiano della...
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    52044, Cignano, Cortona
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 13
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    3 Bedrooms, Sleeps 10Quick View
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    • Parking
    • Private Garden
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, Sleeps 9Quick View
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    Beautiful independent villa with private pool and garden situated in the centre of Camucia, only a few kilometers away from the lovely medieval town of Cortona. This villa, dating back to 19th century, is elegantly furnished with antique pieces and it offers welcoming interiors. The garden...
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 9
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    1 Bedroom, Sleeps 5Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Self catering romantic dependence of an ancient Tuscan farmhouse for your holiday in Tuscany and Umbria. Semi Detached apartment, portion of the main house has its own garden area, and use of the shared swimming pool just a few hundred meters far. Perfect for 2/3 people is also suitable for 5 with...
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    52044, Cortona, Province of Arezzo
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 5
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    9 Bedrooms, Sleeps 18Quick View
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    • Housekeeping Included
    • Sauna
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Washer
    • Hot Tub
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
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    52044, Pietraia, Cortona
    Holiday Rental House - 9 Bedrooms, 8 Bathrooms, Sleeps 18
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    • Private Garden
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    Pet friendly
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    52044, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, Sleeps 11Quick View
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    About this property
    This farmhouse lies on the hills of Cortona, with a great views of the Val di Chiana area. Just a short distance away are the towns of Camucia and Cortona itself (a historical city with Etruscan origins). The house looks out onto a fantastic panorama view and has a beautiful swimming pool which...
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    2 Bedrooms, Sleeps 4Quick View
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    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Balcony
    • Grill
    • Parking
    • Terrace
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In the heart of the Chiana Valley, at the foot of Cortona, lies this graceful stone house Casina La Graziosa. It is a detached house with private garden and pool at guests exclusive disposal. The house is ideal for couples or small families. Casina La Graziosa is a single-storey cozy cottage that...
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    • Satellite TV
    • Mountain Views
    • Grill
    • Patio
    • Housekeeping Included
    • Parking
    • Central Heating
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Review
    3 Bedrooms, Sleeps 6Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
    • Private Garden
    • Wi-Fi
    • Parking
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 8Quick View
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    • Washer
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    Pet friendly
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    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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    52044, Montecchio, Cortona
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    1 Review
    3 Bedrooms, Sleeps 6Quick View
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    • Parking
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    • Private Garden
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    Pet friendly
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    Smoking allowed
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    52044, Pietraia, Cortona
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, Sleeps 2Quick View
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    • Wi-Fi
    • Washer
    • Grill
    • Terrace
    • Central Heating
    • Mountain Views
    • Balcony
    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
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    52044, Cortona, Province of Arezzo
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    1 Bedroom, Sleeps 3Quick View
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    About this property
    “Romina is Tuscany”. In these three words all the soul of this special property can be described. Romina is an ancient farmhouse with swimming pool, perfectly set at the egde of a green hill (”poggio” in Italian) just a few minutes drive away from the pictoresque Cortona. Accessed via a typical...
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    52044, Cignano, Cortona
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    4 Bedrooms, Sleeps 8Quick View
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    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Washer
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casa Gioia's noble origins can be distinguished by the carved stone archways and niches and the handsome masonry of the walls surrounding the villa.  This stone villa-farmhouse has been thoughtfully renovated, preserving its antique charm.  Casa Gioia boasts a lovely rose garden, cypresses, cedar,...
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 4Quick View
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    Charming independent villa with private swimming-pool situated in panoramic location, on the hills around the beautiful medieval town of Cortona, approx. 750 m above sea level. This property is surrounded by beautiful woods and offers tastefully furnished interiors and a cosy atmosphere. The...
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, Sleeps 5Quick View
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    • Parking
    • Private Outdoor Pool (Unheated)
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
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    3-room apartment "Ghezzi", for 5 people, 75 m2, on the ground floor, simple and comfortable furnishings. Living/dining room with satellite TV, open fireplace, dining-table and dinette. Smoking not allowed. Internet (Wireless LAN [WLAN]). 1 sofa bed. Sleeping room with 1 double bed. Sleeping room...
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    52044, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    11 Reviews
    11 Bedrooms, Sleeps 24Quick View
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    • Air Conditioning
    • Hot Tub
    • Terrace
    • Grill
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 11 Bedrooms, 7 Bathrooms, Sleeps 24
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    3 Bedrooms, Sleeps 5Quick View
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    • Terrace
    • Balcony
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    Pet friendly
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    Smoking allowed
    About this property
    Casa Il Pergolato is the perfect place to escape from daily life stress and enjoy a moment of relax in the green and in quiet of the Tuscan hills, away from the hustle and bustle of the city. The house (200 square meters) is made out of stone and is full of classic rustic Tuscan style. Outside it...
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    • Internet Access
    • Grill
    • Washer
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Satellite TV
    • Parking
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 9
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    3 Reviews
    1 Bedroom, Sleeps 2Quick View
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    • Wi-Fi
    • Central Heating
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    About this property
    THE APARTMENT Apartment for 2 person and 1/2, compose by one bedroom + lounge with kitchen + 2 bathroom. internet wifi, TV led, microwave, washing machine, toaster, kettle, spinner, central heating is providing, in the summer months cool fresh air is inside. Central position, near public free...
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    52044, Cortona, Province of Arezzo
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    6 Bedrooms, Sleeps 12Quick View
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    • Satellite TV
    • Grill
    • Private Outdoor Pool (Unheated)
    • Central Heating
    • Washer
    • Balcony
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located only 500 metres from the heart of Cortona in a stunning panoramic position amidst olive-groves “Villa Casale Girifalco” is the ideal location for relaxing and stress-free holidays. The mansion and the two independent, fully-equipped apartments were converted from an old stone farmhouse.
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    1 Bedroom, Sleeps 2Quick View
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    An aristocratic villa built during the middle 800 between the enchanting green, and the sacred silence and the infinite valley. The green, the position and the elegance made the key elements of the main complex (6 beds) and the two depandances “Villa Serenella” and “Villa Limonaia”, two beds each....
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, Sleeps 4Quick View
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    • Wi-Fi
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    The apartment is located in the heart of the historical center of Cortona. Il portale 2 was conceived especially for young couples loving design, comforts and relaxation, to spend an unforgettable vacation in Tuscany. Located on the ground floor, this suite has an independent entrance and is...
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    52044, Cortona, Province of Arezzo
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    9 Bedrooms, Sleeps 16Quick View
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    This villa is a large stone property located on the gentle hills surrounding the beautiful Etruscan town of Cortona, in the heart of Tuscany. The villa lies in a panoramic and quiet position, completely independent and private, immersed in the countryside but at the same time close to the old town...
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 9 Bedrooms, 6 Bathrooms, Sleeps 16
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    2 Bedrooms, Sleeps 4Quick View
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    • Private Garden
    • Satellite TV
    • Central Heating
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    • Terrace
    • Balcony
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    2 Bedrooms, Sleeps 6Quick View
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    Dive in the pool of a rental house in Tuscany! Nice villa, share of a house situated in panoramic location on the hills surrounding Cortona. The rental villa, offering extensive views over the Chiana Valley and Lake Trasimeno, has been skilfully restored and turned into 2 comfortable accommodations...
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, Sleeps 8Quick View
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    • Wi-Fi
    • DVD Player
    • Sauna
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    Pet friendly
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    Smoking allowed
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    Fonte al Vento is immersed in the green landscape of Tuscany, sitting on the typical terraces of the hilly countryside between olive groves, vineyards and other scented Mediterranean plants. The villa is located just a few steps from the Chiesa Monumentale di Santa Maria Nuova and Cortona’s Old...
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    6 Bedrooms, Sleeps 13Quick View
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    • Satellite TV
    • Private Garden
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
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    • Washer
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
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    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...
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 13
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    • Central Heating
    • Private Garden
    • Wi-Fi
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    • Private Outdoor Pool (Unheated)
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    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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    52044, Creti, Cortona
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    2 Bedrooms, Sleeps 6Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
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    3-room apartment "Perbacco", for 6 people, 70 m2, on the ground floor, comfortable and cosy furnishings. Living/dining room with satellite TV and dining-table. Smoking not allowed. Internet (Wireless LAN [WLAN]). 1 double sofa bed. Sleeping room with 2 single beds. Sleeping room with 1 double bed....
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    52044, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, Sleeps 4Quick View
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    • Shared Garden
    • Wi-Fi
    • Air Conditioning
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    • Satellite TV
    • Outdoor Dining Area
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will find 4 spacious apartments for your stay in Cortona, bright and comfortable and an outbuilding between the olive trees.<BR>Farmhouse La Tesa is the best that a country house can give you for your holiday in the heart of Tuscany. You will experience a rejuvenating experience, full of good...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Washer
    • Internet Access
    • Hot Tub
    • Grill
    • Satellite TV
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful, restored 1600s villa nestled in the countryside near Cortona is an inviting retreat for a family or group of friends. The villa is part of a large, family-owned agricultural estate and offers private grounds with a pool and gardens. Lake Trasimeno, the Appenines, Siena, Arezzo and...
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    Cortona, Province of Arezzo
    Holiday Rental House - 6 Bathrooms, Sleeps 14
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    1 Bedroom, Sleeps 4Quick View
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    Dive in the pool of our rental house in Tuscany. A villa for your luxury vacation. Beautiful medieval stone hamlet situated in quiet and panoramic position between olive trees and woods of ancient chestnut trees, typical of Tuscany. The rental villa has been recently restored preserving its...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    • DVD Player
    • Central Heating
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Grill
    • Parking
    • Private Garden
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Fontocchio is situated at the foot of the Etruscan town of Cortona, in an enchanting location among vineyards and olive trees. Thanks to the careful restoration works, the charm of this typical Tuscan farmhouse, with its wooden beams and terracotta floors, has been preserved. A big gate leads...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 17
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    1 Bedroom, Sleeps 4Quick View
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    • DVD Player
    • Private Garden
    • Grill
    • Central Heating
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ' IL FASCINO DELLE MURA ETRUSCHE-MEDIEVALI, UNO STUPENDO E RILASSANTE PANORAMA SULLA VALDICHIANA,UNA STRUTTURA DEL 1200 ARREDATA CON AMORE TRA L'ANTICO E IL MODERNO, UN GIARDINO CHE POGGIA SOPRA LE MURA ETRUSCHE, DA CUI PRENDE IL NOME LA STRUTTURA, IN PROSSIMITA' DI PORTA MONTANINA,UNO DEGLI...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    5 Bedrooms, Sleeps 10Quick View
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    • Mountain Views
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Grill
    • Satellite TV
    • Balcony
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    7 Bedrooms, Sleeps 14Quick View
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    • Private Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    • Mountain Views
    • Washer
    • Air Conditioning
    • Grill
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 14
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    3 Bedrooms, Sleeps 7Quick View
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    About this property
    Nice independent property with private pool situated in panoramic location on the hills around Cortona, at 750 m above-sea-level. The house interiors are nicely furnished in a typical Tuscan style. This estate, surrounded by beautiful woods and valleys, offers extensive views over the surrounding...
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    Location Information
    Cortona, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, Sleeps 4Quick View
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    About this property
    Welcoming, recently restored villa with private pool situated in panoramic location on the hills around Cortona. The villa is built in traditional stone and offers welcoming, carefully finished indoor and outdoor areas. The house interiors are nicely furnished in a typical Tuscan style, outside...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, Sleeps 4Quick View
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    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'Piccolo Porta' is situated in Cortona and can be found a few minutes stroll from centro storico with its galleries, wonderful shops and great restraunts. The beautiful medieval streets lead you to Piccolo Porta where from the second floor you can see over the roof tops of Cortona and down to the...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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