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Vacation Rentals and Villas in Cortona, Italy

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    Travelers to Cortona are booking August dates now. Secure your vacation rental today, and have the perfect trip.
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    5 of 5 stars (4) Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    5 of 5 stars (28) Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 11 | Quick View
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    About this property
    Il Rifugio (The Refuge) is a respectfully restored seventeenth-century stone farmhouse/villa set on a Tuscan hillside surrounded by a centuries' old terraced olive grove and fifty six rolling acres of private property near the Etruscan citadel Cortona. Agriturismo Il Rifugio is the perfect vacation... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 23
    5 of 5 stars (5) Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    The Agriturismo Villa Giarradea is a magnificent mansion builded at the end of 600. Completely renovated keeping the original external appearance (the villa is protected by the "Italian fine arts"), the structure is immersed in the green countryside of Cortona. Giarradea Villa has a large park,... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 18
    5 of 5 stars (9) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    52044, Cortona, Province of Arezzo
    1 / 88
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    52044, Cortona, Province of Arezzo
    1 / 37
    5 of 5 stars (1) Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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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... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 44
    4.5 of 5 stars (5) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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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... View all property information
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    52040, Cortona, Province of Arezzo
    1 / 28
    5 of 5 stars (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    Villa Capezzine 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 "scenic road" that... View all property information
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    52044, Cortona, Province of Arezzo
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    1 / 23
    5 of 5 stars (14) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Located in a beautiful and very peaceful valley of the Cortonese countryside, just 10 mins drive from the lively hilltown, this quaint and atmospheric farmhouse, which has been lovingly restored and tastefully furnished by its Italian-American owners, is cradled in 15 acres of its own olive groves... View all property information
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    52044, Cortona, Province of Arezzo
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    52044, Cortona, Province of Arezzo
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Terrace
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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... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 121
    5 of 5 stars (57) Excellent
    13 Bedrooms, 12 Bathrooms, Sleeps 30 | Quick View
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    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 / 101
    10 Bedrooms, 6 Bathrooms, Sleeps 20 | Quick View
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    • Children's Pool
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    52044, Cortona, Province of Arezzo
    1 / 37
    5 of 5 stars (1) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
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    About this property
    Fonte al Vento is a detached villa wisely set in a large property against a breathtaking landscape that includes an additional accommodation facilities. Each one has its own private garden, swimming pool and spaces for exclusive use to completely respect the privacy of our guests. The Villa is... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 22
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Our house is spacious and full of light - a perfect cool retreat after a warm summer day's exploration in Tuscany. Great for two love birds or a couple with a child, this accommodation in Cortona even has its own little walled garden, where you can sit and chat in the shade. In the evening, you can... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 37
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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 / 36
    4 of 5 stars (1) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Property DescriptionVilla Francesca is a beautiful villa located in the countryside in the green hills on the border between Tuscany and Umbria, a few kilometers from Cortona, a quaint town rich in history and offers shops and services of all kinds. At about 1 km you will find a restaurant and a... View all property information
    Location Information
    52044, Cortona, Province of Arezzo
    9 Bedrooms, 9 Bathrooms, Sleeps 18 | Quick View
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    • Grill
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    About this property
    Villa Paola is an imposing villa of the ‘800, not far from the beautiful Etruscan town of Cortona, which is only 5 km from the historic center. The villa is set in the heart of the Tuscan countryside, among orchards and crops, in a strategic point where even during the hottest hours you will always... View all property information
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    52044, Cortona, Province of Arezzo
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    1 / 16
    5 of 5 stars (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Rasina House is situated in a stunning position at 500m of altitude over the Tuscan hills of Cortona, which give the house a fantastic and unique panoramic view. Rasina house is an ancient rural house that has been recently restored strictly using traditional materials, in accordance with the... View all property information
    Location Information
    52040, Cortona, Province of Arezzo
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Balcony
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    • Pet-friendly
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    • 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 / 20
    5 of 5 stars (5) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    52044, Cortona, Province of Arezzo
    1 / 48
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
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    • Waterfront
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    • x
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    About this property
    Villa Luisella is a charming villa, situated in the heart of the medieval Etruscan city of Cortona, a short walk from the central square, with breathtaking views over the surrounding countryside till the shores of beautiful Trasimeno Lake. The villa's peculiarity is the garden, perfectly set... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 21
    5 of 5 stars (3) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    About this property
    La Fenice is part of an award winning restoration of a substantial farmhouse. The accommodation is over 140sq m restored with terracotta floors and wooden beamed ceilings. Downstairs consists of a large lounge/dining room seating 6 at the table and with comfortable seating around the open... View all property information
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    52044 CORTONA AR, Cortona, Province of Arezzo
    1 / 24
    5 of 5 stars (17) Excellent
    Private Room, 1 Bathroom, Sleeps 7 | Quick View
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    52044, Cortona, Province of Arezzo
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    157sq. Meters (1,690 sq. Ft) This ground floor suite in a stone building with apartments in Tuscany, Cortona, opens up into a spacious living area with doors leading out the private terrace and gardens with spectacular views of the countryside and Cortona . There is a fully equipped kitchen with... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 17
    5 of 5 stars (4) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Satellite TV
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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 / 56
    4.5 of 5 stars (3) Very good
    6 Bedrooms, 6 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Was born at the same time as my friend, the old pine tree Il Vecchio Pino. We are both happy to live in a place like this, surrounded by wild woods full of olive trees, nestling in the large well-kept garden full of plants, flowers, singing birds and a beautiful pool. We are very lucky: I was once... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 10
    5 of 5 stars (2) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Balcony
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    Location Information
    52044, Cortona, Province of Arezzo
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    This suite is on the first floor benefits from the best views of Chiana Valley and Cortona, and opens into a spacious living area with a large authentic wood burning fire place, and spectacular views over the countryside. There is a fully equipped kitchen and 2 double bedrooms, both bedrooms have... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 23
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Shared Yard
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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
    1 / 76
    4.5 of 5 stars (4) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    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 / 20
    5 of 5 stars (2) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Charming Ca de Muito has an idyllic position on the Tuscany side of the Niccone Valley. The views of the stunning countryside are breath-taking, they stretch over the Niccone Valley including 2 picturesque castles, to the village of Preggio on the opposite hillside. Whilst enjoying complete... View all property information
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    52044, Cortona, Province of Arezzo
    1 / 16
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    The house is located in Vicolo Orselli, a central but quiet part of Cortona, next to the Church of Sant' Agostino, at few steps from the main and livelier square of Cortona.<BR> The apartment is situated at less than 100 mt from one of the biggest parking of the town and enjoyes of a panoramic... View all property information
    Location Information
    52044, Cortona, Province of Arezzo
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    The apartment Girasole is situated on the ground floor and it has a separate entrance. It consists of: a living room, a kitchen, two bedrooms, two bathrooms with shower and independent heating.<BR>Apartment cleaning, detergents and waste:<BR>We use non-toxic cleaning products and with clear... View all property information
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    52044, Cortona, Province of Arezzo
    Mercatale
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Set in 2 acres of private olive grove,in the hills above the Niccone valley the house has been restored to a high standard and with larger than normal windows the whole living area is light and airy. There is good access to famous cities in both Tuscany and Umbria,; the nearest village is a 10... View all property information
    Location Information
    06060, Mercatale, Cortona
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Location Information
    52044, Cortona, Province of Arezzo
    4 Bedrooms, 10 Bathrooms, Sleeps 12 | Quick View
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    52044, Cortona, Province of Arezzo
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Outdoor Dining Area
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    The Ciliego is situated on a Tuscan hill in a very peaceful spot that enjoys a breathtaking view of the Chiana Valley. It is an 18th century sand stone farmhouse built on two floors. Ground floor: comfortably furnished sitting room , fully equipped kitchen and dining room. A wooden staircase takes... View all property information
    Location Information
    52044, Cortona, Province of Arezzo
    1 / 23
    4.5 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
    • Air Conditioning
    • Satellite TV
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    • Shared Outdoor Pool...
    • Balcony
    Suitability
    • Pet-friendly
    • Child-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... View all property information
    Location Information
    52044, Cortona, Province of Arezzo
    1 / 17
    5 of 5 stars (11) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 3 | Quick View
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    • Shared Yard
    • Grill
    • Outdoor Dining Area
    • Internet Access
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    Very pacefull 2 bedroom apartment, Located in a portion of Toscany Country Villa,near to Cortona, in the middle of Toscana's country. Close to main railways station (5km),and to main highway (3Km), it is a wondrfull place where you can stay if you have planned to visit Toscana: Firenze (1 hour far... View all property information
    Location Information
    52044, Cortona, Province of Arezzo
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Washer
    • Parking
    • Outdoor Dining Area
    • Private Outdoor...
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    Location Information
    52044, Cortona, Province of Arezzo
    1 / 39
    5 of 5 stars (11) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Grill
    • Private Outdoor...
    • Patio
    • Satellite TV
    • Washer
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Villa Cristina is a romantic 17th century stone farmhouse nestled in luxuriant terraced olive groves and vineyards on a quiet county lane a few steps from the ancient Etruscan hill-town of Cortona. Totally renovated in 2015, Cristina features original 5 meter high brick vaulted ceilings on the main... View all property information
    Location Information
    52044, Cortona, Province of Arezzo
    1 / 12
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Shared Outdoor Pool...
    • Central Heating
    • Wi-Fi
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    • Grill
    • Washer
    • Private Yard
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    52044, Cortona, Province of Arezzo
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Secure Parking
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    • Wi-Fi
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    • Central Heating
    • Washer
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Villa Il Castagno is the heart of the wine estate of the same name, which is located in enchanting hilly position among vineyards and olive groves and from which one can catch sights of the evoking shape of the near town of Cortona. Guests will have the chance to stay in the wonderful residence... View all property information
    Location Information
    52044, Cortona, Province of Arezzo
    1 / 36
    4.5 of 5 stars (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
    • ?
    • 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
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other traveler has booked this property
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    • Private Outdoor...
    • Mountain Views
    • Housekeeping...
    • Balcony
    • Wi-Fi
    • Parking
    • Central Heating
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    Location Information
    52044, Cortona, Province of Arezzo
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other traveler has booked this property
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    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Garibaldi is a finely furnished and welcoming apartment, located on the first floor of a historic building having the same name of the Piazza that leads into the promenade in the centre of Cortona. The architecture of each area is enhanced by the choice of tones and furniture. The apartment offers... View all property information
    Location Information
    52044, Cortona, Province of Arezzo
    1 / 14
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Shared Yard
    • Grill
    • Wi-Fi
    • Private Yard
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    Location Information
    52044, Cortona, Province of Arezzo