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Holiday Rentals with Pools in Province of Arezzo

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    Travellers to Province of Arezzo are booking December dates now. Secure your holiday home today, and have the perfect trip.
    1,979 Matching Rentals in Province of ArezzoView all 3,674 rentals
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    Villa Magnolia1 / 66
    (3)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Tuscany cottage near Castiglion Fiorentino, with Private Pool, BBQ, & Parking1 / 22
    (12)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Newly renovated Villa in Tuscany, spacious suites, Salty pool, outstanding views1 / 31
    (43)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Villa Anita1 / 39
    (1)Very good
    7 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    • Washer
    • Grill
    • Hot Tub
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 September 2016
    Everything is new here, excellent amenities including efficient air conditionning. Nice view on the country side from the large swimming pool. Close to Cortona and lago...
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    About this property
    Nestled in the rolling hills of the Chiana Valley, at the foot of the beautiful town of Cortona, we find ourselves facing a majestic villa which, from its raised position, overlooks and masters the surrounding area, rich in cultivated fields of sunflowers, olive and vineyards: Villa Anita The...
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    52044, Farneta, Province of Arezzo
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 13
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    Villa Della Valle1 / 33
    (1)Average
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    • Central Heating
    • Private Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Della Valle is a charming villa in stone, in true Tuscan style, situated in an elevated position (500 m asl) on the high hills of Cortona, on the border between Tuscany and Umbria. At Villa Della Valle you will experience a holiday in close contact with nature, giving you a break from the...
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    52044, Teverina, Cortona
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    Nice villa in Tuscany hills with large garden and private pool, sleeps 91 / 32
    (4)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 August 2018
    We really enjoyed our stay in this property. The villa is spacious on the inside and especially outdoors! The pool is huge, the climate was great. One thing, though (I can’t...
    Reviewed 7 July 2015
    We just came back from two weeks in this villa. We stayed here with 6 persons: Our friends with their 4 year old girl and me and my wife with our 8 months old baby girl. At...
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    About this property
    Villa Caterina is a nice villa with large garden and private swimming pool. Located in Casavecchia (Capolona) a few Km far from Arezzo on Tuscany hills, Villa Caterina enjoys a spectacular view over the city of Arezzo. Villa Caterina is equipped with 3 spacious bedrooms each with private bath,...
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    52010, Capolona, Arezzo
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 9
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    Villa Borgo delle Spighe- A nice country estate set in a wonderful scenario1 / 35
    (4)Excellent
    7 Bedrooms, 7 Bathrooms, Sleeps 19 Quick View
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    • Private Outdoor Pool (Heated)
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 June 2017
    The whole picture of the house and landscape was perhaps best. We the family - parents, grandparents and children enjoyed this entirety. The pool - little extra fee for heating...
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    About this property
    Located at the foot of Cortona, Borgo delle Spighe lays in the heart of Valdichiana, one of the most evocative scenery in Tuscany. This large red-brick farmhouse, typical of the rural tradition of these valleys, has been completely remodeled and now it can easily accommodate groups up to 14...
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    52044, Cignano, Cortona
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 19
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    Agriturismo Henni pool sauna jacuzzi panoramicview1 / 34
    (5)Excellent
    6 Bedrooms, 8 Bathrooms, Sleeps 15 Quick View
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    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Grill
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 August 2018
    We are on our final night here and just don't want to leave. None of the photos do justice to the area, or the property. The problem is that every view of and from the property...
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    About this property
    Old Farmhouse 'Agriturismo Henni' of 1800th totally renovated with antiseismic criteria in 2016, with swimming pool 6mt x 12mt, hydromassage and sauna with panoramic view. The building is situated upper the hill, around the house there is and olive grove, vineyard and wood. The ideal place for...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 6 Bedrooms, 8 Bathrooms, Sleeps 15
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    Il Mulino1 / 24
    (49)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Patio
    • Mountain Views
    • Washer
    • Central Heating
    • Wi-Fi
    • Grill
    • Waterfront
    • Children's Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 August 2018
    We had a fantastic time staying at the Mill. It’s beautiful and peaceful surroundings but a great location to visit nearby places and some amazing authentic restaurants a short...
    Reviewed 25 August 2018
    Maurice and Angela were both very friendly and helpful from the get go. When we arrived we were shown around the property which was very clean and spacious, comfortably sleeping...
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    About this property
    Il Mulino stands solid and comfortable, perched on a rock where the sound of the river flowing beneath your windows will lull you to sleep at night. The Mill was fully modernised in 2000 but many original features have been retained: cotto and wooden floors, beams and even a breakfast table on the...
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    52032, Badia Tedalda, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Il Bocciolo at La Lombarda1 / 57
    (11)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Central Heating
    • Grill
    • Parking
    • Washer
    • Balcony
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 August 2018
    We had a brilliant holiday at Il Bocciolo and enjoyed everything Tuscany had to offer. Nina and Peter were excellent hosts who were attentive prior to and during our stay...
    Reviewed 5 October 2017
    This was the first time we have stayed away from a city and absolutely loved our experience. Peter and Nina were fabulous hosts and La Lombarda is beautiful. The apartment was...
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    About this property
    La Lombarda, our beautifully restored traditional 18th century Tuscan farmhouse is ideally placed within easy reach of Tuscany and Umbria's wealth of art and cultural centres. Cortona, nestling in its hillside just 20 minutes away, with its medieval cobbled lanes is a delightful and atmospheric...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    La Mimosa at La Lombarda1 / 46
    (11)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Balcony
    • DVD Player
    • Parking
    • Grill
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Central Heating
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 September 2018
    We were looking for a romantic getaway in a part of Tuscany we hadn't yet explored. Not only did we find that, but we became friends with our hosts who couldn't have been nicer...
    Reviewed 10 September 2018
    Absolutely amazing stay at la mimosa. Couldn’t have asked for better hosts than Nina and peter, they were extremely welcoming and very knowledgable about the area. Apartment is...
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    About this property
    La Lombarda, our beautifully restored traditional 18th century Tuscan farmhouse is ideally placed within easy reach of Tuscany and Umbria's wealth of art and cultural centres. Cortona, nestling in its hillside just 20 minutes away, with its medieval cobbled lanes is a delightful and atmospheric...
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    52040, Cortona, Province of Arezzo
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
    • Washer
    • Grill
    • Balcony
    • Terrace
    • Parking
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With patience and enthusiasm we have created a welcoming place to live among olive and ancient fruit varieties, cultivating vegetables and producing honey, all respecting the environment, using the dictates of organic farming. The farm is located about 1.5 km from the town of Monte San Savino, a...
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    52048, Monte San Savino, Province of Arezzo
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    Casa Toppole1 / 27
    (3)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casa Toppole is an old stone farmhouse, full of charm, located in the heart of Tuscany. It is independent, enjoys a panoramic view and is located 6 kilometers from Anghiari, a medieval classified village. The capacity of the house is 6 to 8 people. It was built on the ruins of an eleventh century...
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    52031, Anghiari, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    Villa Alma: the pool is a dream1 / 81
    (4)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Hot Tub
    • Sauna
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you are looking for an exclusive location where time seems to stand still, welcome to Villa Alma. Situated on the Cortona hill, with a breathtaking view on the valley, this villa will ensure you an unforgattable vacation. A charming cherry tree-lined drive takes you to the newly restored...
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Tuscan Dream|Private|Pool|Walk to Cortona|FreeWiFi1 / 57
    (14)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Balcony
    • Wi-Fi
    • Grill
    • Mountain Views
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 October 2017
    Wow! We were very impressed with finding this gem in Cortona. The views are spectacular from this property only drawback is that we were only there for a few days and were out...
    Reviewed 29 March 2017
    The remodelled historic house is the perfect spot to relax and unwind. Open plan living areas with an amazing outlook over the Tuscan countryside. The close proximity to town...
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    About this property
    A dream home just for you. We created our home in Cortona with all the essential mod cons. Music, kitchen, comfy beds, and of course with the essential pool and (Free) Wi-Fi. Villa Rosa is nestled into the Cortona (Tuscan) hillside with only a few minutes drive to the historic hill top town or...
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Villa Rosa - Heaven in Tuscany|Pool|WiFi|Cortona1 / 53
    (15)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Mountain Views
    • Patio
    • Grill
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 October 2018
    Villa Rosa sits comfortably nestled above the high Tuscan hillside town of Cortona.The views, to say the least, are spectacular. The bright and warm mid-September week my wife...
    Reviewed 20 September 2018
    Perfect if you want to relax, unpack, read books, self cater and enjoy the village life and surrounds. Excellent for day trips to Florence, Sienna, Montepulchiano, Arezzo...
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    About this property
    With essential private pool and (Free) Wi-Fi, Villa Rosa is nestled into the Tuscan hillside within a few minutes drive or leisurely walk into vibrant Cortona. Couples love it, families love it. It is heaven. A two bedroom, two bathrooms, fully furnished beautiful private house for your Tuscan...
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Villa Cristina, your wonderful Tuscan dream !!1 / 76
    (38)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 11 Quick View
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    • Washer
    • Hot Tub
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 October 2018
    Located in the hills overlooking Arezzo Italy, Villa Cristina is the perfect location for a vacation in Italy. The Villa has everything: a salt water pool, hot tub, outdoor...
    Reviewed 8 August 2018
    We were once again at Villa Christina, now with our family and children (1, 5 and 8 years old) which was as great as the time with our friends. The house offers everything you...
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    52100, Arezzo, Province of Arezzo
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 11
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    Al Vecchio Fienile1 / 33
    (5)Very good
    6 Bedrooms, 6 Bathrooms, Sleeps 15 Quick View
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    • Parking
    • Washer
    • Private Outdoor Pool (Unheated)
    • Central Heating
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    When, in the 18th century, the Grand Duke Leopold had farmhouses planned and constructed in Tuscany, he never imagined that these would one day become the symbol of Tuscany and that they would become holiday homes for people from all over the world. Even this house has remained unaltered in its...
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    52046, Lucignano, Province of Arezzo
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 15
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Wi-Fi
    • Central Heating
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Grill
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Ginestra is the ideal place for nature lovers and those who want to relax. The villa is located on the hills surrounding the beautiful Etruscan town of Cortona, one of the most beautiful hamlets in Italy and famous throughout for its beauty and quality of life. The villa is elegant and...
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    52044, Teverina, Cortona
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Washer
    • Central Heating
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Balcony
    • Grill
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Due to its scenic location Villa Oleandro offers an unrivaled view over the town of Cortona and the whole Valdichiana. The villa has been carefully restored by the owners who have managed to keep the uniqueness of this beautiful stone farmhouse alive, which, with its rustic Tuscan style, will make...
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    52044, Montalla, Cortona
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    52044, Farneta, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Grill
    • Balcony
    • Private Outdoor Pool (Unheated)
    • Washer
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Immersed in the rolling Tuscan hills, at the foot of the beautiful Etruscan town of Cortona, we are in front of Villa Il Sasso, a majestic and luxurious property that, from its elevated position, dominates the surrounding valley and gazes towards the top of the hill where the beautiful Cortona...
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    52044, Camucia, Province of Arezzo
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 14
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    Villa Cristina - walking distance with pool1 / 41
    (12)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Private Outdoor Pool (Unheated)
    • Patio
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 September 2016
    Beautiful Property will great views, on a lovely hillside looking down to Camuccia town.The pool and accommodation were excellent and Marta from the agency in Cortona looked...
    Reviewed 10 June 2014
    Villa Cristina Contesse was an ideal spot for my family. I traveled with my wife, son (21), and daughter (18) in May. Nick (the host) attended to every need and had the villa in...
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    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...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Villa Conca D'oro1 / 41
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Private Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • DVD Player
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 June 2018
    This was the perfect week in Tuscany. A beautiful farmhouse renovated to ensure complete comfort. Nice bedrooms, bathrooms, a well stocked kitchen, and comfortable living room...
    Reviewed 5 June 2018
    The location is both remote yet so close to Cortona and the other wonderful hill top towns of Tuscany. It was so easy to visit Assisi, Arezzo, Perugia, Siena and other...
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    About this property
    Superb independent property perfectly nestled among the rolling hills surrounding the ancient Etruscan town of Cortona, Villa Conca D'oro is the ideal place to spend a holiday in the spirit of of nature, beauty and relaxation. Only 5 km from the historic center of Cortona and 1.5 km from the small...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Patio
    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In the heart of the tranquil Tuscan countryside, bounded by olive trees and woods, lies this beautiful villa overlooking the Trasimeno Lake. This property consists of 3 independent units, which together can host up to 10 people. A serene corner of the Tuscan countryside, Villa Conti is the perfect...
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    Location Information
    52044, Terontola, Province of Arezzo
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    8 Bedrooms, 9 Bathrooms, Sleeps 22 Quick View
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    • Washer
    • Balcony
    • Terrace
    • Grill
    • Private Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Petraia is a fantastic Tuscan villa, situated in a large garden just a few steps from Valdarno. The villa is on three floors. Near the pool there is an enchanting wellness area with jacuzzi and turkish bath. In the garden there is a large swimming pool in full sun. Relaxing on the loungers...
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    Location Information
    52020, Bucine, Province of Arezzo
    Holiday Rental House - 8 Bedrooms, 9 Bathrooms, Sleeps 22
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    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Patio
    • Parking
    • Grill
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa San Pietro is a beautiful property located in the immediate vicinity of the town of Cortona, whose view of the gentle slopes and monuments creates an unmistakable skyline, visible from the garden of the villa, creating a unique splendour for guests who will have the pleasure of spending their...
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    Location Information
    52044, San Pietro a Cegliolo, Province of Arezzo
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 14
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    Piccolo ulivo  ranch1 / 228
    (12)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Parking
    • Central Heating
    • Terrace
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 September 2018
    We really enjoyed our stay in this beautiful B&B. Paola couldn't have been more friendly, accommodating and welcoming. We loved our terrace, the pool, amazing views, and...
    Reviewed 21 August 2015
    We had an amazing time at the b&b Piccolo Ulivo ranch. Its a very peaceful location but very close to touristic locations like Arezzo, Poppi, Florence, Anghiari.The apartment...
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    Location Information
    52010, Capolona, Arezzo
    Private Room - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Grill
    • Washer
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    • Private Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Civitella is a charming villa with swimming pool ideal for your holiday in Tuscany. It will give you an unforgettable and luxurious experience. Panoramic detached villa with private pool situated in a dominant position above the Val di Chiana, a few kilometers from the town of Civitella. The...
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    Location Information
    52041, Civitella in Val di Chiana, Province of Arezzo
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 9
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Grill
    • Washer
    • Patio
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In the countryside near Cortona, in Castiglion Fiorentino, where this recently restored holiday house is found. The house is situated within a beautiful vegetation setting, bordering a lovely cycle track, suitable for families and per those who love out door sport. The house offers the...
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    Location Information
    52043, Pieve di Chio, Castiglion Fiorentino
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    13 Bedrooms, 10 Bathrooms, Sleeps 31 Quick View
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    • Parking
    • DVD Player
    • Washer
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This large farm tourism enterprise is made up of 5 detached houses located on 300 hectares of woods and pasture land, with deer, roe deer and horses, about 5 km away from the historic centre of Sansepolcro. All the houses have been carefully restored and completed with all amenities offering...
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    Location Information
    52037, Sansepolcro, Province of Arezzo
    Holiday Rental House - 13 Bedrooms, 10 Bathrooms, Sleeps 31
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    Palazzo Rosadi1 / 56
    (2)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • DVD Player
    • Washer
    • Wi-Fi
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 June 2017
    We have been renting this villa for many years to enjoy our family/friends holidays.The Rosadi family is most helpful and offers excellent service. They have become good friends...
    Reviewed 1 May 2016
    This is our group's second stay at Palazzo Rosadi, and a more perfect vacation I can not imagine. From the incredible historical house, to the kindness and generosity of the...
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    About this property
    Palazzo Rosadi is an ancient country house dating back to 1700. In the 2000s it was renovated and became a splendid holiday villa for tourists who love the Tuscan countryside. Perched on the top of a hill, Palazzo Rosadi overlooks the valley of the Monterchi village, also well known because in a...
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    Location Information
    52035, Monterchi, Province of Arezzo
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Terrace
    • Balcony
    • Washer
    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relais Casa del Medico is a beautiful villa in typical Tuscan style with extensive, breathtaking view to the surrounding hills and mountains for 10 (+2) persons. The villa had previously not been rented until the actual owners were conscious that they would enjoy to share with other guests the...
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    Location Information
    52041, Oliveto, Civitella in Val di Chiana
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Central Heating
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Patio
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Fiorentina is the ideal place for a relaxing break immersed in nature. The Villa is surrounded by an olive grove of over two acres and enjoys stunning views of the nearby medieval town of Castiglion Fiorentino. It was recently renovated by the owners who have personally followed the work to...
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    Location Information
    52043, Castiglion Fiorentino, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tuscan holiday farmhouse villa features stunning grounds and pool, sleeps 41 / 23
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Grill
    • Shared Garden
    • Air Conditioning
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 June 2017
    We were so impressed with the beauty and charm of this little farmhouse. The view was incredible, the grounds gorgeous and the hosts just wonderful! We would stay here again in...
    Reviewed 7 August 2016
    Stunning service and personal treatment .the facility was up to dat and well orgnized .great view and area good for hiking location between all the great cities of tuscny...
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    About this property
    Casa Contea was created from an old farmhouse dating back to 1800, completely renovated. With its stone walls, the courtyard, the wooden beams, you can recreate the atmosphere of the ancient past, combined with the comfort of our days. Its elevated position, surrounded by forest, dominates the...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    • Grill
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Lavanda is a beautiful property located in one of the most evocative sceneries of Tuscany. The villa dominates the Valdichiana from an elevated position that will give you a breathtaking view surrounded by nature in complete tranquility, the property is fully fenced and surrounded by a park...
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    Location Information
    52044, Montalla, Cortona
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Balcony
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Marcella is a beautiful apartment situated at the foothill of the ancient town of Cortona, beautiful hamlet dating back to the Etruscans and which today is considered one of the most amazing places not only of Tuscany but of the whole of Italy. Appartamento Marcella (120 sqm- it can accommodate...
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    Location Information
    52044, Terontola, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Typical Tuscany, Privacy and Panorama1 / 29
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Internet Access
    • Terrace
    • Washer
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 May 2017
    We stayed for 12 days and nights in Casa Ronda, 5 persons altogether. Its a lovely place, well maintained, highly situated with a great view over the hills of middle Tuscany. We...
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    About this property
    Casa Ronda is located on the hills of Chianti Valdarno to 450 mt. above the sea level. The house is surrounded by a vineyard Chianti, olive groves and pine forests, in a plot of about 14 hectares, in a natural and untouched environment ideal for those who want peace and freedom to enjoy surround....
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    Location Information
    52024, Loro Ciuffenna, Province of Arezzo
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Terrace
    • Internet Access
    • Children's Pool
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The holiday homes with swimming pool of the farm are located on a high hill, with a wonderful view that sweeps over the vineyards and the woods of Chianti to Siena. The quiet that is breathed in Monte di Rota is total: no car noise passing, no voice, and the same view is relaxing, meeting in the...
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    Location Information
    52020, Montebenichi, Bucine
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    CASOLARE IL CONDOTTIERO HOLIDAY HOUSE1 / 59
    (30)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
    • Patio
    • Wi-Fi
    • Mountain Views
    • Central Heating
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 October 2018
    Loved this house in the Cortona area of Tuscany. Beautiful hillside location overlooking olive trees and the valley below. Stunning pool (which was cleaned every morning) and...
    Reviewed 24 August 2018
    Beautiful views, great pool and lots of space in the villa. Host is easily contactable if you have any problems (not that we did).
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    About this property
    Farmhouse in the hills not far from Castiglion Fiorentino and Cortona. Beautiful rural home placed on the silver hills covered with olives groves between Castiglion Fiorentino and Cortona, in a very panoramic position and a stone's throw away from the magnificent medieval castle of Montecchio...
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    Location Information
    52043, Castiglion Fiorentino, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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    Villa di Max1 / 29
    (1)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 11 Quick View
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    • Washer
    • Parking
    • Grill
    • Cable/satellite TV
    • Central Heating
    • Private Garden
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 July 2017
    Villa Max is a tastefully decorated home with high quality furnishings, that shows care and pride, not the typical furnishing vacation rental. The access road at first daunting...
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    About this property
    Max Weinberg, the long-time drummer for Bruce Springsteen's E Street Band, opens the doors of his marvellous holiday house situated in the gentle verdant hills between Tuscany and Umbria. Max and his wife bought their Tuscan home in 2000, succumbing to an infatuation with Italy after a family...
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    Location Information
    52044, Mercatale, Cortona
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 11
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    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Grill
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A few steps from the ancient Etruscan town of Cortona, only 1 Km from the center, Villa Vittoria sits surrounded by orchards and cultivated fields in a strategic position from which you can enjoy breathtaking views of Val di Chiana. This beautiful villa is immersed in the stunning Tuscan...
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    Location Information
    52044, Montalla, Cortona
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    Tuscany, Cortona - Private Villa for your dream holiday. Pool wifi walk cortona1 / 46
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
    • Mountain Views
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Patio
    • Grill
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 March 2017
    We have visited Villa Rosa twice, and have had a wonderful time on both occasions. Set in olive groves under the walls of a Medici fortress, and a 20 minutes walk from the...
    Reviewed 29 March 2017
    Villa Rosa is a favourite destination where I have stayed a number of times and will keep going back. It is an ideal combination of rural idyll and urban convenience, being...
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    About this property
    A two bedroom, two bathrooms, fully furnished beautiful private house for your Tuscan holiday. Complete with the essential private sparkling pool and Wi-Fi connection, Villa Rosa is nestled into the Tuscan hillside within a few minutes drive or leisurely walk into vibrant and bustling Cortona....
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Best Of Tuscany for Your Family1 / 22
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Internet Access
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 May 2017
    What a nice experience staying in this nice and very well situated Apartment!It was clean, very well furnished and assisted by very efficient and nice owners.I really...
    Reviewed 1 May 2017
    The surrounding is really nice. The flat has everything you want. We didn't miss anything. The hosts are very nice. We are thinking to come again.
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    About this property
    Villa Ceppeto was an old barn and is located on a private property of 7 hectares (70,000 square meters) located on the border of Chianti: there are beautiful walks and mountain bike trails through 750 olive trees, woods and fields of iris. The barn has been completely renovated in the typical...
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    Location Information
    52048, Monte San Savino, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Grill
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Immersed in the heart of Tuscany, nestled on the south side of the hill where the ancient Etruscan town of Cortona is located, lies Tenuta Pomona, a place where one can live an unforgettable experience, in a property of undisputed charm and luxury. The villa enjoys one of the most beautiful views...
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    Location Information
    52044, San Pietro a Cegliolo, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    TUSCANY VILLA PRINCIPE 8 prsns1 / 72
    (4)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
    • Private Outdoor Pool (Unheated)
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 July 2018
    The villa and pool were perfect for our family of six. Lots of room and each bedroom with their own private en suite.The location is just a 10 minute drive from Castiglion...
    Reviewed 23 October 2017
    My husband and I love this house - we've stayed here many times over the past 15 years. The location is great for accessing places of interest in both Tuscany and Umbria - or...
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    About this property
    Podere San Martino is an ancient farm of 9 ectars located in one of the most beatiful and strategic position of the Valle di Chio nearby the Historical towns of Castiglion Fiorentino ( 10 min. ), Cortona ( 20 min. ), Florence ( 1 hour ), Siena ( 1 hour ), Perugia ( 1 hour ), The location on a hill...
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    Location Information
    52043, Castiglion Fiorentino, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Charming 2 bedroom apartment in restored Tuscan farmhouse with pool located in historic Cortona1 / 60
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Wi-Fi
    • Patio
    • Washer
    • Grill
    • Central Heating
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 January 2017
    La Lombarda is an ideal spot for total peace, tranquillity and relaxation; it is exactly as described.With just 3 rented out guest accommodations and another for hosts Nina and...
    Reviewed 3 December 2014
    Nina and Peter were great. We went to see how olives are pressed and made into oil and it was a good learning experience.
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    About this property
    La Lombarda is our charmingly restored traditional 18th century Tuscan farmhouse in the comune of Cortona. La Stufa is a charming two bedroom apartment with wood-beamed ceilings and terracotta floors. There is a comfortable sofa and two armchairs in the lounge, TV, DVD, books, games and videos for...
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    Location Information
    52040, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Central Heating
    • Grill
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Old stone farmhouse, 250 sq. m., in a small hamlet, ideal for up to 10 persons with 5 double bedrooms with private bathroom with shower, a fenced swimming pool, panoramic terrace perfect for outdoor meals, barbecue, wood-burning oven, WiFi and parking. It’s an ideal property for those looking for a...
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    Location Information
    52041, Civitella in Val di Chiana, Province of Arezzo
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Il Cipresso apt in CASA CONTEA view swimming pool1 / 24
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Garden
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 August 2016
    We stayed there with another couple and had the downstairs apartment with two bedrooms and bathrooms either side of the apartment and then a living area and kitchen in between...
    Reviewed 10 August 2016
    This is a lovely place to stay, once you get there! The access road is long and narrow, dusty when it's dry and muddy when wet, so if you're a bit precious about your vehicle...
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    About this property
    Casa Contea was created from an old farmhouse dating back to 1800, completely renovated. With its stone walls, the courtyard, the wooden beams, you can recreate the atmosphere of the ancient past, combined with the comfort of our days. Its elevated position, surrounded by forest, dominates the...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    7 Bedrooms, 6 Bathrooms, Sleeps 13 Quick View
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    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Sauna
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Del Sole is the perfect place for an unforgettable experience! This magnificent property is situated in the heart of the hills of Cortona, in an extremely panoramic position that will offer your eyes all the spectacular splendor of the lush Tuscan countryside. The villa has spacious and...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 13
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