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Cortona Rentals with Pools

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    Travelers to Cortona are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    609 Matching Rentals in CortonaView all 903 rentals
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    Villa BorgoValecchie/ Families&groups friendly/Newly renovated suites&ensuites1 / 30
    (45)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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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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    Agriturismo Henni pool sauna jacuzzi panoramicview1 / 102
    (5)Excellent
    6 Bedrooms, 8 Bathrooms, Sleeps 15 Quick View
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    Il Nido a contemporary countrychic Villa with pool1 / 52
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Patio
    • Secure Parking
    • Wi-Fi
    • Balcony
    • Grill
    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 29, 2016
    A gorgeous property with stunning views, gorgeous pool and garden and lovely interior. Perfect for exploring Tuscany- easy to get to from Perugia airport. Highly recommend.
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    About this property
    Nestled in the colourful Tuscan countryside, just 8km away from the old town of Cortona, Il Nido is a lovely small villa recently restored and finely appointed with a contemporary country-chic style. The skillful ability in matching the soft tones and the tasteful recall to the Arte Povera, give...
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    Location Information
    52042, Montecchio, Cortona
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Tuscany, Cortona - Gorgeous Private Home|Pool|Walk to Cortona|WiFi|Magical1 / 71
    (14)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Washer
    • Balcony
    • Wi-Fi
    • Grill
    • Mountain Views
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 10, 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 March 29, 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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    Location Information
    52044, Cortona, Province of Arezzo
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Villa Rosa - Heaven in Cortona, Tuscany with Pool|WiFi|Walk to Cortona|Privacy1 / 53
    (15)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Mountain Views
    • Patio
    • Grill
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 5, 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 September 19, 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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    Location Information
    52044, Cortona, Province of Arezzo
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Villa Il Giardino di Diana1 / 26
    (9)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Grill
    • Mountain Views
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    We stayed at Villa IL Giardino do Diane in July 2018 and held our wedding reception there after getting married in Cortona. The villa, grounds and local surroundings are all...
    Reviewed July 15, 2018
    The villa was in pristine condition very clean and bedrooms very spacious. It was very comfortable with plenty of room in all areas and beautiful outdoor areas with stunning...
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    About this property
    Located in a beautiful hilly position, Il Giardino di Diana is a genuine stone and brick farmhouse surrounded by the characteristic Tuscan hills with olive groves and vineyards. Both the pool and the attic, boast spectacular panoramic views of the countryside with Cortona's hill in the distance....
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    Location Information
    52044, Montecchio, Cortona
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    Typical house with lovely view and swimmingpool1 / 23
    (3)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Parking
    • Washer
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 14, 2016
    Second time here, very spacious, clean, contemporary house on the hillside with a spectacular view. Orchard with figs, apples, and other fruit. We have seen plenty of wild...
    Reviewed July 5, 2016
    Molbena is what you dream of, when you think of Tuscany....Once through the elegant iron gates, you drive on the tree-lined, winding road to this beautiful stone house perched...
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    About this property
    Surrounded by the enchanting Tuscan countryside, next to a large orchard, woods and terraces of olive trees, Molbena House is the ideal place to fully relax in a luxuriant nature, away from the chaos and crowding, but still being a few minutes away from the artistic treasures of Cortona and the...
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    Location Information
    52040, Cortona, Province of Arezzo
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    Villa Borgo delle Spighe- A nice country estate set in a wonderful scenario1 / 42
    (4)Excellent
    7 Bedrooms, 7 Bathrooms, Sleeps 19 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 5, 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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    Location Information
    52044, Cignano, Cortona
    Rental Home - 7 Bedrooms, 7 Bathrooms, Sleeps 19
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    Private House for your dream holiday -pool,wifi,walk to Cortona-Bliss in Tuscany1 / 72
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Washer
    • Mountain Views
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Patio
    • Grill
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 29, 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 March 29, 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
    Rental Home - 2 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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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Central Heating
    • Grill
    • Parking
    • Washer
    • Balcony
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 15, 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 October 5, 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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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Mountain Views
    • Grill
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Private Yard
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    52044, Cortona, Province of Arezzo
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    Residence Maine Case vacanza Cortona con giardino esclusivo e piscina1 / 35
    (8)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Parking
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    52044, Montecchio, Cortona
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    52044, Cortona, Province of Arezzo
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Cottage Roccaio Cortona1 / 27
    (6)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Central Heating
    • Mountain Views
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 7, 2018
    We came in a heat wave and enjoyed having the pool. We were able to do day trips all around Tuscany. We met the owner in town and traveled along to a dirt road up to the cottage...
    Reviewed September 1, 2018
    Peaceful location overlooking the tuscan countyside. Extremely clean and comfortable 3 bedrooms with extra cots if necessary. Big spacious bathrooms with good quality fixtures...
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    Location Information
    52043, Cortona, Province of Arezzo
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    ANTICO PALLAIO1 / 31
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Sauna
    • DVD Player
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 15, 2015
    The photos on Trip Advisor DO NOT give this place justice. Things got off to a great start with the warm and friendly welcome from Sergio and his family.Fabulous / extensive...
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    About this property
    tipical old house, swimming pool, wifi, tv satelite,bbq, volley ball field, pétanque field, mini tennis field. beatiful wiew over the chiana valley. all the old charme of tuscany. 4bedroom, 4 bathroom Located in the village of Ossaia ( 3 km from Cortona), the property can be used for different...
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    Location Information
    52044, Cortona, Province of Arezzo
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 11
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    6 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Washer
    • Mountain Views
    • Air Conditioning
    • Private Yard
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Il Giardino di Silvana is a typical Tuscan stone house located on an evocative hilly position, a few steps away from the prestigious Santa Maria Nuova church and walk to town. The property preserves its rustic style with cotto flooring, wood beamed ceilings and Pietra Serena stone walls along...
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    Location Information
    52044, Cortona, Province of Arezzo
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 11
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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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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Wi-Fi
    • Patio
    • Washer
    • Grill
    • Central Heating
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 2, 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 December 2, 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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    Villa Augusto the taste of history1 / 24
    (4)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Private Yard
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 26, 2017
    We loved the pool, the beautiful house with all crystal chandeliers, the park with all statues, the cat, the tennis court and the host with all his generousity and tips on what...
    Reviewed June 10, 2017
    We have stayed here on 4 or 5 occasions and fall in love with it again every time we visit. It is in the heart of one of the most beautiful areas of Tuscany - Cortona - an 11th...
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    52044, Cortona, Province of Arezzo
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Set in the majestic Tuscan hills, six bedroom farmhouse with outdoor pool, private garden and gorgeous views1 / 46
    (16)Excellent
    6 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 3, 2015
    I Mandorli is the quintessential Tuscany experience. Rooms are simple and well appointed, one find all he needs in the kitchen, wi fi works well (does not happen all the...
    Reviewed July 23, 2013
    Beautiful location in a silent area with outstanding view. The house and garden is comfortable and well maintained. Well equipped with different amenities and equipment making...
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    About this property
    I Mandorli is an original Tuscan farmhouse. It has been refurbished using traditional materials and techniques to maintain it's rustic character and help stay cool through the long summer days. In autumn and winter you can relax in the spacious living room, in front of the fireplace. From the...
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    Location Information
    52044, Cortona, Province of Arezzo
    Rental Home - 6 Bedrooms, 3 Bathrooms, Sleeps 10
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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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    Location Information
    52044, Teverina, Cortona
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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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 Yard
    • Air Conditioning
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 4, 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 August 7, 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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Villa La Pergola1 / 31
    (7)Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Mountain Views
    • Washer
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 20, 2015
    Wonderful charming old mill house converted to a guest home. Comfortable beds, spacious accomodations. Great hosts. Kitchen is first class. After a full day of touring we...
    Reviewed September 16, 2014
    the house, the people, the owners, the swimming pool, Cortona, the food, the wine all was so beautiful and good , but i have to say, that we had a lot of horse flies and we...
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    About this property
    Villa La Pergola is an authentic private villa in Tuscany, very close to the Etruscan town of Cortona. La Pergola is situated in a cosy village consisting of two other villas each with private swimming pool. The patio, decorated with elegant garden furniture, has a scenic view over the...
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    Location Information
    52044, Cortona, Province of Arezzo
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    8 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Private Yard
    • Sauna
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    tipical old house, swimming pool, wifi, tv satelite,bbq, volley ball field, pétanque field, mini tennis field. beatiful wiew over the chiana valley. all the old charme of tuscany. 4bedroom, 4 bathroom Located in the village of Ossaia ( 3 km from Cortona), the property can be used for different...
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    Location Information
    52044, Cortona, Province of Arezzo
    Rental Home - 8 Bedrooms, 7 Bathrooms, Sleeps 16
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    Beautiful Villa with Pool 10 Minutes from Cortona1 / 24
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Wi-Fi
    • Grill
    • Mountain Views
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 4, 2017
    We stayed at Casaletto for one week on our first trip to Italy and we wish we stayed longer. Casaletto's stone and tile architecture is stunning, the spacious rooms are...
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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...
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    Location Information
    52044, Cortona, Province of Arezzo
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Villa Melody: charming villa very near to Cortona1 / 45
    (6)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Mountain Views
    • Private Outdoor Pool (Unheated)
    • Grill
    • Wi-Fi
    • Washer
    • DVD Player
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 7, 2018
    We stayed at this villa which is now called Gaden Cove for a week in September 2017. It's in the most beautiful area and the accommodation was fabulous, clean and comfortable...
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    About this property
    Casa Melody is an ancient stone farmhouse that lies nestled among the hills near the Medieval town of Cortona. It has been carefully restored with particular care given to its unique architectural features such as the original beamed ceilings, the old Terracotta floors and the wide brick arches. In...
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    Location Information
    52044, Cortona, Province of Arezzo
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tuscan villa with private pool and garden and breathtaking countryside views1 / 20
    (10)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Wi-Fi
    • Secure Parking
    • Private Outdoor Pool (Unheated)
    • Washer
    • Balcony
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 7, 2018
    We saw the pictures and read the reviews so we were excited to go. This feeling was surpassed when we drove up to the property, absolutely amazing. Lots of space and privacy and...
    Reviewed July 11, 2018
    Lovely villa with a separate cottage - easily sleeps 9 but I'm sure can accommodate even more if necessary. Views from the villa and the pool area are stunning, although this...
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    About this property
    Casaccia is a beautiful medieval house on a hilltop with a large private pool and gardens offering incredible views. Fully refurbished, the villa offers 4 large bedrooms (sleeping up to 10), and three bathrooms, including a delightful cottage in the garden with its own bedroom, living space and...
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    Location Information
    06018, Cortona, Province of Arezzo
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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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 June 6, 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 June 4, 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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    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 Yard
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 18, 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
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 11
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Private Yard
    • Mountain Views
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    52044, Cortona, Province of Arezzo
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    Typical house with private pool and stunning view1 / 22
    (4)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Grill
    • Washer
    • Mountain Views
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 15, 2016
    Really friendly and relaxed host. A large beautifully presented property in a stunning rural location. We enjoyed the swimming pool, pizza oven and huge BBQ. Very comfortable...
    Reviewed August 4, 2016
    We had the pleasure of staying here. Family of 5, teenage boys and 2 sets of grandparents... Wonderful views, the owner and caretaker were friendly and responsive. Paradise...
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    About this property
    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...
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    Location Information
    52040, Cortona, Province of Arezzo
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    7 Bedrooms, 4 Bathrooms, Sleeps 11 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
    Rental Home - 7 Bedrooms, 4 Bathrooms, Sleeps 11
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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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    Location Information
    52044, Cortona, Province of Arezzo
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 4 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Grill
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    It 'a beautiful cottage completely restored, was once a barn and a tobacco warehouse. now has 2 bedrooms, a lounge, a kitchen, 2 bathrooms and a dining room that can become an extraordinary study. It has a swimming pool, a large garden, a bocce court, private parking. about 3 km from Cortona, and...
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    Location Information
    52044, Cortona, Province of Arezzo
    Rental Home - 2 Bedrooms, 4 Bathrooms, Sleeps 4
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    Villa Magnolia1 / 66
    (3)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Balcony
    • Grill
    • Central Heating
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 6, 2018
    It is tricky to find a property with enough beds and baths to accomodate 2 families - but Villa Magnolia did just that and more! This farmhouse has been beautifully remodeled...
    Reviewed November 2, 2016
    We were a group of 8 staying at Villa Magnolia. The property is up in the surrounding mountains of the city of Cortona with a beautiful view of the valley below. The...
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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...
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    Location Information
    52044, Teverina, Cortona
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Fantastic 5 bedroom Tuscan farmhouse with panoramic views and swimming pool1 / 30
    (8)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Parking
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Balcony
    • Grill
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid 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...
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    Location Information
    52044, Cortona, Province of Arezzo
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 16
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    Il Villino di Cortona (Relaxing home, exclusive pool, in the Tuscany heart).1 / 23
    (55)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Private Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Patio
    • Housekeeping Included
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 30, 2018
    Now that we have returned home from our 14 day vacation in Italy, I am pleased to sit and write this review above all others. Our time (5 nights) at Il Villino Di Cortona was...
    Reviewed June 24, 2017
    This was our second stay at Il Villino di Cortona and we had a wonderful time once again! The villa is rustically comfortable and the little touches made by Michele (the owner...
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    About this property
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    Location Information
    52044, Cortona, Province of Arezzo
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Grill
    • Private Outdoor Pool (Unheated)
    • Central Heating
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Eleonora will give you a unique stay in a location characterized by quiet and privacy and incomparable views over the beautiful city of Cortona, whose views will accompany you while relaxing in the garden, enjoying the air of the Tuscan countryside in the morning or when you lean out the...
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    Location Information
    52044, Montalla, Cortona
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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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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    Location Information
    52044, Teverina, Cortona
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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 Yard
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 14, 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 August 9, 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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Villa Leccio: a beautiful stone farmhouse1 / 36
    (4)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Central Heating
    • DVD Player
    • Mountain Views
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    52044, Cortona, Province of Arezzo
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    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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    Location Information
    52044, Montecchio, Cortona
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Casa Di Amici1 / 57
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Sauna
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Hot Tub
    • Mountain Views
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In the heart of the Tuscan countryside, the apartment Casa di Amici sits in the main house of a lovely residential complex. Guests can enjoy vast outdoor expanses, a swimming pool adjacent to a barbecue area and sheltered parking. Every apartment also has a neat, private little garden. Casa di...
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    Location Information
    52044, Montecchio, Cortona
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    6 Bedrooms, 6 Bathrooms, Sleeps 11 Quick View
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    • Private Yard
    • Central Heating
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Unheated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 11
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    Casa Contea apt La Quercia with views and pool1 / 23
    (6)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Parking
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 2, 2018
    We really fell for this place when we were exploring Tuscany vacation rentals via Tripadvisor and it was everything we hoped for and more! The view was amazing and the house and...
    Reviewed July 24, 2017
    Valentina and Ivano were very kind, offering everything we needed including their lovely olive oil. We enjoyed alfresco dinners with incredible sunset views, swimming daily in...
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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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tuscany On Your Door Step: Beautiful Home in Cortona, WiFi, Pool, Views, Privacy1 / 82
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Grill
    • Air Conditioning
    • Balcony
    • Mountain Views
    • Washer
    • Wi-Fi
    • Patio
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 25, 2018
    All I wanted was sun and a pool. What I got was much more. Tuscan beauty to delight, Cortona a hill top town within walking distance with so many bars and restaurants...
    Reviewed August 14, 2016
    After busy time in Rome and Florence, my partner and I have visited Cortona. We decided to stayed at this great property. We had a very relaxing time which we needed before...
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    About this property
    Villa Rosa is a private home nestled in the hillside of the historic and vibrant hill top town of Cortona. Only a few minutes drive or a leisurely stroll into the City of Cortona, with expansive views over the valley to the distance shores of Lake Trasimeno, Villa Rosa is a tranquil haven that...
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    Location Information
    52044, Cortona, Province of Arezzo
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Villa Il Giardino di Diana1 / 31
    (2)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Mountain Views
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 23, 2018
    As one of Alex my son's family group, I agree 100% with his review. Our hosts were very helpful. Their villa is well situated for exploring Southern Tuscany and Umbria.
    Reviewed June 12, 2018
    I could not recommend Villa Il Giardino di Diana enough. The house itself is lovely, nice and cool inside even in the heat of the day with lots of big airy rooms and all the...
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    Location Information
    52044, Montecchio, Cortona
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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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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    Location Information
    52044, Montalla, Cortona
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Villa Poggio1 / 35
    (2)Excellent
    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Unheated)
    • Grill
    • Wi-Fi
    • Mountain Views
    • Washer
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 21, 2018
    Villa Poggia is amazing! Andrea could not have been nicer or more accommodating! This villa is perfectly located between Camucia and Cortona- so easy to access. The...
    Reviewed July 23, 2017
    Ever since seeing 'Under the Tuscan Sun, I've dreamt of visiting Tuscany with family and friends and staying in a villa. This was the first time I've rented a vacation home...
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    About this property
    General Description This luxury villa, surrounded by a gorgeous and impressive garden, has been recently restored with great care of details and with respect to Tuscan tradition. What a great location! The villa is ideally located close to village and services offering at the same time absolute...
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    Location Information
    52044, Cortona, Province of Arezzo
    Rental Home - 7 Bedrooms, 5 Bathrooms, Sleeps 14
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    La Pergola, Romantic Villa with Very Nice Loggia1 / 38
    (1)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    • Mountain Views
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 12, 2016
    We really enjoyed the property! The property was very well maintained and spotless. Check-in and check out process, communications with management firm were excellent. We had...
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    About this property
    Villa La Pergola is an authentic private villa in Tuscany, very close to the Etruscan town of Cortona. La Pergola is situated in a cosy village consisting of two other villas each with private swimming pool. The patio, decorated with elegant garden furniture, has a scenic view over the...
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    Location Information
    52044, Cortona, Province of Arezzo
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 11
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