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Holiday Rentals with Pools in Cortona

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    Travellers to Cortona are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    439 Matching Rentals in CortonaView all 658 rentals
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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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    Villa BorgoValecchie/ Families&groups friendly/Newly renovated suites&ensuites1 / 35
    (49)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Beautiful Renovated Tuscan Private Home|Pool|Walk to Cortona|WiFi|Magical1 / 71
    (14)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Villa Il Giardino di Diana1 / 26
    (10)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • 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 January 2019
    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 15 July 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
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    La Mimosa at La Lombarda1 / 46
    (11)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • 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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    Location Information
    52040, Cortona, Province of Arezzo
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Stunning Villa Rosa - Heaven in Tuscany |Relax|Pool|WiFi|Walk to Cortona|Private1 / 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 19 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
    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
    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
    Dream Location Private House  -Pool WIFI Walk to Cortona -Bliss in Tuscany1 / 72
    (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
    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 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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    Cottage Roccaio Cortona1 / 27
    (7)Very good
    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 3 weeks ago
    The grounds of the house are ideal. The outdoor table is in a perfect spot for dining even in the rain. The view is wonderful. However, know that the road leading to this home...
    Reviewed 7 September 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...
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    Location Information
    52043, Cortona, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    ANTICO PALLAIO1 / 31
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • 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 15 October 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
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 11
    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 Garden
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 July 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 10 June 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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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    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 23 June 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 12 June 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
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    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
    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 2 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 beautifully 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...
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    Location Information
    52040, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    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
    8 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Private Garden
    • 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
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 16
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
    • Washer
    • Central Heating
    • Private Outdoor Pool (Unheated)
    • Parking
    • Grill
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa La Rugantina, a typical Tuscan stone farmhouse finely restored, lies in the open countryside surrounded by wheat and sunflowers fields. The property boasts extended gardens and 6 large bedrooms: 5 doubles and a family room that sleeps 4. The whole house then can comfortably accommodate up...
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    Location Information
    52044, Creti, Cortona
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
    Il Villino di Cortona (Relaxing home, exclusive pool, in the Tuscany heart).1 / 24
    (59)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 30 March 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 25 June 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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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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 4 September 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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Celle del Farinaio1 / 27
    (1)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
    • Washer
    • Parking
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house is located on the lower slopes of the hills overlooking the Chiana Valley and where, higher up, stands the Etruscan city of Cortona. The property is immersed in the countryside covered with olive groves, forests and vineyards. This area is located on the border between Tuscany and Umbria...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 14
    Il Cipresso apt in CASA CONTEA view swimming pool1 / 24
    (4)Excellent
    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 23 January 2019
    Have stayed here on three occasions - it's a superb setting. Be warned it's a steep old drive up to the house(s) but it's worth it for the view, privacy, pool and the place...
    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...
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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
    Villa Del Sole1 / 64
    (1)Very good
    7 Bedrooms, 5 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
    Reviewed 13 August 2019
    We had a lovely stay at Villa Del Sole. The location, just a stone's throw away from Cortona, is great and the views absolutely breathtaking.The communal areas were...
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    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, 5 Bathrooms, Sleeps 13
    Set in the majestic Tuscan hills, six bedroom farmhouse with outdoor pool, private garden and gorgeous views1 / 46
    (17)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 4 June 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 23 July 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
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 10
    2 Bedrooms, 4 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Grill
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Private Garden
    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
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 4
    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 2 July 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 24 July 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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Il Giardino di Silvana1 / 30
    (2)Average
    6 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Mountain Views
    • Grill
    • Private Garden
    • Air Conditioning
    • Parking
    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 June 2019
    Country farmhouse located outside Cortona, steep uphill walk/drive to the town. Interior is rustic but pleasant enough. Functional kitchen (although could be better equipped and...
    Reviewed 6 September 2018
    A 20-minute walk to Cortona Old Town (up hill).Great location to tour from if you have transport.Spacious and comfortable accommodation split between four bedrooms / two...
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    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
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 11
    Villa Poggio1 / 35
    (3)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 2 September 2019
    My parents booked this place for a family trip to Italy. I don't think we could have found a better place! We all stayed in the same place by had our own space and separate...
    Reviewed 21 October 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...
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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
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 14
    Gorgeous Home in Cortona -Pool, Wifi, Views,Privacy - Tuscany On Your Door Step:1 / 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 25 September 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 15 August 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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    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
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 16
    Tuscan Private Paradise. Pool,WiFi, Walk to Cortona. Create those happy memories1 / 58
    (14)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Mountain Views
    • Balcony
    • Washer
    • Air Conditioning
    • Patio
    • Private Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 September 2018
    I cannot tell you how often I close my eyes and wish I was back 'Under the Tuscan Sun' in Cortona.As we drove down the Cyprus lined lane and pulled into Villa Rosa, all our...
    Reviewed 16 April 2017
    The house at Cortona is so beautiful, well appointed and welcoming, we felt we'd become part of the wonderful Tuscan landscape and way of life.
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    About this property
    Your holiday to Tuscany is special. You want a home that will provide you with the essential pool and of course the internet. You want to be close to the amenities but far enough away for privacy, seclusion and relaxation. We would love to welcome you to Villa Rosa which has all these features...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Le Casine - Limone Apartment1 / 19
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Grill
    • Shared Garden
    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Parking
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 July 2018
    Had such a great holiday here. The location is great with fantastic views over surrounding countryside and mountains. A great base to explore the area from and would recommend...
    Reviewed 1 August 2015
    My wife and I have just returned from Le Casine apartments in Tuscany and would like to record what a fantastic holiday we had. The apartment we stayed in was the Limone, a...
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    About this property
    This recently renovated country villa is situated in a beautiful rural setting, nestled in a village in the valley below the Etruscan town of Cortona. It has been converted, in traditional Tuscan style, into seven fully-self-contained, apartments which sleep between 2 to 4 visitors each. Each...
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    Location Information
    101 52044, Cortona, Province of Arezzo
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Holiday Villa in Cortona1 / 35
    (2)Excellent
    6 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Heated)
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 6 Bedrooms, 8 Bathrooms, Sleeps 14
    Tuscan Dream Home:Beautifully renovated 450yr Stone Cottage:Pool, WIFI, Magical1 / 53
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Parking
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Grill
    • Wi-Fi
    • DVD Player
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 October 2017
    I have been renting homes (holiday villas, houses, apartments, etc) in Italy, Spain, and Greece for over 25 years; sometimes 2-3x/year. I have never experienced a so enjoyable...
    Reviewed 2 November 2016
    A return visit to this perfect location. The villa has everything you need for a relaxing stay. Quiet with beautiful views of the country with Cortona just down the road...
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    About this property
    A dream home just for you - with all the essential mod cons. Pool, lawn, easy indoor/outdoor living, fully equipped kitchen, comfy beds, and essential (free) Wi-Fi. Villa Rosa is nestled into the hillside and within walking distance to Cortona. Couples love it, families love it. A two...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Mountain Views
    • Grill
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Private Garden
    • 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
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Grill
    • Air Conditioning
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Soak up a timeless ‘La Dolce Vita’ break, from this Tuscan farmhouse apartment with shared pool just 15 minutes’ drive away from captivating Cortona! Surrounded by the romantic rolling countryside of Tuscany, this enchanting refurbished farmhouse residence with on-site pool provides an exclusive,...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Grill
    • Wi-Fi
    • Washer
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bask in the Tuscan sun next holiday, from this lovely retreat in an authentic Tuscan farmhouse, with shared pool and carefree proximity by car to Cortona! Nestled within the enchanting Tuscan countryside, this recently refurbished farmhouse residence with on-site pool offers an exclusive holiday...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Appartamento in affitto per vacanza inToscana ' Casa di Chiarilu'1 / 15
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Children's Pool
    • Washer
    • Housekeeping Included
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
    • 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
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    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
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    Villa Magnolia1 / 69
    (3)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Grill
    • Washer
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 June 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 2 November 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
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Casa Gorgacce1 / 25
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Wi-Fi
    • Central Heating
    • Mountain Views
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Lovely rustic house,ample space for 6 people.everything you could need in a house is there.fab outside space with a lovely pool. Surrounding area is beautiful with a small...
    Reviewed 6 February 2016
    this is a great place. lots for children to do around the pool and the BBQ and the table tennis. We preferred exploring perugia and cortona, wine tours and olive oil tasting. At...
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    About this property
    Casa Gorgacce is an old stone farmhouse with lots of character beautifully converted with all modern comforts. It has a private garden and pool, complete privacy yet with great access and only a few kilometres from 2 lively villages; Meratale di Cortona and Lisciano Niccone where there are shops,...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Cortona villa in beautiful Tuscan countryside1 / 20
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Central Heating
    • Wi-Fi
    • Parking
    • Grill
    • Washer
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 June 2017
    Our time is coming to an end at the wonderful San Silvestro!Cortona and Camucia has provided an excellent base in order to explore the surrounding Tuscan and Umbrian...
    Reviewed 5 September 2014
    We have had a wonderful time at San Silvestro. The villa is a beautiful farmhouse set in a vineyard and a place of tranquility. On our arrival we were greeted with fresh...
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    About this property
    The sitting room has an old open fireplace and impressive, ancient wooden beams. Two comfy sofas are a nice modern addition! The dining room is authentic Italian 1950s decor under more seriously ancient ceiling beams. The atmosphere at San Silvestro is one of homely country simplicity. There's an...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    6 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Washer
    • Mountain Views
    • Air Conditioning
    • Private Garden
    • 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
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 11
    Charming Cortona villa with private pool (Dardano)1 / 11
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Private Garden
    • Central Heating
    • Washer
    • Parking
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 October 2013
    The pictures do not do Dardano justice. Thoroughly enjoyed our stay, Carla and Paolo amazing hosts . Great spot to explore Siena and Umbria. Fantastic local food market 2...
    Reviewed 20 August 2012
    We stayed at Dardano in July of 2012 and enjoyed a wonderful vacation!. Dardano is beautiful, and very comfortable for an extended family (there were 7 of us). It was a warm...
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    About this property
    Dardano is a deceptively large house, full of atmosphere. It is a simple country home, basic even, but with an elemental charm. You drive up to the house with its ancient stone well and to one side there's a little vine-covered area for shady outdoor eating. The garden is a neatly mown meadow...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    2 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Grill
    • Terrace
    • Washer
    • Air Conditioning
    • Balcony
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Luminosa is a beautiful villa in the hills near Cortona. The villa enjoys a picturesque location and is surrounded by olive groves and vineyards, typical of the Tuscan hills. From the pool you have spectacular views of Cortona. In the garden with plants and herbs is a terrace with garden...
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    Location Information
    52044, Montecchio, Cortona
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 12
    2 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    • Grill
    • Terrace
    • Central Heating
    • Shared Outdoor Pool (Unheated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Valentina is a beautiful house from the seventeenth century on a hill with beautiful views over the Tuscan countryside. The villa has been completely renovated and very tastefully renovated and decorated by its owners. The stone villa has beautiful green shutters, terracotta tiles and wooden...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 5 Bathrooms, Sleeps 9
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax by the poolside or discover the captivating beauty of nearby Cortona! Situated in an idyllic former farmhouse residence, this wonderful budget-friendly apartment boasts shared access to a beautiful on-site pool, as well as enviable proximity by car to central Cortona. Inside, the...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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