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Cortona Holiday Homes

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    All 745 Rentals in Cortona
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    Casa Di Amici1 / 57
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    CHARMING COTTAGE NEAR CORTONA, GARDEN, DINING PATIO, OLIVE GROVE, AC,WiFI1 / 57
    (22)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Charming Cortona villa with private pool (Dardano)1 / 11
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Views Views Views!  Incredible Property. Incredible Price.1 / 14
    (13)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Mountain Views
    • Parking
    • Cable/satellite TV
    • Washer
    • Central Heating
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 October 2017
    What a wonderful location in the heart of Cortona. This apartment had everything we needed - comfort, clean, and beautiful! We couldn't have enjoyed the location any more...
    Reviewed 23 August 2017
    I loved my visit to Cortona. I stayed at Casa di Amici in the Marcello, the 2nd Floor apartment. The place has a nice Tuscan and modern charm. It was sparkling clean, with a...
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    About this property
    The Perfect Tuscany VacationThis beautiful penthouse apartment of approximately 55 m2 (600 sq.ft.) has classic Italian beamed ceilings, a wood burning fireplace for cozy winter nights, and unforgettable Tuscan views that everyone dreams of. The completely renovated and decorated separate living...
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    52044, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Alle Pietre1 / 32
    (34)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Central Heating
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 January 2018
    My husband and I spent 4 days in Cortona at the end of December through the New Year. Alle Pietre was a lovely place to stay. The apartment is charming and Ester has done a...
    Reviewed 26 October 2017
    Ester had arranged for the taxi to pick us up at Camucia Station and deliver us to her front door. Ester was waiting for us at her front door with a warm, welcoming smile and...
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    About this property
    My cozy 3-floor house is placed on top of the Etruscan walls of Cortona, at the edge of the historic center, on a very quiet and characteristic street. It can accommodate up to 4 guests. I hope you will enjoy the stunning view on the valley beneath! Caratteristica casa a schiera nel centro storico...
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Tuscan holiday farmhouse villa features stunning grounds and pool, sleeps 41 / 23
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Grill
    • Shared Garden
    • Air Conditioning
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 June 2017
    We were so impressed with the beauty and charm of this little farmhouse. The view was incredible, the grounds gorgeous and the hosts just wonderful! We would stay here again in...
    Reviewed 7 August 2016
    Stunning service and personal treatment .the facility was up to dat and well orgnized .great view and area good for hiking location between all the great cities of tuscny...
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    About this property
    Casa Contea was created from an old farmhouse dating back to 1800, completely renovated. With its stone walls, the courtyard, the wooden beams, you can recreate the atmosphere of the ancient past, combined with the comfort of our days. Its elevated position, surrounded by forest, dominates the...
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Charming 2 bedroom apartment in restored Tuscan farmhouse with pool located in historic Cortona1 / 60
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Wi-Fi
    • Patio
    • Washer
    • Grill
    • Central Heating
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 January 2017
    La Lombarda is an ideal spot for total peace, tranquillity and relaxation; it is exactly as described.With just 3 rented out guest accommodations and another for hosts Nina and...
    Reviewed 3 December 2014
    Nina and Peter were great. We went to see how olives are pressed and made into oil and it was a good learning experience.
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    About this property
    La Lombarda is our charmingly restored traditional 18th century Tuscan farmhouse in the comune of Cortona. La Stufa is a charming two bedroom apartment with wood-beamed ceilings and terracotta floors. There is a comfortable sofa and two armchairs in the lounge, TV, DVD, books, games and videos for...
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    52040, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    La Mimosa at La Lombarda1 / 46
    (8)Excellent
    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 14 August 2017
    We stayed for a week , what a wonderful experience , our villa is situated in a privileged place , close to everything , all wonderful Tuscany , we had a car and can move to...
    Reviewed 4 April 2017
    Peter and Nina are great hosts, full of local knowledge and great ideas for meals / days out. La Stufa was our very comfortable home and the pool provided a wonderful way to...
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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
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    Casa Contea apt La Quercia with views and pool1 / 23
    (5)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 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
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    Cortona villa in beautiful Tuscan countryside1 / 12
    (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
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Private Garden
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Set in the heart of the Tuscan countryside, at the foot of Cortona, apartment Casa di Adrienne is part of the main farmhouse in a lovely residential complex. Guests have at their disposal large outer spaces, the swimming pool with the adjacent BBQ area and the covered parking lots. In addition,...
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    Location Information
    52044, Montecchio, Cortona
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    52044, Montecchio, Cortona
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Tuscan villa with private pool and garden and breathtaking countryside views1 / 20
    (8)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Secure Parking
    • Private Outdoor Pool (Unheated)
    • Washer
    • Balcony
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 December 2015
    I can hardly put into words what a glorious place this is! It suited us perfectly - comfortable, extremely well-equipped with thoughtful information left by the owners. Sure...
    Reviewed 6 August 2015
    We had an amazing time here! The main house is full of character, with old wooden beams, an ancient fireplace and quirky features - we were not surprised to learn that it could...
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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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Il Cipresso apt in CASA CONTEA view swimming pool1 / 24
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Garden
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 August 2016
    We stayed there with another couple and had the downstairs apartment with two bedrooms and bathrooms either side of the apartment and then a living area and kitchen in between...
    Reviewed 10 August 2016
    This is a lovely place to stay, once you get there! The access road is long and narrow, dusty when it's dry and muddy when wet, so if you're a bit precious about your vehicle...
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    About this property
    Casa Contea was created from an old farmhouse dating back to 1800, completely renovated. With its stone walls, the courtyard, the wooden beams, you can recreate the atmosphere of the ancient past, combined with the comfort of our days. Its elevated position, surrounded by forest, dominates the...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    P.B MOSS  HOUSE1 / 10
    (3)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Balcony
    • Washer
    • Central Heating
    • Parking
    • Porch
    • Mountain Views
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 August 2017
    Had a fabulous stay in Cortona .The apartment was very comfortable, well equipped, private and convenient .With stunning views from the outdoor area which was perfect for...
    Reviewed 24 September 2015
    This apartment was charming, clean, very comfortable, and really like a second home. The owner lives upstairs and with his perfect English helped us to immediately orient...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    villa ai cedri1 / 35
    (25)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Wi-Fi
    • Mountain Views
    • Grill
    • Cable/satellite TV
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 October 2017
    Our stay at the Villa ai cedri was perfect. Definitely a beautiful, charming Villa and the views are outstanding. We loved every moment and hope to visit again. Giovan the...
    Reviewed 3 October 2017
    Seriously. The beautiful views from the porch, the pool and the rooftop deck were beyond beautiful. Exploring the details of the olive trees, picking vegetables and fruit...
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    About this property
    'The agriturismo can accommodate 8 - 10 guests. The villa (250sqm) is set on the hillside and, from both the house and the gardens, one can enjoy the spectacular 180 degree views over the Valdichiana valley to the hills of Montepulciano beyond. The colours change throughout the seasons; from the...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Casa Zeni - Signorelli1 / 30
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 May 2017
    We stayed for 3 nights to allow us time in Cortona before moving on through Tuscany, the apartment was all that we expected and more. The pictures do show what's on offer but...
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    About this property
    Casa Zeni Signorelli is a little gem located in the heart of the ancient Etruscan town of Cortona, a short walk from all the services and the beauty of the town but at the same time in a peaceful and quiet place. You will be immersed in an elegant and charming atmosphere, in a tasteful environment...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cortona walking distance villa1 / 16
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Balcony
    • Air Conditioning
    • Grill
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 January 2018
    If you are looking for a villa that is under 10 minute walk from the beautiful hilltop town of Cortona, look no further. The villa is well equipped, the garden and pool perfect...
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    About this property
    This lovely small villa is located at 400 m from the charming town of Cortona, one of the most beautiful and renowned towns of Tuscany. An important Etruscan settlement, Cortona today is a medieval jewel on the side of a hill dominating the Val di Chiana. The villa, 65 sq. m, can comfortably...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    La Terrazza sulla Valle1 / 53
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Balcony
    • Grill
    • Mountain Views
    • Air Conditioning
    • Wi-Fi
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Perched just outside the town wall of Cortona, La Terrazza was the perfect location for us. We were only 100 meters from the main bus stop at Piazza Mercato. A 10 minute ride...
    Reviewed 27 June 2015
    We loved our time in this Cortona apartment. Everything was new and so well planned. We had 2 full bathrooms, a beautiful kitchen and the terrace was such a treat. The owners...
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    About this property
    Beautifully freshly renovated 2 bedroom/2 bathroom apartment with a private terrace overlooking the Valley. Master bedroom with a big mirror closet, fireplace, stunning view of the valley from the window and access to private terrace. The other bedroom has a closet and a nice private bathroom...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Washer
    • Central Heating
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Balcony
    • Grill
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Due to its scenic location Villa Oleandro offers an unrivaled view over the town of Cortona and the whole Valdichiana. The villa has been carefully restored by the owners who have managed to keep the uniqueness of this beautiful stone farmhouse alive, which, with its rustic Tuscan style, will make...
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    Location Information
    52044, Montalla, Cortona
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Perfect Stay at Incredible Prices1 / 20
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Mountain Views
    • Cable/satellite TV
    • Central Heating
    • DVD Player
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 March 2017
    We stayed at Marcello apartment over Christmas and New Years and fell in love with Cortona and Casa di Amici! We had the best sleeps in years, and the apartment was very nice...
    Reviewed 25 May 2016
    We had the fortunate opportunity to choose this lovely apartment for our three month stay in Tuscany. We felt very much at home in the apartment since it was well equipped for...
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    About this property
    Two bedroom spacious apartmentTaking up the full second floor, you will find the Marcello at Casa di Amici. The largest of the apartments, the Marcello is approximately 65 m2 (700 sq. ft.), and is the perfect apartment for couples or families that like a little more room and that need to...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Casa dell'Ermanna1 / 53
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Balcony
    • Wi-Fi
    • Terrace
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 January 2016
    This well-located apartment in the center of Cortona offers Old World charm with modern comfort and convenience. The interior is imaginatively and artistically decorated. Of...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Villa in Tuscany, Cortona(hiking, bikes, pathways, waterfalls)(wine&olive oil)1 / 31
    (41)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Grill
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 April 2018
    This property has a 1 bedroom apartment, 2 2 bedroom apartments and a 4 bedroom villa. We stayed in one of the 2 bedroom apartments. I can't say enough about this place. The...
    Reviewed 15 October 2017
    Borgo Valecchie is absolutely gorgeous! It’s tucked away in a very quiet area right outside of downtown Cortona and it’s a little slice paradise. My wife and I were treated like...
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    About this property
    Our villa offers an ideal combination of elegant simplicity and historical charm which create a unique experience and can comfortably accommodate up to 10 guests. Located just five minutes away from The Hill town Cortona. Along with a private swimming pool, this holiday accommodation, immersed...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Borgo di Vagli1 / 14
    (9)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Shared Garden
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    A fabulous restored village . Simply beautiful . Food is amazing and service excellent . Close to pretty much anything as long as you have a rental car . 20 minutes to Cortona...
    Reviewed 22 November 2017
    Secluded, yet modern. So friendly! Just a great way to experience Italy at its finest. This is not a city hotel, this is living in the Italian countryside, exploring small towns...
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    About this property
    Located in the heart of the Tuscan countryside, Borgo di Vagli is a quaint, meticulously restored 14th century Hamlet surrounded by a protected area of olive groves, fruit trees and ancient oaks. From the terraces, you can enjoy panoramic views of the breathtaking Tuscan hills, including a...
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    Location Information
    52040, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Appartamento Luna1 / 31
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • DVD Player
    • Wi-Fi
    • Central Heating
    • Grill
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 October 2017
    The view can't be beat and the location was perfect for us. This apartment will make you feel like you're an Italian. The Italian family who owns the apartment live on sight and...
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    About this property
    Appartamento Luna is a beautiful ground floor studio with 2 bedrooms and two bathrooms in a panoramic position in Cortona; situated on the cone hill of Cortona, an Etruscan town of rare charm and beauty, it will give you an unrivaled view over the Valdichiana which stretches right in front of you...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Villa San Martino beautiful hilly position1 / 36
    (1)Average
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Washer
    • Grill
    • Hot Tub
    • Central Heating
    • Balcony
    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 May 2017
    We booked this as it was advertised with a pool but we were told on arrival that the pool would not be ready before May. We had excellent weather all week (25degrees) and had...
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    About this property
    Set in beautiful hilly position, the farmhouse is named after the 800 olive trees that surround the property and from which the owners obtain great olive oil. San Martino agli Ulivi is the result of a long and accurate renovation of the family estate. On one of the stones of the old barn you can...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Villa Poggio1 / 35
    (1)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 24 July 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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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 14
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    Il Bocciolo at La Lombarda1 / 57
    (10)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Central Heating
    • Grill
    • Parking
    • Washer
    • Balcony
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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...
    Reviewed 21 April 2017
    We enjoyed our stay here.Well set up,good bed & helpful owners. It's convenient to lots of great little towns & attractions. The winery next door is a great place for a...
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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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    Villa Rosa - Heaven in Tuscany|Pool|WiFi|Cortona1 / 33
    (13)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 19 September 2017
    This is the second time we have stayed in Villa Rosa. We had our daughter and her husband with us and we stayed for 7 nights. Everything in the villa was to a very high standard...
    Reviewed 30 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...
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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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Mountain Views
    • Grill
    • Patio
    • Wi-Fi
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    52044, Pietraia, Cortona
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Ciliegio, nice apartment in lovely hilly position1 / 19
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Outdoor Dining Area
    • Mountain Views
    • Grill
    • Wi-Fi
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 November 2016
    The Drive up to the Villa is challenging, however once there the views are amazingWe barbecued on five nights sitting around the stone table which is excellent.The views...
    Reviewed 2 August 2016
    The views from the property are phenomenal as you can see for 20 miles. The swimming is like an infinity pool as you are constantly stare at the Chiana Hills and beyond. We made...
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    About this property
    The Ciliego is situated on a Tuscan hill in a very peaceful spot that enjoys a breathtaking view of the Chiana Valley. It is an 18th century sand stone farmhouse built on two floors. Ground floor: comfortably furnished sitting room , fully equipped kitchen and dining room. A wooden staircase takes...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Casa del Balestriere In Centro Storico1 / 13
    (7)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 January 2017
    I spent four weeks at Luca's rental in May and June last year. It was perfect. It was close enough to town to be able to easily walk to every restaurant, the grocery store...
    Reviewed 3 October 2016
    Our expectations were exceeded in every way. My wife and I had a delightful two weeks in Cortona, staying at this apartment within the city. Pre-trip communication with Luca...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    VillaStefania Old Farmhouse Great View on Cortona1 / 20
    (4)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Grill
    • Wi-Fi
    • Secure Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 June 2016
    We recently returned from a one week stay at Villa Stefania. We had 11 people in our party and rented both apartments. The views of the surrounding area were fabulous and we...
    Reviewed 11 January 2016
    We were 3 Family with several Kids spending three days, including the new year´s eve in the Cortona area. Stefania and her husband was very kind, available and flexible to...
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    About this property
    Stone-built farmhouse that has recently been restored with great care and is situated in the hills approximately three kiliometers from Cortona. The property is situated in a well reserved country place but not remote, very near to all necessity. The Villa is divided into two indipendent units...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Under the Tuscan Sun1 / 33
    (28)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • DVD Player
    • Balcony
    • Mountain Views
    • Central Heating
    • Terrace
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 October 2016
    We stayed 5 nights in this lovely apartment and it was the highlight of our 20 day trip through Italy. The apartment has everything one needs - it is clean, nicely decorated...
    Reviewed 22 July 2016
    We just drove down from Cortona to Rome after spending two weeks in this apartment. Put simply, this apartment is wonderful. The view from the living room is as advertised...
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    About this property
    This charming apartment, made of stones, consists of bedroom with queen size bed and a big wardrobe/closet, living room with a convertible sofa-bed and a breath taking view of the Val di Chiana Valley, full kitchen with dish washer, breakfast table and the same beautiful view as the living room....
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Il Villino di Cortona (private property, private pool, wi-fi, air conditioning)1 / 23
    (46)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 31 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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    Agriturismo Henni pool sauna jacuzzi panoramicview1 / 34
    (4)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
    About this property
    Old Farmhouse 'Agriturismo Henni' of 1800th totally renovated with antiseismic criteria in 2016, with swimming pool 6mt x 12mt, hydromassage and sauna with panoramic view. The building is situated upper the hill, around the house there is and olive grove, vineyard and wood. The ideal place for...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 6 Bedrooms, 8 Bathrooms, Sleeps 15
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    Home-from-home comfort in the Tuscan hills1 / 19
    (12)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Secure Parking
    • Washer
    • Grill
    • Wi-Fi
    • Patio
    • DVD Player
    • Mountain Views
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 October 2017
    What wasn’t to like? In need of break far from the madding crowd, we couldn’t have found a more perfect spot. Tucked away amidst the magnificent scenery of Tuscany - a perfect...
    Reviewed 19 September 2016
    My husband and I stayed in this lovey flat in the Tuscan hills outside of Cortona for 5 nights with another couple in late August/early September 2016. Kate and Andrew were very...
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    About this property
    Get above and beyond it all in our hillside retreat. Here we offer Spring and Autumn self catering holidays, with a focus on hill walking and relaxing in spacious, well presented accommodation that spans the lower two levels of our secluded farm cottage, located in tranquill hills 12 km (plus 2 km...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Central Heating
    • Cable/satellite TV
    • Mountain Views
    • Grill
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ca de Lelli is a spacious cottage modernised and fully equipped for family or group holidays at a very affordable price. Situated on a well maintained rural road close to Mercatale in the beautiful Niccone valley which straddles the Tuscan Umbrian border. The cottage has two double bed rooms the...
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    Location Information
    06019, Mercatale, Cortona
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    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
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Garibaldi, splendid apt in the centre Cortona1 / 37
    (2)Average
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Washer
    • Balcony
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 June 2017
    Apartment is located at one end of the main Via Nationale right in the very centre of Cortona. This give you access to all of the superb restaurants, wine bars and cafes on...
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    About this property
    Garibaldi is a finely furnished and welcoming apartment, located on the first floor of a historic building having the same name of the Piazza that leads into the promenade in the centre of Cortona. The architecture of each area is enhanced by the choice of tones and furniture. The apartment offers...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Casa vacanze CASA BIAGIOTTI1 / 24
    (5)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Wi-Fi
    • Mountain Views
    • DVD Player
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 September 2017
    From the very start, we were made to feel most welcome by the warmth and generosity of the lovely owners, Loriano and Roberta. Nothing was too much trouble for them and they...
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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Charming top floor Historic Cortona1 / 43
    (9)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Private Garden
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 August 2017
    Myself and 3 other ladies came to Italy to celebrate two birthdays. We stayed at Paulo and Daniella's charming villa in Cortona; it was beautiful!The bedrooms were spacious with...
    Reviewed 1 August 2017
    The accommodations were outstanding. And Daniela and Pablo were a pleasure to deal with. They provided excellent recommendations for places to visit and restaurants. Truly...
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    About this property
    Three double rooms each with private bathrooms and showers, dining room, kitchen. In the garden a cabin with a wood oven, barbecue, table and chairs and deckchairs. From june 15 to august 31 the price per night includes air conditioning. In the kitchen ceiling fan. The spacious apartment 'La...
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    52044, Cortona, Province of Arezzo
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Appartamento Cara Mia1 / 20
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Washer
    • Cable/satellite TV
    • Central Heating
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 September 2017
    Throughly enjoyed our stay here, it was a home away from home.Ideal location, right around the corner from the main square.2 separate bathrooms both with showers, which was...
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    About this property
    Casa Cara Mia is an apartment of 67 square meters on the first floor of an old building, right in the heart of the historical center of the beautiful town of Cortona, an ancient Tuscan village among the most beautiful in Italy. The apartment, despite being in the old city, is cool and quiet, ideal...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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 21 May 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 16 September 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
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Tuscan Dream|Private|Pool|Walk to Cortona|FreeWiFi1 / 38
    (14)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Balcony
    • Wi-Fi
    • Grill
    • Mountain Views
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 October 2017
    Wow! We were very impressed with finding this gem in Cortona. The views are spectacular from this property only drawback is that we were only there for a few days and were out...
    Reviewed 30 March 2017
    The remodelled historic house is the perfect spot to relax and unwind. Open plan living areas with an amazing outlook over the Tuscan countryside. The close proximity to town...
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    About this property
    A dream home just for you. We created our home in Cortona with all the essential mod cons. Music, kitchen, comfy beds, and of course with the essential pool and (Free) Wi-Fi. Villa Rosa is nestled into the Cortona (Tuscan) hillside with only a few minutes drive to the historic hill top town or...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Please contact me for discount which depends on the group size. 5 stunning Double studio apartments all with own sitting room and bathroom. The house was renovated, decorated and furnished by local artist Edo Perigrino from a ruin which belonged to the neighbouring castle. The property contains...
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    Location Information
    52044, Mercatale, Cortona
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    4 Bedrooms, 5 Bathrooms, Sleeps 7 Quick View
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    • Ocean Views
    • Mountain Views
    • DVD Player
    • Washer
    • Central Heating
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The elegant apartment is situated on the second and the third floor of an old building once property of titled people, at the entrance of Piazza del Duomo and offers magnificent glimpses of the alleys and the rooves of Cortona, wonderful sunsets and a stunning view on the Valdichiana. The warm...
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    Location Information
    52044, Cortona, Province of Arezzo
    Condo/Apartment - 4 Bedrooms, 5 Bathrooms, Sleeps 7
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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
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 16
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    Cottage Roccaio Cortona1 / 27
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • 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 November 2017
    3 Spacious bedrooms with 3 full baths. Good kitchen with large dining, great outdoor space. This place is as good as the pictures. We were met at a local gas station and lead...
    Reviewed 24 July 2017
    Cottage very comfortable and used the pool everyday. Great place to stay and explore Tuscany. Ideal location for visiting Cortona, Arezzo, Siena, Montepulciano. We enjoyed...
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    52043, Cortona, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    La Fiorita Farmhouse in Cortona,Apartment Ortensia1 / 80
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • Patio
    • Mountain Views
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 March 2016
    We were looking for a central location in Tuscany, near Cortona, from which we could explore the countryside. La Fiorita was perfect for that. Although about 12 km outside of...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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