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Holiday Rentals with Pools in Province of Arezzo

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    Travellers to Province of Arezzo are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    1,816 Matching Rentals in Province of ArezzoView all 2,643 rentals
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    Villa Cristina, your wonderful Tuscan dream !!1 / 82
    (26)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    QUIET COUNTRY HOUSE (TOSCANA - AREZZO - ANGHIARI) DOG FRIENDLY, EXCLUSIVE USE1 / 25
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    ilpuggio1 / 25
    (5)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Tuscany Villa Bellavista1 / 48
    (9)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Central Heating
    • Washer
    • Grill
    • Private Outdoor Pool (Unheated)
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 June 2017
    The villa was charming and very well equipped with a good swimming pool. My only quibble is that it was not really"accessible"( an important feature when booking) Though...
    Reviewed 4 August 2016
    Had a wonderful holiday and Daniele could not have been more helpful. He even came and found us when we arrived and were lost to direct us to the villa. Beautiful scenery and a...
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    About this property
    San Martino is an ancient farm ( XIII century ) with three Farm Houses: Villa Bellavista ( 4 sleeps ), unique stone Villa with a relaxing atmosphere, lovingly restored and furnished. The Villa has own Private Pool 12mt x 5mt. The pivacy is guaranted. The property consist of 9 ectares located in...
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    Location Information
    52043, Castiglion Fiorentino, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Washer
    • Balcony
    • Wi-Fi
    • Grill
    • Mountain Views
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    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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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Podere Verdi Colline - Antico podere con piscina privata in Toscana1 / 74
    (9)Excellent
    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Children's Pool
    • Wi-Fi
    • Satellite TV
    • Patio
    • Housekeeping Included
    • Balcony
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 June 2017
    Tucked away in a small village in the hills of Tuscany. So peaceful, quiet and located in a beautiful scenery. Lovely apartment with super fresh new kitchen and comfortable big...
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    52014, Poppi, Province of Arezzo
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    Villa di Max1 / 29
    (1)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Washer
    • Parking
    • Grill
    • 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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    52044, Mercatale, Cortona
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 11
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    Borgo di Vagli1 / 14
    (7)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Central Heating
    • DVD Player
    • Satellite TV
    • Wi-Fi
    • Shared Garden
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 August 2017
    Every morning I just wanted to gaze out over the hills as the sun came up, actually, I also wanted to gaze out as the sun went down as well, in-between I was extremely happy...
    Reviewed 11 April 2017
    The staff was very friendly and helpful.The food was delicious.Extremely remote and difficult to drive at night..
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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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    6 Bedrooms, 6 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Private Garden
    • Central Heating
    • Wi-Fi
    • Washer
    • Satellite TV
    • Grill
    • Private Outdoor Pool (Unheated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Max Weinberg, the long-time drummer for Bruce Springsteen's E Street Band, opens the doors of his marvellous holiday house situated in the gentle verdant hills between Tuscany and Umbria. Max and his wife bought their Tuscan home in 2000, succumbing to an infatuation with Italy after a family...
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    52044, Mercatale, Cortona
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 11
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    La Mimosa at La Lombarda1 / 46
    (8)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Balcony
    • DVD Player
    • Parking
    • Grill
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Central Heating
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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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    52040, Cortona, Province of Arezzo
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Casale La Rosa dei Venti1 / 26
    (3)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Patio
    • Private Garden
    • Housekeeping Included
    • Central Heating
    • Washer
    • Grill
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    52033, Caprese Michelangelo, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Beautiful 3-bedroom house with garden and private secluded pool1 / 28
    (9)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Terrace
    • Grill
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • DVD Player
    • Balcony
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 August 2014
    We always look for a property with a pool, a view and somewhere shady to sit to enjoy the scenery. Capanno del Lupo ticked all the boxes and offered so much more.As a group of 5...
    Reviewed 29 July 2014
    We have just returned from a fantastic stay at Capanno del lupo. Whilst we would certainly echo the praises of other reviewers on the excellent facilities and location, it was...
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    About this property
    Capanno Del Lupo is a beautiful 300 year old, stone farmhouse, recently restored, which stands in 10 acres of hillside that merge into chestnut groves and woodland. It's position high in the Tuscan hills offers amazing views, seclusion and tranquillity and is perfectly located for walking...
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    52033, Caprese Michelangelo, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Casa la Bozza, IL Bozzino1 / 50
    (6)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Parking
    • Satellite TV
    • Central Heating
    • Grill
    • Private Garden
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 August 2016
    We had a fantastic stay here in this beautiful old house. I was very pleased with how clean it was when we arrived. Fresh clean sheets, new, good quality mattresses and...
    Reviewed 27 May 2015
    What a wonderfully relaxing visit! We enjoyed spending time here on the property as much as visiting the nearby Tuscan cities of Arezzo, Cortona and Assisi. The home is lovely...
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    About this property
    THE HOUSE IS SPLIT IN 2 INDEPENDENT APARTMENT OF THE SAME SIZE, BOT WITH A PRIVATE GARDEN, ENTRANCE AND PARKING, WE CAN RENT ONE OF THEM FOR 6+1 OR THE ENTIRE HOUSE FOR 12+2. THE DESCRIPTION BELOW REFERS TO Il Bozzino, the ground floor oneBUT APPLY TO BOTH. PLEASE READ TO HAVE MORE DETAILS OR ASK....
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    52044, Montalla, Cortona
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Il Bocciolo at La Lombarda1 / 57
    (10)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 2 weeks ago
    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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    52044, Cortona, Province of Arezzo
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Casa Gorgacce1 / 25
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Wi-Fi
    • Central Heating
    • Mountain Views
    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 31 May 2014
    I would like to start this review by saying Casa Gorgacce was exactly what we were looking for in a Tuscany farm villa. We loved it. This place puts you in the middle of the...
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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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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Villa Merelli1 / 50
    (3)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Washer
    • Grill
    • Private Garden
    • Private Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    52040, Alberoro, Province of Arezzo
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Casa dei Noce1 / 25
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • Central Heating
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Wi-Fi
    • Washer
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 June 2016
    We were lucky enough to stay for a wonderful week in this peaceful traditional casa which has been beautifully and lovingly restored to a high standard by the owners.We spent...
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    About this property
    We bought the house back in 2004 as a ruin and spent the next 3 years creating a house that we ourselves would love to stay in and we are very proud of it The house is the last one up the valley with no near neighbours and has wonderful views which you can never tire of. Its on 3 floors with 1...
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    52036, Pieve Santo Stefano, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    AGRITURISMO MENCHETTI - appartamento IL SALICE1 / 10
    (3)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Parking
    • Children's Pool
    • Patio
    • Washer
    • Shared Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fattoria il Salice is a farm house where guests can stay in three attractive holiday apartments, two of which (Il Salice and Il Granaio) are built into the renovations of the old cattle byre, while the other (Il Giardino) occupies the first floor of the owner's house. All around the houses a large...
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    52045, Foiano Della Chiana, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Cortona, Tuscan Retreat, Serene, WiFi, Pool, Bliss1 / 32
    (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 17 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.
    Reviewed 31 March 2017
    A picturesque villa perched in the hills of Cortona with abundant sunshine, butterflies, wild lavender and rosemary, a large terrace for outdoor entertaining, and a refreshing...
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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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    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Best Of Tuscany for Your Family1 / 22
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 May 2017
    What a nice experience staying in this nice and very well situated Apartment!It was clean, very well furnished and assisted by very efficient and nice owners.I really...
    Reviewed 1 May 2017
    The surrounding is really nice. The flat has everything you want. We didn't miss anything. The hosts are very nice. We are thinking to come again.
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    About this property
    Vacation Home Villa Ceppeto was an old barn and it lies on a 17.30 acres (70.000 sq.meters) private property located on the border of Chianti: there are beautiful walks and mountain bike trails through 750 olive trees, woods and fields of irises. The barn has been completely restored in the typical...
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    52048, Monte San Savino, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    TUSCANY VILLA PRINCIPE 8 prsns1 / 33
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
    • Private Outdoor Pool (Unheated)
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 November 2015
    We have stayed at this villa 5 times and will be staying there again next May (2016).Our first stay was for 2 weeks in 2001. We were a party of 6 including my 80 year old...
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    About this property
    Podere San Martino is an ancient farm of 9 ectars located in one of the most beatiful and strategic position of the Valle di Chio nearby the Historical towns of Castiglion Fiorentino ( 10 min. ), Cortona ( 20 min. ), Florence ( 1 hour ), Siena ( 1 hour ), Perugia ( 1 hour ), The location on a hill...
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    52043, Castiglion Fiorentino, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Casentino house & exclusive pool. Dogs welcome1 / 31
    (3)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Mountain Views
    • Patio
    • Grill
    • Central Heating
    • Private Outdoor Pool (Unheated)
    • Washer
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 August 2015
    Beautifull house, (very well equipped) lovely pool. Nice views over the mountains. Very relaxing, sitting on the balcony or by the pool, sipping wine.
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    About this property
    The splendour of Casa Giardino is found in the rural, medieval, tiny village of Spalanni which enjoys spectacular views across the Casentino valley. The exclusive and sun drenched pool, the large beautiful gardens with an abundance of fruiting trees and herbs, all combine to make unforgettable...
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    52018, Castel San Niccolo, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Casa Vacanze Villa Maria - appartamento Donatella1 / 10
    (9)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • Hot Tub
    • Wi-Fi
    • Grill
    • Housekeeping Included
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 June 2017
    Wonderful location, great host and amazingly decorated apartments! We could not have asked for more! Perfect for families and couples and plenty to visit around!
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    52031, Anghiari, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Parking
    • Grill
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • Central Heating
    • Washer
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casa Fontelunga is a lovely country house placed in an enchanted location hillside, between our olive plantation and just a few minutes from the beautiful art city of Cortona, made famous worldwide from the book and movie 'Under the Tuscan Sun'. Privacy and quietness are the main features of this...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Molino le Gualchiere1 / 25
    (37)Excellent
    11 Bedrooms, 15 Bathrooms, Sleeps 20 Quick View
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    • Hot Tub
    • Washer
    • Wi-Fi
    • Grill
    • Central Heating
    • Sauna
    • Balcony
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 days ago
    Perfect spot for those who enjoy quietness and want take it easy under the Tuscan sun. It's situated a half an hour walk from Loro Ciuffenna that has restaurants and cute old...
    Reviewed 7 March 2017
    If you love tranquility and history – this is the place for you. The farm is located in true Tuscanian country side surrounded by olive trees and vineyards and consists of 5...
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    52028, Loro Ciuffenna, Province of Arezzo
    Holiday Rental House - 11 Bedrooms, 15 Bathrooms, Sleeps 20
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    Tuscany, Cortona - Private Villa for your dream holiday. Pool wifi walk cortona1 / 30
    (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 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...
    Reviewed 29 March 2017
    Villa Rosa is a favourite destination where I have stayed a number of times and will keep going back. It is an ideal combination of rural idyll and urban convenience, being...
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    About this property
    A two bedroom, two bathrooms, fully furnished beautiful private house for your Tuscan holiday. Complete with the essential private sparkling pool and Wi-Fi connection, Villa Rosa is nestled into the Tuscan hillside within a few minutes drive or leisurely walk into vibrant and bustling Cortona....
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Casale Ruffignano1 / 20
    (5)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Parking
    • Central Heating
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Washer
    • Private Garden
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 June 2017
    Eight of us loved staying a week here - only great things to say: quiet, clean, gorgeous, comfortable. The owners take wonderful care of the property inside and out. We loved...
    Reviewed 18 August 2016
    We were a group of 19. 11 Adults and 8 children age 3 to 13years.This was an amazing location the villa was a wonderful historic building with loads of character.Views of...
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    About this property
    Villa Ruffignano is a luxury property, recently reconstructed respecting the traditional characteristics combined with the necessities of modern life. Villa Ruffigano dates back to the 16th century and was the centre of an antique farm on which 30 people worked. Guests can get a taste of the...
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    Location Information
    52044, Portole, Province of Arezzo
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 16
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    6 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Washer
    • Grill
    • Private Outdoor Pool (Unheated)
    • Parking
    • Private Garden
    • Air Conditioning
    • Wi-Fi
    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
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    villa ai cedri1 / 35
    (24)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Wi-Fi
    • Mountain Views
    • Grill
    • Satellite TV
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    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...
    Reviewed 12 September 2017
    The propert was breathtaking! Everything you need is available. The owners are extremely gracious as well.
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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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    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 4 weeks ago
    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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    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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    Il Nido a contemporary countrychic Villa with pool1 / 52
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Secure Parking
    • Wi-Fi
    • Balcony
    • Grill
    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 August 2016
    A gorgeous property with stunning views, gorgeous pool and garden and lovely interior. Perfect for exploring Tuscany- easy to get to from Perugia airport. Highly recommend.
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    About this property
    Nestled in the colourful Tuscan countryside, just 8km away from the old town of Cortona, Il Nido is a lovely small villa recently restored and finely appointed with a contemporary country-chic style. The skillful ability in matching the soft tones and the tasteful recall to the Arte Povera, give...
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    Location Information
    52042, Montecchio, Cortona
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, 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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    Location Information
    52040, Cortona, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    La Certosa1 / 33
    (5)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Parking
    • Balcony
    • Washer
    • Internet Access
    • Patio
    • Terrace
    • Private Garden
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 April 2017
    From the minature cyclamen which fill the forest leading to the villa, to the orchards and cypress and mind-blowing view you find when you arrive, La Certosa is full of graceful...
    Reviewed 15 April 2017
    Twice, I have had the pleasure of staying at La Certosa with friends old and new. Italy has never felt so comfortable and beautiful to me than on those two visits. The...
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    About this property
    Description: A spacious farmhouse located in a spectacular, private and tranquil hillside setting that includes 15 acres of terraced olive groves and fruit trees (pears, plums, cherry and apple.) Cortona, with its shops, restaurants and open air market is a 20-minute walk away along a quiet lane...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Cottage Roccaio Cortona1 / 27
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Central Heating
    • Mountain Views
    • Satellite TV
    • Wi-Fi
    • Washer
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 7 September 2016
    This was one of the best vacation I ever took and most of it due to the house. The pictures don't do it justice. It is even prettier and it's surrounding is breathtaking.
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    Location Information
    52043, Cortona, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    La Graziosa, graceful cottage with lovely pool.1 / 30
    (3)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Washer
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Grill
    • Patio
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 June 2015
    We're staying here and really enjoying it. Great location just down the hill from Cortona, actually just beyone Camucia. That means access to Cortona, Camucia's more real-life...
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    About this property
    In the heart of the Chiana Valley, at the foot of Cortona, lies this graceful stone house Casina La Graziosa. It is a detached house with private garden and pool at guests's exclusive disposal. The house is ideal for couples or small families. Casina La Graziosa is a single storey cozy cottage that...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Tuscany Villa Principe1 / 59
    (6)Excellent
    5 Bedrooms, 10 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Private Garden
    • Private Outdoor Pool (Unheated)
    • Mountain Views
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 August 2016
    Second visit to this villa and I cannot fault it, the owner Daniele is the nicest guy and will do anything to help your stay wonderful. The villa is situated at the top of a...
    Reviewed 7 November 2015
    We have stayed at this villa 5 times and will be staying there again next May (2016).Our first stay was for 2 weeks in 2001. We were a party of 6 including my 80 year old...
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    About this property
    San Martino is ancient farm of 13th century of 9 ectars located in one of the most beatiful and strategic position of the Valle di Chio and Val di Chiana nearby the Hisorical Towns of Castiglion Fiorentino ( 10 min ), Cortona ( 25 min ), Arezzo ( 30 min ), Montepulciano ( 45 min ), FLORENCE , SIENA...
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    Location Information
    52043, Castiglion Fiorentino, Province of Arezzo
    Holiday Rental House - 5 Bedrooms, 10 Bathrooms, Sleeps 10
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    CASALE IL TRECENTO Castiglion Fiorentino1 / 37
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Wi-Fi
    • Satellite TV
    • Hot Tub
    • Grill
    • Balcony
    • Washer
    • Patio
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 August 2017
    Oh how I loved this villa! It was even nicer in reality than in the description online. The villa is spacious with a perfect layout for two families. It is decorated with style...
    Reviewed 19 July 2016
    The farmhouse is classic, the pool is stunning and the inside is better than advertised. And thie owner and his family are so warm and helpful. And such good cooks! Definitely...
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    About this property
    Property DescriptionOld farmhouse of peasant origins, where on the ground floor you can still appreciate the old stables. Located 1,5 km away from the town of Castiglion Fiorentino which can also be reached on foot. Castiglion Fiorentino is one of the most renowned towns of Valdichiana and has...
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    Location Information
    52043, Castiglion Fiorentino, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
    • Washer
    • Balcony
    • Wi-Fi
    • DVD Player
    • Central Heating
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming stone farmhouse, equipped with every comfort, in an extraordinarily scenic location. Located in Valdarno, in front of the Chianti hills, between Florence and Arezzo is only half an hour from Siena. Due to its location, is an excellent starting point to visit the most famous tourist...
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    Location Information
    52024, San Giustino Valdarno, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Il Villino di Cortona (private property, private pool, wi-fi, air conditioning)1 / 23
    (44)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Private Outdoor Pool (Unheated)
    • Washer
    • Satellite TV
    • Patio
    • Housekeeping Included
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 1 October 2016
    Just completed s wonderful week's stay at the villa! Michele looked after us very well and his enthusiasm and generosity have no boundaries!A great pool and all amenities on...
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    About this property
    "Il Villino di Cortona", cosy holiday home nestled in the green heart of the Chiana Valley in Cortona (Tuscany), an oasis of peace, tranquility and relaxation. Your holiday in contact with nature ... "Il Villino di Cortona”, is a small holiday home, nestled in the Val di Chiana, in the heart of...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    La Bozza , country apartment with private garden1 / 42
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Balcony
    • Parking
    • Private Garden
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 August 2016
    La Bozza is a wonderful place where I spent my holidays with my family. We relaxed at the clearly blue pool and we felt well in the clearless flat. It is like a second home for...
    Reviewed 14 August 2016
    I celebrated my 60th at La Bozza with my daugher and best friend. The villa was everything i dreamed of, spacious with 3 double bedrooms, 2 baths and well equipped living...
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    About this property
    Started officially as a busines in 1994 but with previous experience of property rental in the precedent 10 years, Agriturismo Fontelunga is now a reference poit for those searching for a true Tuscan experience. W own same of the nicest accommodation in the traditional country stile in the Cortona...
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    Location Information
    52044, Montalla, Cortona
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Casa Maria Laura1 / 30
    (5)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Satellite TV
    • Grill
    • Washer
    • Patio
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 August 2017
    We have been back to to this Villa year after year as it's so perfect. Too be honest it's so good I have delayed writing a review as wanted to keep it secret.The villa is tucked...
    Reviewed 8 May 2017
    The house and the location was wonderful! We spent four days here and only left the house once to go to a vineyard, otherwise we just stayed at the house enjoying the sun...
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    Location Information
    52044, Cortona, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Chianti Villa , Florence, Siena, Arezzo, Tuscany1 / 55
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • DVD Player
    • Parking
    • Terrace
    • Grill
    • Housekeeping Included
    • Balcony
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    52022, Cavriglia, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Il Moro Novo1 / 24
    (1)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 3 Quick View
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    • Air Conditioning
    • Satellite TV
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Equipped with chairs, shades, and beach beds. It has been restored with respect for the original stile and all the furniture are antique, you will have a warm and relaxing feeling when you enter Il Moro Novo. The house is located just outside a small country village, so it is not easy to reach and...
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    Location Information
    52044, Montalla, Cortona
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 3
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    Villa la Foce: breathtaking panoramic view1 / 47
    (5)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Central Heating
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 June 2014
    We had an amazing time in the Villa from the minute we arrived by car. The owner was very friendly and helped recommended places to eat. The Villa was exactly as it was in the...
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    About this property
    Villa La Foce is situated on a charming hillside, just a few kilometres from Castiglion Fiorentino and Cortona. This beautiful independent villa enjoys a breathtaking panoramic view on the surrounding countryside and villages. An excellent choice for those seeking privacy and peace. The Villa,...
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    Location Information
    52043, Castiglion Fiorentino, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Villa Monterosi1 / 27
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Balcony
    • Satellite TV
    • Grill
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 August 2016
    We were two families with four kids that had a fantastic week at Villa Monterosi. The house was very nice with a good kitchen and everyone enjoyed making pizza in the outside...
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    About this property
    Set in 40 acres of olive groves, oak woods and fields full of wild flowers, Villa Monterosi is a jewel of peace with it's own private swimming pool, rolling gardens and terraces. A place to dream of, this stone built house has been renovated to the highest ecological standards whilst maintaining...
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    Location Information
    52031, Anghiari, Province of Arezzo
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Trilocale Iole in casale di campagna1 / 29
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Air Conditioning
    • Private Garden
    • Parking
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    52045, Foiano Della Chiana, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Farmhouse - Casa Maesta1 / 22
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Balcony
    • Grill
    • DVD Player
    • Patio
    • Central Heating
    • Mountain Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 September 2015
    We could not have asked for anything more from our stay .We had everything we needed .The house is beautiful and well looked after.. The pool was esquisit The...
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    About this property
    A Tuscan farmhouse located 5km from the medieval town Anghiari and 10km from the Roman town Sansepolcro. The town of Anghiari is nicely situated in the heart of the Upper Tiber Valley (Alta Valtiberina). Officially listed as “Uno dei Borghi piú belli d'Italia” (one of the most beautiful towns in...
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    Location Information
    52031, Anghiari, Province of Arezzo
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    'La Villa di Valeria' Piscina e Parco Arezzo1 / 28
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Grill
    • Air Conditioning
    • Patio
    • Children's Pool
    • DVD Player
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    52100, Arezzo, Province of Arezzo
    Private Room - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Molino le Gualchiere - Apt. La Capanna 2 camere1 / 28
    (2)Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Grill
    • Terrace
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Sauna
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 July 2017
    My wife and my 2 older children (ages 16 and 22) stayed here in July for a family vacation. This was the perfect location for our needs. The apartment was roomy enough for all...
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    Location Information
    52028, Loro Ciuffenna, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 4 Bathrooms, Sleeps 4
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