Cortona Vacation Home Rentals

On your next trip, consider a Cortona vacation home rental for your accommodations. There are 12 vacation homes in Cortona resorts. Vacation home rentals are generally appealing for many reasons. Some of the foremost being cost savings, more space, and no tips or service charges that are associated with hotel rooms. Vacation rental homes have kitchens for cooking, living rooms for gathering... read more
On your next trip, consider a Cortona vacation home rental for your accommodations. There are 12 vacation homes in Cortona resorts. Vacation home rentals are generally appealing for many reasons. Some of the foremost being cost savings, more space, and no tips or service charges that are associated with hotel rooms. Vacation rental homes have kitchens for cooking, living rooms for gathering together and offer the appeal of living in a real neighborhood and soaking up the rhythm of the locals.

With our friendly, responsive customer service and extensive informational website, renting a Cortona vacation home from Owner Direct Vacation Rentals is a breeze. Find your perfect location and home size to suit your needs, no matter what your criteria.
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Cortona Vacation Activities

12 Vacation Home Rentals

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  • Villa with Air

    Cortona: Villa
    6 BDR • 3 BA • Sleeps 13 • #256711
    475 to 485 EUR/night
    Our villa is a lovely holiday villa ,near to the enchanting town of Cortona, famous worldwide by the movie "Under the Tuscan Sun". It is just a short distance away too from the splendid towns of Montepulciano, Arezzo, Montalcino, Trasimeno Lake and Val d'Orcia. It is the ideal location to enjoy relaxing days, enjoying the Tuscan countryside and the gorgeous sunsets, the splendid food and wine of the hills of Tuscany, exploring the corners of this south area called Valdorcia , Valdichiana. The Tuscan villa, furnished in modern luxury Tuscan style, is perfect for groups and families, hosting up to 13 guests, with its 6 double bedrooms and 3 large bathrooms. Guests will enjoy the private swimming pool (measuring 6x12m) from which you can enjoy a panoramic view of the rolling hills nearby. The Tuscan villa is divided over two floors: on the ground floor, you will find the large living area and kitchen and two l double bedrooms and one large bathroom, accessible to wheelchairs or disabled guests. The top floor has 2 double bedrooms with view on the countryside, a bathroom with shower and two more bedrooms facing in the opposite direction with a panoramic view and luminious bathroom with shower. The open space living area and kitchen have everything you need to make your stay comfortable and relaxing. The kitchen has a dishwasher, all the utensils you need to enjoy meals at home, a kettle pot, toaster, and moka coffee machine for your morning brew, while the living room has a large TV Wifi internet , and comfortable sofa to enjoy a relaxing break. Wifi is available in this entire area. The patio and garden is easily accessible from this area, where you will enjoy the bbq area, drink a good glass of wine and good Tuscany meals , under the gazebo nearby the pool . The olive trees and other local plants around the pool and villa will remind you of the gorgeous Tuscan setting you find yourself in. The entire ground floor and external garden area and pool is easily accessible to any guest with mobility handicaps. The small village of Montecchio di Cortona where it's located the villa has a wonderful bakery, a small supermarket, a cafe-tabacchi, icecream (called bar in Italian), a pharmacy and bus stop to go in the Cortona Town, Camucia village where is a train station, larger supermarket and other shops. You should find most everything you need without having to go too far away.
  • Beautiful one Bedroom

    Cortona: Cottage
    1 BDR • 1 BA • Sleeps 3 • #202180
    79 to 166 EUR/night
    PLEASE NOTE: The posted rates are for 2 people, with an additional cost of 70 EUR per person, per week for the 3rd guest. This extra person charge is paid locally on arrival, and is NOT included in the total quoted by Owner Direct. Beautiful detached cottage in a fantastic position with wonderful views of the Chiana valley beyond. It has a lovely garden and a large swimming pool that both also enjoy the pretty panorama. The cottage is furnished to a very high standard and the location is perfect for visiting the famous region of Southern Tuscany. It is situated on a typical Tuscan estate which has been recently lovingly restored. It is composed of the owners farmhouse and the cottage which is completely detached, the cottage has a lovely garden where you can relax whilst enjoying the view, or have a meal al fresco cooked leisurely over hot coals on the barbecue. On the estate there is a large swimming pool (12m x 6m) which is reserved for the guests and the occasional use of the owners who are friendly and helpful but will not disturb your privacy. The house is composed of a comfortable living room, which is furnished in typical Tuscan style with some antique pieces. It has a country style kitchen / dining area, a sitting area with settee, armchairs, and cosy fireplace. The bedroom is spacious, has beamed ceilings and there is a modern bathroom. It is excellently located for touring the area with the towns of Montepulciano, renowned for its excellent wine, Pienza, for its pecorino cheese, and beautiful Cortona all being close by.
  • This farmhouse has been

    Cortona: Villa
    9 BDR • 7 BA • Sleeps 20 • #42066
    720 to 850 EUR/night
    High on a hilltop near Cortona is our farmhouse with a marvelous panoramic views of the Niccone Valley. The unit is decorated in traditional Tuscan style. It has good lighting with simple, classic furnishings. Each apartments have TV SAT, CD Player, stereo and hairdryer in each bathroom. In a common area there are laundry facilities: washing machine, clothes lines, iron and iron board. The garden is perfect for al fresco meals in the long summer months. Walkers and nature lovers can take advantage of the many tracks and paths that wind through the surrounding countryside. The house lies in extensive gardens and has a large, well-kept swimming pool . Furnished with tables and chairs, and equipped with a barbecue and oven, the garden is perfect for al fresco meals in the long summer months. Walkers and nature lovers can take advantage of the many tracks and paths that wind through the surrounding countryside, even strolling down to the Castello di Pierle and one of Tuscany's most striking castles.
  • Charming Villa

    Cortona: Villa
    5 BDR • 5 BA • Sleeps 11 • #250530
    414 to 686 EUR/night
    This Villa, a recently built house, together with other near villas is part of a small residential area situated in wonderful hilly position surrounded by greenery and spotted with olive groves. The facade is enhanced by the stone patio from which one can enjoy a stunning view on the valley underneath. On the several levels in the outer space there is the swimming pool, an outer cooking space with BBQ and wood-burning oven and, on the lower level, a covered park (1 car). The house, sleeping up to 11 people, is developed on four floors. On the ground floor the sunny living area gives access to the garden both from the sitting room with sofa and fireplace and the fully-equipped kitchen, connected to the pergola, ideal to comfortably eat in the open air. On the same floor there is also a double bedroom and a bathroom with shower. 2 double bedrooms, each with private bathroom, are located on the first floor from which it is possible to enjoy an evoking view on the Valdichiana. An additional twin bedroom (2 single beds) with bathroom with tub, ideal for kids, is at guests' disposal in the attic.The Taverna on the ground level is composed of a double bedroom plus an extra bed, with bathroom with shower. All the windows are equipped with mosquito nets and all rooms dispose of air conditioning, except for the cool basement room, accessible from the sitting room, where one can find a double bedroom, a kitchenette and a small bathroom with shower. Cotona is only 5 km far, while within 2 km there are supermarkets and main amenities. This Villa is ideal for those who want to spend a pleasant holiday in Tuscany.
  • Private Balcony with a

    Cortona: Villa
    3 BDR • 1 BA • Sleeps 6 • #42061
    105 to 140 EUR/night
    High on a hilltop near Cortona is our farmhouse with a marvellous panoramic views of the Niccone Valley. The unit is decorated in traditional Tuscan style. It has good lighting with simple, classic furnishings. The garden is perfect for al fresco meals in the long summer months. Walkers and nature lovers can take advantage of the many tracks and paths that wind through the surrounding countryside. This unit has also has a beautiful patio on the ground floor to have a pleasant moment reading a book or sunbathing. The house lies in extensive gardens and has a large, well-kept swimming pool . Furnished with tables and chairs, and equipped with a barbecue and oven, the garden is perfect for al fresco meals in the long summer months. Walkers and nature lovers can take advantage of the many tracks and paths that wind through the surrounding countryside, even strolling down to the Castello di Pierle - owned by the same family as the Villa, and one of Tuscany's most striking castles.
  • Nido is a Country-Chic

    Cortona: Villa
    2 BDR • 2 BA • Sleeps 4 • #258499
    123 to 286 EUR/night
    Nestled in the colourful Tuscan countryside, just 8km away from the old town of Cortona, this 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 to the property a particular atmosphere: fresh, relaxing and homey. The villa is spread on the ground floor, it has got an spacious living area, with the dining table and lounge area, fully-equipped kitchenette. There is also a double bedroom with en suite shower-room, a twin and another mutual shower room. You can find the same care for details and attention to comforts in the outdoor spaces where the covered area is the ideal place to unwind or just having alfresco dining enjoying the landscape of the valley with the distinctive shape of Cortona's hill light up by the vibrant red lights of the stunning sunsets that only this part of Tuscany can offer. From the full-equipped pool, your eyes will be delighted by the view of the typical Tuscan landscape distinguished by the shape of the several farm houses and manors as far as you eye can reach and it has the taste of old times gone by. The villa it's only a few minutes from Camucia, an ideal place to reach with ease historical and artistic places of interest.
  • Beautiful Farmhouse

    Cortona: Villa
    4 BDR • 4 BA • Sleeps 10 • #258436
    286 to 489 EUR/night
    The Casa, located in wonderful panoramic position with a view over the Valdichiana, is a beautiful farmhouse holding all the peculiar architectural features of the Tuscan style, such as loggia, terracotta floors and wooden beams. The house is developed on three floors, each with direct access from the outside. The main entrance leads to the large kitchen, provided with every comfort and fully equipped, and to the outer veranda, ideal to taste great dinners while enjoying the landscape. An arch door separates the kitchen from the cosy living room with sofas where the stone fireplace stands out. On the first floor there is the sleeping area, composed of three bedrooms. One of the doubles has ensuite bathroom with shower; the other two bedrooms (a double and one with French bed and additional single bed on the lovely mezzanine) share a bathroom with shower. The fourth bedroom, a double with extra single bed, is located in the tavern, in which guests also find a bathroom with shower, a small "gym corner" with tapis roulant and cyclette, and laundry room. Outside the house is surrounded by 1.500 sqm of terraced and totally fenced garden, which represents the ideal place where to spend lovely relaxing moments underneath the olive and oak trees. A small corner is dedicated to the BBQ and wood-burning oven. The beautiful swimming pool area can be reached through a characteristic stone staircase and is equipped with sunbeds, deck chairs and umbrellas. Adjacent to the swimming pool there is a small annex with kitchenette and bathroom with shower. The Casa is only few km far from the well-known Etruscan town of Cortona rich in traditions, culture, art and culinary history. Its strategic position also makes it the perfect starting point to visit the major cultural and city centres in Central Italy.
  • La Noce, a Small Stone

    Cortona: Villa
    2 BDR • 2 BA • Sleeps 4 • #258487
    129 to 286 EUR/night
    In a beautiful hillside location with views of Cortona, this small stone farmhouse with a peculiar profile and a charming soul. ... "I deeply love my house, it speaks of myself, of my life and of my habits, I would like to consider the tenants as my personal guests, friends whom I wish to be happy in Cortona" ... With these words the owner opens her warm and welcoming house which spreads on two levels. On the ground floor, the living area is characterized by carefully chosen pieces of furniture and charming exotic colours. The kitchen has direct access to the garden, fully equipped for al fresco dining, while the fireplace in the living room is ideal to enjoy some pleasant moments of relaxation and cosiness even in chillier seasons, punctuated by the ancient rhythms of nature and the intense colours of this corner of Tuscany. The ground floor is completed by a lovely bathroom with bathtub. Upstairs the sleeping area provides two bedrooms: one double and a twin, matchable upon request. They both share a bathroom with shower and a wonderful view. From the garden, characterized by silvery olive trees, the eye sweeps free on the Valdichiana dominated by the nearby Cortona, an Etruscan jewel which turns pinkish with the beautiful sunsets the valley offers. The home, located just a short drive away from the most beautiful historical towns of Umbria and Tuscany, is the perfect base to tour this beautiful area and to taste its best comfort food.
  • Renovated and Furnished

    Cortona: Villa
    3 BDR • 2 BA • Sleeps 8 • #258089
    200 to 256 EUR/night
    Our Casa stands in a tiny rural village, once devoted to agriculture. The property, once an old rural farmhouse, has now been renovated and furnished with modern and fancy style. Its tucked position let it overlooks all Chiana valley and makes easy to reach out the main Tuscan highlights such as Florence, Arezzo, Siena, Perugia and Cortona, the latter within just 10m driving. This 100sq.M. Farmhouse develops on two floors, both linked internally: the living area is located on the ground floor and it is accessible from the outer area thanks to the many different entrances; it is composed by living room with fireplace, kitchen with dining room and loggia where to comfortably eat “al fresco”, a full bathroom with shower and a double bedroom. The sleeping area is located on the upper floor and it is equipped with one double bedroom, one twin bedroom and one full bathroom with shower. All windows are provided with mosquito nets. The pool area is screened by tall trees and it is equipped with sunbeds and parasols. Pool is at exclusive use of guests and its size is 5x10m with variable depth (1,20m min, 1,50m max). The whole property is surrounded by a well refined garden where to find a fully equipped loggia and a brick BBQ.
  • A Privileged Front-Row

    Cortona: Villa
    4 BDR • 5 BA • Sleeps 10 • #258439
    283 to 486 EUR/night
    From this charming villa and its splendid hilltop position, guests can join a privileged front-row seat on the underlying Valdichiana valley. Surrounded by gentle olive tree hills, the villa offers a spectacular scenario on Cortona: the Etruscan city. The relaxing pool, located on a lower level, and the wide terrace furnished meticulously, ensure the perfect places for guests that want to chill out under the warm summer sun. Both can comfortably host up to 10 people gathering beautiful convivial moments altogether, even during chillier autumn and winter evenings thanks to the internal welcoming living room: in fact this charming Tuscan corner is splendid all the year round. The Villa develops into two opposite sides linked by a luminous central living room. On the ground floor guests can join the living area with its sitting room, a bathroom and a spacious fully equipped kitchen. Thanks to the different accesses, guests can easily move from the indoors to the outdoors and the spectacular terrace and the gorgeous internal courtyard with loggia. An elegant staircase leads to the sleeping area upstairs composed by three double bedrooms with en-suite bathrooms with shower box and a twin bedroom adjacent to a full bathroom equipped with whirlpool tub. Design furniture and the harmonic interior house painting were accurately chosen by owners in order to give a touch of warmth and hospitality. This beautiful property, located really close to the town centre, is the perfect spot for a holiday in the pursuit of harmony and relax. Within a few minutes driving you can reach the closer Umbrian borders with its historical amenities and well equipped Lake Trasimeno's beaches that give tourists the possibility to visit its islands and enjoy recreational fishing experiences.
  • Tuscany - an Air

    Cortona: Villa
    6 BDR • 4 BA • Sleeps 10 • #247237
    324 to 468 EUR/night
    Newly renovated in 2018, this very fine family villa makes a great home in Tuscany. Easy access, modern features and a wonderful private pool to enjoy. Day trips to Cortona, Pienza, Montepulciano, Chianti, Siena and a train service too to Florence. The Villa offers a lovely air conditioned home in Tuscany for both large families and groups of friends to thoroughly enjoy. The Villa traces its history over 400 years and now for 2019, has been fully restored and renovated to provide a warm and comfortable stone house with lovely views to enjoy The villa offers large landscaped gardens and a super private pool which is one of the many the focal points for guests to relax. . The large gardens and pool are complemented by a large covered gazebo providing the perfect spot to enjoy shaded relaxed lunches and romantic suppers in this marvelous setting. When you arrive at the Villa you will discover the spacious living room which has a large hand carved stone fire place. On this floor, is the modern fully equipped kitchen, and separate dining room. The first of the six bedrooms are also found on the ground floor: a capacious double bedroom with bathroom with bathtub and shower. Using the large staircase, you will reach the first floor where most of the sleeping accommodation is found. Here there are 3 large double bedrooms, and 2 single bedrooms along with 3 bright and modern bathrooms with each with showers. The Villa easily lends itself to become you 'home in Tuscany', with a wealth of features and amenities and of course, fresh and high quality bed linens and towels. For the owners, this villa means a lot to them. It is not just an historic stone house, but where generations of their family grew up and helped make the area what it is today - A little piece of Tuscan history. The large and Private pool (12m x 6m) is open from last week of May until the end of third week of September All linens are included and are changed every week. Additional changes can be arranged at additional cost. A maid service, chef and other services are also available at additional cost. Heating is not included and charged by consumption.
  • Tuscany, Views, Infinity

    Cortona: Villa
    3 BDR • 3 BA • Sleeps 6 • #230025
    315 to 470 EUR/night
    The view from here is - "just stunning but wait until you see the pool..." ... Villa is - "simply beautiful " Two comments form guests in August 2016 Villa is for sure, a really special property for both friends and families to enjoy. Tucked away on the sleepy hillside of Castiglion Fiorentino and where guests can make this their "home from home" - The property welcomed its first guests in May 2016, - The villa is set within an olive grove where the visible ruins of an ancient defence castle of Castiglion Fiorentino can be explored and enjoyed. Adjacent to the larger villa is a (deconsecrated) church from the 12th century which has also being restored. The Villa and its annex provide three bedrooms, three bathrooms, modern kitchens, 2 sitting rooms, a vast terrace with some of the loveliest views of the valley and the town of Castiglion along with the private Infinity Edge pool - strategically situated to enjoy the fabulous views. It is about 3 km from the town, where there are many restaurants, bars and shops and, there is also small shop,bar and restaurant just across the valley if you did not want to travel into the town, Much like the other villas here, this is also a good location - an excellent base to explore Tuscany its many hill towns, festivals, wineries and countryside including easy easy day trips to Cortona, Pienza, Montepulciano, Siena etc - Florence is also easy by either car (1 hour) or by train from our local station. This is one of our first reviews from May 2016. A first review says: “The houses are surrounded by a beautiful old olive grove. There are two terraces overlooking the valley and a very nice infinity swimming pool. The view is breathtaking. I have been in this valley before but the view here beats everything. There is a small terrace in the back to catch the early morning sun. The large (Giant) terraces in the front catch the sun from 10 am to sunset. For people like me who love to read in the shade : plenty of shade available under the surrounding trees. The olive groves around the houses are actually grassy meadows, ideal for children's play. In the woods on top of the hill behind the house lie the remains of a 13 th century castle. You have to drive up a drivable access road from the valley floor to reach this house. The next and only other house is 100 m down. The road continues up the hill for another 1.6 km, winding through beautiful olive groves and forests, offering breathtaking views. Then then for easy hiking, road changes into a hiking trail that joins the hiking trail that circumvent the valley. We were the first occupants in a newly developed property. We were two couples and stayed a week in May 2016. The property consist of two houses. The smaller one , just a few meters away, has one bedroom, with a king size bed, bathroom and a living space with kitchen. Tho main house has two bedrooms, with king size bed and the other with two single beds. The main house has two bathrooms. A dining room, sitting room and separate kitchen. Hendrik, NL. Also in the area are tennis courts, horse riding and , now the new Golf Course at Cortona -
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  • Lovely Three Bedroom

    Poppi: Cottage
    3 BDR • 2 BA • Sleeps 6 • #202349
    132 to 225 EUR/night
    The cottage is situated in a beautiful position on a lovely estate with wonderful views of the countryside and the Castle of Poppi. Originally a barn, it has now been fully restored retaining many original characteristics and furnished in classic Tuscan style whilst being fitted with modern comforts. The ground floor of the cottage opens onto the own garden area perfect for dining al fresco, and the first floor balcony has pretty views towards the shared swimming pool which is situated in a gorgeous position in the grounds enjoying a lovely panorama. In the grounds is also a large gazebo, and for guests use there are barbeques, a laundry room with coin operated washing machine and iron, WiFi internet connection, and a communal room with large covered terrace area for events. Also on the estate is a lovely stone farmhouse, which houses eight apartments, and a further detached cottage. Just 1.5km away is the picturesque town of Poppi with a good selection of amenities including a supermarket, shops and restaurants. The Casentino area of Tuscany, much of which is a national park, has many hidden treasures, the lovely local hill towns are a joy to leisurely explore and the main art cities of Florence and Arezzo are within an hours’ drive. Other wonderful Tuscan towns such as Siena, San Gimignano and Cortona are lovely days out.
  • 6 Bedroom Detached Villa

    Poppi: Villa
    6 BDR • 7 BA • Sleeps 15 • #201475
    294 to 544 EUR/night
    This villa lovely Tuscan Manor house on an estate in the hills between Arezzo and Florence. It is spacious and comfortably furnished in country style and retains many original characteristics such as oak beams, and stone fireplaces creating a warm and inviting atmosphere. The private swimming pool in the garden is the perfect spot for relaxing and enjoys pretty views. Surrounding the villa are spacious gardens with lawns, where there is a private swimming pool (12m x 6m) enjoying a beautiful view of the countryside. Close to the house is an annex building now converted into a large dining area with fully equipped kitchen with pizza oven, and shaded outside terrace with barbecue creating the perfect spot for the whole party to prepare delicious meals and dine al fresco together. Near the house is another farm building housing the owners farm equipment, and his well cared for vegetable garden, where he proudly grows an abundance of produce which can be sampled locally as well as a lovely beauty farm (payable locally), with indoor swimming pool (8m x 4m), hydro massage vitality tub, sauna, cromo therapy shower, and relaxation room.
  • Casa Outside the Medieval

    Anghiari: Villa
    7 BDR • 7 BA • Sleeps 14 • #248645
    271 to 500 EUR/night
    This is an ancient stone farmhouse adorned with traditional geraniums & ortenzie. Over three floors, the farmhouse comprises of seven double bedrooms (all with an en-suite) and a large living accommodation with terrace on the mezzanine floor plus large living accommodation including kitchen on the ground floor with entrance to the covered patio and equipped to relax, listen to music, talk with friends, dine al fresco or read a good book on sunny summer days. Outside the house there is a large fenced garden including luxurious private swimming pool area surrounded by lush landscape gardens with tall trees, fabulous aromatic plants including jasmine, lavender and herbs such as sage, rosemary and wisteria. This area also hosts sunloungers, outside dining plus a barbecue. There is further seating dotted around the extensive gardens. Outside the garden, in the secular oak wood, a play area for children and adults - including bowling green, table tennis, soccer field, trampoline - overlooking a beautiful vineyard and sunflower fields. The house has a balcony where you can enjoy the views of the Tuscan countryside.
  • Tuscany Large Noble Villa

    Arezzo: Villa
    11 BDR • 10 BA • Sleeps 34 • #234379
    1,200 to 1,286 EUR/night
    This Villa, near to lovely Tuscan town of Arezzo, only 10 minutes on foot is ideally positioned for a holiday vacation, located in the middle of Tuscany in a fantastic and peaceful hill of Castelsecco, and close to all amenities of the city, supermarkets, museum, bar, pub, bakery, shops. The vacation villa is equipped with a 10 hectare park which is an inviting place to relax, a gazebo with large bbq, panoramic pool ,it's a perfect place to refresh and enjoy the scenery of the skyline of the cathedral and historic palazzos in the town below and beautiful sunsets. The villa can accommodate a total of 34 people - the perfect setting for a destination wedding, family reunion or group celebration, holidays with friends of any kind. Completely furnished with the most up to date of amenities, you can rely on the owners to assist you with any questions, itineraries or special requests you may have. This is their family home, which they have painstaking restored to its original design and they look forward to sharing its traditions and stories with you on your holiday in Tuscany. The villa has common area with kitchen for stay and eat together, large gazebo outdoor, big bbq and relaxing area with sofa, tables, chairs and all garden equipment. Next to villa it's available a restaurant Casina Rossa only open for the guests .
  • Old Stone Farmhouse Full

    Anghiari: House
    3 BDR • 3 BA • Sleeps 8 • #126337
    90 to 170 EUR/night
    Nestling in a Tuscan hamlet named Toppole, is a 130 square meter farmhouse built on the ruins of an eleventh century stronghold. It is independent, enjoys a panoramic view and is located 6 km from Anghiari, a medieval village classified as "one of the most beautiful villages in Italy”: the battle which took place there inspired Leonardo da Vinci. A few km along the road, you will find Caprese, the town where Michelangelo was born, and Sansepolcro, home town of the famous artist Piero della Francesca. The house has beamed ceilings and terracotta floors. It is quiet and restful with charming surroundings. There is a covered terrace with a large wooden table – very pleasant for al fresco dining in summer. The garden is strewn with olive trees, vines, lavenders, rose bushes, a fig tree, a giant rosemary bush, thyme and basil. There is a superb pizza oven, also useful for grills. An outside shower allows you to refresh yourself in the open air. In the cellar, two mountain bikes are available. A car is essential. Electricity: international plug
  • Beautiful Villa Located

    Castiglion Fiorentino: Villa
    3 BDR • 4 BA • Sleeps 6 • #258497
    286 to 472 EUR/night
    The Villa is situated among the enchanting hills surrounding the lively towns of Castiglion Fiorentino and Cortona. This old Tuscan farmhouse offers a breathtaking view on the surrounding landscape and represents the ideal choice for those who wish privacy and tranquility. The renovation of this magnificent villa of pietra serena was carried out with refinement and taste. The property was elegantly furnished and provided with every modern comfort. Subtle colours, large spaces and wide French doors in wrought iron, stone and terracotta floors and beam of whitened wood make the ambiance a relaxing and gentle one. The ground floor, characterized by large arcades, hosts the living area. The access through large French doors leads to the living room with comfortable sofas and spacious dining room. A single bright location, separated only by big arcades which hosts also a bathroom and a fully equipped kitchen on the same ground. The kitchen, equipped with all the modern devices, is very spacious and provided with dining area, ideal to have breakfast or a quick lunch. A wooden staircase leads to the first floor where guests find a second living area with direct access to the garden. The sitting room is furnished with sofas, armchairs and big TV screen. The sleeping area is composed of 3 suites, each with ensuite bathroom (2 with bathtub and 1 with shower) and characterized by unique colours and decorations. The two main bedrooms have both their own access through a private staircase and are provided with spacious ensuite bathroom. All of the three bedrooms have a queen-size double bed at their disposal. The big garden hosts the big infinity pool. The garden also offers to the guests a relax area around the swimming pool consisting of wide equipped pergola, ideal to enjoy wonderful BBQs and to eat in the open air. On the terrace there is a lovely loggia, furnished with table and chairs and perfect to taste a great breakfast or to relax sipping a good glass of wine. The owner, a very discreet American gentleman, lives in a small annex with private entrance inside the property and will be at your disposal to give his support or some useful advice to spend a nice holiday. The villa, the swimming pool and the garden are for guests' use only and will not be used by the owner.
  • An Incredible Place for

    Monte San Savino: Villa
    3 BDR • 2 BA • Sleeps 6 • #258086
    186 to 315 EUR/night
    This private retreat offers wild open lush country views and a peaceful atmosphere, an incredible place for children to play and for adults to destress from the busy daily routine. The ground floor is characterized by an open plan room which includes a bright living and dining area with a comfortable sofa and two dining tables and fully equipped and recently remodelled kitchen boasting a large electric hob, a beautiful stone counter and designed features. Two large French windows open on the garden, providing both light and a direct access to the outdoor. The rustic cotto tiles along with the solid wood beamed ceiling are harmoniously blended with the modern shades of the wall plasters characterized by warm colours which make every room very welcoming. On the same floor we find a large double bedroom with wrought iron bed and period wood furniture. The bedroom has an en suite bathroom with shower. A metal staircase leads on the upper floor which holds another double bedroom with en suite bathroom with shower and a joint single room, perfect to accommodate a child in close distance to the parents. The second floor can be accessed directly from an external staircase and private access. Air-conditioning and wireless internet are also available throughout the house. A large private swimming pool equipped with loungers along with the outdoor dining area with BBQ makes this the perfect place to relax. The home is located just a few minutes from Foiano della Chiana and Monte San Savino. The popular Etruscan town of Cortona, renowned for its history, beauty and good food, is just a short drive away.
  • Nestled within Large

    Castiglion Fiorentino: Villa
    2 BDR • 2 BA • Sleeps 4 • #258495
    286 to 358 EUR/night
    Nestled within large grounds among rolling hills, this villa provides a private peaceful country retreat, but is ideally located just a short drive from the old towns of Castiglion Fiorentino and Cortona. In a delightful elevated setting, this detached house is designed to take full advantage of uninterrupted views over the valley. The villa, spread on two levels, is characterized by modern and stylish interiors boasting any comfort. On the ground level we found the living are and the fully fitted kitchen. On the ground floor there's also a double bedroom with two single beds and en suite bathroom with shower. On the first floor the superb master bedroom with a big comfortable double bed, designed interiors and a large window that provides an incredible view stretching out to the horizon. It is so entertaining to watch the unspoilt panorama that you will lose yourself in it at any time of the day enjoying the different colours from dawn to dusk. The master bedroom is served by a large en suite bathroom with large shower box. The garden is meticulously maintained and enhanced by the beauty of the infinity pool that blends with the outstanding panorama behind. During the warm summer nights, enjoy al fresco dining in the fully equipped area outside that provides also a BBQ. The property has a private parking space, central heating, Satellite TV, WIFI and many other comforts. This villa is the ideal place fon an unforgettable holiday, plenty of privacy in a peaceful and quaint corner of Tuscany.
  • Wonderful Tuscan Cottage

    Castiglion Fiorentino: Cottage
    3 BDR • 1 BA • Sleeps 5 • #204108
    135 to 145 EUR/night
    Part of the ancient Il Borgo Tranquilitta, this cottage is an enchanting and cozy cottage with a fabulous shared pool, nestled in olive groves with views of one of Tuscany's most gorgeous valleys. One of just three properties, this independent detached cottage was recently restored and is built from the local sandstone, “Pietra Serena,” with its soft ochers and grays. Lovingly preserved, it retains its rustic charm and makes the perfect home for your vacation in Tuscany. The cottage can sleep between 3 and 5 guests. It has two bedrooms, (one double and one single), plus the option to use the second sitting room as a bedroom which has a comfortable sofabed. In addition, the cottage has a lovely sitting room, kitchen/diner and bathroom. The cottage has its own private furnished terrace with stunning views and, with access to the old stone oven and barbecue pit for ’al fresco’ dining. The swimming pool has been idyllically positioned to benefit from the gorgeous views of the valley and the distant Tuscan towns. The house has central heating, and also has a large open fireplace welcoming early and late season visitors. Our closest towns are Castiglion FIorentino and Cortona both tracing their roots back 3000 years. Both are protected by magnificent stonewalls and city gates over 2000 years old. Other places not to be missed are Arezzo, Pienza, Montepulciano, the Chianti region, Assisi, Siena,
  • Charming Tuscan Home with

    Castiglion Fiorentino: Cottage
    2 BDR • 1 BA • Sleeps 4 • #204110
    135 to 145 EUR/night
    The villa is an enchanting cozy cottage with a fabulous pool, nestled in olive groves with views of one of Tuscany's most gorgeous valleys. One of three properties, this independent detached cottage was recently restored and is built from the local sandstone, “Pietra Serena,” with its soft ochers and grays. Lovingly preserved, it retains its rustic charm and makes the perfect home for your vacation in Tuscany. The cottage can sleep up to 5. It has two bedrooms, (one double and one single), plus the option to use the adjacent annex which provides sleeping for an additional 2 guests by way of a sofa-bed and additional bathroom. The cottage has a lovely sitting room, kitchen/diner and bathroom. It has a private furnished terrace with access to the old stone oven and barbecue pit for ’al fresco’ dining. The swimming pool has been idyllically positioned to benefit from the stunning views of the valley and the distant Tuscan towns. Although the cottage has central heating, it also has a large open fireplace welcoming early and late season visitors. A laundry room on site is available for guests’ use. Our closest towns are Castiglion FIorentino and Cortona both tracing their roots back 3000 years! Both are protected by magnificent stonewalls and city gates over 2000 years old. Other places not to be missed are Arezzo, Pienza, Montepulciano, the Chianti region, Assisi, Siena, & by train, Florence is just an hour from the local rail station
  • Great Value for up to 4

    Castiglion Fiorentino: Cottage
    2 BDR • 1 BA • Sleeps 4 • #202867
    135 to 145 EUR/night
    Part of the small ancient hamlet of Il Borgo Tranquilitta, this charming stone cottage for three guests is the perfect place to start your vacation in Tuscany, Traditionally furnished, full of charm and character. From every room you can enjoy stunning views of the valley, the historic town of Castiglion Fiorentino, the gardens, olive groves and the large swimming pool. Cottage has two bedrooms, (One double and one single) a charming sitting room with open fireplace, fully equipped kitchen and dining area, terraces for outside dining – where there is also a barbeque for those warm summer afternoons and al-fresco dining. There are only three cottages in the village and lots of private spaces to enjoy this wonderful spot. The village has been totally and caringly renovated by local artisans retaining its natural charm and character whilst providing warm and inviting interiors. "Our first vacation to Italy. We had two cottages here, two patios - one for the morning sun and one for the afternoon and evenings when we are outside enjoying the sunsets. The apartments are set in real country setting, olives and other vegetation the views are really wonderful. The highlight though was the pool which, for the most part we had to ourselves and this, plus incredibly warm weather made it a great combination!"
  • Grazia, Tuscany Italy

    Castiglion Fiorentino: Villa
    4 BDR • 3 BA • Sleeps 8 • #241783
    389 to 465 EUR/night
    THIS CHARMING LARGE FARMHOUSE VILLA IN TUSCANY PROVIDES A PERFECT SETTING FOR A FAMILY OR FRIENDS HOLIDAY. THE LARGE GARDENS AND TERRACES PROVIDE THE PERFECT OUTSIDE SPACE FOR RELAXING. THERE IS A PRIVATE SWIMMING POOL FOR YOU TO ENJOY AND A LOVELY SHADED GAZEBO COMPLETE WITH TABLE AND CHAIRS FOR ALFRESCO DINING. A FABULOUS FEATURE OF THIS VILLA ARE THE VIEWS. These are easy to enjoy from any number of settings around the villa including the villas own terraces, the pool and the gardens. The pool and terraces are perfect spots to enjoy a glass of wine and watch the sunset over the ancient Castle of Montechio and the Tuscan hill town of Castiglion Fiorentino. Villa is about 3-4 km outside of the town of Castiglion where there is an abundance of restaurants, supermarkets and small artisan shops to enjoy. Just a half hour drive is Arezzo, the charming town used as the backdrop for Roberto Benigni's "Life is Beautiful." and 20 minutes to the bustling town of Cortona - also famed by books and films along The terraced areas surrounding the house and pool are filled with roses, vines, lavender, dog-rose, oak trees. The pool overlooks the castle of Montechio and, is one of the loveliest places to enjoy a warm summers evening. Villa offers and easy and accessible location as well as total privacy with huge sense of space. The villa has its own parking area. The villa has many Tuscan features including rustic terracotta tiled floors, beamed ceilings and original stone walls. The villa is furnished with simply with country-style pieces and the three reception areas ensure space for everyone.. There are four bedrooms, three large double bedrooms and a fourth which is loft style and possible better for children. Each of the three floors has a bathroom with shower. Two kitchens - one for easy access to the pergola and another offering more space for lavish cooking. The main entrance leads to a cozy kitchen and living area with TV, and access to a terrace with views. There are also two guest bedrooms and a bathroom.The kitchen has all amenities to help make your stay a pleasure. The lower floor leading to gardens has a large sitting area along with the main kitchen. There is also another double bedroom and bathroom. The first floor offers the fourth bedroom in loft style space. There is also another bathroom The pool is open from May until the end of September.

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Cortona News and Events

Cortona is a small but fascinating city in the province of Arezzo, Tuscany, central Italy, situated on a commanding hill, and overlooking Lake Trasimeno. Its cyclopean walls reveal its Etruscan origins. It was one of the twelve cities of Etruria and in its vicinity many Etruscan ruins and tombs may be seen. Cortona sided against Rome until 310 B.C. when Fabius Rullianus defeated the Etruscans and took Perugia. Perugia, with other cities, including Cortona, then made peace with Rome. Later Cortona was destroyed by the Lombards but was soon rebuilt. In the 14 C, it was governed by the Casali and afterwards became part of the Grand Duchy of Tuscany.

Sights & Attractions

Museo Diocesano: Little is left of the original Romanesque character of Cortona's duomo , which is situated northwest of Piazza Signorelli and has been rebuilt several times in a less-than-felicitous fashion. Fortunately, its wonderful artworks have been saved and are on display in this museum, which occupies the former church of the Gesù on the opposite side of the piazza.

Room 1 features a remarkable Roman sarcophagus decorated with a frenzied battle scene between Dionysus and the Amazons, but the real treasures are in Room 3. These include a moving Crucifixion (1320) by Pietro Lorenzetti and two beautiful works by Fra' Angelico: Annunciation (1436) and Madonna with Child and Saints (1436–7).

Museo dell'Accademia Etrusca: The rather plain facade of the 13th-century Palazzo Casali was added to the original building in the 17th century. Inside, this fascinating museum displays substantial local Etruscan and Roman finds, Renaissance globes, 18th-century decorative arts and contemporary paintings. The Etruscan collection is the highlight, particularly those objects excavated from the tombs at Sodo, just outside town.

Eremo Le Celle: This Franciscan hermitage is set amid dense woodland 3km north of Cortona. Its buildings sit next to a picturesque stream with an 18th-century stone bridge, and the only sounds to disturb the tranquil atmosphere are the bells that call the resident friars to vespers and mass in the cave-like Chiesa Cella di San Francesco.

Festivals & Events of Cortona, Italy
Giostra dell'Archidado (June)
A crossbow competition held in late May or early June usually on the Sunday of Pentecost (Whitsunday). The contest is held in Piazza Signorelli.

Lonely Planet - Cortona
With a layout indicative of someone spilling a bucket of 'Etruscan town' down a hillside, rooms with a view are the rule, not the exception in Cortona. In the late 14th century Fra Angelico lived and worked here, and fellow artists Luca Signorelli (1450–1523) and Pietro da Cortona (1596–1669) were both born within the walls.

Large chunks of Under the Tuscan Sun, the soap-in-the-sun film of the book by Frances Mayes, were shot in Cortona. (You'll look in vain, though, for the fountain in which the eccentric Englishwoman cavorts; it was built specially for filming and is now dry.)

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