Gaiole in Chianti Villas with Pool
Results 381 - 400 of 416
Castello D'Ombrone
Wonderful independent holiday home with private pool, A/C, WIFI, TV, panoramic view, near Montalcino
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18
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9
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8
Description
Castello D'Ombrone is located 6 km (3 mi) from Buonconvento, Italy and only 18 km (11 mi) from Montalcino in the tourist area "Orcia Valley". Castello D'Ombrone is a beautiful holiday home with WiFi internet, private pool and air conditioning. The property can sleep up to 18 guests comfortably in nine bedrooms with eight bathrooms. There is a golf course nearby if you'd like to get in a round or two while on holiday.
The property is located within a wildlife reserve, which is why wild animals can sometimes be seen on the grounds. However, they usually do not come close to the houses.
The Experience
After arriving you will be greeted by the owner or manager where you’ll find a beautiful clean well-maintained property perfect for a relaxing vacation in Tuscany. After a hectic day of sightseeing, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to relax at the end the day.
Visit the Area
Most people enjoy visiting close-by cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Montalcino 18 km (11 mi), Siena 35 km (21 mi), Montepulciano 45 km (28 mi), Arezzo 68 km (42 mi) and Cortona 71 km (44 mi).
Some other major tourist destinations you should consider visiting are: Florence 102 km (63 mi), Viareggio 196 km (122 mi), Forte Dei Marmi 203 km (126 mi), Rome 221 km (137 mi), Venice 353 km (219 mi) and Milan 394 km (245 mi).
Additional Information
Check-In Time: 15:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 29 April - 30 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 117 km (72 mi), Pisa (psa) 150 km (93 mi), Bologna (blq) 201 km (125 mi), Roma Ciampino (cia) 230 km (143 mi) and Roma Fiumicino (fco) 242 km (151 mi).
Additional Services
Cooking Lessons - If you're interested in discovering more about Tuscan cooking, ask about the cooking lessons that can be scheduled at the property. It's a pleasant way to spend time with friends and family while discovering the techniques required to master Tuscan cuisine. For more details and the supplemental cost, please contact us.
Professional Chef - Are you looking for a real treat during your vacation? Why not book a professional chef to prepare and serve you a sumptuous meal using local produce? The chef will arrange the meal based on your preferences and dietary requirements. The chef will offer suggestions for the various courses and the wine. Ask for more details and the extra costs.
Maid Service - Upgrade your vacation with maid service. This service can be organized by the owner. Inquire for more details about the supplemental cost.
Borgo Castelrotto
Description
Property Summary
This charming vacation rental occupies a beautifully renovated portion of a traditional farmhouse set in an excellent panoramic position in the countryside near San Giovanni D'asso, Italy, close to the renowned town of Montalcino. The property comprises two adjoining apartments within an independent farmhouse structure, offering flexible accommodation for families or groups seeking an authentic Tuscan experience. You will enjoy convenient amenities including a private swimming pool and dedicated parking area within the fenced grounds. The elevated location provides sweeping views over the surrounding rural landscape, creating an idyllic setting for a relaxing retreat in one of Tuscany's most celebrated wine-producing regions.
Outdoors
The outdoor space features a refreshing non-heated swimming pool measuring 6.50 by 3.50 meters with a depth of 1.40 meters, available for your use from May 1st through October 31st. The property is surrounded by a 180 square meter fenced garden that ensures privacy and security throughout your stay. Within the garden you will find a gazebo providing shaded outdoor living space, perfect for relaxing during the warmest hours of the day. A barbecue is available for preparing al fresco meals, allowing you to dine outdoors while taking in the panoramic countryside views that characterize this exceptional location.
Unit Layout
The farmhouse is divided into two adjoining apartments that together accommodate a maximum capacity of 7 guests across 4 bedrooms and 2 bathrooms. Apartment A sleeps 4 guests and is arranged over two floors. On the ground floor you will find a living room and dining room with fireplace, television, and a kitchenette equipped with an oven. The first floor houses a double bedroom, a twin bedroom, and a bathroom with shower. Apartment B accommodates 3 guests and is similarly distributed across two levels. The ground floor contains a living room with kitchenette including an oven, a single bedroom, and a small bathroom. On the first floor there is a double bedroom. This configuration provides flexible sleeping arrangements suitable for families or groups traveling together while maintaining separate living spaces.
Amenities Included
Your accommodation is equipped with a washing machine for your convenience during longer stays. The barbecue facilities enable outdoor cooking and dining experiences in the garden setting. The fireplace in Apartment A provides both warmth and ambiance during cooler months. Heat is available throughout the property to ensure comfort during autumn, winter, and early spring visits. Television is provided in Apartment A for entertainment. The kitchenettes in both apartments include ovens for preparing meals. All windows are fitted with mosquito nets to ensure comfortable ventilation during warm weather while keeping insects out.
Other Information
Check-in is available between 3 pm and 7 pm, and check-out is required by 10 am. The rental price includes water, gas, final cleaning, and linen for both bedrooms and bathrooms, with linen changes provided on a weekly basis. Upon arrival you will be required to provide a security deposit which will be returned at the end of your stay minus the cost of any damages incurred. A tourist tax may be required upon arrival according to the regulations of the local municipality. The fenced garden provides secure outdoor space throughout the property.
Distances and Attractions
The property is located in the countryside near the historic hilltop town of Montalcino, one of Tuscany's most prestigious wine destinations famous for its Brunello wines. This excellent rural position offers panoramic views while maintaining convenient access to local amenities, wineries, restaurants, and the cultural attractions of southern Tuscany. The surrounding area provides opportunities for wine tasting, exploring medieval villages, and experiencing the authentic character of the Tuscan countryside.
Costs & Services
Extra costs
- Heating consumption: payable locally based on consumption
- Security deposit: €500.00
- Pets: €25.00 per week
- Baby cot: €30.00 per week
- Extra bed: €80.00 per week Il Bosco
Torre di Vignale
Superb independent vacation home with WIFI, private pool and TV
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16
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7
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6
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400 m2
Description
SPECIAL OFFER 15% DISCOUNT From 15th April until 20th June 2026 - FOR 1 WEEK BOOKINGS
The 14th century, when this strip of land near Arezzo, which marked the border between the two Italies, the Lombard and the Byzantine, saw the construction of an imposing square building dominated by a mighty tower at about 570 metres above sea level.
La Torre di Vignale, with its distant military origins, still witnessed today by traces of battlements and a few embrasures, has been renovated, has regained the importance and charm of the past, standing out again majestically among dense forests of oak and chestnut trees and ready to welcome you, perfect for groups of families or friends who want a relaxing holiday in contact with nature.
The house is surrounded by a large and panoramic garden, full of flowers and equipped with a very special pergola, made in the old pigsty, with wooden table and benches and coloured cushions. At your disposal there is also a barbecue and a wood-burning oven placed not far from the pergola, a perfect corner for your dinners and barbecues with family and friends.
At the edge of the garden, on a terrace in a dominant position with respect to the house and the valley below, you will find the beautiful swimming pool (size 9x9 m - depth 1.20-2.20 m - open from 01st May to 30th September), equipped with sunbeds and a wooden gazebo, if you prefer to enjoy it sheltered from the hot summer sun.
La Torre di Vignale offers its visitors a charm of other times and a delightful hospitality, even your small size four-legged friends are welcome here. Also the furnishings, comfortable and rational, with warm and welcoming colours, are for the most part composed of antique furniture that contribute to giving the house a very special fascination.
Paola, the owner, with her kindness and courtesy will make you feel immediately at home. You will instantly became friends with her and she will be a fundamental reference point for your holiday. Do not forget to ask her to prepare you some of her typical Tuscan dishes, our word, you will not regret it! Torre di Vignale
Podere D'Asso
Independent Villa with private pool, WIFI, A/C, TV, patio, panoramic view, near Montalcino
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12
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6
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8
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778 m2
Description
Podere D'Asso is a beautiful stone building (778 sq m) with WiFi internet, air conditioning and private pool. The property can accommodate up to 12 people comfortably in six bedrooms with eight bathrooms. Conveniently located 2 km (2 mi) from San Giovanni D'asso, Italy in the tourist area "Orcia Valley" and only 20 km (12 mi) from Montalcino.
What to Expect
After arriving you will be welcomed by the owner or manager where you’ll find a beautiful clean well-maintained property with views of the hills perfect for a splendid holiday in Tuscany. Regardless of how you spend your days - shopping, visiting museums, sightseeing or just driving in the countryside, when you arrive home you can relax with your family and friends at the pool for a perfect ending to another day in Tuscany. Also available outside are a barbecue grill and patio. Dining with friends and family is a big part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your holiday. The kitchen includes coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 12 people. Dine 'al fresco' like a real Tuscan, the fully furnished veranda is the perfect setting to enjoy food, family and the nice Tuscan weather.
Visit the Area
Most people enjoy visiting close-by cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Montalcino 20 km (12 mi), Montepulciano 31 km (19 mi), Siena 47 km (29 mi), Cortona 47 km (29 mi) and Arezzo 53 km (33 mi).
Some other major tourist destinations you should consider visiting are: Florence 132 km (82 mi), Viareggio 219 km (136 mi), Forte Dei Marmi 226 km (140 mi), Rome 214 km (133 mi), Milan 419 km (260 mi) and Naples 405 km (251 mi).
Additional Information
Check-In Time: 15:00 - 20:00
Check-Out Time: 09:00 - 12:00
Pool Open: 20 May - 1 November (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 137 km (85 mi), Pisa (psa) 200 km (124 mi), Roma Ciampino (cia) 223 km (138 mi), Bologna (blq) 224 km (139 mi) and Roma Fiumicino (fco) 235 km (146 mi).
Special Services
Cooking Lessons - Discover from a local chef the techniques vital to master Tuscan cuisine. The owner can organize to have a chef come to the property for a cooking lesson for any number of people in your group. It's a fun way to spend time with friends and family while discovering the secrets vital to prepare mouth-watering Tuscan meals when you return home. For more details and the supplemental cost, please contact us.
Professional Chef - Are you looking for a real treat during your holiday? Why not book a professional chef to prepare and serve you a delicious meal using local produce? The chef will schedule the meal based on your preferences and dietary needs. The chef will offer advice for the various courses and the wine. Inquire for more details and the additional costs.
Tours - The owner can arrange custom tours for your group. To learn about the tours available, speak to the owner after arriving or inquire prior to booking. The cost will vary depending in the exact tour and number of people.
Maid Service - If you'd like maid service during your stay that can be organized by the owner. Inquire for more details about the supplemental cost.
Pre-Stocked Fridge - If you'd like to have the fridge and pantry stocked before you check-in that is possible at Podere D'Asso. Inquire for more details, including the supplemental cost and how to arrange this service.
Baby Sitting - If you're traveling with children and would like an evening alone, a babysitter can be organized. Speak to the owner directly about this service upon arrival.
Podere Verninelle
Cadellura
Pretty private property with WIFI, pool, A/C, TV and patio
Special Offer-
5
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2
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2
Description
Property Summary
Nestled in the tranquil Santa Firmina district, just 4 km from the heart of Arezzo, Italy, the single-family house "Cadellura" offers an exceptional holiday rental experience that seamlessly blends privacy with convenience. This beautiful home provides a quiet and peaceful retreat from the energy of the city, while keeping you close enough to enjoy everything that Arezzo and its surroundings have to offer. The property sits within a generous 10,000 m2 fenced estate, where a terraced garden of lawn, trees, and an orchard creates a lush and serene setting. A kidney-shaped swimming pool measuring 10 x 5 m invites you to relax and enjoy the warmth of the Italian sun during the seasonal period from May 1st to September 30th. Wireless internet connection is available throughout the property, ensuring you remain connected throughout your stay. Parking is conveniently provided on the premises, and the expansive yard surrounding the house adds an extra layer of seclusion and natural beauty to your experience.
Outdoors
The outdoor spaces at "Cadellura" are truly one of the property's most remarkable features. The 10,000 m2 fenced grounds encompass a beautifully terraced garden with lawn areas, mature trees, and a productive orchard, offering ample space to unwind and explore in complete privacy. The kidney-shaped swimming pool, measuring 10 x 5 m, is available seasonally from May 1st to September 30th and serves as the centerpiece of the outdoor leisure area. Surrounding the pool, you will find a dedicated pool house equipped with a refrigerator, an outdoor shower, and comfortable patio furniture, creating an ideal setting for long, relaxing days in the open air. Whether you choose to dine al fresco, lounge by the water, or simply stroll through the orchard, the outdoor environment of "Cadellura" offers a genuinely immersive Italian countryside experience.
Other Information
"Cadellura" is equipped with a burglar alarm system, providing you with an added sense of security and peace of mind throughout your stay. It is worth noting that the owner resides on the same property, ensuring that assistance is readily available should you need anything during your visit. Further details regarding check-in and check-out times, house rules, and any additional policies can be confirmed directly with the property management prior to your arrival.
Distances and Attractions
"Cadellura" enjoys an enviable location that places a wide range of amenities and attractions within easy reach. A local shop is situated just 500 m from the property, while a supermarket can be found approximately 2 km away, making it straightforward to stock up on everything you need. Public transportation is conveniently accessible, with a bus stop located only 500 m from the house. The Arezzo railway station is just 4 km away, providing excellent connections to the wider region. The historic city center of Arezzo itself is a mere 4 km from the property, offering an abundance of cultural, culinary, and architectural attractions for you to explore during your stay. Cadellura
Agriturismo del Talozzo
Pretty property with pool, TV and patio
Special Offer-
2
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1
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1
Description
Property Summary
Nestled in the tranquil district of Sant'Anastasio, just 7 km from the historic center of Arezzo, Italy, Agriturismo del Talozzo is a charming holiday rental immersed in the breathtaking Tuscan countryside. This fenced property offers guests a shared and serene environment, ideal for those seeking a peaceful retreat surrounded by nature. The estate features a beautifully maintained garden with trees and open meadow areas, providing a lush and relaxing setting throughout your stay. A large swimming pool measuring 11 x 6 metres is available for guest enjoyment from May 1st to September 30th, kept in excellent condition by the resident owner and gardener. Ample parking is available directly on the premises, accessible via a short 50-metre stretch of unmade road, ensuring a convenient and straightforward arrival experience.
Outdoors
The outdoor spaces at Agriturismo del Talozzo are a true highlight of the property, offering guests a generous and well-kept environment in which to unwind and connect with the surrounding Tuscan landscape. The expansive garden is adorned with mature trees and open meadow areas, creating a naturally shaded and picturesque setting perfect for leisurely afternoons outdoors. The large swimming pool, measuring 11 x 6 metres, serves as the centrepiece of the outdoor area and is available for use from May 1st through September 30th. It is regularly maintained by the owner and gardener to ensure it remains in pristine condition throughout the season. The fenced grounds provide an added sense of security and privacy, allowing guests to enjoy the outdoor spaces with complete peace of mind.
Other Information
Agriturismo del Talozzo is a working agricultural estate, and guests have the unique opportunity to observe animal husbandry activities taking place on the property during their stay, offering an authentic and enriching rural experience. The owner resides in a separate semi-detached house located on the estate, ensuring that guests maintain their privacy while benefiting from the attentive presence of the host. Please be aware that the owner keeps a dog on the premises. The property is fully fenced, contributing to a safe and private atmosphere for all guests. The surrounding countryside setting ensures a quiet and restful environment, making this an ideal destination for those looking to escape the pace of everyday life and immerse themselves in the natural beauty of the Tuscan hills.
Distances and Attractions
Agriturismo del Talozzo enjoys a privileged location that places guests within easy reach of some of the most celebrated destinations in Tuscany and beyond. The center of Arezzo, with its rich artistic and cultural heritage, is just 7 km away, while the "Arezzo" railway station is conveniently located only 5 km from the property, making regional travel straightforward and accessible. A local shop and supermarket are situated just 1 km away, ensuring that everyday essentials are always within close reach. For those wishing to explore the wider region, the medieval town of Castiglion Fiorentino is 15 km away, the renowned city of Cortona lies 24 km from the property, and the scenic Lago Trasimeno can be reached in approximately 40 km. The Equestrian Center Arezzo is just 3.5 km away, offering a wonderful activity for horse enthusiasts. The cultural and artistic treasures of Firenze are also accessible, situated 88 km from the estate. Agriturismo del Talozzo
Olivo
Pretty independent villa rental with private pool, WIFI and TV
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6
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4
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3
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100 m2
Description
Olivo is a characteristic and very old farmhouse that you will find almost hidden among the silver foliage of the olive trees that cover the hillside, giving the villa an atmosphere and peace of times gone by. You will find it nestled between the cities of Arezzo and Castiglion Fiorentino, and its location will offer you countless possibilities for visiting museums, monuments or simply for shopping in the centre of Arezzo.
In Arezzo, to which we advise you to dedicate at least one day, you will find a marvellous historic centre, made up of cobbled alleyways and ancient buildings, some of which date back to the Medieval period, as well as designer shops and typical restaurants and cafés, where you can spend an afternoon or a lazy summer evening. Just 4 km away is also the Arezzo Equestrian Centre where internationally renowned equestrian events are held throughout the year.
The beautiful panoramic swimming pool (size 5x10 m, depth 0.90-1.80 m - open from 10 May to 30th September) was built on a large green terrace, just a few metres from the house. In the completely enclosed garden, your children can play freely in absolute tranquillity in the shade of the olive trees and century-old trees, while you, by the side of the pool, can enjoy the sun while admiring the fantastic panorama of the valley below. For the little ones' playtime there is also a playhouse in a tree.
At the back of the house you will have at your disposal, for dinners or lunches in the open air, a comfortable equipped area, wood-burning oven and barbecue, where you can enjoy your meals in company.
Olivo is a rustic-style farmhouse, reminiscent of the old peasant houses, whose warmth provided shelter for the large families of our ancestors. The strong point of the house in our opinion is the fact that here you will feel as if transported to a past made up of ancient traditions, rituals and moments spent with the family, in a warm, welcoming atmosphere that will accompany you throughout your holiday, making you feel at home. Olivo
Villa Cecilia
Beautiful independent holiday home with private pool, A/C, TV and pets allowed
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6
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2
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2
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150 m2
Description
Villa Cecilia is an old farmhouse dating back to before 1800. You will find it perched on a hill in the heart of the Valdichiana, about 4 km from Castiglion Fiorentino, a characteristic village where you will find shops, restaurants, supermarkets and all necessities.
The farmhouse has been recently and carefully restored under the careful guidance of the owners, who strongly wished to maintain its ancient origins and characteristics. The original terracotta tiled floors, the high ceilings with wooden beams, all coordinated with quality furnishings, with fine antiques, are a perfect match for the characteristics of the villa. You will feel a sense of warmth at the villa, you will feel welcomed and pampered, perfectly in harmony with your surroundings.
The history of the farmhouse is also fascinating. In ancient times, the Valdichiana was a swamp and before the land reclamation took place, its waters lapped the land of the property and just a few steps from the house there was a small harbour for boats that connected by water to the surrounding villages.
Today the villa is part of a farm that includes vineyards, cereal crops, farmyard animals and beautiful horses. About 1 km away, at the owners' residence, you will be able to enjoy the organic produce from their vegetable garden free of charge. Their paddocks, should you travel with your horses, will be at your disposal (service available for a fee).
Around the villa, you will enjoy a large, completely fenced green space perfect for your morning or evening walks even with your four-legged friends. Inside the park there is also a woodland path (approx. 500 m) where you can relax, walk and organise cool snacks.
For your days at home, there is a beautiful infinity swimming pool (size 6x12 m, depth 1.35 m - open from 01 May to 30 September), with a Roman staircase, bicycles at your disposal, a beautiful porch well equipped with outdoor furniture, where you can enjoy a book or an aperitif in company, the barbecue for your cookouts and also games for your children. Villa Cecilia
Villino Alba
Fabulous independent villa with WIFI, private pool and TV
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13
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6
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5
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200 m2
Description
There is something special about this beautiful property situated in the wooded hills separating the Chiana and Arno valleys, which, because of its location, also enjoys easy access to the cities of Arezzo, Florence and Siena.
Perhaps it is the well-kept, panoramic garden shaded by tall pines and completely fenced, the lovely private swimming pool (size 6 x 9 m - depth 1.20 m - open from 01st May to 30th September) or perhaps the Jacuzzi (6 seats - extra charge) set among the olive trees...? Or, could it be the very idea of the country villa, its secluded but not isolated location, and the warm atmosphere created inside with pastel colours and rustic style furniture.
Whatever you think it is, you will love this beautiful villa and it will be the ideal place for a family holiday or even with your group of friends. Even your small size four-legged friends are welcome here. There is an outdoor area with games for children, a comfortable porch very well equipped with table, chairs and barbecue for dinners and barbecues with friends. For the more sporty, there is also a small gym so you don't miss a workout even on holiday.
Due to its own objective characteristics (independent entrances and three kitchens) this property is particularly suited to accommodate several families who decide to spend their holidays together, while maintaining each one's autonomy.
The owners are very friendly and courteous and offer a special welcome by providing a welcome basket with basic food on arrival.
In addition, in full compliance with energy saving regulations, the house is equipped with solar panels. Villino Alba
Villa Quattro Mori
Amazing independent holiday home with WIFI, private pool, TV and terrace
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8
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4
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3
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300 m2
Description
A short distance from the city of Arezzo, an ideal starting point for visiting Tuscany, we find Villa Quattro Mori, a charming villa that once belonged to an ancient and noble family of Counts of Arezzo. It has in fact maintained its charm, in the furnishings of the elegant bedrooms, the lounge, the swimming pool adorned with marble and statues, and the large park shaded by centuries-old pines.
Just 500 m away, in the small village of Tregozzano, which is easily reached on foot, there is a bar, a pharmacy and some small food shops.
Just outside the village you will also find a typical trattoria.
You can easily reach Arezzo, a beautiful city of art that houses, among others, Piero della Francesca's masterpieces such as the Legend of the True Cross, by public transport, or in 5 minutes by car along the provincial road that passes near the villa. Here, if you love shopping, the old main street, today “Corso Italia”, offers elegant and exclusive shops. There are also supermarkets, restaurants and services of all kinds. We recommend you spend an evening in the small alleys of the historic centre, sitting on the stone steps of an ancient basilica, with a glass of wine in your hand.
The highlights of the villa, in our opinion, are certainly the splendid swimming pool with Roman staircase (size m 16x6, depth m. 1.40-2.00 - open from 27 June to 5 September) decorated with precious marble and with changing room and bathroom with shower, the characteristic pergola covered with wisteria and roses with marble fountain and wooden benches where you can spend dreamy days in the company of your book.
But above all, the large glass veranda overlooking the swimming pool, with its billiard table, table football, comfortable sofas, dining table, fridge and bathroom with shower, will be the perfect place for your days with friends, your dinners and your most beautiful family moments.
Your small size four-legged friends are also welcome. Villa Quattro Mori
Borgo di Usciano
Beautiful private vacation rental with WIFI, private pool, TV, terrace and pets allowed
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20
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10
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8
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250 m2
Description
Usciano is an ancient village of medieval origin, located a few kilometres from the city of Arezzo. It is located on a panoramic position, perched on a high hill, surrounded by olive groves and green woods of oak and holm-oak. The stone farmhouse and its two small houses date back to 1851, when the small village was inhabited by woodcutters, farmers and chestnut growers, the atmosphere alone will immediately take you back to those times.
The hamlet has been restored preserving its original features and using ancient materials such as terracotta, stone and old wooden beams. Even the furniture, functional and comfortable, has been chosen in respect of rural traditions.
Borgo di Usciano can be reached by an unpaved road through the woods of about 1.5 km, which is well maintained and suitable for all types of cars.
Only 2.5 km away is the village of Palazzo del Pero where you will find a couple of restaurants and some shops.
Only 9 km away is the city of Arezzo and its monuments, shops for shopping enthusiasts, supermarkets, restaurants and all kinds of services. But we also recommend that you spend wonderful days discovering the old town centre, its narrow streets and the works of art by Piero della Francesca, Cimabue and Vasari, scattered throughout the city.
The outdoor area of Borgo di Usciano is divided into various panoramic terraces, and you'll be spoilt for choice whether to relax in the solarium by the beautiful infinity pool (size 7x14 m, depth 1-1.60 m - open from 01st May to 30th September), in the shade of a cool tree in the lower part of the garden, or climb the hill with a 360° panorama and a good book to keep you company.
Adjacent to the kitchen is the paved area with a stone barbecue and wood-burning oven, and equipped with tables and chairs, where you can enjoy pizza and barbecue with your family or friends. To make your holiday even richer and more enjoyable, you can request tastings of typical Tuscan products, massages with experts in the field and guided mountain bike tours of the area. Edoardo, the owner, will be happy to help you.
Pets are welcome (extra charge could be required). Borgo di Usciano
Villa Leopoldina
Fabulous private holiday villa with WIFI, A/C, private pool and TV
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12
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6
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6
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450 m2
Description
If you decide to spend your holiday at Villa Leopoldina, you can stay in a historic building, a splendid example of a typical Tuscan house designed in the 18th century by the architects of Grand Duke Leopold of Lorraine, with the characteristic four overlapping arches on the façade. It will be a plunge into the past, when families were very numerous and these huge homes housed several generations under the same roof.
In front of the villa you will find the private garden and on the right-hand side the beautiful swimming pool (size 12x5 m, depth 1.40 m, completely enclosed - open from 01st May to 30th September). From here, every day, you can enjoy a splendid panoramic view over the city of Arezzo and its valleys, a view that becomes even more suggestive at night with the thousands of tiny lights that seem to chase each other. You will reach the centre of Arezzo in less than 10 minutes by car and here you will find all the necessary amenities and services, as well as museums, magnificent churches, cathedrals and monuments to visit.
One of the villa's bonuses is certainly its location. It is located within the Pomaio winery, a renowned winery that produces its excellent wines following the rules of eco-sustainability. Pomaio is listed as one of the 13 most beautiful Design Cellars in the Region of Tuscany for the Toscana Wine Architecture project, and this 'Green' philosophy was also followed for the renovation of the villa. In fact, thanks to the materials used, the villa has a high energy-saving rating, with positive effects both for the environment and for those who stay there in all seasons.
Therefore, in addition to living in the midst of an almost enchanted place, amidst splendid rows of vines that slope down towards the silhouette of the city, you will be able to taste the excellent wines in the wine cellar when you feel like taking a little walk and reaching it.
Villa Leopoldina is on two levels connected by a covered outdoor staircase. You will have two fully equipped kitchens, a washing machine and a dryer on each floor, Wi-Fi, air conditioning, and satellite TV. Villa Leopoldina is your perfect location for a holiday with all the comforts on an authentic 100-year-old residence.
On arrival day you will have the opportunity to enjoy a dinner offered by the owners (for stays of a minimum of 7 nights) and a welcome basket for breakfast the following day. Thanks to a wooden bridge at the back of the villa, the first floor is also accessible to persons with reduced mobility. Villa Leopoldina
Villa Mandorlo
Stunning private accommodation with WIFI, private pool, A/C, TV and terrace
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10
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5
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6
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280 m2
Description
You will find Villa Mandorlo inside the ancient Podere di Pomaio, just outside Arezzo. It is an old farmhouse that has been renovated following all of today's eco-sustainability standards, which are similarly applied to the entire estate, which produces and exports excellent Tuscan IGT and DOCG wines. Podere Pomaio's Bio-architecture winery is listed among the 14 most beautiful Design Cellars in Tuscany for the Toscana Wine Architecture project.
At the winery you can also book wine tastings and tours of the estate, we also recommend a visit to the beautiful vineyards, it is an experience not to be missed!
At Villa Mandorlo you will have at your disposal a private garden (about 5000 square metres) and a splendid swimming pool extremely panoramic, overlooking the valley, the surrounding chain of hills and the beautiful city of Arezzo, which, day and night, will offer you truly suggestive sceneries.
In Arezzo you will find all the conveniences of a big city. There are shops, supermarkets and typical restaurants, as well as valuable works of art by renowned artists such as Piero della Francesca and Giorgio Vasari.
The swimming pool, truly splendid, has the particularity of being shell-shaped (size 6.50x8.40 m - depth 1.30 m - open from 01st May to 30th September), and is just a few steps from the bright dining room, definitely one of the highlights of the villa. The dining room, with its large windows, offers not only a fantastic panorama but also the possibility of unforgettable dinners by the pool.
At Villa Mandorlo you will find yourself immersed in the atmosphere and charm of old Tuscan farmhouses. The excellent furnishings and equipment, as well as comfortable and functional, will allow you to spend a memorable holiday.
On the day of your arrival, the owners will be happy to offer you dinner (for stays of a minimum of 7 nights) and a welcome basket with ingredients for breakfast the following day. Villa Mandorlo
Montalcino 17
Unique multi-unit property with WIFI, pool, TV, patio, pets allowed and panoramic view
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5
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24
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10
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10
| Accommodation | Sleeps | Bedrooms | Bathrooms | Floor Area | Price |
|---|---|---|---|---|---|
| Torrenieri 17.1 | 6 | 2 | 2 | 100 m2 | € 135 /Night |
| Asciano 17.2 | 6 | 2 | 2 | 90 m2 | € 145 /Night |
| Siena 17.3 | 4 | 2 | 2 | 65 m2 | € 135 /Night |
| Pienza 17.4 | 4 | 2 | 2 | 85 m2 | € 135 /Night |
| Monteroni 17.5 | 4 | 2 | 2 | 70 m2 | € 135 /Night |
| All 5 Accommodations | 24 | 10 | 10 |
Description
Property Summary
Nestled among rolling fields and vineyards in the heart of Tuscany, Italy, Podere San Giuseppe is a beautifully renovated country house offering an authentic and tranquil retreat in the countryside near San Giovanni D'Asso. Positioned on top of a sun-drenched hill, this charming residence comprises 6 individually designed and furnished apartments, each reflecting a unique character and style. Whether you are seeking a peaceful escape or a base from which to explore the rich cultural heritage of the region, this holiday rental delivers an exceptional experience in one of Italy's most celebrated landscapes. The property features a shared swimming pool measuring 8 x 16 metres, with a depth of 140 cm throughout, available seasonally from 1 April to 30 October, offering a refreshing retreat during the warmer months. A dedicated children's pool is also available for younger guests. Connectivity is well catered for with WiFi available throughout the house, ensuring you remain effortlessly connected during your stay. A reception service is on hand to assist with your needs, and a shared washing machine is available for guest use. Linen change is available at a supplementary charge, and room cleaning can be arranged on request at an additional cost. A cook service is also available upon request for an extra fee. Please note that all houses and apartments are individually designed and furnished, and the photographs provided are intended as representative examples only.
Outdoors
The outdoor spaces at Podere San Giuseppe are a true highlight of the property, inviting you to immerse yourself in the serene Tuscan countryside. The shared swimming pool, measuring 8 x 16 metres with a consistent depth of 140 cm, is maintained by the owner and gardener, ensuring impeccable conditions throughout its seasonal availability from 1 April to 30 October. A children's pool provides a safe and enjoyable space for younger guests, while an outdoor shower offers convenient poolside facilities. A spacious terrace completes the outdoor offering, providing an ideal setting for alfresco dining, relaxation, and taking in the sweeping views of the surrounding vineyards and natural landscape. The property sits within a natural state estate, preserving the unspoiled beauty of the environment and enhancing the sense of seclusion and tranquillity that defines this remarkable countryside retreat.
Other Information
Parking is available directly on the premises for your convenience. Please be aware that access to the property involves a 3 km bumpy motor road leading to the grounds, and guests are advised to plan accordingly. Baby equipment is included at no additional cost, making the property well suited for families travelling with young children. Podere San Giuseppe is also suitable for events, offering a distinctive and atmospheric setting for special occasions. Guests are kindly reminded that the wearing of bathing caps is obligatory when using the swimming pool.
Distances and Attractions
Podere San Giuseppe enjoys a well-connected countryside location, with the town of Buonconvento reachable in approximately 7.5 km, where you will find a range of everyday conveniences including shops, a grocery store, a supermarket, and restaurants. The bus stop and railway station of Buonconvento are also located 7.5 km from the property, providing practical transport links for those wishing to explore the wider region without a car. The renowned town of Montalcino, celebrated worldwide for its exceptional Brunello wine, lies 16 km away and is well worth a visit for its medieval architecture and vibrant local culture. The historic city of Siena, a UNESCO World Heritage Site, is situated 35 km from the property, while the enchanting Renaissance town of Pienza can be reached in the same distance. For those wishing to venture further, the elegant hilltop town of Montepulciano is approximately 50 km away, offering outstanding wine, gastronomy, and panoramic views across the Val d'Orcia. Montalcino 17
Montegufoni
Comfortable flat with WIFI, pool, A/C, terrace and panoramic view
-10% Special Offer-
39
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159
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68
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56
| Accommodation | Sleeps | Bedrooms | Bathrooms | Floor Area | Price |
|---|---|---|---|---|---|
| Villa Acciaioli | 8 | 4 | 3 | 180 m2 | € 174 /Night |
| Montegufoni 3 | 5 | 2 | 1 | 75 m2 | € 87 /Night |
| Montegufoni 10 | 2 | 1 | 1 | 45 m2 | € 82 /Night |
| Montegufoni 11 | 3 | 1 | 1 | 45 m2 | € 82 /Night |
| Montegufoni 13 | 4 | 1 | 1 | 75 m2 | € 87 /Night |
| Montegufoni 17 | 4 | 1 | 1 | 55 m2 | € 92 /Night |
| Montegufoni 18 | 5 | 2 | 1 | 80 m2 | € 92 /Night |
| Montegufoni 22 | 2 | 1 | 1 | 32 m2 | € 87 /Night |
| Montegufoni 23 | 6 | 3 | 1 | 120 m2 | € 122 /Night |
| Montegufoni 27 | 5 | 2 | 1 | 100 m2 | € 107 /Night |
| Montegufoni 28 | 3 | 1 | 1 | 70 m2 | € 87 /Night |
| Montegufoni 29 | 3 | 2 | 1 | 65 m2 | € 96 /Night |
| Montegufoni 30 | 4 | 2 | 2 | 80 m2 | € 112 /Night |
| Torre | 2 | 1 | 1 | 75 m2 | € 96 /Night |
| Torre 2 | 2 | 1 | 1 | 35 m2 | € 92 /Night |
| Acciaioli 1Bis | 6 | 3 | 3 | 120 m2 | € 158 /Night |
| Acciaioli 4 | 5 | 2 | 2 | 70 m2 | € 122 /Night |
| Acciaioli 14 | 6 | 3 | 3 | 113 m2 | € 158 /Night |
| Acciaioli 3 | 2 | 1 | 2 | 90 m2 | € 92 /Night |
| Tiglio | 5 | 2 | 2 | 90 m2 | € 122 /Night |
| Tettoia | 4 | 2 | 2 | 85 m2 | € 117 /Night |
| Guardiano | 3 | 1 | 1 | 70 m2 | € 87 /Night |
| Bellavista | 2 | 1 | 1 | 50 m2 | € 87 /Night |
| Giardino | 4 | 1 | 1 | 75 m2 | € 122 /Night |
| Fattoressa | 4 | 1 | 1 | 70 m2 | € 92 /Night |
| Camino | 2 | 1 | 1 | 25 m2 | € 87 /Night |
| Segretario | 5 | 2 | 1 | 100 m2 | € 132 /Night |
| Tramonto | 4 | 2 | 2 | 80 m2 | € 122 /Night |
| Archi | 4 | 1 | 1 | 45 m2 | € 179/Night |
| Forno | 4 | 2 | 1 | 65 m2 | € 92 /Night |
| Montegufoni 19B | 5 | 3 | 2 | 80 m2 | € 127 /Night |
| Cappella | 3 | 1 | 1 | 45 m2 | € 82 /Night |
| Bastione | 2 | 1 | 1 | 65 m2 | € 102 /Night |
| Galleria | 9 | 4 | 3 | 310 m2 | € 291 /Night |
| La Grotta | 5 | 2 | 2 | 100 m2 | € 147 /Night |
| Cardinale | 6 | 3 | 2 | 110 m2 | € 132 /Night |
| Teatro | 3 | 1 | 1 | 90 m2 | € 107 /Night |
| Montegufoni 7 | 4 | 1 | 1 | 60 m2 | € 122 /Night |
| Cupola | 4 | 2 | 1 | 75 m2 | € 112 /Night |
| All 39 Accommodations | 159 | 68 | 56 |
Description
Castello di Montegufoni is an exclusive location to spend wonderful holidays in the heart of Chianti Region.
Dating back to the 12th century and restored in the 17th century by the noble family of Acciaioli, the Castle has a magnificent tower built on the model of the one of Palazzo Vecchio in Florence.
Montegufoni Castle is part of a large estate comprising vineyards and olive trees and is surrounded by the beautiful Chianti landscape. In the castle there are 39 apartments and a large garden with a nice swimming pool: the perfect spot to relax and have fun with your family and friends.
The Chianti Region is one of the most renowned charming area in Italy for its cultural, historical and enogastronomic traditions. This luxurious Castle offers to our guests incredible holiday experiences (on request) such as cooking lessons, event location, guided tours and more!
Distances from the villa: the small village of Montagnana V.P. with food shops 1 km, Montespertoli with all kinds of shops approx. 5 km, Florence 20 km, Pisa approx. 70 km.
A bus stop with busses to Florence is only a few meters from the castle away. Bikes and scooters for rent are available in Montespertoli.
At guests’ disposal: large and very charming terraced park furnished with garden furniture and table tennis, beautiful Italian gardens (dating back to the 18th century) with lemon trees and swimming-pool (12 x 6 m - open from 01/04 to 31/10). Reception open from 9.00 to 12.30 and from 14.30 to 18.30. The outbuildings of the castle as well were restored and turned into charming apartments. The castle is run by the Posarelli family. A nice restaurant offering nice recipes of the local Chianti tradition is open every night (from April to October except on Tuesdays). Laundry with shared washing-machine (€ 4,- / per washing). WI-FI internet connection available in some apartment, in the reception and restaurant area.
Extra services: on request possibility of renting a baby bed (€ 50,- / per week) and an extra bed (€ 100,- / per week) both payable locally.
Please carefully check if there are any extra costs to be paid on site! Montegufoni
Villa Cincinelli
Fabulous independent villa with private pool, WIFI, TV and pets allowed, near Arezzo
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18
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8
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5
Description
Villa Cincinelli is a nice holiday home with private pool and WiFi internet. The property can accommodate up to 18 people comfortably in eight bedrooms with five bathrooms. Villa Cincinelli is located 5 km (3 mi) from Capolona, Italy and only 18 km (11 mi) from Arezzo in the tourist area "Arezzo And Surroundings".
What to Expect
The villa is internally composed by five independent apartments, each with its own entrance and not communicating internally; in spite of this one offers a large dining area with a table suitable to seat the entire group (ground floor, in front of the pool).
Outside, dining together is possible by joining some tables - in the part of the garden facing the swimming-pool.
in case the clients are less than the villa can sleep and the relative discount is applied, one or two apartments with 1 bedroom each will not be available.
When you arrive at Villa Cincinelli you’ll find a nice clean well-maintained property perfect for a relaxing vacation in Tuscany. After a hectic day of sightseeing, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to relax at the end the day.
Places Nearby
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Arezzo 18 km (11 mi), Cortona 45 km (28 mi), Montepulciano 66 km (41 mi), Greve In Chianti 86 km (53 mi) and Siena 88 km (55 mi).
Some other major tourist destinations you should consider visiting are: Florence 102 km (63 mi), Viareggio 189 km (117 mi), Forte Dei Marmi 196 km (122 mi), Rome 238 km (148 mi), Venice 345 km (214 mi) and Milan 387 km (240 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on vacation that is not a problem at Villa Cincinelli. If you have a large dog or multiple pets, please inquire for permission prior to booking.
Check-In Time: 15:30 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 15 June - 15 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 109 km (68 mi), Pisa (psa) 170 km (105 mi), Bologna (blq) 194 km (120 mi), Roma Ciampino (cia) 247 km (154 mi) and Roma Fiumicino (fco) 260 km (161 mi).
Villa Cincinelli
Il Circolo
Pretty private accommodation with private pool, WIFI, TV and panoramic view
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6
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3
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2
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150 m2
Description
Beautiful country house in a panoramic position, recently restored maintaining and enhancing the rustic style and at the same time providing it with all comforts to ensure a relaxing and welcoming environment. Located in the beautiful area of the "Val di Sieve", a few kilometers from Florence, the house is on two floors, with nice furnishings and some period furniture. The property has a nice garden of 3000sqm. equipped with above ground pool for the exclusive use of guests (7m. x 3m. prof. 130cm.) and provided with area equipped for outdoor dining with barbecue. Private parking in the property.
The house is located at 5,5km. from "Rufina", at 23km. from Florence, at 17km. from "Vicchio" (birthplace of Giotto and Fra Angelico) at 40km. from the "Barberino Designer Outlet" (over 100 stores of major brands of Italian and international fashion). Il Circolo
Villa Marietta
Amazing private vacation rental with A/C, WIFI, private pool, TV and panoramic view, close to Arezzo
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14
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7
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5
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400 m2
Description
Charming villa with private swimming pool on the hills near Arezzo, Tuscany.
This property has been recently renovated. Inside, this villa has lovely interiors and it's fuelly equipped with any possible comfort. Outside, it is provided a large garden with private swimming pool and an outdoor patio furnishe with barbecue, table and chair for al-fresco dining. Villa Marietta is just a short drive away from Arezzo, Castiglion Fiorentino, Cortona and Chiana Valley.
At guests' disposal WI-FI internet connection (free wi-fi), air-conditioning in each bedroom, large common areas, private swimming pool (14m x 5m; depth: 1,40m), private garden, outdoor area (by the kitchen) furnished with table and chairs for al-fresco dining, 2 baby beds (on request at the time of the reservation), shower room by the pool with 2 showers, parking
Distances:Frassineto (food bar) 1 km away, Cesa in Valdichiana (shops of any kind) 7 km away, Castiglion Fiorentino 10 km away, Arezzo 18 km away, Cortona 21 km away, Montepulciano 40 km away, Pienza 45 km away, Siena 60 km away, Firenze 85 km away, San Gimignano 100 km away, Volterra 115 km away.
Please carefully check if there are any extra costs to be paid on site! Villa Marietta
Antica Villa della Lana
Unique private property with WIFI, private pool, A/C, TV, veranda and pets allowed, near Arezzo
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10
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5
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5
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220 m2
Description
Antica Villa Della Lana is located 960 m (3115 ft) from Santa Firmina, Italy and only 2 km (2 mi) from Arezzo in the tourist area "Arezzo And Surroundings". Antica Villa Della Lana is a lovely stone building (220 sq m) with private pool, WiFi internet and air conditioning. The property can sleep up to ten guests comfortably in five bedrooms with five bathrooms.
Your Experience
When you arrive you’ll find a beautiful clean well-maintained property ideal for a splendid vacation in Tuscany. Regardless of how you spend your days - shopping, sightseeing, visiting museums or just driving in the countryside, when you arrive home you can unwind with your family and friends at the pool for a perfect ending to another day in Tuscany. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to ten people.
Places Nearby
Most people enjoy visiting close-by cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Arezzo 2 km (2 mi), Cortona 29 km (18 mi), Montepulciano 51 km (31 mi), Montalcino 72 km (45 mi) and Siena 73 km (46 mi).
Some other major tourist destinations you should consider visiting are: Florence 93 km (58 mi), Viareggio 179 km (111 mi), Forte Dei Marmi 186 km (116 mi), Rome 232 km (144 mi), Venice 338 km (210 mi) and Milan 381 km (237 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on holiday that is not a problem at Antica Villa Della Lana. If you have a large dog or multiple pets, please inquire for permission prior to booking.
Pool Open: 15 April - 31 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 98 km (61 mi), Pisa (psa) 160 km (99 mi), Bologna (blq) 188 km (117 mi), Roma Ciampino (cia) 242 km (150 mi) and Roma Fiumicino (fco) 245 km (152 mi).
Antica Villa Della Lana
Private Villa with WIFI, private pool, A/C, TV, patio, panoramic view, close to Montepulciano
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4
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1
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1
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100 m2
Description
Vineyard’s Cottage With Pool, Ac, Wifi - Siena is located 7 km (4 mi) from Sinalunga, Italy and only 22 km (14 mi) from Montepulciano in the tourist area "Orcia Valley". Vineyard’s Cottage With Pool, Ac, Wifi - Siena is a lovely stone building (100 sq m) with air conditioning, private pool and WiFi internet. The property can sleep up to four people comfortably.
The property is fully fenced with dog-proof enclosure.
Your Experience
Upon arrival you’ll find a lovely clean well-maintained property with views of the hills perfect for a splendid holiday in Tuscany. For your pleasure you will find a private pool where you can relax while enjoying a nice cold beverage after a busy day of sightseeing. Outside you will also find a patio and barbecue grill. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, stove and refrigerator, as well as, plenty of tableware and cutlery for up to four people.
Places Nearby
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Montepulciano 22 km (14 mi), Montalcino 36 km (22 mi), Arezzo 38 km (23 mi), Cortona 39 km (24 mi) and Siena 48 km (30 mi).
Some other major tourist destinations you should consider visiting are: Florence 123 km (77 mi), Viareggio 210 km (130 mi), Forte Dei Marmi 217 km (135 mi), Rome 205 km (127 mi), Milan 410 km (255 mi) and Naples 396 km (246 mi).
Additional Information
Check-In Time: 17:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 May - 30 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 129 km (80 mi), Pisa (psa) 191 km (119 mi), Roma Ciampino (cia) 214 km (133 mi), Bologna (blq) 215 km (134 mi) and Roma Fiumicino (fco) 227 km (141 mi).
Additional Services
Tours - The owner can organize custom tours for your group. To learn about the tours offered, speak to the owner after arriving or inquire prior to booking. The cost will vary depending in the exact tour and number of people.
Vineyard’s Cottage With Pool, Ac, Wifi - Siena