Autumn Vacation Rentals in Borgo alla Collina
Results 321 - 340 of 351
Il Cottage Roccaio
Stunning private holiday rental with A/C, WIFI, private pool, TV, patio and pets allowed
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8
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3
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3
Description
Property Summary
Nestled among the rolling fields and vineyards of the Tuscan countryside, Cottage Roccaio is a cosy and characterful semi-detached house offering a truly authentic rural retreat just 3 km from the historic centre of Castiglion Fiorentino, Italy. Spread across 2 storeys, this rustic yet comfortable holiday rental combines traditional charm with all the comforts needed for a relaxing stay in one of Italy's most celebrated regions. The property enjoys a secluded and peaceful position, making it an ideal escape for those seeking tranquillity and natural beauty. Guests have access to a private, well-kept fenced garden that frames the home beautifully and provides a sense of complete privacy. A private swimming pool measuring 8 x 4 metres with a depth of 150 cm and filled with salt water is available for guests to enjoy from 1 May to 30 October, with maintenance carried out by the owner and gardener. Wireless internet connection is available throughout the property, ensuring you remain connected during your stay. Parking is conveniently available directly on the premises, accessible via a 600-metre unmade road from the main motor access point.
Outdoors
The outdoor spaces at Cottage Roccaio are a true highlight of the property, offering an inviting and serene environment surrounded by the natural beauty of the Tuscan landscape. The private fenced garden is well maintained and provides ample space to relax, unwind, and enjoy the fresh countryside air. The salt water swimming pool, measuring 8 x 4 metres with a depth of 150 cm, serves as the centrepiece of the outdoor area and is available seasonally from 1 May through to 30 October. Pool upkeep is managed by the owner and gardener, ensuring the water and surroundings are kept in excellent condition throughout the season. The garden and outdoor setting, framed by vineyards and open fields, create a picturesque backdrop that perfectly complements the rustic character of the cottage.
Other Information
Cottage Roccaio is equipped with a laundry room and washing machine, offering practical conveniences for longer stays. Please be aware that the owner resides on the same property, which may provide an added sense of security and local assistance during your visit. The owner also keeps a dog on the premises. Given the rural location of the property and the nature of the surrounding road network, the use of a private car is strongly recommended to make the most of your stay and to access nearby towns, services, and attractions with ease.
Distances and Attractions
Cottage Roccaio benefits from a well-connected position within the Tuscan countryside, placing a wide range of services and cultural destinations within easy reach. A grocery store is located just 2 km away, while a supermarket can be found at 4 km. A restaurant is situated 3 km from the property, and the nearest bus stop is also 3 km away. The charming hilltop town of Castiglion Fiorentino lies just 3 km from the cottage, offering a wealth of local history, architecture, and authentic Italian atmosphere. The celebrated town of Cortona, renowned for its Etruscan heritage and stunning panoramic views, is 11 km away, while the vibrant city of Arezzo, famous for its medieval piazza and antique market, is 22 km distant. The elegant wine town of Montepulciano can be reached in approximately 38 km, and the magnificent city of Florence, with its world-class museums and Renaissance landmarks, is 100 km away. Nature lovers will also appreciate the proximity of Lago Trasimeno, one of Italy's most well-known lakes, situated just 29 km from the property. Il Cottage Roccaio
Olivo
Private Vacation home with private pool, WIFI, A/C, TV, patio, pets allowed, panoramic view
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4
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2
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1
Description
Property Summary
Nestled in a serene and secluded setting just 500 metres from the centre of Castellina in Chianti, Italy, the newly renovated Country house "Olivo" is a charming and detached vacation rental that offers an exceptional retreat in the heart of the Tuscan countryside. Positioned in a beautifully sunny location, the property provides guests with an outstanding sense of privacy and tranquillity, making it an ideal base for those wishing to explore one of Italy's most celebrated regions. The fully fenced 500 square metre yard surrounding the property ensures a safe and secure environment in which to relax and unwind, while the inviting swimming pool offers a refreshing escape during the warmer months. Guests can remain connected throughout their stay thanks to internet WiFi available on the premises, and parking is conveniently provided on-site, ensuring a seamless and comfortable experience from arrival to departure.
Outdoors
The outdoor spaces at Country house "Olivo" have been thoughtfully designed to offer guests a complete and enjoyable alfresco experience. The beautifully maintained 500 square metre garden, fully enclosed by fencing, provides a private and peaceful setting ideal for relaxation. At its heart lies a refreshing swimming pool measuring 8 x 3 metres with a depth of 130 centimetres, available for use during the seasonal period from 01 April to 31 October. A pergola offers welcome shade during the warmer hours of the day, while the outdoor shower adds a practical touch for guests returning from a swim. The garden is furnished with comfortable garden furniture, perfect for lounging and enjoying the stunning Tuscan surroundings, and a barbecue is available for those who wish to dine outdoors, making the space ideal for alfresco meals and convivial gatherings.
Other Information
Heating is available at Country house "Olivo" from 01 November to 07 April and is to be paid for directly on-site. Guests are encouraged to note that the property is within walking distance of grocery stores and supermarkets, making it straightforward to stock up on everyday essentials without the need for lengthy travel.
Distances and Attractions
Country house "Olivo" enjoys an enviable location that places guests within easy reach of some of Tuscany's most celebrated destinations. The centre of Castellina in Chianti is just 500 metres away, while the historic city of Siena can be reached in approximately 26 kilometres and the magnificent city of Florence lies approximately 48 kilometres from the property. For those seeking relaxation and wellness, the renowned thermal baths of "Rapolano Terme" are situated approximately 52 kilometres away. The surrounding area is rich in cultural and scenic attractions, with the charming towns and villages of San Donato in Poggio, Radda in Chianti, Panzano in Chianti, Greve in Chianti, Monteriggioni, San Gimignano, and Volterra all accessible within a short drive. Guests can immerse themselves in the breathtaking Tuscan landscape through a wide range of activities, including hiking and cycling, or spend their time discovering the picturesque villages and historic towns that define this extraordinary region. Olivo
Il Sogno di Pietro
Independent Holiday rental with WIFI, private pool, A/C, TV, patio, pets allowed, panoramic view
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11
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5
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4
Description
Property Summary
Nestled among trees and rolling fields in the heart of Tuscany, Italy, the villa "Il Sogno Di Pietro" is an exceptional holiday rental offering a harmonious blend of privacy, comfort, and natural beauty. Located just 6 km from the centre of Castiglion Fiorentino, this elegant property comprises a main house and a separate outbuilding, set within a fully fenced private estate of 6,500 m2. The grounds provide a true sense of seclusion, with a lush lawn and mature vegetation creating a serene and restorative atmosphere. A generously sized private swimming pool measuring 12 x 4 m with a depth of 140 cm is available for guests to enjoy seasonally from 1 April to 30 October, with pool maintenance carried out regularly by the owner's gardener. The estate benefits from ample private parking accommodating up to 6 cars directly on the premises. Wireless internet is available throughout the property, ensuring guests remain connected during their stay. The expansive yard surrounding the villa enhances the overall sense of space and tranquillity, making "Il Sogno Di Pietro" a truly remarkable retreat in the Tuscan countryside.
Outdoors
The outdoor spaces of "Il Sogno Di Pietro" have been thoughtfully designed to encourage relaxation and al fresco living at its finest. The private swimming pool, measuring 12 x 4 m with a depth of 140 cm, takes centre stage in the garden and is available for use from 1 April to 30 October. For guests who wish to enjoy the pool outside of the warmer months or prefer a heated swimming experience, the pool can be heated at an additional cost, subject to prior booking of the service. An outdoor shower is conveniently located nearby for rinsing off after a swim. A charming pergola provides a shaded area ideal for dining or relaxing during the warmer parts of the day, and the garden furniture ensures that outdoor seating is both comfortable and plentiful. A barbecue is also available for guests who wish to enjoy outdoor cooking and dining under the Tuscan sky. The fully fenced grounds of 6,500 m2 encompass a well-maintained lawn and natural surroundings that offer complete privacy throughout your stay.
Other Information
The annex at "Il Sogno Di Pietro" consists of a living room with a kitchenette, 1 double bedroom, and a bathroom with a shower, providing a comfortable and self-contained space ideal for additional guests. Inside the main house, guests have exclusive access to an infrared sauna and a dedicated spa area, both of which are included in the rental. The property is managed with care and attention, with the owner's gardener attending to pool maintenance and the upkeep of the grounds on a regular basis. Please be aware that the owner does not accept any youth groups. All specific services requiring prior arrangement, such as pool heating, must be booked in advance to ensure availability during your stay.
Distances and Attractions
"Il Sogno Di Pietro" enjoys a privileged location that places a wide range of amenities and cultural attractions within easy reach. A grocery store and supermarket are both situated approximately 3 km from the property, while a restaurant can be found just 1 km away, making everyday conveniences readily accessible. A bus stop is located 1.5 km from the villa, offering a practical connection to the surrounding area. The renowned thermal baths of "Rapolano Terme" are approximately 37 km away, providing a wonderful opportunity for relaxation and wellness. The bathing lake of Trasimeno is also within reach, offering a scenic natural destination for swimming and leisure. Among the nearby cultural highlights, the historic town of Cortona is just 13 km away, while the celebrated city of Arezzo can be reached in approximately 16 km. The charming village of Lucignano lies 20 km from the property, and Passignano Sul Trasimeno is situated 31 km away. Castiglione Del Lago is approximately 33 km from the villa, and the iconic Renaissance town of Pienza is reachable within 47 km, making the property an ideal base for exploring the rich artistic and historical heritage of Tuscany and the surrounding regions. Il Sogno di Pietro
Cerretino Group House 14 Sleeps
Unique private vacation rental with WIFI, private pool, A/C, TV, patio and panoramic view
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14
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7
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6
Description
Property Summary
Nestled in the heart of the Tuscan countryside in Castellina in Chianti, Italy, this charming and historical country house, known as "Cerretino group house 14 sleeps," offers an authentic and memorable holiday rental experience for large groups seeking comfort, character, and natural beauty. Spread across 2 storeys, the property is composed of a main house and an outbuilding, harmoniously surrounded by meadows, open fields, and rolling vineyards that define the iconic Chianti landscape. Positioned just 1 km from the centre of Castellina in Chianti and only 200 m from the edge of a forest, the property enjoys a wonderfully sunny aspect that enhances its rural charm throughout the seasons. The private swimming pool, measuring 6 x 12 m with a depth ranging from 100 to 180 cm, is available seasonally from 15 May to 15 October and serves as a refreshing centrepiece for warm Tuscan days. The generous yard surrounding the property provides ample space to relax and enjoy the natural setting, while Wi-Fi internet connectivity ensures that guests remain comfortably connected throughout their stay. Parking is conveniently available directly at the house, offering ease of arrival and departure for all guests.
Outdoors
The outdoor spaces of this property are thoughtfully arranged to make the most of the stunning Tuscan countryside that envelops the estate. The private swimming pool, set within the natural grounds, is complemented by an outdoor shower, making it a fully equipped and refreshing retreat during the warmer months. A well-appointed terrace provides the perfect setting for alfresco dining and relaxed gatherings, furnished with garden furniture that invites guests to linger over meals and enjoy the panoramic views of the surrounding landscape. A barbecue is also available, allowing guests to prepare and savour outdoor meals in true Italian countryside style. Pool maintenance is carried out regularly by the owner and gardener, ensuring that the facilities are always in excellent condition throughout the season. Walking paths are accessible directly from the property, beginning just 200 m away, offering guests the opportunity to explore the surrounding natural environment on foot.
Other Information
The property is equipped with a central heating system and air conditioning, ensuring a comfortable indoor climate regardless of the season. A washing machine and tumble dryer are also available within the house, providing practical convenience for longer stays. Guests should be aware that access to the property is via a 300 m long motor road that is notably narrow and uneven, and care should be taken when approaching by vehicle. Baby equipment is included in the stay at no additional cost, making the property well suited for families travelling with young children. Groups of teenagers are accommodated on request only, and guests are kindly asked to make prior arrangements in this regard.
Distances and Attractions
The property's location places guests within easy reach of a wide range of everyday conveniences and cultural destinations. A shop, grocery store, supermarket, restaurant, and bakery are all located within 1 km of the property, while a bar can be found just 500 m away. A pedestrian zone is accessible at 1 km, and a bus stop is conveniently situated only 300 m from the house. For those wishing to explore the coast, the sandy beach of "Cecina Mare" is located 88 km away, while the renowned thermal baths of "Rapolano Terme" offer a relaxing retreat at a distance of 50 km. The surrounding Chianti region is rich in historic towns and cultural landmarks, with Panzano in Chianti just 13 km away, Greve in Chianti and Gaiole in Chianti both at 20 km, and the magnificent city of Siena reachable in approximately 26 km. San Gimignano, famous for its medieval towers, lies 42 km from the property, while the art-filled city of Florence is situated 50 km away, making it an ideal destination for a day excursion. Cerretino Group House 14 Sleeps
San Donato
Great holiday home with WIFI, pool, pets allowed and panoramic view, close to Greve In Chianti
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2
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14
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5
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5
| Accommodation | Sleeps | Bedrooms | Bathrooms | Floor Area | Price |
|---|---|---|---|---|---|
| San Donato 1 | 6 | 2 | 2 | 70 m2 | € 129 /Night |
| San Donato 2 | 8 | 3 | 3 | 180 m2 | € 182 /Night |
| All 2 Accommodations | 14 | 5 | 5 |
Description
Nice property with pool situated near the beautiful medieval hamlet of San Donato in Poggio, half-way between Florence and Siena. This property comprises 2 comfortable apartments all of which recently restored and tastefully furnished. Beautiful vineyards and olive groves surround the estate and produce excellent Chianti Classico wine and olive oil (available for the clients to be tasted and purchased). This property is situated among green hills but at the same time it is very close to the small town of San Donato (walking distance) offering nice restaurants, pizzerias and all main services.
The access to the property is via an unpaved but well-maintained road suitable for any kind of car.
Distances: San Donato in Poggio with all kinds of shops 500 m away, Greve in Chianti 15 km, the charming medieval town of San Gimignano 18 km, Florence 20 km, Siena 35 km away, Pisa (airport) 95 km away, Arezzo approx. 100 km, Cortona 140 km away. Rome is approx. 300 km away.
At guests’ disposal: large outside areas, garden furnished with tables, chairs and sun-beds, shared swimming-pool (6 x 12 m – min. depth 1,2 m, max. depth 1,4 m; opening hours: 9:00 AM – 7:00 PM), splendid park for walks along nice paths leading to a small lake.
The apartments San Donato 1 and 2 provide WI-FI internet access (free of charge).
Parking within the grounds.
A large common room is available upon request to organize nice dinners as well as tasting of the products of the estate (wine, olive oil, “vin santo”).
The apartments San Donato 1 and 2 can be connected to accommodate 10/14 persons.
Please carefully check if there are any extra costs to be paid on site! San Donato
La Casa di Pino
Amazing private holiday rental with WIFI, A/C, private pool and TV, near Cortona
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4
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1
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1
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55 m2
Description
La Casa di Pino, a small jewel of rural architecture dating back to the year 1200, is located in the heart of the Val di Chio, on the border between Tuscany and Umbria and a few kilometers from the town of Castiglion Fiorentino. All around green woods that are part of the farm, where you can also admire the beautiful 'Majesty' in the grove, a few hundred meters from the house.
In our opinion the main feature of Casa di Pino, which makes it perfect for couples and romantic holidays, is the atmosphere that the owners have managed to create in this small space. In addition to the fact that it resembles a nest, the warm colors chosen for the rooms and the furniture itself, give the feeling of being at home, in an intimate and welcoming place.
In the wide garden the beautiful swimming pool (size 4x8 m., depth 1,20-1,50 m. - open from 01st May to 30th September) with Jacuzzi corner, barbecue and wood burning oven next to the gazebo and an equipped porch. A few meters from the house passes a panoramic side road that crosses the hills and connects Castiglion Fiorentino to the town of Cortona and the nearby region of Umbria. The property accepts small size pets. La Casa di Pino
Galleria di Brolio
Pretty independent property with private pool, A/C, WIFI, TV and veranda, close to Cortona
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10
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4
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3
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170 m2
Description
Galleria di Brolio is an old stone farmhouse whose origins date back to 1800, located between two of the most important towns of the Valdichiana, Castiglion Fiorentino and Foiano, and which is now part of the owners' farm. You will find the farmhouse just a few kilometres from the two towns and in both, as well as various monuments and sites of artistic interest that are definitely worth a visit, you will have shops, restaurants and all kinds of services. The small historic centres of the villages will be a pleasant destination for your aperitifs or dinners at the restaurant.
The farmhouse takes its name from the Galleria di Brolio, a conduit that is still in operation today and is located on the edge of the olive grove. The conduit is part of the canal built between 1932 and 1940 to improve the flow of water towards the Arno, planned by the engineer Vittorio Fossombroni for the reclamation of the valley at the end of the 18th century.
Galleria di Brolio is situated on the edge of a wood of about 20 hectares of oaks and pines used as a hunting reserve for the repopulation of animals; they live here in the utmost freedom and if you love wildlife you will frequently see hares and pheasants running in the olive grove, the vineyard and even in the house lawn.
On the ground floor there is the apartment where the owners live, as well as a cellar and a shed for the farm's agricultural tools, while the first floor is reserved for you. The furnishings are very nice and comfortable, enriched with local antiques, and blend in perfectly with the old features of the house. Not far away, on the other side of the wood, passes the railway line that connects central Italy with the main cities of the peninsula (Florence, Bologna, Rome, Milan), so it will be easy to move around even without a car.
A few metres from the house, surrounded by silver olive trees, you will find a beautiful swimming pool completely fenced and for your exclusive use (size 11x5 m, depth 1.10-1.40 m - open from 01st May to 30th September), together with a gazebo equipped with garden furniture, which will allow you to shelter from the hot summer sun.
There is also a large pergola supplied with wrought iron furniture for eating outside, equipped with a barbecue and a wood-burning oven, for those evenings when you want to enjoy a pizza or a grill “al fresco”.
The owner, on request, will prepare excellent typical Tuscan dinners and pizzas in the wood-fired oven which, we are told by customers who have stayed at the house, are truly delicious.
Galleria di Brolio
La Casa del Nonno
Fantastic flat with private pool, WIFI, TV and pets allowed
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4
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2
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1
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55 m2
Description
From the village of Castiglion Fiorentino, with its shops and services, following the suggestive road that crosses the entire Val di Chio and climbs the wooded hills and represent the natural border between Tuscany and Umbria, you will arrive at a small cluster of houses set on the slopes of the hill and overlooking a beautiful wooded landscape. The last stretch of road, about 200 m, is unpaved and sloping. La Casa del Nonno is a small, old stone house that is part of this original rural settlement once inhabited by farming families. Here you will find guaranteed peace; lazy summer days by the pool and in the solarium enjoying the sun, without hearing any noise except those of nature.
A careful renovation has brought La Casa del Nonno back to life. Rustic style furniture, old beams on the ceilings, the old fireplace in the living room, give it a warm atmosphere reminiscent of times gone by, when the house and the open fire were the shelter of the farmers after a hard day's work.
The house will be your own little nest, well-finished, comfortable and cosy and will immediately give you the feeling of being welcome.
In front of the house there is an outdoor area arranged on natural terraces connected by steps, completely fenced and equipped with garden furniture, barbecue and a small house with laundry. For your exclusive use there is also a beautiful swimming pool (size 6x4 m, depth 1.20 m - open from 1 May to 30th September), with a panoramic view and equipped with sunbeds, deckchairs and sunshade.
For your open-air dinners in the summer evenings, the owners have organised a special corner on a terrace in the garden, equipped with a wrought iron table and chairs and covered by a large parasol. La Casa del Nonno
Fornacino
Great apartment with pool, A/C, TV and panoramic view, near Siena
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6
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17
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9
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10
| Accommodation | Sleeps | Bedrooms | Bathrooms | Floor Area | Price |
|---|---|---|---|---|---|
| Fornacino 1 | 2 | 1 | 2 | 68 m2 | € 209 /Night |
| Fornacino 2 | 4 | 2 | 2 | 78 m2 | € 263 /Night |
| Fornacino 3 | 2 | 1 | 2 | 57 m2 | € 209 /Night |
| Fornacino 4 | 2 | 1 | 1 | 41 m2 | € 198 /Night |
| Fornacino 5 | 5 | 3 | 2 | 87 m2 | € 300 /Night |
| Fornacino 6 | 2 | 1 | 1 | 46 m2 | € 198 /Night |
| All 6 Accommodations | 17 | 9 | 10 |
Description
Ancient farmhouse with adjoining barn situated on a large and renowned farming estate producing excellent wine and olive oil. This property has been carefully restored and turned into 6 comfortable apartments, all of which offering nice interiors furnished in a rustic style with some antiques. The location, among vineyards and olive groves is peaceful and dominates the Chianti Classico hills. Beautiful panoramic views with Siena in the distance are afforded. This property provides a well-kept large garden (6000 m2) with infinity pool whose use is to be shared among the 6 apartments.
Distances: Ponte a Bozzone with a food shop, a restaurant and a butcher is 5 km away, Siena with all kinds of shops and railway station 12 km, San Gimignano approx. 50 km, Florence 70 km away, Pisa 115 km , Rome 250 km away.
At guests disposal: large panoramic garden (6000 m2), shared infinity swimming-pool (5,5 x 15 m – maximum depth 1,8 m – open from 01/05 to 30/09), solarium terrace with open-air shower (cold water), barbecue, oven for pizza, furnished loggia (35 m2), table tennis. Shared laundry with washing-machine and ironing facilities. All of the apartments provide alarm system, satellite TV, hair-dryer, heating system and table and chairs (in a common area).
Parking within the grounds.
Extra services included in the rental price: linen change on Wednesdays.
Extra services to be paid on the spot: Baby bed available upon request at € 70,- / per week (payable on site).
The produce of the estate is available for clients to be purchased.
Please carefully check if there are any extra costs to be paid on site! Fornacino
Casa Angela
Stunning private villa with private pool, A/C, WIFI, TV, balcony, pets allowed, near Cortona
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8
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3
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3
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170 m2
Description
An old farmhouse completely renovated, located near Castiglion Fiorentino. Casa Angela will be the ideal place where you can rediscover the flavours of the past, of a simple and quiet life. You will have at your disposal a large vegetable garden where you can pick up genuine fresh seasonal vegetables every morning. In the vicinity of the farmhouse there are farmyard animals, fruit trees and vineyards, making your stay a true country life experience.
Of this holiday you will surely remember the slow and warm days that village life, still regulated with rhythms of other times, gives us.
For your lazy summer days the beautiful swimming pool completely fenced and for your exclusive use (size mt. 6x12, depth mt. 1,20-1,50 - open from 16 May to 30th September) will be the ideal place also for your evening aperitifs, relaxed in the gazebo, with a good red wine in your glass and with the lights of Castiglion Fiorentino, which climbs up the hill, as a backdrop.
For children there is a large green outdoor space to explore with a five-a-side football goal for fun times with friends. The house is definitely perfect, in our opinion, for family holiday with children or for a small group of friends who want to discover the beauty of Tuscany and the nearby Umbria, renting a villa with private pool.
Pets are welcome (extra charge could be required).
We guarantee that you will leave your heart in Castiglion Fiorentino. A small town of steep, paved alleyways, ancient buildings, stone stairways and arches and mighty walls dominated by the imposing Cassero tower, guarding the valley. Many trattorias and restaurants invite you to go out in the evening and enjoy a dish of fresh, handmade pasta or a famous Florentine steak.
In Castiglion Fiorentino you will also find supermarkets for your daily shopping, other shops and all necessary services. From the house you can easily walk to a restaurant which is just 1 km far.
A few km away is the border with the region of Umbria, in 15 minutes by car you will be able to reach the golden beaches of Lake Trasimeno, with its characteristic villages and islets to discover. Casa Angela
Collina dei Fiori
Wonderful private vacation home with WIFI, A/C, private pool, TV and pets allowed, close to Arezzo
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9
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4
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3
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150 m2
Description
Collina dei Fiori is the result of a painstaking restructuring of an old country house situated in an extremely panoramic position, waiting for you to spend unforgettable holidays with your family or friends. This beautiful villa is at the top of a hillside covered in age-old olive trees and green woods, where many small roads climb up the steep hills revealing enchanting views at every turn.
In a few minutes’ drive from the house you can easily reach Castiglion Fiorentino, Cortona, Arezzo and Lake Trasimeno, ideal destinations for day trips, to alternate with relaxing days at the swimming pool (size 5x10 m, depth 1,20-2,20 m - open from 01st May to 30th September) and funny tennis and table tennis tournaments. The tennis court is located a few hundred meters from the house and is shared only with the guests of the other two houses VILLA DEGLI OLIVI and VILLA GIOTTO.
Adjacent to the kitchen there is a pergola furnished with table and benches and a barbecue where you can spend your evenings together with family and friends, enjoying grilled meats and sipping a glass of wine. The large enclosed garden offers privacy and security for your family and your four-legged friends (a supplement may be charged for pets). If you want to stretch your legs in the hills around the house there are countless hiking trails, also suitable for children. Collina dei Fiori
Podere i Gigli
Amazing private villa rental with A/C, private pool, WIFI, TV and terrace, close to Cortona
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6
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3
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3
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170 m2
Description
Podere I Gigli is a farmhouse just a few steps away from the centre of Castiglion Fiorentino, which you can easily reach on foot in less than 10 minutes when you want to stretch your legs. The railway station, which is 500 metres from the property, is also within easy reach and makes the house particularly suitable for all types of travel should you wish to visit Tuscany and Central Italy without taking a car.
The farm mainly produces cereals, but around the house you can also enjoy the view of vineyards, olive groves and fruit trees. The owners will be happy to let you taste and buy their pure Sangiovese wine, extra virgin olive oil and other products of the farm, proudly handed down from father to daughter.
The house is surrounded by a large, well-kept garden, shaded and filled with flowers and plants. In the relaxation area, furnished with table and chairs, you can comfortably enjoy your meals in the open air. At the back of the house, in a sunny position, there is a swimming pool measuring 4.5x9m, 1.50m deep and completely fenced ( open from 16 May to 30 September) for the safety of your children.
Another corner that we think you will appreciate is the sun terrace on the first floor, where you will find a small lounge with a sun umbrella, table and chairs, ideal for aperitifs in the cool of summer evenings.
There is also a vegetable garden with fresh seasonal vegetables that you can pick daily.
Podere I Gigli is an old stone farmhouse, dating back to the early 1900s, which has recently been renovated and brought back to life while maintaining the structure, which still exudes ancient history and farming traditions. The grit floors and exposed beams have been preserved and together with the rustic furnishings and antiques and local crafts, personally and carefully chosen by the owner, make the house a truly ideal place for your holidays.
The owners who live next door, although discreet, will be a sure reference point for any need you may have. Podere i Gigli
Le Vasche
Comfortable holiday home with pool, WIFI, TV and panoramic view, near Florence
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4
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19
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10
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7
| Accommodation | Sleeps | Bedrooms | Bathrooms | Floor Area | Price |
|---|---|---|---|---|---|
| Vasche 1 | 4 | 2 | 2 | 100 m2 | € 119 /Night |
| Vasche 2 | 4 | 2 | 1 | 60 m2 | € 108 /Night |
| Vasche 3 | 6 | 3 | 2 | 200 m2 | € 169 /Night |
| Vasche 4 | 5 | 3 | 2 | 150 m2 | € 161 /Night |
| All 4 Accommodations | 19 | 10 | 7 |
Description
Four charming apartments in a farmhouse (composed in total by 4 units) that was originally a watchtower during the war between the Florence and Siena republics. Today it is the guesthouse of a 16th century villa, where the property owners reside. The property is in a tranquil location at the center of a 12 hectare farm that produces wine and olive oil. At the same time it is just 350 m from the center of a small, charactaristic village where a bus can take you to Florence in just 20 minutes. Beautiful view of the countryside. Each apartment has its own large, private outdoor space, and the beautiful, enclosed, shared pool sits among olive trees, overlooking the country landscape (85 m from the house). Upon request, it is possible to visit the garden of the main villa, with its ancient interconnecting pools fed by a natural spring and age-old lemon trees. The apartments are furnished in simple, rustic style. Access to the property is via a 250 m unpaved but well-maintained road.
Distances: general stores and bars 300 m away, Cerbaia with all kinds of shops, restaurants and tennis 2 km, San Casciano with all kinds of shops 5,5 km away, Florence (airport) 17 km, San Gimignano 41 km away, Siena 64 km, Castellina in Chianti 72 km away, Pisa (airport) 74 km, Tirrenia (beaches) 85 km, Rome approx. 300 km away.
At guests’ disposal: fenced-in pool (7 x 14 m – depth from 1,4 m to 2,2m – open from 8:00 to 20:00) with outdoor shower (cold water). Each apartment has its own private outdoor space and a barbecue (portable). Laundry with washing machine (€ 3,- / wash), iron and ironing board. WI-FI internet connection available in the apartments as well as in the garden area.
Parking within the grounds.
Extra services to be paid on the spot: Extra single bed available upon request (€ 80,- / week), use of a double sofa-bed in Vasche 1 (€ 120,- / per week), baby bed with linen (€ 50,- / week), high chair (€ 50,- / week). Maid service (€ 12,- / hour). Upon request it is possible to purchase products from the farm.
Please carefully check if there are any extra costs to be paid on site! Le Vasche
Casa Chiara
Pretty private house with WIFI, A/C, TV, terrace, pets allowed and panoramic view
Special Offer-
4
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2
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1
Description
Property Summary
Nestled in the heart of Tuscany, Italy, "Casa Chiara" is a beautifully appointed two-story vacation rental that combines modern comfort with the timeless charm of the Chianti countryside. Built in 2009, this thoughtfully designed property is situated just 300 meters from the center of Castellina in Chianti, offering guests the rare combination of a peaceful, sun-drenched setting and effortless access to local amenities. The house accommodates families and groups seeking a refined retreat in one of Italy's most celebrated wine regions. Connectivity is seamlessly provided through Wi-Fi internet access, ensuring you remain connected throughout your stay. For those arriving by car, the property offers convenient on-site parking as well as a private single garage located directly at the house. The surrounding yard, a private terraced garden spanning 40 square meters, adds a charming outdoor dimension to the property, inviting you to enjoy the gentle Tuscan climate in a tranquil and intimate setting.
Outdoors
The outdoor spaces of "Casa Chiara" have been designed to make the most of the property's sunny and sheltered position. The private terraced garden extends across 40 square meters, offering a welcoming green retreat where you can relax and soak in the warmth of the Chianti hills. While the garden is not fenced, it provides a sense of seclusion and calm that complements the overall atmosphere of the property. The terraced layout adds visual interest and makes excellent use of the natural topography of the site, creating distinct areas where you can unwind, dine al fresco, or simply enjoy the surrounding landscape at your leisure.
Other Information
"Casa Chiara" is a two-story house built in 2009, offering a modern and well-maintained living environment suited to a variety of guests, including families traveling with young children, as baby equipment is included with the rental. The property is set in a quiet and sunny location, ensuring a restful atmosphere throughout your stay despite its proximity to the village center. Walking paths spanning 500 meters are easily accessible from the property, making it an excellent base for leisurely outdoor exploration on foot. For those seeking aquatic leisure, an outdoor swimming pool is available 3 kilometers from the house, while an indoor pool can be found 12 kilometers away.
Distances and Attractions
"Casa Chiara" enjoys an enviable position that places a wealth of Tuscan attractions within easy reach. The center of Castellina in Chianti is just a 3-minute walk from the property, and within that short distance you will find a pedestrian zone, a restaurant, and a bar. Everyday conveniences including a shop, grocery store, and supermarket are all within walking distance, while a bus stop is located just 200 meters away for those wishing to travel further afield. For a truly restorative experience, the thermal baths at "Rapolano Terme" are situated 50 kilometers from the house. Golf enthusiasts will appreciate the presence of an 18-hole golf course just 35 kilometers away. Among the surrounding towns, Radda in Chianti is 12 kilometers away, Greve in Chianti is 20 kilometers away, and the magnificent city of Siena lies just 26 kilometers from the property. San Gimignano, renowned for its medieval towers, is 34 kilometers away, while the Renaissance splendor of Florence can be reached in approximately 50 kilometers. For those planning onward travel, Pisa is located 100 kilometers from "Casa Chiara." Casa Chiara
Terrazza sul Chianti
Wonderful villa rental with WIFI, A/C, TV, patio and panoramic view
Special Offer-
10
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4
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4
Description
Property Summary
Nestled in the heart of Tuscany, Italy, "Terrazza sul Chianti" is a large, modern holiday rental set across 2 storeys and fully renovated in 2025. Located in Castellina in Chianti, this impressive residence sits 1.2 km from the town centre in a secluded, elevated position on a slope within a quiet residential district. The property benefits from a desirable west-facing orientation, offering a sense of openness and light throughout the day. Situated within a residence of 2 houses, the property provides a private and refined retreat for those seeking an authentic Tuscan experience. Guests have access to a generously sized yard in its natural state, which is fully fenced, ensuring both privacy and security. Convenient on-site parking is available directly at the house, making arrivals and departures effortless. Wireless internet connection is available throughout the property, keeping guests connected during their stay.
Outdoors
The outdoor spaces at "Terrazza sul Chianti" reflect the natural beauty of the surrounding Chianti landscape. The fenced yard, maintained in its natural state, provides ample room to relax and enjoy the fresh Tuscan air in a tranquil and private setting. The west-facing position of the property ensures that the exterior areas are bathed in warm afternoon and evening light, creating an ideal atmosphere for outdoor leisure. An outdoor swimming pool is located 1 km from the property, offering guests easy access to additional recreational facilities during their stay.
Other Information
Guests should be aware that part of the house is closed and unoccupied during the stay, and the owner resides on the same property. A main road is located close by. Baby equipment is included in the rental at no additional cost. Groups of teenagers are accommodated on request only. The property is part of a small residence comprising 2 houses in total, and the shared outdoor areas are available for guest use.
Distances and Attractions
"Terrazza sul Chianti" enjoys an excellent position for exploring some of the most celebrated destinations in Tuscany. The bus stop "Chiantigiana" is just 30 m from the property, providing convenient public transport access. Essential amenities are within easy reach, with a grocery store and supermarket both 1.3 km away, and a restaurant just 1 km from the property. The railway station "Castellina Scalo" is 7 km away, while the sandy beach of "Cecina Mare" can be reached in approximately 95 km. Among the most notable nearby attractions, Radda in Chianti is 12 km away, while both Siena and Greve in Chianti are 20 km from the property. Gaiole in Chianti lies 22 km away, and the iconic medieval town of San Gimignano is 27 km distant. The magnificent city of Florence is reachable within 44 km, making it an ideal destination for a day trip. The surrounding Chianti region offers a wealth of opportunities for wine tasting, scenic drives through rolling vineyards, and the discovery of historic hilltop villages. Terrazza sul Chianti
Fiore di Mandorlo
Comfortable flat with WIFI, A/C, TV and patio
Special Offer-
5
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2
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1
Description
Property Summary
Nestled in the serene Tuscan countryside of Castellina in Chianti, Italy, the charming apartment house "Fiore di Mandorlo" offers an exceptional holiday rental experience in a secluded and sun-drenched setting, just 4 km from the centre of Castellina in Chianti. This beautifully renovated historical residence carries the character and warmth of its origins while providing all the comforts expected of a refined country retreat. The property sits within a natural state estate, offering guests the exclusive use of a private garden and yard where the tranquillity of the Tuscan landscape can be fully appreciated. Convenient private parking is available directly at the house, ensuring effortless arrivals and departures. Wifi internet connectivity is provided, allowing guests to remain connected throughout their stay while enjoying the peaceful rural surroundings.
Outdoors
The outdoor spaces of "Fiore di Mandorlo" invite guests to immerse themselves in the beauty of the Chianti countryside. The private garden, maintained in its natural state, provides a genuine and unspoilt environment ideal for relaxing and enjoying the abundant Tuscan sunshine. The surrounding grounds offer ample space for outdoor leisure, with the property's secluded position ensuring complete privacy and a deep sense of calm. For those wishing to swim, an outdoor swimming pool is accessible just 3 km from the property.
Other Information
Baby equipment is included as part of the property offering, making "Fiore di Mandorlo" a thoughtful choice for families travelling with young children. A car is recommended in order to make the most of the property's countryside location and to reach the surrounding towns, services, and attractions with ease.
Distances and Attractions
The property is ideally positioned to explore the rich cultural and gastronomic heritage of Tuscany. The centre of Castellina in Chianti is located just 4 km away, where guests will find a selection of local shops and a supermarket, both reachable within the same distance. The bus stop "Chiantigiana" is situated 2 km from the property. The magnificent city of Siena, renowned for its medieval architecture and the famous Piazza del Campo, is approximately 25 km away, while Florence, one of the world's most celebrated art and cultural destinations, can be reached in approximately 45 km. This privileged location places guests within easy reach of the finest vineyards, hilltop villages, and landscapes that define the heart of the Chianti region. Fiore di Mandorlo
Volpe
Beautiful holiday home with A/C, WIFI, TV, balcony and pets allowed
Special Offer-
4
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2
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2
Description
Property Summary
Welcome to "Volpe," a beautiful and comfortable detached 2-family house nestled in a peaceful residential area of villas, just 1 km from the centre of Castiglion Fiorentino, Italy. This thoughtfully renovated holiday rental offers an ideal retreat for those seeking a refined and tranquil escape in the heart of Tuscany. The property benefits from a private garden of 250 m2, providing a serene outdoor space exclusively for your enjoyment, while a shared fenced garden of 2,000 m2 is also available for common use. Connectivity is seamlessly ensured with Internet WiFi access throughout the property. Parking is conveniently available directly on the premises, and an EV charging station is provided for guests travelling with electric vehicles, reflecting a thoughtful commitment to modern comfort and sustainability.
Outdoors
The outdoor spaces at "Volpe" are a true highlight of the property, offering a generous and well-maintained environment in which to relax and enjoy the Tuscan landscape. The private garden of 250 m2 provides an intimate and exclusive setting, ideal for outdoor dining, leisure, or simply unwinding in the fresh air. For those seeking more space, the shared fenced garden of 2,000 m2 offers ample room to stroll, play, or gather in a secure and well-kept environment. The surrounding residential area of villas ensures a calm and pleasant atmosphere throughout your stay.
Other Information
A car is recommended to make the most of the surrounding area and to reach nearby attractions with ease. The owner of the property resides on the same premises in a separate semi-detached house, ensuring a welcoming and attentive presence while fully respecting your privacy. Please be aware that the owner does not accept bookings from youth groups.
Distances and Attractions
"Volpe" enjoys an exceptionally convenient location with a wide range of services and attractions within easy reach. A grocery store is located just 400 m away, while a supermarket can be found at 500 m. A restaurant and a bar are both situated approximately 1 km from the property, and a bus stop is only 300 m away. The railway station "Firenze-Roma" is reachable within 3 km, making regional travel straightforward and accessible. Nature lovers will appreciate the proximity to the bathing lake "Trasimeno," just 20 km away, and the renowned thermal baths "Rapolano" at 45 km. The area is also rich in cultural and historic destinations, with Cortona at 11 km, Arezzo at 16 km, Passignano sul Trasimeno at 29 km, Castiglion Del Lago at 29 km, Pienza at 45 km, and the magnificent city of Siena at 60 km. Volpe
Vignole
Pretty independent vacation home with WIFI, TV, patio, pets allowed and panoramic view
Special Offer-
4
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2
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1
Description
Property Summary
Nestled in the heart of the Tuscan countryside in Castellina In Chianti, Italy, "Tenuzta di Vignole" is a beautifully renovated semi-detached cottage that offers an exceptional holiday rental experience for those seeking peace, tranquility, and an authentic connection with the natural landscape. Elevated on top of a hill and surrounded by fields and vineyards, this charming property enjoys a secluded position that affords unparalleled views of the rolling Tuscan countryside. The property covers an impressive 210,000 m2 and features a large, fenced garden filled with a rich variety of plants and trees, creating a serene and private environment for guests to enjoy throughout their stay. Wireless internet wifi is available throughout the cottage, ensuring you remain connected whenever needed. Upon arrival via the 2.4 km motor road leading to the property, you will find ample parking space conveniently available on site.
Outdoors
The outdoor spaces at "Tenuzta di Vignole" are a true highlight of the property, offering a remarkable setting in which to relax and immerse yourself in the beauty of the Tuscan landscape. The large, fenced garden is generously planted with trees and greenery, providing natural shade and a sense of seclusion that makes it ideal for quiet moments outdoors. The elevated hilltop position ensures that the surrounding views of vineyards and countryside are visible from the exterior areas of the property, creating a breathtaking backdrop for outdoor dining and leisure. The natural environment of the estate, spanning across its vast grounds, invites you to explore and appreciate the unspoiled rural scenery that defines this remarkable corner of Tuscany.
Other Information
The owner of "Tenuzta di Vignole" resides on the same property and is readily available to assist guests during their stay, offering a warm and personal touch to the hospitality experience. Baby equipment is available upon request, making the cottage a considerate choice for families traveling with young children. Additionally, the owner is happy to provide local farm products, giving you the opportunity to enjoy fresh, authentic Tuscan produce during your visit. Please note that a car is strongly recommended for getting around the area, as the property is accessed via a 2.4 km bumpy motor road and the surrounding region is best explored by private vehicle.
Distances and Attractions
"Tenuzta di Vignole" enjoys a privileged location that places a wealth of Tuscan destinations within easy reach. The center of Panzano is just 3 km away, while the charming town of Greve in Chianti is approximately 7 km from the property, both offering local shops, restaurants, and a genuine taste of Chianti village life. Further afield, the historic town of Radda in Chianti is easily accessible and well worth a visit for its medieval character and scenic surroundings. The renowned hilltop town of San Gimignano, famous for its striking medieval towers, can also be reached without difficulty, as can the magnificent city of Siena, one of Italy's most celebrated cultural and artistic destinations. The region as a whole offers an abundance of experiences, from wine tasting among the vineyards to exploring centuries-old villages and landscapes that have inspired travelers for generations. Vignole
Villa degli Olivi
Independent Villa rental with A/C, private pool, WIFI, TV, terrace, pets allowed, close to Arezzo
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14
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7
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7
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360 m2
Description
Villa degli Olivi is a beautiful holiday villa with attractive architectural features situated just outside Castiglion Fiorentino, a typical Tuscan town on the hills of the Valdichiana, surrounded by age-old olive groves and ancient cypress trees. The origins of the town date back in history. Today it's a quiet town which offers its visitors numerous cultural and eno-gastronomic events planned throughout the whole year.
The villa is situated on the slopes of a hill looking onto the Valdichiana below and is certainly the ideal spot for anyone wanting to spend their holiday in a charming country villa, without sacrificing any of the comforts of modern life. The internal fittings, equipment and furnishings of the house are of an high standard and ensure the maximum comfort.
Around the villa a large park of centuries-old olive trees, completely fenced in with a fence and equipped with gazebo, garden furniture, barbecue and wood-burning oven will be the ideal place to spend relaxing evenings in good company. For the amusement of adults and children there are: the beautiful fenced-in infinity pool (size m. 6 x 12, depth m. 1,20-3,00 - open from 01st May to 30th September), the table tennis and approx. 2 km far the private tennis court (size 18x36 m.) to be shared only with the guests of other 3 villas COLLINA DEI FIORI, CASALE IL TRECENTO and VILLA GIOTTO. Villa degli Olivi
Podere Orietta
Lovely home with WIFI, pool, A/C, terrace, pets allowed and panoramic view
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4
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14
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6
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5
| Accommodation | Sleeps | Bedrooms | Bathrooms | Floor Area | Price |
|---|---|---|---|---|---|
| Orietta 1 | 3 | 1 | 1 | 55 m2 | € 83 /Night |
| Orietta 2 | 3 | 1 | 1 | 55 m2 | € 83 /Night |
| Orietta 3 | 2 | 1 | 1 | 30 m2 | € 78 /Night |
| Orietta 4 | 6 | 3 | 2 | 100 m2 | € 129 /Night |
| All 4 Accommodations | 14 | 6 | 5 |
Description
Four nice apartments in a farmhouse situated on a large farming estate (30 hectares) with woods, vineyards, horses and “cinta-senese” breeding (kind of pig typical of the area around Siena). This property, offering a total of 4 units, is in quiet and panoramic location and enjoys extensive views over the surrounding landscape. All of the apartments are simply but nicely furnished, in a typical Tuscan style.
The access to the property is via an unpaved road of 2,3 km.
The property, thanks to its spacious interiors and its large exteriors, guarantees a pleasure and safe stay. All the areas, including the swimming pool, are carefully sanitized and sterilized for the health and tranquility of guests.
Distances: Castelnuovo Berardenga with all kinds of shops 10,5 km away, Siena 28 km, Radda in Chianti 40 km, Florence 77 km. Horse-back riding facilities 6 km away.
At guests’ disposal: large well-kept furnished garden, swimming-pool (5,5 x 13,5 m – maximum depth 2,4 m – open from 01/05 to 03/10), solarium (30 square meters) set in panoramic location. Small barbecues. Laundry with washing-machine and dryer (€ 3,- / per washing). WI-FI internet access and computer available (free of charge). Covered parking within the grounds.
Extra Services: Baby bed and high-chair available at € 10,- / per week each (to be paid on the spot). Maid service available by arrangement (€ 12,- / per hour to be paid locally).
Pets are allowed by paying an extra charge of € 10,- / per week (payment on site).
Check-in between 16.30 and 19.30
Please carefully check if there are any extra costs to be paid on site! Podere Orietta