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La Salciaia

: EAS16468

Wonderful independent property with WIFI, private pool, A/C, TV, patio, panoramic view, near Arezzo

  Special Offer
  • Sleeps
    15
  • Bedrooms
    6
  • Bathrooms
    4
  • Private Pool
  • Cancellation insurance (included)
From € 249per Night

Description

Property Summary

Nestled in the sun-drenched Tuscan countryside of Monte San Savino, Italy, this beautifully restored farmhouse with its characteristic pigeon-loft is an exceptional villa offering a truly immersive rural retreat. Originally built in 1814 and thoughtfully renovated, the property sits within a generous 6-hectare estate surrounded by sweeping meadows and golden sunflower fields, evoking the timeless charm of a period residence. The interiors are rich with authentic character, featuring a spacious living room with a fireplace, a large dining table, terracotta flooring, and high beamed ceilings that speak to the building's storied history. Guests are welcomed by a sense of complete seclusion, as the property is enclosed by automatic gates and benefits from total privacy, given that the adjacent annex is not designated for residential use. A fenced garden of 2,000 m2 with a well-maintained lawn provides ample space for outdoor enjoyment, while the fenced swimming pool measuring 6 x 12 m, with a depth ranging from 120 to 230 cm, invites relaxation during its seasonal availability from 06 April to 05 October. Parking is available on the property, and high-speed internet wifi ensures that guests who need to remain connected can do so with ease throughout their stay.

Outdoors

The outdoor spaces of this remarkable property are designed to make the most of the Tuscan landscape and climate. A large porch equipped with a barbecue, a pizza oven, a dishwasher, and a dedicated worktop creates an ideal setting for al fresco dining beside the swimming pool, which features an internal staircase for easy access. A gazebo and a wood-burning oven further enrich the exterior, offering additional options for outdoor cooking and leisurely gatherings. The fenced garden is thoughtfully appointed with garden furniture, an arbour, and a table tennis table, providing entertainment for guests of all ages. A children's playground complete with a slide adds a family-friendly dimension to the outdoor offering, while an outdoor shower ensures convenience after a swim. The entire estate extends across 6 hectares of private land, encompassing lush meadows that frame the property and contribute to its atmosphere of peaceful seclusion.

Other Information

This property is well-equipped to ensure a comfortable and convenient stay throughout the year. The farmhouse is fitted with a central heating system, which is available exclusively from 01 November to 07 April and must be paid for on the spot. A washing machine is available for guests' use. Room cleaning and the services of a private cook can be arranged upon request for an additional fee. The property is suitable for hosting events, making it an excellent choice for special occasions in a stunning Tuscan setting.

Distances and Attractions

The property enjoys an outstanding location for exploring the finest destinations in Tuscany. The centre of Monte San Savino is just 3 km away, while the charming town of Lucignano is 7 km from the estate. The nearest motorway access is only 2 km by road, equivalent to 800 metres in flying distance, making regional travel exceptionally convenient. The railway station of "Monte San Savino" is situated 3 km from the property. Among the most celebrated cultural and historical destinations within easy reach are Arezzo at 12 km, Montepulciano at 33 km, the thermal baths of "Serre di Rapolano" at 34 km, Pienza at 39 km, Siena at 40 km, Cortona at 42 km, and Montalcino at 46 km. This central position within the Tuscan landscape makes the property an ideal base from which to discover the region's world-renowned art, architecture, gastronomy, and natural beauty. La Salciaia

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Wonderful independent vacation rental with A/C, private pool, WIFI, TV, patio and pets allowed

  • Sleeps
    8
  • Bedrooms
    3
  • Bathrooms
    3
  • Private Pool
  • Cancellation insurance (included)
From € 213per Night

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

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Il Tiglioré

: EAS221918

Superb independent holiday villa with WIFI, A/C, private pool, TV, patio and pets allowed

  Special Offer
  • Sleeps
    4
  • Bedrooms
    2
  • Bathrooms
    1
  • Private Pool
  • Cancellation insurance (included)
From € 100per Night

Description

Property Summary

Nestled among the rolling fields of the Tuscan countryside, "Il Tiglioré" is a modern and cosy semi-detached holiday rental that has been thoughtfully renovated to offer a comfortable and welcoming retreat. Located just 5 km from the charming town of Castiglion Fiorentino, in the heart of Italy, this property combines contemporary living with the timeless beauty of the surrounding landscape. The house benefits from a private, well-kept fenced garden that creates a peaceful and secure outdoor environment, perfect for relaxing in complete privacy. Guests have access to a dedicated parking area directly on the premises, ensuring a convenient and stress-free arrival. The property is equipped with internet Wi-Fi, allowing you to stay connected throughout your stay. The above-ground swimming pool, measuring 6 x 3 m with a depth of 132 cm, is available seasonally from 1 June to 31 August, offering a refreshing escape during the warm Tuscan summer months.

Outdoors

The outdoor spaces of "Il Tiglioré" are designed to make the most of the beautiful natural surroundings. The fenced garden is carefully maintained and features a wildlife garden area alongside mature trees, creating a lush and tranquil atmosphere. An arbour provides a shaded spot ideal for relaxing or enjoying a meal outdoors, while the garden furniture offers comfortable seating for al fresco dining and leisure. A barbecue is also available, making it easy to enjoy outdoor cooking and convivial evenings under the Tuscan sky. The above-ground swimming pool, with its generous dimensions and seasonal availability from 1 June to 31 August, serves as the centrepiece of the outdoor area and is perfectly suited for cooling off during the warmer months.

Other Information

"Il Tiglioré" is a semi-detached property, and it is worth noting that the owner resides within the same residence, ensuring a welcoming and attentive hosting experience. A car is recommended to make the most of the property's location and to easily access the surrounding towns, attractions, and services in the area.

Distances and Attractions

The property's location places you within easy reach of a wide range of everyday conveniences and cultural destinations. A supermarket is situated just 3.3 km away, while a restaurant can be found at a distance of 3 km, and a bus stop is conveniently located only 600 m from the property. The historic town of Castiglion Fiorentino, with its rich heritage and local character, lies just 5 km away. For those wishing to explore further, the renowned hilltop town of Cortona is 16 km away, while the vibrant city of Arezzo, celebrated for its art and architecture, is 19 km from the property. The picturesque town of Montepulciano, famous for its exceptional wines and medieval streets, can be reached in approximately 33 km, and the iconic city of Firenze is situated 99 km away, making it an achievable day trip destination. Nature lovers will also appreciate the proximity of Lago Trasimeno, one of the most well-known lakes in central Italy, located just 40 km from the property. Il Tiglioré

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Villa Chio

: EAS190185

Superb independent property with private pool, WIFI, TV and panoramic view, near Cortona

  • Sleeps
    6
  • Bedrooms
    3
  • Bathrooms
    3
  • Floor Area
    200 m2
  • Private Pool
From € 508 per Night

Description

Villa Chio is a lovely stone building (200 sq m) with private pool and WiFi internet. The property can accommodate up to six people comfortably in three bedrooms with three bathrooms. Conveniently located 4 km (3 mi) from Castiglion Fiorentino, Italy in the tourist area "Cortona And Surroundings" and only 14 km (9 mi) from Cortona.

The Experience
When you arrive at Villa Chio you’ll find a lovely clean well-maintained property ideal for a splendid vacation in Tuscany. After a hectic day of shopping, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to relax at the end the day. There is a kitchen including microwave, toaster and refrigerator, as well as, plenty of tableware and cutlery for up to six people. If you prefer to dine 'al fresco', there is a fully furnished garden where you can enjoy the weather while dining outdoors.

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: Cortona 14 km (9 mi), Arezzo 21 km (13 mi), Montepulciano 40 km (25 mi), Perugia 63 km (39 mi) and Montalcino 65 km (40 mi).

Some other major tourist destinations you should consider visiting are: Florence 112 km (70 mi), Viareggio 199 km (123 mi), Forte Dei Marmi 206 km (128 mi), Rome 213 km (132 mi), Venice 355 km (221 mi) and Milan 396 km (246 mi).

Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 09:00
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) 118 km (73 mi), Pisa (psa) 180 km (112 mi), Bologna (blq) 204 km (127 mi), Roma Ciampino (cia) 222 km (138 mi) and Roma Fiumicino (fco) 235 km (146 mi).


It is forbidden to organize parties and events. Villa La Ghiandaia

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La Salciaia

: EAS182413

Independent Vacation home with WIFI, private pool, A/C, TV, patio, pets allowed, panoramic view

  Special Offer
  • Sleeps
    19
  • Bedrooms
    8
  • Bathrooms
    6
  • Private Pool
  • Cancellation insurance (included)
From € 320per Night

Description

Property Summary

Nestled in the sun-drenched Tuscan countryside of Monte San Savino, Italy, this beautifully renovated farmhouse dating back to 1814 is an exceptional vacation rental for those seeking privacy, comfort, and an authentic Italian rural experience. A distinctive pigeon-loft adds character to the property, which is surrounded by picturesque sunflower fields and lush meadows, creating a serene and secluded atmosphere. The villa is very large, beautiful, and comfortable, with interiors evocative of a period home, featuring a spacious living room with a fireplace, a generous dining table, terracotta flooring, and high beamed ceilings that speak to the property's rich heritage. Guests benefit from a private fenced garden of 2,000 m2 with a well-maintained lawn, offering ample space for outdoor leisure and relaxation. A private swimming pool measuring 6 x 12 m, with a depth ranging from 120 to 230 cm and equipped with an internal staircase, is available seasonally from April to October, providing a refreshing retreat during the warmer months. The property is fully equipped with Internet WiFi, and private parking is available directly on site. Automatic gates ensure total privacy throughout your stay, making this farmhouse a truly exclusive retreat in the heart of Tuscany.

Outdoors

The outdoor spaces of this remarkable Tuscan farmhouse are designed to offer an unparalleled al fresco living experience. The private fenced garden of 2,000 m2 is laid with lawn and provides generous space for relaxation and recreation. The swimming pool, measuring 6 x 12 m with a depth of 120 to 230 cm and featuring an internal staircase, is available seasonally from April to October and serves as the natural centrepiece of the outdoor area. A gazebo and an arbor offer shaded retreats ideal for outdoor dining or simply unwinding in the Tuscan sun. The porch is equipped with a barbecue, a pizza oven, and a dishwasher for added convenience, while a wood-burning oven and grill further enhance the outdoor culinary possibilities. An outdoor shower is available for use after a swim, and garden furniture is provided throughout the exterior spaces to ensure comfort. Younger guests will enjoy the children's playground complete with a slide, and a table tennis table is also available outdoors for additional entertainment.

Other Information

The villa is equipped with a central heating system, which is available from November to April and is payable on the spot upon arrival. A washing machine is available inside the villa for guests' convenience, and a table tennis table is also located within the interior spaces. Room cleaning and cook services are available upon request at an additional cost. The annex situated next to the property is not for residential use. The property was originally built in 1814 and has since been thoughtfully renovated to combine historic charm with modern comfort. Check-in and check-out times are not specified in the available information. Guests should note that the automatic gates ensure complete privacy and security throughout their stay.

Distances and Attractions

The farmhouse enjoys an exceptionally convenient location in the Tuscan countryside, situated just 3 km from the centre of Monte San Savino and 7 km from the centre of Lucignano, both of which offer local shops, restaurants, and cultural points of interest. The property is located approximately 2 km from the motorway access, making it an ideal base for exploring the most celebrated towns and destinations across Tuscany. Arezzo, Montepulciano, Pienza, Siena, Cortona, and Montalcino are all within comfortable reach, offering guests a wealth of art, history, gastronomy, and natural beauty to discover during their stay. Whether you are visiting for a special event or simply seeking a relaxing retreat surrounded by the timeless landscapes of central Italy, the property's strategic position ensures that the very best of Tuscany is always close at hand. La Salciaia

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Independent Holiday rental with WIFI, private pool, A/C, TV, patio, pets allowed, panoramic view

  • Sleeps
    11
  • Bedrooms
    5
  • Bathrooms
    4
  • Private Pool
  • Cancellation insurance (included)
From € 788per Night

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

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Pretty independent property with private pool, A/C, WIFI, TV and veranda, close to Cortona

  • Sleeps
    10
  • Bedrooms
    4
  • Bathrooms
    3
  • Floor Area
    170 m2
  • Private Pool
From € 197per Night

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

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Superb private villa rental with A/C, private pool, WIFI and TV, close to Cortona

  • Sleeps
    4
  • Bedrooms
    1
  • Bathrooms
    1
  • Floor Area
    55 m2
  • Private Pool
From € 141per Night

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

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Fantastic flat with private pool, WIFI, TV and pets allowed

  • Sleeps
    4
  • Bedrooms
    2
  • Bathrooms
    1
  • Floor Area
    55 m2
  • Private Pool
From € 95per Night

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

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Casa Angela

: EAS193085

Stunning private villa with private pool, A/C, WIFI, TV, balcony, pets allowed, near Cortona

  • Sleeps
    8
  • Bedrooms
    3
  • Bathrooms
    3
  • Floor Area
    170 m2
  • Private Pool
From € 205per Night

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

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Beautiful private villa rental with WIFI, private pool, TV and pets allowed

  • Sleeps
    10
  • Bedrooms
    4
  • Bathrooms
    4
  • Floor Area
    240 m2
  • Private Pool
From € 195per Night

Description

Palazzolo Alto is a beautiful villa on the edge of the tiny village of Palazzuolo, located in the area north of Monte San Savino. It has always been the natural border between the provinces of Arezzo and Siena, two of the most important cities in Tuscany, equidistant from the villa and easily reachable in about 30 minutes driving. Moreover, if you like cycling or if you love motorbikes, the road between Monte San Savino and Siena offers beautiful views and breathtaking landscapes.
In Palazzolo Alto you will find a large, panoramic garden. On hot summer days you can relax on the sun terrace of the private swimming pool (size 6x12 m, depth 1.00-1.40 m, completely fenced - open from 17 May to 30th September) and enjoy a refreshing dip. The barbecue in front of the large porch is great for delicious meals with your family or friends, or if you prefer you can enjoy a good Tuscan dinner cooked by one of our chefs. The villa is spacious and well furnished with local antiques.
But what will strike you most about this villa is undoubtedly the view from the house, the garden and also from the swimming pool. A view that overlooks natural landscapes of intense beauty, from the Crete Senesi to the gates of Siena. An entire valley to satisfy the eye, prosperous vineyards, green wooded areas, silver olive trees, in short, Tuscany from your window! Palazzolo Alto

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Amazing private villa rental with A/C, private pool, WIFI, TV and terrace, close to Cortona

  • Sleeps
    6
  • Bedrooms
    3
  • Bathrooms
    3
  • Floor Area
    170 m2
  • Private Pool
From € 140per Night

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

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Wonderful private vacation home with WIFI, A/C, private pool, TV and pets allowed, close to Arezzo

  • Sleeps
    9
  • Bedrooms
    4
  • Bathrooms
    3
  • Floor Area
    150 m2
  • Private Pool
From € 350per Night

Description

SPECIAL OFFER 10% DISCOUNT From 20th June until 03rd July 2026 and From 01st until 25 September 2026 - FOR 1 WEEK BOOKINGS

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

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Beautiful private house with private pool, A/C, WIFI and TV, near Arezzo

  • Sleeps
    4
  • Bedrooms
    2
  • Bathrooms
    1
  • Floor Area
    110 m2
  • Private Pool
From € 217per Night

Description

Villa Gioiosa is an old stone house that once belonged to the nearby Benedictine monastery and was used by the monks as a chestnut dryer, of which the surrounding woods are rich. Today the house has been completely restored, maintaining the characteristics of the old Tuscan farmhouse, both in the architectural features and in the furnishings, enriched with local antiques.
A few kilometres away is the village of Monte San Savino, famous for its ceramics and its beautiful alleyways and buildings, offering shops, supermarkets, restaurants and services of all kinds.
In the large garden adorned with medicinal plants, flowers and olive trees, there is on one side a beautiful swimming pool with a Roman staircase (size m. 5 x 10, depth m. 1.50 - open from 01st May to 30th September), and on the other a large barbecue and wood-burning oven in a beautiful wooden gazebo furnished with table and chairs, where you can spend enjoyable evenings in the company of family and friends. In the garden there are many relaxing corners where you will be spoilt for choice, whether reading a book under the porch, sunbathing by the pool or taking long, relaxing walks through the woods and cultivated fields within the property, which extends over several hectares.
Villa Gioiosa offers a holiday in a cosy and genuine atmosphere combining the uniqueness of a Tuscan farmhouse with the comforts of modern life such as air conditioning and Wi-Fi internet access.
To reach the house you have to drive about 1 km of unpaved road, well maintained but not recommended for sports cars; but don't let that scare you because when you get to the house you will know that it is really worth it. Villa Gioiosa

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Beautiful private villa with A/C, WIFI, private pool, TV, terrace and pets allowed, near Arezzo

  • Sleeps
    14
  • Bedrooms
    7
  • Bathrooms
    7
  • Floor Area
    360 m2
  • Private Pool
From € 515per Night

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

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Pozzonovo

: EAS48357

Nice holiday home with pool, WIFI, TV and pets allowed, close to Cortona

  • Accommodation
    3
  • Sleeps
    10
  • Bedrooms
    3
  • Bathrooms
    3
  • Swimming Pool
€ 72 per Night
  Accommodation   Sleeps   Bedrooms   Bathrooms   Floor Area Price
  Il Susino 2 1 1 31 m2 € 72 /Night
  Il Ciliegio 4 1 1 49 m2 € 79 /Night
  Il Pesco 4 1 1 40 m2 € 79 /Night
All 3 Accommodations 10 3 3

Description

Pozzonovo is an old farmhouse divided into 3 comfortable apartments and is the result of the skilful and careful renovation of a stone building. The three units have independent entrances and in the garden their own area equipped with a table, chairs, sun umbrella and barbecue, perfect for enjoying your meals in the open air.
You will find the farmhouse immersed in the Valdichiana countryside and, at the same time, close to the village of Castiglion Fiorentino, which can be easily reached on foot with a walk of about 1.5 km. From the railway station in Castiglion Fiorentino it will be easy to travel by train for day trips to Florence, Rome and other interesting cities in central Italy.
We advise you to immerse yourself in the life of the small village, its shops, bars and restaurants; you will get a glimpse of country life that still harks back to ancient traditions and customs.
The stone walls, wooden and brick ceilings and simple but comfortable furnishings give the apartments a special charm. You will immediately feel at home, welcomed by a warm atmosphere and by Mrs Rita, the owner, who is always ready to assist her guests in times of need.
Together with the owner, you will be able to make use of the large outdoor area, a cool, large 6 x 12 m swimming pool (depth 0.90-1.40 m - open from 01 May to 30 September) located in front of the house, the badminton court, table tennis and bowling green.
Internet access available only in the garden. Pozzonovo

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Fantastic accommodation with WIFI, pool, TV and terrace

  • Accommodation
    4
  • Sleeps
    16
  • Bedrooms
    7
  • Bathrooms
    7
  • Swimming Pool
€ 65per Night
  Accommodation   Sleeps   Bedrooms   Bathrooms   Floor Area Price
  Casa Ghigo 4 2 2 75 m2 € 100/Night
  Casa Gesuina 4 2 2 75 m2 € 100/Night
  Casa Linda 2 1 1 50 m2 € 65/Night
  Casa Vana 6 2 2 140 m2 € 107/Night
16 7 7

Description

The Agriturismo Bevignano, at the centre of a thriving farm with 70 hectares of woodland and 1,200 silver olive trees, has ancient origins. They date back to 1600 when there was a monastery here, and you can still admire an ancient little church inside the property. This ancient village, located on the border between the provinces of Arezzo and Siena, nestled in the wooded hills north of Monte San Savino, still retains its architectural features that make it a place full of charm and history. You will feel as if catapulted into another century, in contact with nature and the simplicity of country life.
The town of Monte San Savino with its shops, supermarkets and services of all kinds is about 10 km away. The town also offers typical restaurants where you can enjoy the famous Chianina beef, Tuscan red wines and also excellent pizzas.

The property is divided into two stone buildings, which in turn are divided into four independent apartments. Casa Vana and Casa Linda and the house where the owners live are in the first farmhouse, and Casa Ghigo and Casa Gesuina are in the second farmhouse. Each apartment has an independent entrance and will have a private outdoor area equipped with table and chairs for your outdoor meals.
The owners, after a careful study of the origins and traditions of the place, have decided to keep the original core of the hamlet unaltered, enriching it with sober and essential finishes and furnishings, which will give you the opportunity to experience a holiday in contact with nature and the country lifestyle, together with the comforts of modern life.

The Agriturismo is located in an extremely scenic area, the view you will enjoy from your windows will remain etched in your memories for many years to come. In the farm's woods and olive groves it will be fantastic to take long, relaxing walks; if you love trekking, this is absolutely the place for you.
At your disposal, on hot summer days, is the large swimming pool (size 7x14 m. - depth 1.00-2.50 m. - open from 01 May to 30 September). For sports enthusiasts the tennis court, the table tennis table, and for dinners and grills with friends and family, a barbecue and a wood-burning oven. Laundry service and Wi-Fi Internet connection available (Internet on request at the house and in the owner's garden). Even your small four-legged friends will be welcome (extra charge could be required). On arrival and throughout your holiday, you will benefit from the owners' assistance in English and French and you will be able to taste and purchase an excellent organic extra virgin olive oil. Agriturismo Bevignano

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Wonderful holiday home with WIFI, private pool, TV and panoramic view, near Montepulciano

  • Sleeps
    8
  • Bedrooms
    4
  • Bathrooms
    4
  • Floor Area
    150 m2
  • Private Pool
From € 231per Night

Description

Independent portion of a stone farmhouse dating back to the 15th century. This property, which has been, completely restored in 2012, offers 2 independent units separated by fences and hedgerows. Outside guests can enjoy use of a large furnished garden ideal for al-fresco dining and of a nice private pool.
This property is situated in the splendid Val d’Orcia region, in easy access to the charming towns of Pienza, San Quirico d’Orcia, San Casciano dei Bagni.
The access to the property is via an unpaved but well-maintained road suitable to any cars.
Distances: San Quirico with general stores 8 km away, Bagno Vignoni 4 km, Pienza 10 km away, Montepulciano 16 km, Siena 50 km away, Cortona 52 km, Arezzo 70 km, Florence (airport) 135 km, Rome (airport) 190 km.
At guests’ disposal: large furnished garden with table, chairs barbecue and swing, private swimming-pool (12 x 6 m – min. depth 1,1 m – max. depth 1,3 m – open from 01/05 to 30/09), open-air shower by the pool (only cold water).
Parking within the grounds.

Please carefully check if there are any extra costs to be paid on site! Villa Cassia

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Superb private holiday home with A/C, private pool, TV, patio and panoramic view

  -5% Special Offer
  • Sleeps
    10
  • Bedrooms
    4
  • Bathrooms
    4
  • Floor Area
    300 m2
  • Private Pool
From € 625per Night

Description

Casale Sunset is located 4 km (3 mi) from Paciano, Italy and only 33 km (21 mi) from Montepulciano. Casale Sunset is a nice vacation rental (300 sq m) with air conditioning and private pool. The property can accommodate up to ten guests comfortably in four bedrooms with four bathrooms.

The Experience
After arriving at Casale Sunset you’ll find a lovely clean well-maintained property ideal for a splendid holiday in Umbria. Regardless of how you spend your days - sightseeing, shopping, 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 Umbria. Also available outside are a patio and barbecue grill. 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. If you prefer to dine 'al fresco', there is a fully furnished veranda where you can enjoy the weather while dining outdoors.

Places Nearby
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: Montepulciano 33 km (21 mi), Cortona 37 km (23 mi), Perugia 45 km (28 mi), Montalcino 61 km (38 mi) and Assisi 66 km (41 mi).

Some other major tourist destinations you should consider visiting are: Florence 146 km (91 mi), Viareggio 232 km (144 mi), Forte Dei Marmi 239 km (149 mi), Rome 173 km (107 mi), Venice 389 km (241 mi) and Milan 431 km (268 mi).

Additional Information
Check-In Time: 16:00 - 19:00
Check-Out Time: 08:00 - 10:00
Pool Open: 15 April - 15 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) 147 km (91 mi), Roma Ciampino (cia) 182 km (113 mi), Roma Fiumicino (fco) 194 km (121 mi), Pisa (psa) 213 km (132 mi) and Bologna (blq) 237 km (147 mi).


Casale Sunset

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Casa Catia

: EAS95460

Stunning private villa with private pool, WIFI, TV, pets allowed and panoramic view, close to Arezzo

  • Sleeps
    12
  • Bedrooms
    5
  • Bathrooms
    4
  • Floor Area
    170 m2
  • Private Pool
From € 159per Night

Description

Comfortable holiday home ideally located close to the traditional village of Castiglion Fiorentino. From this area located south of Siena, known as “Chiana Valley”, guests can easily reach Cortona, Siena, Orcia Valley, Umbria, etc.
The villa is independent, furnished in a traditional rustic Tuscan style and is provided with a private garden and private swimming pool. Access to the property is via 300m of unpaved road in good conditions. Next to the villa, a landing path for ultralight aircrafts is available on request and at disposal of the guests in case they wish to live the unusual experience of a flight over the surrounding countryside.

At guests’ disposal: large furnished garden, gazebo, barbecue, wood oven, private swimming pool for the exclusive use of the guests (size: 10mx5m; depth: 1,5m; open from 01/05 to 30/09), outdoor shower (cold water); baby cot; pets are allowed.

Distances: Castiglion Firoentino (with shops of any kind) 7 km away, Arezzo 18 km away, Cortona 19 km away, Lake Trasimeno 35 km away, Rapolano Terme (with thermal spas) 32 km away, Montepulciano 35 km away, Pienza 42 km away, Siena 55 km away, Montalcino (famous for its “Brunello” wine) 58 km away, Florence 95 km away, Orvieto 105 km away.

Please carefully check if there are any extra costs to be paid on site! Casa Catia

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