Caprese Michelangelo Villas with Pool
Results 81 - 100 of 159
Villa Crispinino
Independent Villa with WIFI, A/C, private pool, patio, pets allowed, panoramic view, close to Arezzo
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- 4
- 4
Description
This is an independent villa boasting beautiful views and its own swimming pool. Its dominating position, overlooking the Val di Chiana, is not far from the town of Civitella.
The villa itself has been recently refurbished however, it still holds its original character such as terracotta floors, wooden beams and stone arches.
Outside there is a large terrace and a large garden, both offering privacy and somewhere to relax in the open air. The property is surrounded by fencing.
Villa Crispinino is perfectly positioned for anyone hoping to visit Tuscany’s famous sites. About 20 km from the property, in the town of Arezzo, you can catch a train to destinations such as Rome, Florence, Orvieto and Siena.
Access to the property is via a dirt road (in great condition).
Distances: The nearby town of Civitella (4 km) can offer you food shops while Battifolle (10 km) can offer a large selection of shops. Arezzo lies 20 km away and slightly further afield are the cities of Siena (50 km), Florence (80 km), Assisi and Perugia (90 km).
Available to guests: Large, well-kept and furnished garden, swimming pool reserved exclusively for guests (10 x 5 m - depth 1.4 m) and barbecue.
The rental has free WI-FI and a Play Station.
Parking available on the grounds of the property.
Extra Services: Upon request, two children’s cots are available at no extra charge.
Please carefully check if there are any extra costs to be paid on site! Villa Crispinino
Book your vacation for the period from 04 April 2026 to 30 May 2026 and save 10% (minimum 7 nights).
Book 15 days or less before the arrival date and receive a 15 % discount off the published rental rates.
This Offer is valid only for stays of 7 nights minimum and can not be combined with any other special offers.
Casa Angela
Superb independent villa with private pool, WIFI, A/C, TV, balcony and pets allowed, near Cortona
- 8
- 3
- 3
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
Civitella
Beautiful private property with WIFI, hot tub, private pool, TV, panoramic view, close to Arezzo
- 8
- 4
- 2
Description
Independent house with private swimming pool located in a very scenic area in Valdichiana and surrounded by the countryside of Arezzo. Hectares of woodlands that circle the property ensure maximum privacy and a closeness with nature. The interior is in a rustic style. Outside, the guests can enjoy a private garden and a beautiful swimming pool with a great view and wooden solarium furnished with tables and chairs. Beside the swimming pool there is also a hot tub to enjoy.
This is an ideal set-up for those looking to spend a holiday in absolute tranquility.
The house is accessed via a stretch of roughly 4km of dirt road which is not adapted to low-lying/sports cars.
Distances: Civitella della Chiana with food stores and restaurants - 6 km, Battifolle with a wide variety of shops - roughly 15 km, Arezzo (train station) - 25 km, Monte San Savino - 25 km, Siena – roughly 75 km, Florence (airport) - 80 km, Perugia - 100 km.
Available: outdoor private and furnished area with tables, chairs and sun umbrellas, swimming pool reserved for the exclusive use of guests (9 x 3 m - depth 1,1 m – open from 01/04 to 15/10), outdoor shower with hot water (solar heated), barbecue, wood-burning pizza oven.
Onsite parking.
Please carefully check if there are any extra costs to be paid on site! Civitella
Villa degli Olivi
Private Accommodation with A/C, WIFI, private pool, TV, terrace, pets allowed, close to Arezzo
- 14
- 7
- 7
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 i Gigli
Amazing private holiday rental with WIFI, A/C, private pool, TV and terrace, close to Cortona
- 6
- 3
- 3
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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- 8
- 4
Description
La Quiete is a very old farmhouse that preserves intact the characteristics of the rural architecture. The villa is lovingly preserved by its owners, and if you are lucky enough to stay here, its wooden ceilings, ancient brick arches, Tuscan terracotta floors and elegant furnishings will welcome you into a very special charm, made of old, simple and essential things. At La Quiete you will feel at home, in a warm and cosy atmosphere.
The villa is located at the foot of the first wooded hills, which mark the border between Valdichiana and Valdarno, from here you can make even daily excursions, towards the two valleys, dotted with small villages nestled in the Tuscan countryside. In Monte San Savino, which is just a few kilometres away, it will be pleasant to spend evenings out, dining in typical restaurants or enjoying an aperitif sitting at tables in the colourful cobbled streets.
From the windows of the villa you can admire the imposing Castello di Civitella with its characteristic 'Torre Spaccata'. We absolutely recommend a visit to this small village, a real jewel of the Valdichiana, with its ancient cistern, panoramic square and medieval buildings.
La Quiete, in our opinion, is perfectly suited for your holidays with children, or in the company of large groups of friends. Around the house you will find a large green area equipped with outdoor furniture, barbecue, table tennis, table football, children's games, volleyball court and five-a-side football pitch. A splendid swimming pool (size 6x12 m, depth 1.10-2.00 m - open from 01st May to 30th September) will brighten your summer days, and the large furnished portico outside will be the setting for your breakfasts, lunches and dinners in the open air. La Quiete
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- 4
- 3
Description
Property Summary
Casa Clotilde is a charming, renovated country house located in the tranquil countryside just 4 km from the center of Monte San Savino and 5 km from the center of Civitella In Val Di Chiana, Italy. This vacation rental features a private, fenced garden of 350 m2 with a lawn and trees, as well as a large swimming pool (13 x 7 m) available from 09.Apr. to 30.Sep. with a depth of 120 - 180 cm, ideal for both adults and children. Guests can enjoy internet access and central heating system within the house.
Outdoors
The property boasts a private, fenced garden of 350 m2 with a lawn and trees, as well as a large swimming pool (13 x 7 m) that is available from 09.Apr. to 30.Sep. The pool has a depth of 120 - 180 cm, making it ideal for both adults and children. The garden also features an outdoor shower, volleyball court, arbour, garden furniture and a barbecue, providing plenty of opportunities for outdoor activities and relaxation.
Other Information
Breakfast and half board are available upon request at an extra cost, as well as a pre-arrival grocery service. The property also has a roofed parking area for two cars. For those who enjoy fishing, a permit is required and the property offers the option of purchasing local farm products.
Distances and Attractions
Nearby attractions include the beautiful city of Arezzo, situated only 15 km away, and the picturesque town of Montepulciano, which can be reached in 40 km. There is also an equestrian center in Arezzo, just 10 km away, making it a convenient location for those interested in horseback riding. Casa Clotilde
Casale Il Giglio
Beautiful private house with private pool, WIFI, TV, pets allowed and panoramic view
- 10
- 5
- 5
Description
Property Summary
Civitella In Val Di Chiana, Italy is home to a charming cottage that has recently undergone renovations. Divided into two spacious parts, each with its own private garden spanning 400 square meters, this property offers a peaceful retreat surrounded by a large fenced garden shared with the owner's nearby residence. The cottage boasts well-maintained interiors, featuring terracotta and parquet flooring, beamed ceilings, stone archways, and bedrooms equipped with ceiling fans and wrought iron beds. A highlight is the refreshing swimming pool, complemented by an outdoor hot water shower, offering stunning views of the sunflower fields that characterize the Tuscan landscape. Additionally, guests can enjoy private gated access and a video entry phone for added security and convenience during their vacation rental stay.
Outdoors
The outdoor spaces of this property are truly remarkable. Guests can indulge in a refreshing swim in the stunning swimming pool, complete with an outdoor hot water shower while taking in the breathtaking views of the sunflower fields, a quintessential part of the Tuscan landscape. As the sun sets, the famous Gargonza castle provides a picturesque backdrop. The property also features a spacious, fenced garden of 800 square meters, providing ample space for outdoor activities and relaxation. The uniquely shaped pool is surrounded by various amenities, including an outdoor shower, table tennis, boules, and comfortable garden furniture, ensuring a delightful holiday rental experience.
Other Information
The charming working farm "Casale il Giglio" offers a cozy and authentic experience for guests. Renovated in 2004, this property is conveniently located just 5 kilometers from the center of Monte San Savino. Guests can enjoy a range of amenities during their stay, including WiFi, table football, and bicycles (4). Heating is available for an additional fee from November 1st to April 15th. The property is well-suited for families and seniors, and the owner resides on the same premises.
Distances and Attractions
The property's prime location offers easy access to numerous attractions in the surrounding areas. Lucignano is just 12 kilometers away, while Rapolano Terme is 28 kilometers from the property. Cortona (32 km), Montepulciano (37 km), and Gaiole in Chianti (45 km) are also within convenient driving distances. Guests should note that having a car is recommended to fully explore the region's charms during their vacation rental stay. With its proximity to renowned destinations, this property provides an ideal base for discovering the rich cultural heritage and natural beauty of Tuscany. Casale Il Giglio
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- 2
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Description
Property Summary
Cottage "Santa Lucia" is a beautiful semi-detached holiday rental located near the center of Castiglion Fiorentino, a picturesque village in Tuscany. This charming cottage boasts a 3-hectare orchard, a private garden lawn with trees, and a highlight 12 x 6 meter swimming pool with a depth of 140-200 cm, available seasonally. You can enjoy the outdoor spaces, including an outdoor shower and parking on the premises, while staying connected with wifi internet.
Outdoors
The property is surrounded by a vast 3-hectare orchard, perfect for nature lovers and outdoor walks. You'll have access to a private garden lawn and trees, ideal for relaxing and soaking up the Tuscan sun. The swimming pool, measuring 12 x 6 meters with a depth of 140-200 cm, is a true highlight, available seasonally from May 1st to September 30th, providing a refreshing escape on hot summer days.
Other Information
Cottage "Santa Lucia" offers wifi internet access, allowing you to stay connected during your holiday rental. The property also features an outdoor shower and parking on the premises for your convenience.
Distances and Attractions
Castiglion Fiorentino, a charming village with shops and supermarkets for your daily needs, is just 2.5 km away. The railway station "Castiglion Fiorentino" is conveniently located 2.5 km from the cottage, making it easy to explore nearby areas. The Trasimeno lake, perfect for water sports enthusiasts, is 35 km away. Fashion lovers will appreciate the Valdichiana Outlet Village, located 25 km from the property. Additionally, the cities of Arezzo and Cortona, popular destinations in the region, are 20 km and 12 km away, respectively. Santa Lucia
Il Borgo di Gebbia
Private Holiday home with private pool, WIFI, TV, terrace, panoramic view, close to Arezzo
- 10
- 5
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Description
Property Summary
Il Borgo di Gebbia is a charming country house located in Civitella In Val Di Chiana, Italy. Renovated in 2014, it offers a tranquil and private holiday rental getaway. The property spans over 2 hectares and features an above-ground swimming pool, internet WiFi, and parking facilities, providing you with a comfortable and enjoyable vacation experience.
Outdoors
The country house boasts a fenced, above-ground swimming pool, measuring 7 x 4 meters with a depth of 120 cm, available seasonally from May to September. The property is perched atop a hill, offering breathtaking views of the Val Di Chiana countryside and a serene outdoor environment.
Other Information
Weekly room cleaning is provided, and for an additional fee, a cook can be arranged upon request. Breakfast service is also available for an extra charge. Guests can park their vehicles on the premises and have access to nearby amenities, including shops, supermarkets, and restaurants within close proximity.
Distances and Attractions
Il Borgo di Gebbia is conveniently located, with Civitella in Val di Chiana just 3.5 km away, Arezzo 23 km away, and Siena 52 km away. Nearby attractions include the thermal baths of Rapolano Terme (44 km), Castiglion del Lago bathing lake (69 km), an 18-hole golf course (23 km), tennis courts (14 km), and horseback riding opportunities (6 km). Additionally, Castelnuovo Berardenga (36 km), Cortona (42 km), Gaiole in Chianti (63 km), Montepulciano (63 km), Pienza (63 km), and Florence (84 km) are all within driving distance, offering guests a wealth of cultural and recreational activities. Il Borgo di Gebbia
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- 1
- 1
Description
Property Summary
The "Nido del Sorbino" cottage offers a tranquil vacation rental nestled in the heart of Tuscany, situated on a private 2,000 square meter fenced plot with a terraced and natural garden. The property boasts a small seasonal swimming pool, a yard, internet WiFi access, and parking facilities, providing you with a comfortable and convenient stay.
Outdoors
The cottage embraces the beauty of the outdoors with its terraced and natural garden, creating a serene setting for outdoor activities. Indulge in the refreshing experience of the small swimming pool, measuring 3 x 2 meters with a depth of 140 centimeters, available seasonally from May 1 to September 30.
Other Information
Castiglion Fiorentino, Italy, serves as the idyllic location for this holiday rental, offering easy access to nearby amenities and attractions. Situated at an elevation of 460 meters above sea level, the cottage is a mere 4 kilometers from the town center and 15 kilometers from Arezzo. A narrow motor access of 200 meters via an unmade road leads to the property.
Distances and Attractions
The surrounding area offers a wealth of attractions and conveniences. The nearest shop is just 1.5 kilometers away, while a supermarket is conveniently located 2 kilometers from the property. The "Castiglion Fiorentino" railway station is situated 4 kilometers away, providing easy access to transportation. Outdoor enthusiasts can enjoy the sandy beach of "Castiglione della Pescaia" located 160 kilometers away or the "Trasimeno" bathing lake, which is 35 kilometers from the cottage. Additionally, a golf course with 18 holes is a short 15-kilometer drive away. Nearby towns and cities worth exploring include Cortona (15 km), Firenze (100 km), and Valdichiana Outlet Village (25 km). A car is highly recommended to fully experience the surrounding attractions. Nido del Sorbino
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- 3
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Description
Property Summary
House "La Felcaia" is a vacation rental located in the beautiful countryside of Tuscany, Castiglion Fiorentino, Italy. It offers a peaceful retreat away from the city's hustle and bustle while still being conveniently located near the village. The property boasts a terraced garden filled with trees spanning 3 hectares, providing ample outdoor space. You can enjoy exclusive access to a swimming pool measuring 11 x 5 meters, with a depth of 90 - 190 cm, available from May 1 to October 6. The private property spans across 500 m2 and is surrounded by a fenced terraced garden. Amenities include internet WiFi, roofed parking for two cars, and a burglar alarm system.
Outdoors
The property offers a range of outdoor amenities for your enjoyment. For shared use, there is a 50 m2 pergola, garden furniture, and a table tennis table. Within the private fenced terraced garden, you can find a swimming pool with a WC and an outdoor shower in the pool area. Additional recreational facilities include a table tennis table and table football available inside the house. The terraced garden is filled with trees, creating a serene and natural environment for your vacation rental experience.
Other Information
House "La Felcaia" is situated on the owner's property, who resides on the same premises. To explore the surrounding areas, it is recommended that you have a car during your stay. The property is located at an elevation of 600 meters above sea level, providing a beautiful and scenic environment. The owner's presence on the property ensures assistance and support if needed.
Distances and Attractions
House "La Felcaia" enjoys a strategic location with easy access to various nearby attractions. The village center of Castiglion Fiorentino is just 2.5 km away, while the center of Cortona is 10 km away. Shops and supermarkets are conveniently located 2.5 km and 3.5 km away, respectively. The Castiglion Fiorentino railway station is 3.5 km away, making it easy to explore the region. For beach enthusiasts, Castiglione della Pescaia sandy beach is 160 km away, and Lago Trasimeno, a bathing lake, is 35 km from the property. Golf enthusiasts can enjoy the 9-hole golf course located 13 km away, and hiking enthusiasts can explore the walking paths directly from the house. Popular tourist destinations like Arezzo (25 km), Florence (100 km), and Valdichiana Outlet Village (20 km) are within easy reach. La Felcaia
Le Terrazze
Pretty private holiday villa with hot tub, WIFI, private pool, TV, patio and pets allowed
- 6
- 3
- 3
Description
Property Summary
Le Terrazze is a charming rustic house with two storeys, terraced and located just 4 kilometers away from the center of Monte San Savino and 5 kilometers away from the center of Civitella Val di Chiana in Italy. It boasts a beautiful garden with a lawn and trees, as well as a large seasonal swimming pool measuring 12 x 5 meters. Guests can enjoy internet access, parking on the premises, and the option for breakfast and half board meals for an additional fee. The vacation rental also offers a pre-arrival grocery service for added convenience.
Outdoors
The property is situated on a massive 2-hectare lot that features a natural pond for shared use. The private property is fenced and covers an area of 600 square meters. Guests can enjoy the outdoor shower, table tennis, arbour, and garden furniture in the spacious outdoor area.
Other Information
The nearest shop, restaurant, and bar are all just 600 meters away, while the railway station "Albergo" is only 1 kilometer away. For those interested in horseback riding, a riding stable is located just 700 meters from the property. Farm products are available for local sale, and a permit is required for fishing, with an additional fee. The owner of the property lives on the same lot, and there are animals in the neighborhood.
Distances and Attractions
Nearby attractions include Arezzo, which is just 15 kilometers away, Montepulciano, located 40 kilometers away, and well-known lakes such as Trasimeno, easily accessible at just 50 kilometers away. Additionally, a lovely lake is situated just 500 meters away from the property. Le Terrazze
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- 2
- 2
Description
Property Summary
"Il Sorbino" is a charming rustic cottage located in Castiglion Fiorentino, Italy. Offering a tranquil holiday rental experience, the property boasts a private fenced area of 2,000 square meters with a terraced garden lawn. The highlight is the 10 x 5-meter swimming pool with depths ranging from 12 to 220 centimeters, available for use from May 1 to September 30. Guests can enjoy an outdoor shower, terrace, garden furniture, and the pool is maintained by the owner or gardener. Additionally, the property provides Internet WiFi and parking on the premises.
Outdoors
The property features a private area of 2,000 square meters, which is fenced and includes a terraced garden lawn. Guests can enjoy the highlight of the property, the swimming pool, measuring 10 x 5 meters with a depth ranging from 12 to 220 centimeters. The swimming pool is available for use from May 1 to September 30. An outdoor shower, terrace, and garden furniture are also provided, and the pool is maintained by the owner or gardener.
Other Information
Access to the property can be a bit challenging as the motor access is 200 meters long, bumpy, and narrow, making it recommended for guests to arrive by car. Parking is available on the premises. Bicycles are also available for an additional fee. The nearest shop is 1.5 kilometers away, while the supermarket is 2 kilometers away.
Distances and Attractions
The property is situated 4 kilometers away from the center of Castiglion Fiorentino, 15 kilometers from the center of Arezzo, and 35 kilometers from the lake. The railway station "Castiglion Fiorentino" is 4 kilometers away, and the sandy beach "Castiglione della Pescaia" is 160 kilometers away. For swimming, the bathing lake "Lago Trasimeno" is 35 kilometers away. Additionally, there is a 9-hole golf course located 15 kilometers away. Nearby attractions include the town of Cortona at 15 kilometers, Florence at 100 kilometers, and the Valdichiana Outlet Village at 25 kilometers. Il Sorbino
Il Sogno di Pietro
Wonderful private house with A/C, WIFI, private pool, TV, patio, pets allowed, panoramic view
- 11
- 5
- 4
Description
Property Summary
Il Sogno Di Pietro is a beautiful and comfortable villa surrounded by trees and fields in Castiglion Fiorentino, Italy. The property features a main house and an outbuilding, offering a spacious and private setting. It boasts a fenced 6,500 square meter grounds with a lush lawn, a seasonal swimming pool (12 x 4 meters, depth 140 cm, available from April 15 to October 30), an outdoor shower, a pergola, garden furniture, a barbecue area, and parking on the premises. With amenities like Internet Wi-Fi, it provides a perfect setting for a relaxing vacation rental.
Outdoors
The property offers an idyllic outdoor experience with its expansive 6,500 square meter fenced grounds. Guests can enjoy the well-manicured lawn, perfect for lounging or outdoor activities. The highlight is the seasonal swimming pool, measuring 12 x 4 meters with a depth of 140 cm, available from April 15 to October 30. Enhance your alfresco experience with the outdoor shower, pergola, garden furniture, and barbecue area. Just an example, you can savor delightful meals prepared on the grill while enjoying the beautiful surroundings.
Other Information
The property is conveniently located near essential amenities. A grocery store and a supermarket are just 3 km away, ensuring easy access to supplies. For dining options, a restaurant is only 1 km from the villa. The "Firenze-Roma" railway station is 3 km away, providing convenient transportation links. Those seeking relaxation can visit the thermal baths at "Rapolano Terme," situated 37 km from the property, or the bathing lake "Trasimeno." The owner does not accept youth groups, ensuring a peaceful atmosphere for families and couples.
Distances and Attractions
Il Sogno Di Pietro offers a prime location to explore the region's rich cultural and historical attractions. Nearby destinations include Cortona (13 km), Arezzo (16 km), Lucignano (20 km), Passignao Sul Trasimeno (31 km), Castiglione Del Lago (33 km), and Pienza (47 km). These charming towns and cities offer a glimpse into the region's rich heritage, with stunning architecture, museums, and picturesque landscapes to explore. Whether you're seeking cultural immersion or natural beauty, this holiday rental provides a convenient base to experience the best of the area. Il Sogno di Pietro
Zen
Fabulous independent holiday home with private pool, WIFI, TV, balcony, panoramic view, near Cortona
- 15
- 6
- 6
Description
Property Summary
Villa "Zen" is a renovated and detached house offering a unique holiday rental experience in the Tuscan countryside. Surrounded by trees and fields, it boasts beautiful views of the estate's olive groves. The property features a private, fenced garden and a swimming pool measuring 12 x 7 meters with a depth of 140 centimeters, available seasonally from May 1st to October 15th. Additionally, it provides amenities such as Internet Wifi, a washing machine, and parking on the premises.
Outdoors
The property's outdoor spaces are truly remarkable. You can relax and enjoy the stunning views while taking a refreshing dip in the private swimming pool, complete with an outdoor shower, garden furniture, and a barbecue. The fenced garden offers a serene and secluded retreat amid the picturesque Tuscan countryside.
Other Information
Villa "Zen" is conveniently located, with motor access via an unmade road, mountain road, and ramp. While a car is recommended for your stay, you'll find a restaurant just 2 kilometers away and a grocery store and supermarket within 5 kilometers. The property also offers internet access and a washing machine for added convenience.
Distances and Attractions
Situated 350 meters above sea level and perched on top of a hill, Villa "Zen" is just 5 kilometers from the center of Castiglion Fiorentino, 15 kilometers from Cortona, and 25 kilometers from Arezzo. For those seeking a day by the water, the bathing lake "Trasimeno" is approximately 20 kilometers away. Nearby attractions include the charming villages of Castiglion Fiorentino and Cortona, as well as the historic city of Arezzo, offering ample opportunities to explore the region's rich cultural heritage. Zen
Il Tiglioré
Pretty independent villa rental with private pool, A/C, WIFI, TV, patio and pets allowed
- 4
- 2
- 1
Description
Property Summary
Il Tiglioré presents a modern and cosy semi-detached house that has been thoughtfully renovated, positioned amidst tranquil fields just 5 km from the centre of Castiglion Fiorentino, Italy. This holiday rental features a well-maintained, fenced private garden adorned with a wildlife garden and mature trees, creating a serene outdoor environment. The property includes an above-ground swimming pool measuring 6 x 3 m with a depth of 132 cm, available seasonally from 01.Jun. through 31.Aug. You will benefit from convenient parking on the premises, ensuring ease of access throughout your stay. Internet WiFi connectivity is available to keep you connected during your visit. The spacious yard provides ample outdoor space for relaxation and recreation, complemented by an arbour, garden furniture, and barbecue facilities for outdoor dining and entertainment.
Outdoors
The outdoor spaces at Il Tiglioré offer you an inviting retreat surrounded by nature. The property's well-kept, fenced garden features a charming wildlife garden and established trees that provide natural shade and privacy. The above-ground swimming pool, measuring 6 x 3 m with a depth of 132 cm, is available for your enjoyment from 01.Jun. until 31.Aug., offering refreshing respite during the warmer months. An arbour provides a shaded spot for outdoor relaxation, while the garden furniture and barbecue facilities create perfect opportunities for al fresco dining and entertaining. The peaceful surroundings of fields enhance the tranquil atmosphere of this semi-detached residence.
Other Information
Please note that a car is recommended for convenient access to the property and surrounding areas. The owner resides in the same residence. A supermarket is located 3.3 km from the property, while restaurant options can be found 3 km away. A bus stop is situated 600 m from Il Tiglioré for those wishing to use public transportation.
Distances and Attractions
Il Tiglioré enjoys a favourable location for exploring the renowned attractions of Tuscany and Umbria. The historic town of Cortona is situated 16 km from the property, while Arezzo can be reached within 19 km. The celebrated hilltop town of Montepulciano lies 33 km away, and the cultural capital of Firenze is accessible at 99 km. Nature enthusiasts will appreciate the proximity to Lago Trasimeno, a well-known lake that can easily be reached at 40 km from the property. The property is positioned 5 km from the centre of Castiglion Fiorentino, Italy, providing convenient access to local amenities and attractions. Il Tiglioré
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| Accommodation | ||||
|---|---|---|---|---|
| La Castellana | 2 | 1 | 1 | |
| Canto al Sole | 2 | 1 | 1 | |
| Bellina | 2 | 1 | 1 | |
| Canto alla Luna | 4 | 1 | 1 | |
| Lilla | 2 | 1 | 1 | |
| Cecilia | 2 | 1 | 1 | |
| All 6 Accommodations | 14 | 6 | 6 |
Description
Hospitality, Osteria "Gentile" with veg garden, Cooking School and a stunning infinity pool overlooking the valley: il Canto del Maggio, owned by Simona and her family, isn’t just a place to sleep — it’s a place where you meet a family deeply rooted in this land and in its rhythms.
Here guests are welcomed into six charming units that reflect a rare and authentic form of hospitality: the Albergo diffuso—literally, a ‘scattered hotel’. Developed in Italy, this model revitalizes once-abandoned villages by blending comfort with local tradition in a truly immersive experience- in fact the "borgo" is a shared community between locals that live here permanently, and travelers that was born in the late 1980's.
Our collaboration with this placa was born to promote a network of local chefs, farmers, winemakers, guides, and hospitality professionals — all working together to create meaningful moments that we hope will make your stay one to remember.
My team (I am Tuscany) and I will take care of the accommodation side of your experience — from the moment you book to the day you arrive. Before your stay, we’ll coordinate with you to plan any extra services or personalized experiences, so everything is ready and tailored to your needs before you arrive.
Simona, the soul of this place, will welcome you into her world: her home, her kitchen, around her table, or walking through the vegetable garden — the orto. On the plate, a cuisine that arises spontaneously: the garden decides the menu, and we simply follow its lead.
Together, we can plan special dinners in the garden or by the pool, enjoy breakfast on the terrace or your private patio, and explore much more — from local farmers’ markets and tastings to our favorite go-to places in the area.
Available experiences include:
-Harvesting ingredients directly from the garden and discovering the joy of simple, farm-to-table cooking
-Themed culinary workshops (vegetarian, pastry-making, regional cuisine)
-Activities that immerse you in the natural beauty, culture, and traditions of the area
-Private meals (including breakfast) served anywhere on the property
-Pop-up events hosted by the restaurant or the outdoor kitchen
-Private events and retreats tailored to your needs Il Canto Del Maggio
Special Offer for Canto al Sole
Book now and save 10%. Offer valid until 30 June 2026 and for a minimum stay of 7 nights.
Last-Minute Offer for Lilla
Book 10 days or less before the arrival date and receive a 15 % discount off the published rental rates.
This Offer is valid only for stays of 5 nights minimum and can not be combined with any other special offers.
Il Cottage Roccaio
Pretty independent holiday villa with A/C, WIFI, private pool, TV, patio and pets allowed
- 8
- 3
- 3
Description
Property Summary
Cottage Roccaio is a cosy, rustic, and comfortable semi-detached house featuring two storeys, nestled in a secluded and quiet position surrounded by fields and vineyards, located 3 km from the centre of Castiglion Fiorentino, Italy. This charming holiday rental offers a private, well-kept fenced garden and a seasonal swimming pool with salt water, available from 1st May to 30th October, with regular maintenance provided by the owner or gardener. The property includes convenient amenities such as a laundry room with a washing machine, ensuring a comfortable stay for guests. Internet WiFi connectivity keeps you connected throughout your visit, while a spacious yard provides ample outdoor space for relaxation. Private parking is available on the premises, with motor access to the house via a 600 m unmade road. Please note that the owner lives on the same property and has a dog, adding to the authentic countryside experience.
Outdoors
The outdoor spaces at Cottage Roccaio provide an idyllic setting for relaxation and enjoyment of the Tuscan countryside. You will have access to a private, well-kept garden that is fully fenced, offering both privacy and security. The seasonal swimming pool features salt water and is available for use from 1st May through 30th October, providing a refreshing retreat during the warmer months. The property is surrounded by picturesque fields and vineyards, creating a tranquil atmosphere perfect for unwinding. The pool maintenance is regularly handled by the owner or gardener, ensuring the facilities remain in excellent condition throughout your stay.
Other Information
Access to the property is via motor vehicle along a 600 m unmade road, and a car is recommended for your stay. The owner resides on the same property and has a dog. Essential amenities are conveniently located nearby, with a grocery store 2 km away, a supermarket 4 km from the property, and a restaurant situated 3 km from Cottage Roccaio. Public transportation is accessible via a bus stop located 3 km from the house.
Distances and Attractions
Cottage Roccaio is ideally positioned for exploring the renowned attractions of Tuscany and Umbria. The charming hilltop town of Cortona is just 11 km away, while the historic city of Arezzo can be reached within 22 km. The picturesque town of Montepulciano, famous for its wine, is located 38 km from the property, and the magnificent city of Firenze is 100 km away. Nature enthusiasts will appreciate the proximity to Lago Trasimeno, a well-known lake that is easily accessible at 29 km from the house. The property's location in Castiglion Fiorentino, Italy, serves as an excellent base for discovering the cultural and natural treasures of the region. Il Cottage Roccaio
Villa Chio
Stunning private holiday rental with private pool, WIFI, TV and panoramic view, near Cortona
- 6
- 3
- 3
Description
Villa Chio is located 4 km (3 mi) from Castiglion Fiorentino, Italy and only 14 km (9 mi) from Cortona in the tourist area "Cortona And Surroundings". Holiday home Villa Chio is a beautiful stone building (200 sq m) that includes private pool and WiFi internet. The property can sleep up to six guests comfortably in three bedrooms with three bathrooms.
Your Experience
After arriving you will be welcomed by the owner or manager where you’ll find a lovely clean well-maintained property ideal for a peaceful holiday in Tuscany. For your pleasure you will find a private pool where you can relax while enjoying a nice cold beverage after a busy day of sightseeing. Sharing a meal with friends and family is a huge part of the Tuscan culture. Take advantage of the kitchen to prepare meals using local produce while on your vacation. The kitchen includes microwave, toaster and refrigerator, as well as, plenty of tableware and cutlery for up to six people. Dine 'al fresco' like a real Tuscan, the fully furnished garden is the ideal setting to enjoy food, family and the nice Tuscan weather.
Visit the Area
Most people enjoy visiting close-by cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: 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
