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Vacation home rentals in Casentino

Find and book unique vacation home rentals on Airbnb

Top-rated vacation home rentals in Casentino

Guests agree: these vacation home rentals are highly rated for location, cleanliness, and more.

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Guest favorite
An aerial view captures the serene layout of the estate, surrounded by lush greenery and rolling hills. The inviting pool is situated centrally, accompanied by sun loungers. Stone buildings harmonize with the natural landscape, reflecting the tranquil beauty of the Montagnola Senese.
Vacation home in Sovicille
4.97 out of 5 average rating, 150 reviews

Podere La Castellina - No. 1 COTTAGE

Independent stone and brick cottage inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The cottage can comfortably accommodate 5 people and includes: - large living room with TV and fireplace - kitchen with oven - master bedroom - bedroom with three single beds - bathroom with shower Guests have access to a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.

Top guest favorite
An aerial view captures a charming Tuscan farmhouse nestled within lush green vineyards and rolling hills. The property features a rustic stone exterior and a terracotta roof, complemented by surrounding greenery and a clear blue sky.
Vacation home in Poggibonsi
4.95 out of 5 average rating, 182 reviews

Vittoria Chianti Vacations 🍇🍷

Vittoria Chianti Vacations is the ideal solution for those seeking peace and tranquility in the heart of Chianti, close to all comforts. Typical Tuscan farmhouse halfway between Florence and Siena, is located in a strategic position to quickly reach Florence, Siena, San Gimignano, Monteriggioni, Volterra and the Chianti hills. Siena Eye Laser Clinic 2 min. Private parking, two bedrooms, equipped kitchen, private bathroom, Wi-Fi, private garden, barbecue, a wonderful view of the Chianti hills.

Guest favorite
Vacation home in Reggello
4.88 out of 5 average rating, 151 reviews

The Florentine Barrels

Bellissima botte abitativa completamente fatta in legno, la botte è una delle più grandi al mondo 3,5 metri di diametro per 8 metri di lunghezza. Dispone di cucina, ampio bagno ,spaziosi armadio e comodo letto. La botte è situata in una tenuta agricola in Toscana nel mezzo di una bellissima oliveta . Massima tranquillità con vista mozzafiato e idromassaggio. Zona molto strategica per visitare le migliori città toscane, come Firenze, Siena e Arezzo . Esperienza fantastica e rilassante.

Top guest favorite
A cozy living area features exposed wooden beams and stone walls. A dining table is set near a window, with a vintage chandelier overhead. A small TV is placed on a wooden cabinet, and a fireplace is flanked by a red couch and a decorative rug.
Vacation home in Arezzo
4.95 out of 5 average rating, 172 reviews

Renovated apartment in historic barn Chianti zone

Enter in this compendium of history surrounded by nature. The atmosphere of this barn will warm your heart along a path that passes through the Tuscan style, the Italian design of the 70s and 80s and the use of natural materials such as wood, lime and glass You can relax, sipping a glass of wine and admiring the sunset reflected in the mirror of water of the swimming pool, sitting comfortably in an armchair in the garden behind the apartment. Stroll among the vineyards and olive trees.

Top guest favorite
A stone farmhouse is situated on a spacious grassy area, surrounded by trees and blooming flowers. The sky is partly cloudy, revealing blue skies. A sunshade is visible near the house, and a picturesque hillside can be seen in the background, enhancing the natural setting.
Vacation home in Chiaveretto
4.97 out of 5 average rating, 108 reviews

Alloro, a charming studio apartment in Val di Nima, Arezzo

12 km from Arezzo, a delightful studio furnished with care on the ground floor of a typical Tuscan stone farmhouse from the early twentieth century. Surrounded by the woods and overlooking a village, the farmhouse is located in a hilly position within a large 5 hectars property. Through a path immersed in the woods with a pleasant walk you can reach the stream that flows into the valley. Until the end of July about (depending on the years) you can swim in a small natural pool.

Superhost
Vacation home in Impruneta
4.84 out of 5 average rating, 289 reviews

Lovely farmhouse Tuscany

Tuscan farmhouse of 140 square meters with two bedrooms up to four people, very large living room with fireplace with terracotta floors and typical ceilings, kitchen equipped for cooking with fridge and microwave, external courtyard in ancient stone with table and chairs and private garden with olive trees. Customers are requested to come by car. If you want the heating is paid and according to consumption and can only be switched on from the period established by the region.

Guest favorite
The rustic stone facade of the house features abundant greenery and wisteria blooms cascading from the upper balcony. The entrance is accessible via a stone pathway, and wooden beams frame the windows, enhancing the traditional Tuscan architecture.
Vacation home in San Martino Sopr'Arno
4.94 out of 5 average rating, 118 reviews

Casa Manu

CARATTERISTICA CASA TOSCANA in pietra immersa nelle colline della provincia di Arezzo. Vicino a Siena, Firenze, Cortona, Perugia, Sansepolcro e alle Foreste Casentinesi. Ideale per trekking, turismo enogastronomico (a pochi km si trovano alcune tra le migliori cantine della Toscana), per appassionati di arte e cultura. A disposizione esclusivamente per gli ospiti un grande terrazzo panoramico, molto riservato. Vi accoglieremo con un presente di benvenuto.

Guest favorite
An ancient stone farmhouse with a rustic red-tiled roof is surrounded by lush greenery. The building sits within a mountainous landscape, framed by trees. The open sky above reveals soft clouds and sunlight, hinting at the serene atmosphere of the rural environment.
Vacation home in Chiusi della Verna
4.96 out of 5 average rating, 142 reviews

Experience rustic off-grid life in the wilderness

This ancient farmhouse lies within a national park in one of the largest areas of forests in Europe. Solar power, wood stoves and the bumpy road offer an authentic off-grid experience. A rare privilege to go into the wild and take a break from urban life and modern conveniences. Hike to the monastery of St.Francis and the sacred forests of La Verna...or simply sit and enjoy the peace of this magical remote place.

Guest favorite
A charming rustic farmhouse is set against a dramatic sky, framed by lush green trees. The exterior features warm-toned walls and a tiled roof, while a spacious yard includes seating arrangements for outdoor relaxation, inviting guests to enjoy the serene countryside.
Vacation home in Simignano
4.92 out of 5 average rating, 213 reviews

Casa al Gianni - Quercia

Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

Guest favorite
The rustic kitchen area features exposed stone walls and a warm, earthy tone. A small wooden table with two chairs sits adjacent to a red cabinet. A sink with a vintage faucet and decorative items can be seen, complemented by soft lighting from an overhead fixture.
Vacation home in Figline e Incisa Valdarno
4.93 out of 5 average rating, 376 reviews

Romantic stay at a bio-agritourism in Florence

Escape the crowd of Firenze and be ready for an authentic rural Tuscan lifestyle experience ... The deers graze the fields near the house, you can hear the wild boars grunting and the crickets singing. Healthy food, good wine, a bio sauna and a jacuzzi in the olive grove; a real re-charge and re-connection in Nature in an eco-friendly and cozy accommodation .

Guest favorite
An outdoor area is presented, featuring a stone-paved patio with several potted plants. The entrance to the house is framed by arched doors, which open to a cozy seating arrangement. Views of the surrounding landscape are visible in the background.
Vacation home in Faella
4.93 out of 5 average rating, 126 reviews

Historic apartment Il Prato in Castelfranco

Il Prato is a historic Tuscan farmhouse on the outskirts of Castelfranco di Sopra, finely restored and surrounded by olive trees, orchards, and woods. It has a beautiful garden where you can relax and eat. Equidistant from the great cities of art of Siena, Florence, and Arezzo.

Guest favorite
A terrace is showcased, featuring a wooden table accompanied by white chairs. The scene includes expansive views of rolling hills and vineyards, framed by tall cypress trees. The sky reveals warm sunset hues, creating a serene atmosphere.
Vacation home in Greve in Chianti
4.92 out of 5 average rating, 114 reviews

Stunning Tuscan apartment for 2

This apartment - tucked away privately and enjoying a stunning view from its terrace - is part of an 'agriturismo' farm which produces organic Chianti Classico. Spacious and light, it has 1 double bedroom, 1 sitting room, 1 bathroom and a kitchen.

Popular amenities for Casentino vacation home rentals

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