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Holiday home rentals in Casentino

Find and book unique holiday home rentals on Airbnb

Top-rated holiday home rentals in Casentino

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

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Guest favourite
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.
Holiday home
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 favourite
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.
Holiday home
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 favourite
Holiday home
4.86 out of 5 average rating, 242 reviews

Lovely house with fabulous view....

Typical Tuscan farmhouse with splendid views of the Chianti, suitable for 2 people. The house is furnished in Tuscan style being a former barn, has been recently renovated and is 70 square meters. Double bedroom with bathroom, large living room with sofa and nice mezzanine, kitchen equipped with stove, refrigerator, etc. 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.

Top guest favourite
A modern bedroom showcases vibrant artwork on the walls, contributing to its artistic ambiance. A spacious bed is complemented by a gray blanket and colorful decorative accents. Natural light illuminates the room from a nearby window, enhancing the creative atmosphere.
Holiday home
4.93 out of 5 average rating, 166 reviews

The Artist's House

Enjoy a real art experience at Casa dell'Artista, the perfect place for your holiday in Florence – a spacious and modern open space, bright and equipped with every comfort. Located in one of the most traditional districts of the old town, it’s the perfect choice for families, couples and friends (rooms are separated but not closed by doors). Here you will enjoy a unique stay, surrounded by the artworks of host and painter Annalisa and a few steps from Florence’s most popular attractions.

Top guest favourite
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.
Holiday home
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 apartment 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
Holiday home
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.

Guest favourite
A stone archway leads into a historic entrance, flanked by rugged walls covered with greenery. The pathway, lined with a metal railing, guides visitors through a tranquil setting enhanced by the natural surroundings.
Holiday home
4.94 out of 5 average rating, 282 reviews

La casina sulle Mura with garden

La Casina è situata nella parte alta di Cortona, nella zona denominata "il Poggio". Si puo' giungere in auto fino al suo ingresso. Il Centro citta' e' raggiungibile a piedi in pochi minuti, percorrendo strade e vicoli caratteristici. Gode di una splendida vista su Cortona e la Valdichiana. E' facile parcheggiare nelle vicinanze. Gli ospiti che giungono in treno in una delle stazioni vicine, su richiesta, possono essere prelevati e accompagnati a destinazione.

Guest favourite
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.
Holiday home
4.94 out of 5 average rating, 117 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 favourite
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.
Holiday home
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 favourite
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.
Holiday home
4.92 out of 5 average rating, 212 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 favourite
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.
Holiday home
4.93 out of 5 average rating, 375 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 favourite
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.
Holiday home
4.93 out of 5 average rating, 126 reviews

Historic apartment Il Prato in Castelfranco

Il Prato is a historic Tuscan farmhouse at the gates 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 art cities of Siena, Florence and Arezzo.

Popular amenities for holiday home rentals in Casentino

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