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Holiday rentals in Rocca San Casciano

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Top-rated holiday rentals in Rocca San Casciano

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A stone structure with a tiled roof is framed by greenery, surrounded by rolling hills. A spacious outdoor area features a wooden table, inviting relaxation. Large trees and thriving shrubs enhance the tranquil setting, with a backdrop of a serene sunset illuminating the landscape.
Home
4.98 out of 5 average rating, 220 reviews

The Chianti Classico Sunset

Se cercate una location idilliaca nel cuore del Chianti classico, immersi nei vigneti e oliveti delle splendide colline toscane, nel podere di una Villa storica del ‘500, allora venite nel nostro fienile!! Ha una posizione dominante con una vista strepitosa, dove è possibile godersi tramonti mozzafiato. La totale indipendenza della casa, l'accogliente giardino, il grande loggiato permettono di trascorrere soggiorni in totale tranquillità. Le nostre recensioni sono la vostra migliore garanzia.

Guest favourite
The spacious room is characterized by sloped wood-beamed ceilings, large windows allowing natural light, and a comfortable seating area with two armchairs facing a small wooden table. A neatly made bed with light linens is positioned in the background, creating an inviting atmosphere.
Apartment
4.93 out of 5 average rating, 124 reviews

Mansardina Pasquin (Corso della Repubblica)

In a very central and strategic position, in the city center, the accommodation is suitable for comfortably reaching, even on foot, the Fabbri Theater, the University Campus, the San Domenico Museum, the station, etc. The accommodation has a double bed, private bathroom, kitchen with stove and large refrigerator with internal freezer compartment available, breakfast corner. Wi-Fi and temperature-controlled thermostat. (Day use bookings are not accepted). CIN: IT040012C2ETXG92WB

Top guest favourite
The exterior of the castle is showcased at sunset, with vibrant orange and purple skies providing a dramatic backdrop. Stone towers rise from the landscape, surrounded by greenery and colorful flora, reflecting the historic charm of the property.
Castle
4.99 out of 5 average rating, 210 reviews

Il Castello di Ferrano - Castle in Tuscany

Try the experience to stay in a real Castle! Il Castello di Ferrano offers to his hosts the chance of doing an unforgettable experiece:you will be the only guests in the castle and everythig will be for you (private pool from June to September, gardens ecc.)Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.

Top guest favourite
A charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.
Farm stay
4.99 out of 5 average rating, 446 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Top guest favourite
A cozy bedroom features a rustic stone wall with warm lighting illuminating the space. A spacious bed is draped with a soft blanket, and a small dining area with two chairs and a table is positioned by a window. The room captures a blend of comfort and simplicity.
Apartment
4.96 out of 5 average rating, 253 reviews

The Teodorano ruin, in the countryside.

This is a typical early 1900s Romagna farmhouse, nestled in the Romagna hills between Forlì and Cesena. 40 km from the Romagna Riviera, you are immersed in the middle of the green and sunny hills where in addition to relaxing in the available swimming pool (seasonal summer opening), you can practice various outdoor activities, including trekking, bike excursions and much more. A BBQ area and a shaded area for outdoor dining are available for guests.

Superhost
A spacious freestanding bathtub is filled with water, adorned with floating flowers and candles. A small wooden table beside it holds a bucket of champagne and two glasses. Soft towels and a decorative rose are also visible, contributing to a relaxing ambiance.
Home
4.98 out of 5 average rating, 281 reviews

"La limonaia" - Romantic Suite

Romantic Suite immersed in the enchanting hills of Fiesole. It is the ideal place fot those looking for unique and exclusive experience of its kind characterized by suggestive views and unforgettable sunsets. The accommodation is part of an old 19th century Tuscan farmhouse surrounded by its own olive groves and woods. This is an ideal place for a relaxing holiday and privileged base for visiting the major centers of interest in Tuscany.

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
4.97 out of 5 average rating, 144 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
Farm stay
4.88 out of 5 average rating, 309 reviews

Romantic apartment in the Tuscan village

The house is located in an ancient medieval village that has been completely renovated while maintaining the charm of its history. In the village you will find two swimming pools, a restaurant, many gardens and much more... It is in a strategic position to be able to reach the main attractions such as the Chianti Region, Florence, Arezzo and Siena!

Top guest favourite
An elegant medieval castle is surrounded by lush olive trees, showcasing its stone façade and characteristic towers. Soft lighting emanates from the windows, creating a warm ambiance as dusk approaches. The castle is set against a backdrop of gently rolling hills, enhancing its historic charm.
Castle
4.88 out of 5 average rating, 119 reviews

Suite in Castello di Valle

A unique experience in a historical dwelling located in the Chianti region. This medieval castle is situated in a strategic position, surrounded by the major Tuscan touristic attractions. The suite is at the entrance floor level: double bedroom with bathroom, sofa bed for two people, kitchenette, fireplace.

Top guest favourite
A rustic stone house is situated among lush greenery, framed by old trees displaying autumn foliage. The building features multiple windows and a welcoming presence, surrounded by a mostly open landscape with gentle slopes and natural stone elements.
Flat
4.99 out of 5 average rating, 108 reviews

Podere La Quercia

Immersed in the woods of Casentino, surrounded by firs, oaks and hazels and protected by a secular oak that surrounds it, our most beloved house is the ideal place for those who want to spend a few days in a warm and welcoming atmosphere and to take refuge in nature in an area rich in art and mysticism.

Top guest favourite
A private terrace is featured, equipped with a small dining table and chairs. Scenic views of the surrounding historic rooftops and towers are visible, showcasing the charm of the Oltrarno district under a clear blue sky.
Flat
4.96 out of 5 average rating, 124 reviews

Panoramic loft with terrace near Ponte Vecchio

Luminoso e silenzioso loft all'ultimo piano nel quartiere Oltrarno del centro storico. Vicino a tutti i monumenti e trasporti pubblici. Offre tutti i comfort per un soggiorno rilassante. Splendida vista su Palazzo Pitti e sui giardini di Boboli. Nessun ascensore. Per 1-2 persone.

Guest favourite
A beautifully restored stone building features a sloped roof and large windows that offer expansive views of the surrounding landscape. A well-maintained garden, framed by potted plants, leads to a patio area with outdoor seating set against a backdrop of rolling hills.
Home
4.93 out of 5 average rating, 227 reviews

Casa Bada - Barn

Historic 12th-century barn restored in 2019, with attention to every detail. 180-degree panoramic view of the Chianti Rufina hills. Private house with private entrance, spacious garden, private parking and pool shared with one other apartment.

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