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Vacation rentals in Rocca San Casciano

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Top-rated vacation rentals in Rocca San Casciano

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Top guest favorite
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 in San Casciano In Val di Pesa
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.

Top guest favorite
Home in Vaiano
5 out of 5 average rating, 259 reviews

The MOONLIT & SUNNY COTTAGE near Florence

IL COLLE DI FALTUGNANO: immersed in an olive grove on a Tuscan hills and with an amazing view of the valley, the stone cottage has been remarkably recovered a few months ago, a caravanserai a few century ago. In a strategic position close to Florence is a good base for exploring Tuscany and be independent at the same time with supermarkets and restaurants just a few minutes away. Close to a farmhouse you can buy fresh local organic ingredients, such as bio vegetables, eggs or cheese.

Top guest favorite
A private outdoor pool is framed by lush greenery, featuring a clear blue water surface. The pool area includes tiled edges and steps leading into the water, situated within a serene garden setting that contributes to a peaceful environment.
Castle in Ferrano
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 favorite
A serene outdoor pool area is framed by lush green grass, featuring several sun loungers and umbrellas. The clear water in the pool reflects the blue sky, while tall cypress trees provide a natural backdrop to the tranquil setting.
Farm stay in Greve in Chianti
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 favorite
An inviting outdoor pool is framed by a spacious wooden deck. Sun loungers are placed nearby on the lush green lawn, with shaded seating under a pergola visible in the background. Surrounding trees enhance the peaceful countryside setting.
Condo in Teodorano
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.

Guest favorite
An exterior view showcases a charming suite with a terracotta facade. The entrance features large arched windows, while a patio is furnished with two cozy chairs and a small table surrounded by potted plants. A serene dog relaxes on the stone-paved terrace.
Home in Fiesole
5 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 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
4.97 out of 5 average rating, 145 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.

Top guest favorite
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 in Barberino Tavarnelle
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 favorite
The stone exterior of the house is surrounded by lush greenery and trees, featuring arched windows with wooden shutters. A charming pathway of stones leads to an inviting entrance, enhancing the natural setting. Sunlight illuminates the facade, creating a serene atmosphere.
Apartment in Pratovecchio - Stia
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.

Guest favorite
Apartment in Santo Spirito
4.99 out of 5 average rating, 573 reviews

Romantic spring in the secret garden

"A relaxing bath in the spectacular freestanding bathtub enjoying the tranquility and beauty of Boboli' s garden ..." Welcome to Relais il Ronco a luxurious and quiet apartment with large garden located in the center of Florence in the district of San Frediano in a secluded and exclusive street.

Top guest favorite
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.
Apartment in Santo Spirito
4.96 out of 5 average rating, 125 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 favorite
Home in San Martino
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.

Popular amenities for Rocca San Casciano vacation rentals