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Vacation rentals in Rocca San Casciano

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Top-rated vacation rentals in Rocca San Casciano

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

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Top guest favorite
Home in Greve in Chianti
4.99 out of 5 average rating, 113 reviews

Relaxation and charm in the Chianti hills

Beautiful stone farmhouse, detached, surrounded by olive trees and the Chianti hills, with private garden and panoramic swimming pool. Ground floor with large living rooms, antique fireplace and wood-burning oven, bright living room and fully equipped kitchen. On the first floor, three suites consisting of a bedroom, study and private bathroom. Access via gate and white road on private property just 500 meters from the village of Strada in Chianti. Ideal for peace and relaxation. Convenient location for visiting Tuscany.

Guest favorite
Vacation home in Brisighella
5.0 out of 5 average rating, 5 reviews

Palazzo Metelli: Historic Art Flat & Garden Oasis

Historic residence where beauty, nature, and tradition come together. The Demetra apartment is part of a historic building protected under the Code of Cultural Heritage and Landscape (Legislative Decree 42/2004). It is located just 300 meters from the ancient Via degli Asini and the Medieval Village. The property features a secluded outdoor area nestled within the Palazzo. As our guest, this intimate space is yours to enjoy exclusively. ***Su richiesta è possibile aggiungere un letto.***

Guest favorite
Home in Civitella di Romagna
4.91 out of 5 average rating, 11 reviews

Sode del Mardello Farm

Completely renovated apartment in a semi-detached house in the hills of Civitella di Romagna. Located in the countryside, the apartment, which is on the ground floor, is surrounded by fields and woods that offer quiet and natural views. It has parking and is 30 km from Forlì, 50 km from the Romagna Riviera, 10 km from Santa Sofia where you can relax in the waters of the Bidente River and 23 km from the Ridracoli Dam in the Foreste Casentinesi Park. It is 2.8 km from the center of Civitella.

Top guest favorite
Villa in Bertinoro
4.98 out of 5 average rating, 82 reviews

LUXURY VILLA BELVEDERE - Sea View with Pool & Spa

Providing a truly authentic italian experience, the spacious and gorgeously decorated Villa Belvedere is magnificently set in a unique corner of the ancient village of Bertinoro, with breathtaking views of the peaceful and pictoresque Romagna hills, sea and coastline. Infinity pool heated upon request, hot tub, sauna, steambath, professional gym; cinema room, billiard, bar corner with wine cellar, fully furnished and carefully designed and maintaned garden with barbecue and outdoor games.

Top guest favorite
Condo in Castrocaro Terme e Terra del Sole
5.0 out of 5 average rating, 21 reviews

Elegant 2-Suite Residence, near the Thermal Baths

Relax with the whole family in this newly renovated, quiet, bright and cozy accommodation in a quiet area. It has 2 comfortable Suites . 2 bathrooms complete with every comfort. Large open-plan living room with two comfortable sofas, one of which becomes the third double bed. Watch your favorite programs on the 55'' Samsung Smart Tv with Netflix and Youtube. In the fully equipped adjacent kitchen you can cook and dine at the 6-seater table. The accommodation is fully air-conditioned.

Guest favorite
A rustic country house is nestled in a lush green landscape, surrounded by tall trees. The stone exterior is complemented by a red-tiled roof. A porch with outdoor seating is visible, and neatly stacked firewood is arranged nearby, adding to the serene rural setting.
Cabin in Galeata
4.81 out of 5 average rating, 52 reviews

Country house “The Big Oak” (Villa Casone).

On the ancient borders of the Grand Duchy of Tuscany "Romagna since 1923", in a territory that combines the best traditions of the two regions, a recently renovated country house where you can experience the tranquility of a natural environment 70 km from Florence, Arezzo, Ravenna and Rimini. A few kilometers away you can visit the Casentino forest park and enjoy the culinary, cultural and historical emotions of our region. An old wood-burning oven is attached to the cottage.

Top guest favorite
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 in Ferrano
4.99 out of 5 average rating, 226 reviews

Il Castello di Ferrano - Castle in Tuscany

Try the experience of staying in a real Castle! Il Castello di Ferrano offers to its hosts the chance of living an unforgettable experience: you will be the only guests in the castle, and everything will be for you (private pool from June to September, gardens etc..). 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
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 510 reviews

Farmhouse in Chianti with Swimming Pool

Agriturismo Il Colle is located on one of the Chianti hills. The structure has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car The apartment is located on the ground floor of the main farmhouse, with independent access and private space. The care taken in the restoration and furnishing make the house particularly welcoming, respecting the rural style.

Top guest favorite
The historic tower-penthouse villa is surrounded by lush greenery and trees. The three-story structure is characterized by its earthy facade and wooden shutters. Well-maintained gardens with various plants create a serene outdoor environment, enhancing the villa's tranquil charm and historical significance.
Castle in Bagno A Ripoli
4.96 out of 5 average rating, 138 reviews

Tower Penthouse in small castle near Florence

900 year old Tower-Penthouse apartment in Chianti Villa, spacious & super-scenic historical home that combines magical atmosphere with space, light, history, convenience. (AC throughout). Painting-like 360° views of Tuscan Hills all the way to Florence; sun-filled, private grounds. Perfect location for an unforgettable family stay. Ample private property (including forest). Walking distance from village shops. Convenient location, Florence in sight.

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, 157 reviews

Experience rustic off-grid life in the wilderness

This ancient rustic farmhouse lies within a national park in one of the largest areas of forests in Europe. Solar power, wood stoves, the bumpy road and the lack of phone signal 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 spacious bedroom features a king-size bed with neutral bedding, complemented by decorative pillows. Soft lighting is provided by wall sconces, while natural stone walls add texture. A small bedside table and an armchair enhance the inviting ambiance.
Home in Sarsina
4.95 out of 5 average rating, 64 reviews

Nature Retreat | Peace & Relax in the Hills

A stone house immersed in nature, in the heart of Romagna, between the Apennines and historic villages. A peaceful and quiet place for those seeking slow living, intimacy and relaxation, with a private hot tub. La Cappelletta holds generations of memories and is now a space to live slowly: sleep, cook, taste, meditate and enjoy the silence. Perfect for romantic stays, escapes from the city, retreats with friends or weekends away from the noise.

Top guest favorite
Aerial view of La Collina showcases the rustic farmhouse surrounded by lush vineyards under a warm sunset. The panoramic swimming pool sits beside the house, and rolling hills extend into the horizon, reflecting the serene beauty of the Italian countryside.
Villa in Castel bolognese
5.0 out of 5 average rating, 47 reviews

Beautiful hilltop farmhouse with swimming pool

Nestled at the top of picturesque and peaceful vineyards in the gentle rolling hills of Romagna, La Collina is the perfect Italian getaway destination. Experience the rustic charm of countryside living with the comforts of modern living due to a recent full restoration. You will enjoy panoramic views to the Adriatic Sea and the Tuscan Appenines with breathtaking uninterrupted sunrises and sunsets over the surrounding valleys.

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