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Holiday rentals in Rocca San Casciano

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Top-rated holiday rentals in Rocca San Casciano

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Top guest favourite
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
4.98 out of 5 average rating, 52 reviews

[Hot Tub and Nature] Entire Home in the hills

A stone house surrounded by nature, in Romagna, between the Apennines and the villages. Here live the memories of generations, of a village, of three brothers who have decided to reopen their doors for those seeking intimacy, nature, taste. La Cappelletta is where you can sleep, cook, taste, meditate. Whether it is for a romantic getaway, an escape from the city, a vacation with grandparents, a retreat among friends, a corporate team building sprint, a weekend away from the chaos to find peace.

Top guest favourite
The elegant villa is set against a twilight sky, featuring an inviting infinity pool surrounded by stylish sun loungers. Lush gardens and pathways lead to the spacious terrace adorned with ambient lighting, enhancing the serene atmosphere of the outdoor space.
Villa in Bertinoro
4.97 out of 5 average rating, 66 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 favourite
The rustic stone buildings are set within a lush green landscape, surrounded by trees and hills. A swimming pool is positioned in the foreground, with a stone barbecue nearby. A vehicle is parked close to the entrance, emphasizing the property's spacious outdoor area.
Holiday home in Marradi
5 out of 5 average rating, 47 reviews

Relax in the woods-Pian di Lazzaro

Holiday 🌲 Home in the Heart of the Forest - Pian di Lazzaro Immersed in the quiet of a dense forest and surrounded by a splendid panoramic view, Pian di Lazzaro is an ancient renovated farmhouse located just 3 km from Tredozio and 15 km from Marradi The property consists of two independent apartments, perfect for families, couples or groups of friends looking for relaxation in nature: 🏡 Apartment: Living room with fireplace, Fully equipped kitchen Rooms: triple and one double

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 in Ferrano
4.99 out of 5 average rating, 210 reviews

The Castle of 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 in Greve in Chianti
4.99 out of 5 average rating, 434 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 in Teodorano
4.96 out of 5 average rating, 252 reviews

The Theodoran 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.

Top guest favourite
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 in Fiesole
5 out of 5 average rating, 273 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
The historic tower apartment, part of a small castle, is surrounded by lush greenery and trees. The building features multiple windows, showcasing traditional architectural elements. A picturesque garden with low shrubs and budding flowers provides a tranquil atmosphere, inviting exploration of the outdoor space.
Castle in Bagno A Ripoli
4.92 out of 5 average rating, 559 reviews

TOWER apartment in small castle near Florence

Romantic, Historically unique, Magical atmosphere, 360 degree views of the countryside and Florence. Great retreat for digital nomads, or simply to retreat from the hustle and bustle. Convenient for Chianti and Tuscany explorations. A/C in 2 rooms. Cooking class and wine tasting available. If you'd like to add more space and comfort, book the TOWER PENTHOUSE: double the space, a large kitchen, another bathroom. Perfect for families!

Top guest favourite
A bright living area features a wooden ceiling with exposed beams. Natural light enters through a window, highlighting a gray sofa and a yellow pillow. A chair sits nearby, while a staircase leads to an upper level, enhancing the spacious feel of the room.
Flat in Marradi
4.96 out of 5 average rating, 91 reviews

In a historic building between Florence, Bologna and Ravenna

The apartment is located in the main square of the village 10 minutes walk from the Railway Station. Marradi is located in the heart of the Tuscan-Romagna Apennines, from where you can easily reach the cities of art Florence, Bologna and Ravenna. Due to its characteristics, the apartment is also suitable for long stays. In 2025, the railway may be affected by momentary closures due to work on the line. Check on the Trenitalia App

Top guest favourite
The two-story residence features a light-colored facade with green shutters, reflecting in the inviting pool. Surrounding landscaping adds texture, while clear skies create a serene atmosphere. A covered patio extends from the building, providing an outdoor space to enjoy the picturesque views.
Apartment in Faenza
5 out of 5 average rating, 48 reviews

Mantignano Power

Panoramic apartments in Romagna. Wonderful apartments on the Romagna hills, where you can enjoy a breathtaking view. It is a magical place where you can enjoy a wonderful golden sunrise every morning that rises from the sea and in the evening of an orange sunset in the rolling hills of Romagna. Vines, apricots, peaches, and meadows create harmonious colors and shapes to daydream in place truly out of the ordinary.

Top guest favourite
A serene outdoor space features a private swimming pool surrounded by lush greenery, providing scenic views of rolling hills and trees. Two lounge chairs and an umbrella are positioned near the pool, enhancing the tranquil atmosphere of the area.
Apartment in Tredozio
4.97 out of 5 average rating, 34 reviews

Country House La Clombera 1

The apartment is part of a cozy country house located on the border between Romagna and Tuscany. The house is surrounded for three-quarters by about nine thousand square meters of land and it’s spread on four stories. On the second one two apartments are located and have been recently renovated. Both the apartments are fully furnished in order to provide our guests with a great comfort!

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 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.

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