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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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Guest favorite
The exterior of a two-story building is portrayed, featuring a warm orange facade and contrasting blue shutters. A wooden door with an arched window is centered beneath a decorative stone plaque, while a small potted plant is placed near the entrance.
Condo in Marradi
5 out of 5 average rating, 17 reviews

heaven and earth under the stars

In the historic center of Marradi, but in a quiet area with a narrow street and traveled only by residents, you will find a two-story building. My wife and I live on the ground floor. On the first floor, you will find the Airbnb Cielo e Terra and a recently renovated attic consisting of 2 large double bedrooms, a small hallway where you can have breakfast and a small but fully equipped bathroom, shower, toilet, sink and hydraulic brush, free Wi-Fi, private parking and a large garden adjacent to the house

Top guest favorite
Farm stay in Ruscello
4.99 out of 5 average rating, 499 reviews

Farmhouse Fattoria La Parita

Provencal-style apartment nestled between vineyards and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 km from the highway. The song of jays and cuckoos will be the soundtrack to the stay while the roe deer graze among the olive trees. A basic Italian breakfast is included (coffee, tea, milk, biscuits, etc.), but if you prefer a richer breakfast served at the table, the cost is €15 per person (€10 from 5 to 15 years, free under 5 years). EV wallbox available.

Guest favorite
A bright and spacious living room features a large marble coffee table and a pair of elegant chaise lounges. A striking painting hangs above a contemporary white sofa adorned with colorful cushions. Antique furnishings and a patterned rug enhance the room's sophisticated ambiance.
Apartment in Centro
4.94 out of 5 average rating, 363 reviews

Museum Suite - Luxurious unit with a River View -

After 13 wonderful years of hosting on Airbnb, the time has come to close this incredible chapter and embrace the next. These upcoming 7 months will be the final season for MuseumSuite, in Jan 2027, the property will be sold and transformed into a private family residence. It has been an absolute honor and a privilege to welcome guests from all walks of life. Each of you has deeply enriched my journey, and I hope that MuseumSuite has left a beautiful, lasting impression on your lives as well.

Superhost
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
4.78 out of 5 average rating, 46 reviews

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

Sugli antichi confini del Granducato di Toscana “Romagna dal 1923”,in un territorio che coniuga le migliori tradizioni delle due regioni, un casolare di campagna recentemente ristrutturato dove è possibile vivere la quiete di un ambiente naturale a 70 Km da Firenze, Arezzo, Ravenna e Rimini. A pochi Km potete visitare il parco delle foreste casentinesi e godere delle emozioni culinarie, culturali e storiche del nostro territorio. Annesso al casolare è disponibile un antico forno a legna.

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, 218 reviews

The Castle of 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
Apartment in Faenza
5 out of 5 average rating, 52 reviews

Podere Mantignano 2

Panoramic apartments in Romagna ideal and recommended for an ADULT AUDIENCE. Wonderful apartments in 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 an orange sunset over the gentle Romagna hills in the evening. Vines, apricot trees, peach trees and meadows create harmonious colors and shapes to daydream in a truly extraordinary place.

Top guest favorite
A living area features a brick fireplace, surrounded by a comfortable seating arrangement. A dining table is set for meals, with natural light streaming through large windows, showcasing the picturesque surroundings. The ceiling showcases wooden beams, adding to the room's character.
Villa in Tavarnelle Val di Pesa
5 out of 5 average rating, 25 reviews

Tuscan Luxury Villa • Natural Pool & Privacy

Immagina di svegliarti in totale privacy, circondato dalle colline del Chianti, con la tua piscina naturale, la spiaggia e il chiringuito. Non è solo un soggiorno, ma una vera “private luxury experience” toscana. Tenuta Virgilio nel Chianti è una villa immersa nella natura, perfetta per chi cerca relax, silenzio ed esclusività in Toscana. Oltre 3 ettari di uliveto e totale privacy: nessuno spazio condiviso, solo la tua esperienza in Toscana.

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, 133 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, character, convenience. 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.

Top guest favorite
Casa particular in Florence
5 out of 5 average rating, 44 reviews

Palazzina Maresa - Loft 4

Palazzina Maresa is a 1920s building carefully restored to host eight independent apartments, each shaped by the vision of a different young local designer. The project reflects on early 20th-century aesthetics through a contemporary lens, blending architecture, design, and artistic research. Located in a quiet residential area with private and shared gardens, the building is just a short walk from Florence’s historic center.

Guest favorite
A shaded outdoor patio is framed by greenery, providing a peaceful retreat. Comfortable seating is arranged around a small table, while sun loungers are positioned nearby. The surrounding landscape showcases hills and trees, enhancing the serene environment of the private garden.
Farm stay in Cavriglia
4.9 out of 5 average rating, 210 reviews

Chianti La Pruneta, Caravaggio apartment

A Jewel of an apartment in the heart of Tuscany. Stunning views over cypress and olive trees. Beamed ceilings, marble floors, all recently refurbished. The apartment includes an antique wooden bed and Venetian lights. You can relax and eat 'Al Fresco' in your own private garden where sun loungers a BBQ and a shaded eating area are all provided, enjoying the beautiful views.

Top guest favorite
The entrance to the house features a green door with steps leading up to it. A stone bench sits beside the entrance, adorned with pink roses. Vibrant flower pots add color to the pathway, creating a welcoming exterior in a serene garden setting.
Guesthouse in Fiesole
4.99 out of 5 average rating, 168 reviews

Fiesole in Giardino Home & breakfast B&B

WELCOME TO FIESOLE IN GIARDINO HOME 🌿 Enjoy a peaceful stay in Fiesole, the charming hill overlooking Florence. A small independent house with bedroom, kitchen/living area and private bathroom, fully renovated and surrounded by greenery. Breakfast is included in the price. During spring and summer, breakfast is served on the panoramic rooftop terrace with a beautiful view.

Guest favorite
Apartment in Premilcuore
5 out of 5 average rating, 8 reviews

House on the screaming caves Ponte Nuovo Premilcuore

Apartment located above the Screaming Caves of the charming town of Giumella - Premilcuore, a place surrounded by the nature of the Casentino Forest Park. Gualchiera from the 1500s/1600s, renovated in 2025 Great starting point for hiking, info on site Possibility of a closed and safe place for your bicycles. For small children, a camping bed with high sides is available.

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