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House vacation rentals in Rocca San Casciano

Find and book unique houses on Airbnb

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Popular amenities for Rocca San Casciano house rentals

House rentals with a pool

Top guest favorite
A salt-water pool is set within a manicured lawn, surrounded by sun loungers and shaded umbrellas. The stone-clad building in the background features rustic architecture, complemented by lush greenery and distant hills under a clear blue sky.
Home in Poppi
5 out of 5 average rating, 51 reviews

Villa Podere Cerretino

Emma KamperRating, 5 stars3 weeks ago
Fabulous place in amazing surroundings. The pool area is wonderful and the garden beautiful. We had an amazing time and enjoyed the entire place - especially the outdoor pizza oven. Nicola was very helpful and fast in his responses.
Top guest favorite
Home in Barberino Tavarnelle
5 out of 5 average rating, 108 reviews

Infinity pool in Chianti area

KrisRating, 5 stars2 weeks ago
"Perfect" is the only word that comes to mind for Anna's place. Such a serene location and perfect for a family. The view is just spectacular. We felt so at home and loved sitting out in the yard and by the pool. Anna provided us with a list of so many amazing things to do/see near and far. A must do is the pasta making with Vilma at the house-the most memorable and delicious meal from our trip! Can't wait to go back there to live more of the Tuscan life and enjoy the most beautiful view. Thank you, Anna, for hosting such a gem!
Guest favorite
A serene outdoor space features a large, clear swimming pool surrounded by carefully manicured hedges and tall trees. The rustic stone house stands in the background, complemented by a few lounge chairs near the pool, offering a peaceful setting for relaxation.
Home in Cavriglia
4.93 out of 5 average rating, 80 reviews

Wonderful country house

MichaelRating, 5 stars1 week ago
We had a brilliant week at Jakob and Margit’s house. Margit was so friendly and helpful (and gave us some wine and fresh eggs!). The views from the gardens are incredible and having the swimming pool was perfect. The local area has lots of great vineyards to visit and the house is close to Florence/Siena/Arezzo for day trips. It had everything we needed like a washing machine etc.
Superhost
A shared swimming pool is surrounded by a fenced area, featuring several sun loungers with striped cushions and umbrellas for shade. Olive trees and lush greenery create a peaceful backdrop, while the clear blue sky adds to the serene atmosphere.
Home in Reggello
4.8 out of 5 average rating, 82 reviews

House with pool among olive trees plantation

KarolinaRating, 5 stars9 months ago
The apartment is located in the picturesque surroundings. It takes quite a while to get there up the hill, but the views reward it! The place was clean and well-prepared for our stay. Good spot if you look for some peace and quiet and want to stay away from the noise!
Superhost
A serene outdoor seating area features white iron chairs adorned with floral cushions, set against a rustic stone wall. A nearby tree provides shade, surrounded by greenery and a view of the countryside, creating a peaceful spot for relaxation.
Home in Galluzzo
4.84 out of 5 average rating, 265 reviews

Old barn The Nepitella

ErinRating, 5 stars4 weeks ago
We loved our stay at Michaela’s house. The views were beautiful and it was a nice and relaxing atmosphere. Great location, very short walk to the town or easy bus ride into the center of Florence. We will definitely be back!
Superhost
A private swimming pool is surrounded by wooden decking and lush greenery, offering expansive views of the rolling hills and valleys in the distance under a clear blue sky. A small ladder is available for easy access to the water.
Home in Rufina
4.86 out of 5 average rating, 104 reviews

Ancient Tuscan Rural Residence

Jóna BergþóraRating, 5 stars1 week ago
Great house with amazing views. We used the pool a lot as it was very hot during our stay. Francesco and Serena were very nice and helpful. They booked a cooking class for us, which I highly recommend. The location is very convenient for visiting Florence, as it only takes about half an hour by train from Rufina.
Superhost
A private terrace features a wooden deck with a cushioned lounge chair beside a mini pool. Lush greenery surrounds the area, providing a serene view of the valley and hills in the background under a bright blue sky with scattered clouds.
Home in Londa
4.96 out of 5 average rating, 26 reviews

Luxury Country Retreat near Florence with Jacuzzi

JacquelineRating, 5 stars1 month ago
We felt very comfortable at Adriana's and the accommodation was very modern, clean and well maintained. The outdoor area with the hot tub was also super nice. The way to the accommodation is a bit narrow and curvy, which can be a bit challenging for inexperienced Italian vacationers, but it is quite feasible.
Guest favorite
A private swimming pool is set against a backdrop of lush hills, displaying clear blue water. Surrounding the pool, a paved area offers space for relaxation, featuring lounge chairs along the perimeter. A wooden fence provides a natural boundary, enhancing the tranquil outdoor atmosphere.
Home in Sogliano Al Rubicone
4.95 out of 5 average rating, 112 reviews

Country house with private pool

AndrewRating, 5 stars4 weeks ago
What a beautiful little space in the Italian countryside. I am so sad we could not stay longer. We had a wonderful welcome and our stay far exceed our expectations. Our host helped us book dinners every night in local restaurants and we loved the proximity to San Marino and nearby wineries.

Weekly house rentals

Top guest favorite
A modern sleeping area features a spacious bed dressed in a textured blanket, complemented by neatly rolled towels. An elegant freestanding bathtub is positioned against a rustic stone wall, while a potted plant adds a touch of greenery to the setting.
Home in San Marino
4.96 out of 5 average rating, 25 reviews

Casa Cicetta Accommodation 1296

BenRating, 5 stars3 weeks ago
Our stay here was amazing! The host was extremely friendly and helped us bring our suitcases in when she saw us struggling to bring them up the hill. She gave us a map of the area along with recommendations for restaurants and things to do. She was super communicative and helpful whenever we needed anything! The airbnb is beautiful and I wish we could’ve stayed longer. The view is amazing and we felt super comfortable and welcome. We fell in love with San Marino and will definitely be back with the same hosts and place!
Guest favorite
The exterior of a recently modernized house is shown, featuring large glass doors and a pergola casting striped shadows. A landscaped garden surrounds the property, with olive trees visible nearby. The clear blue sky complements the serene rural setting.
Home in Borgo San Lorenzo
4.95 out of 5 average rating, 57 reviews

The Diospero

VasilyRating, 5 starstoday
I am from California and stayed at 50 different Airbnb properties so far, mostly in the US, and most were very good, some were great, but none were like this property. this place is more than a place to stay. This was a very special and unique experience made possible by the great hospitality and generosity of the owners. I stayed for the entire Mugello MotoGP 2025 weekend and this location could not be more perfect to attend the race events every day. The views, the road to the property, the whole area and history or the area are all amazing. I got to learn a great deal about this beautiful part of the world and felt like I was an “Italian” for a few days. Highly recommended.
Top guest favorite
A spacious bed is centered against a textured white wall, complemented by two wooden nightstands on either side. Each nightstand features a simple lamp and a decorative yellow object. Natural light enters through the window, accentuating the soft bedding and neutral decor.
Home in Savignano sul Rubicone
4.98 out of 5 average rating, 58 reviews

Casa Castelvecchio

ChristinaRating, 5 stars2 weeks ago
Honestly, Deborah was the perfect host for several reasons. Beyond being incredibly kind and understanding, she really tuned into what I needed. I mentioned that this was my first time in a town like this and that I was hoping to hibernate for a few days, and her place felt like the perfect fit. She went above and beyond to make the check-in process smooth, even offering to pick me up from the train station and take me to the grocery store—on a Sunday, no less, when most places were closed and options were limited. Her home was serene, even more beautiful than the photos, and I immediately felt safe and at ease in the neighbourhood. I also loved how central it was to most things, like a spa, fruit/vegetable store, cafes, restaurants and convenience stores. In a world that often feels like it’s growing less kind, Deborah truly understands the heart of hospitality. :)
Top guest favorite
The exterior of a restored barn is showcased amidst a scenic landscape. Natural elements include lush green grass, a tall tree, and a gentle slope leading to a hill. A wooden pergola provides shade, and rustic stone walls feature a blend of earthy tones.
Home in Pontassieve
5 out of 5 average rating, 28 reviews

La Quercia House in the countryside

Ishlah BimoRating, 5 stars4 days ago
Renza and Mauro prepared the house nicely during our trip! The house was spotlessly clean and they even provided an ample amount of amenities which we found quite helpful for us. Thank you for such a hospitality! :)
Guest favorite
A traditional stone house with a sloped roof features wooden shutters and a central door. An awning provides shade over a dining table set on a well-maintained lawn. Surrounding flowers and greenery create a peaceful outdoor setting, reflecting a serene countryside ambiance.
Home in Greve in Chianti
5 out of 5 average rating, 61 reviews

La Loggia – Casine al Sole

PeterRating, 5 stars1 month ago
Spontaneously booked. And can easily arrange everything necessary at short notice. Federico is calmly communicative and can refine the stay with good recommendations. The location is special. The place has a good effect on the body and mind. WeiläuAbout but not far for shopping or restaurants. A beautiful pool. Tasteful spaces. Wifi junckies could sometimes hate something with the net, but the overall picture is not diminished. Everything else necessary is on site or will be promptly provided by Federico. A wonderful starting point for Visit in Florence or Chianti. Lots of rustic trattorias,winemakers and olive farmers nearby.
Top guest favorite
A spacious bedroom is presented featuring two beds, one being convertible, and artwork depicting a mountain landscape. Natural light enters through a nearby window, enhancing the modern decor. A small bedside table and decorative elements, including a plant, add warmth to the space.
Home in San Marino
4.97 out of 5 average rating, 77 reviews

House "Independent" close to the Historic Center

ShawnRating, 5 starstoday
Awesome stay! Very friendly host
Top guest favorite
A charming stone villa is framed by lush greenery and tall trees. Natural stone pathways lead to the entrance, where wooden shutters are seen beside arched windows. Shadows from the surrounding foliage create a tranquil ambiance, reflecting the serene countryside setting.
Home in Radda in Chianti
5 out of 5 average rating, 20 reviews

Villa le Scope 5*

ColeRating, 5 stars3 weeks ago
Beautiful home. Extremely clean. Riccardo was extremely responsive and made our check in process very easy. Definitely would stay again!
Top guest favorite
The bedroom features a spacious bed with a patterned bedspread. A wooden headboard adds warmth, complemented by two small bedside lamps. Large windows allow natural light to fill the space, with views of the surrounding landscape. Two paintings adorn the walls, enhancing the room's charm.
Home in Poggibonsi
4.92 out of 5 average rating, 59 reviews

Agriturismo Podere San Martino (apartment for two)

LukasRating, 5 stars1 month ago
Everything was just like in the pictures. We had a great time. The view was amazing and Maddalena was really helpful. Thank you!

Private house rentals

Guest favorite
A stone house with a rustic charm is enveloped by lush greenery and blooming wisteria. Large windows and a distinctive arched window enhance the facade, while vibrant plants add warmth to the exterior. The surrounding landscape features rolling hills in the distance under a partly cloudy sky.
Home in Fiesole
4.97 out of 5 average rating, 32 reviews

Scenic country house with large pool near Florence

ChristopherRating, 5 stars1 month ago
Absolute Perfection in Fiesole!** Michael’s villa in Fiesole is nothing short of spectacular. From the moment we arrived, we were mesmerized by the breathtaking views of the Tuscan countryside and Florence in the distance. The location is ideal—peaceful, romantic, and just a short drive from the heart of Florence, making it the perfect blend of serenity and convenience. The villa itself is stunning—spacious, elegantly decorated, and equipped with every amenity you could need. The outdoor terrace was our favorite spot, where we enjoyed morning coffee with panoramic views and evening wine under the stars. The lush gardens and private pool added an extra touch of luxury to our stay. Michael was an exceptional host—attentive, welcoming, and full of great local recommendations. His hospitality truly made our experience unforgettable. If you’re looking for a dreamy Tuscan escape with world-class scenery, impeccable style, and top-notch service, this is the place. We can’t wait to
Superhost
A tranquil swimming pool is surrounded by a well-maintained garden, reflecting the soft colors of the sunset. Lush greenery and vineyards are visible in the background, enhancing the serene atmosphere, while comfortable loungers are placed nearby for relaxation.
Home in Barberino Tavarnelle
4.76 out of 5 average rating, 55 reviews

7 min Cantina Antinori | Pool | Casa Sala & Pepe

RyanRating, 5 stars1 month ago
Beautiful home near Chianti. Clean and comfortable, with amazing vineyard/sunset views. The hosts were very responsive and friendly, and they gave clear instructions. One thing to note is that the property is listed as "Entire Home", but it is actually a condominium that shares walls and outdoor common areas with the neighbors. There is a divider in the backyard between us and the neighbors, but it is not completely private. Overall, we had a great time here.
Top guest favorite
An outdoor swimming pool is surrounded by a stone patio and a secure fence. Lush greenery and rolling hills provide a scenic backdrop, while terracotta pots with plants are positioned at the pool's edge, adding to the natural ambiance.
Home in Castel Focognano
5 out of 5 average rating, 21 reviews

Tuscan Rustic

GeorgRating, 5 stars4 days ago
Such an amazing place! We loved our stay there and definitely want to come back! The outdoor area is great, the views amazing and the house very clean, beautiful and we had such a nice time
Superhost
A panoramic view of rolling green hills and distant mountains is displayed, with patches of forest and farmland. The image features several rustic stone buildings nestled among trees, connected by winding paths and open fields, inviting a sense of peace and connection to nature.
Home in Bagno di Romagna
5 out of 5 average rating, 3 reviews

Terrace overlooking the park (La Legnaia)

DarcyRating, 5 stars20 months ago
Delightful people. Incredibly kind and helpful. I'm so pleased I chose to stay with Mauro. Very accomodating.
Guest favorite
A comfortable living area is highlighted by a beige sofa adorned with decorative pillows. A modern floor lamp stands beside the sofa, illuminating the space. An artificial Christmas tree with golden decorations adds a festive touch, contrasting with the light-colored walls.
Home in Forli
4.92 out of 5 average rating, 59 reviews

Cielo Apartment

IrenaRating, 5 stars1 month ago
This is a very clean and comfortable flat in the centre of Forli, just steps away from Corso della Repubblica. It's a 25 minutes' walk or a very short taxi ride from the train station. The communication with Gian Luca was smooth quick, I felt well looked after. The flat is very well kept, there are amenities as well as special details on the part of the hosts that made my stay pleasant and comfortable. The area in front of the flat is well lit at night, which made me feel safe, as well as there being cameras on the outside and the owner living nearby. The bed was comfortable. There was hardly any traffic in the street, however there were occasionally loud passers-by at night who disturbed me as I'm a light sleeper, but no major noises.
Guest favorite
A stone terrace is framed by arched supports, illuminated by gentle lighting. Wooden furniture is arranged for relaxation, with potted plants adding natural elements. The backdrop showcases the medieval bridge, seamlessly integrating the outdoor space with the historic architecture.
Home in Mercatello sul Metauro
4.95 out of 5 average rating, 40 reviews

The house on the bridge

Sara & LeonardoRating, 5 stars1 week ago
Not only does Giovanna's accommodation satisfy for its excellent and particular location (right under a Romanesque bridge, a stone's throw from the square, restaurants and the river), but the welcome is something unique. No one in an Airbnb had ever made us find a homemade cake for breakfast (and with what skill from Giovanna's mother) and had taken so much care of the well-being of our dog as well as ours. Mercatello sul Metauro is a small gem and this house completes the picture. We will definitely be back!
Top guest favorite
A private swimming pool is framed by a sun terrace furnished with several white loungers. A shaded seating area provides a relaxing spot nearby, surrounded by lush greenery and trees. Natural stone steps lead along the edge of the space, enhancing the tranquil outdoor setting.
Home in Montevarchi
5 out of 5 average rating, 25 reviews

Casa San Ripa: Relax Oasis with Private Pool

CarolinaRating, 5 stars4 days ago
We had an amazing time in Casa San Ripa. The house is even nicer than it looks in the pictures, the view is amazing and the outside area is lovely, with all the lights in the trees at night. The whole property was very clean, including the inside and the pool, the instructions were easy and Giulia is super responsive and extremaly nice and helpful. We had a great stay and would highly recommend!
Top guest favorite
A spacious sitting area features a comfortable grey sofa adorned with decorative pillows. Natural light enters through a stained glass window, illuminating the textured beige walls. A wooden table sits in the center, complemented by a patterned area rug and artwork displayed on the walls.
Home in Greve in Chianti
4.97 out of 5 average rating, 35 reviews

Sweet life in Tuscany , but so close to Florance

JulieRating, 5 stars2 weeks ago
We had a lovely stay and Simona was keen to ensure that we were happy. The villa has a lovely rustic feel. Ignore the no entry sign at the end of the dirt track road and drive up through the trees. You park right outside the house. It was a little more expensive for us as we were only 2, staying in a place for 4. The dog was lovely and friendly ( although looks as though he might not be as Alsatian breed I think ). There is a lovely restaurant in San Polo with a lovely garden out the back… about 7 mins away.

Destinations to explore