Vacation rentals in Rocca San Casciano

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Rocca San Casciano

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

0 of 0 items showing

1 of 3 pages

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 Storico

4.95 out of 5 average rating, 341 reviews

Museum Suite - Luxurious unit with a City View -

Decorated with ornate elegance, the apartment exudes an air of grandeur. Touches of white Carrara marble and stone floors add a richness to this bright and open space. Entering through a large stone archway into the grand foyer, your eye is immediately drawn to the captivating views of the arno river. Magnificent stone columns lead into the large living room of the apartment. Furnished with a combination of antiques and modern fixtures, this room offers a wonderful space to entertain at home while enjoying the breathtaking views of the city. Just off the living room you will find the fully equipped professional kitchen. A spectacular stone mantle serves as the hood for the stove and makes an elegant statement in this lovely cooking area. The main bedroom is completely spacious and well lit, the second bedroom is smaller and doesn't have the river view but is indeed very cozy. Both have queen beds and full marble ensuite bathrooms. The combination of antiques furnishings with modern design elements is truly a step into Italian Luxury. This fantastic apartment offers you the chance to immerse yourself into the heart of ancient Florence. The prime location is a perfect starting point for exploring all of the city’s most notable landmarks. The magical views from all rooms of this accommodation surround you in the beauty of Florence all day and night. There is a supermarket conveniently located 150 meters from the apartment. The Ponte Vecchio is 200 meters away and in a 5 minutes walk, you can reach the city center. The water boiler sometimes needs to be restarted. It's outside of the kitchen, there in an on/off button, you just need to turn it on and off. If all the utilities are on at the same time the light may go down, the breaker is next to the main entrance, inside the apartment. I also work for a hot air balloon company, if you are up for some adventure, you just need to ask me. The apartment is in the heart of ancient Florence—perfect for exploring the many nearby landmarks. You won't need a car, everything is at walking distance. In case you will arrive with a rented car, there is a parking next to the aparment that charges 35eur/day.

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

4.98 out of 5 average rating, 100 reviews

House "Independent" close to the Historic Center

This independent house, located a few steps from the walls surrounding the historic center of the Republic of San Marino, is the top place for those seeking relax, privacy and a breathtaking view of the surrounding mountains. The house, modern and with attention to detail, is perfect for families, couples or small groups who want to live an unforgettable experience. Large and well-organized spaces are designed for your every comfort. Free parking a few steps from the front door. Pets are welcome

Guest favorite

An expansive outdoor deck offers a serene view of rolling hills under a clear sky. An infinity pool transitions seamlessly into the landscape, with two soft seating cushions placed nearby, inviting relaxation and contemplation of the stunning panoramic scenery.

Home in Casale

4.88 out of 5 average rating, 185 reviews

Infinity view

Completamente ristrutturata posizione con vista mozzafiato sul Valdarno. Il piano terra è composto da soggiorno con due vetrate che danno sul patio, camino, divano letto, bagno con grande doccia e cucina moderna con isola in acciaio, con tre porte finestre per accedere alla zona pranzo esterna con bbq. Il primo piano è composto da due camere matrimoniali ognuna dotata del proprio bagno con doccia. Giardino è moto curato,ci sono vari angoli relax, prendisole è una piscina infinity ad idrolisi

Guest favorite

The exterior of the cottage is surrounded by greenery, featuring a sunlit terrace with a dining table and umbrella. Potted plants add color to the entrance, while the rustic charm of the stone and tiled details enhances the natural setting.

Home in Vaiano

4.99 out of 5 average rating, 237 reviews

Cottage in Toscana in antica Villa con giardino

Il Cottage è parte di una proprietà della famiglia Bernocchi, già presente nelle mappe della zona del 1500 ed e' situata proprio su di una antica via Romana che attraversava i monti della Calvana. Distante circa 9 km da Prato e 20 da Firenze. Il Cottage, liberi su tre lati, e' situato in posizione panoramica circondato da un parco privato, ideale per camminate e sport. Una vera e propria casa, con cucina, salotto, camera e bagno. Ampi spazi esterni, giardino e orto botanico.

Top guest favorite

A rustic living area features a wooden table surrounded by two elegant armchairs and a beige sofa. A stone fireplace, stocked with logs, stands as a focal point, while wooden beams adorn the ceiling. An inviting atmosphere is created by warm, natural colors and soft furnishings.

Home in Anghiari

4.99 out of 5 average rating, 241 reviews

Casa Rosmarino Eco-Wellness Country Home

Price includes the WELLNESS & COMFORT package as follow: - Organic Wooden Fired Hot Tub w/Jacuzzi (1 water filling good for 4 days of use) - Infrared Sauna - Wood for Fireplace & Hot Tub - Fire starters - Heating/Air Conditioning - Laundry/Dryer - Shower Gel/Shampoo/Bathrobes - Welcome Appetizer w/Wine - Italian Ground Coffee - Treats during your stay Extra activities (not included) : - Massages, Cooking Classes, Tours & Tasting Please INQUIRE for price & availability.

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, 207 reviews

The Chianti Classico Sunset

If you are looking for an idyllic location in the heart of the classic Chianti, immersed in the vineyards and olive groves of the beautiful Tuscan hills, in the farm of a historic Villa of the ‘500, then come to our barn!! It has a dominating position with a stunning view, where you can enjoy breathtaking sunsets. The total independence of the house, the cozy garden, the large loggia allow you to spend stays in complete peace of mind. Our reviews are your best guarantee.

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, 201 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 favorite

An inviting villa surrounded by lush greenery and vibrant flowers, featuring blooming rose bushes and olive trees. The gravel pathway leads to the entrance, showcasing a two-story structure with balconies. Sunlight highlights the colorful landscape, creating a serene atmosphere.

Villa in Impruneta

5 out of 5 average rating, 150 reviews

The Tower

Ancient Tuscan villa, beautiful, with exclusive private garden, completely renovated, surrounded by the beautiful and gentle Tuscan hills. The villa has a breathtaking view, is very sunny, well furnished and equipped with all amenities, quiet and not isolated. The house is located in Bagnolo, a small hamlet of Impruneta at the gates of Chianti, an area of olive groves, vineyards and peace. The house is about 10 km by car from the center of Florence.

Top guest favorite

The living area features a spacious gray sofa and two modern armchairs positioned around a circular coffee table. Large windows provide unobstructed views of the cityscape, with natural light illuminating the space. A decorative wall art adds a touch of character to the room.

Apartment in Centro Storico

4.99 out of 5 average rating, 201 reviews

Ponte Vecchio Suite with balcony on Arno river

The suite is about 592 square feet with a wide living and a lovely balcony facing Arno River. It has an amazing view of the Ponte Vecchio as well as the Ponte Santa Trinita. The living room is open to a dining area and a fully equipped kitchen. The bedroom has a queen size bed and 2 closets. A large bathroom with 2 windows, double sinks and a walk-in shower, is connected with the bedroom. Wi-Fi and air conditioning system are provided.

Top guest favorite

A spacious outdoor area features a swimming pool surrounded by lush green lawns and dotted with comfortable sun loungers. Umbrellas provide shade, and the serene landscape is framed by tall trees and gentle hills in the background.

Farm stay in Greve in Chianti

4.99 out of 5 average rating, 386 reviews

Typical Tuscan country house

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence. This apartment is one level, totally independent with private garden. Restored and furnished with great care to make the guest's stay as comfortable and relaxing as possible, in the full respect of the Tuscan rural style.

Guest favorite

A charming balcony is adorned with potted greenery, featuring a small round table and chairs. An unobstructed view of the Florence Cathedral and its intricate façade is visible, with people gathered in the square below, capturing the lively atmosphere of this historical setting.

Apartment in Centro Storico

4.93 out of 5 average rating, 149 reviews

Antelux South: your private balcony next to Duomo

Antelux Firenze: South wing, an exclusive apartment located in the same building as our famous Window to the Duomo. This boutique space is in the oldest part of this historical building from the 1200’s, with original frescoes, Italian antiques & crystal chandeliers. It features 2 bedrooms with in-your-face Duomo views, 1 bath, living-dining room, kitchenette, and a GORGEOUS BALCONY connecting the master bedroom and living room.

Top guest favorite

A serene bedroom space features a spacious bed adorned with soft, neutral-toned linens. Sheer white drapes create a cozy atmosphere, while the open doors offer a view of the lush outdoors, inviting natural light into the room.

Farm stay in Arezzo

4.97 out of 5 average rating, 237 reviews

Explore nature in the center of Vigneti Chianti

Feel close to the land in a rustic building on a Tuscan farm. Old stone walls, ceilings with exposed beams and terracotta floors are the backdrop to a characteristic apartment with fireplace. Plunge into an infinity pool for a unique view of the surrounding landscape. Dine outdoors, with the fresh air caressing you, sit and relax admiring the sunset under the ancient cypresses.