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Holiday rentals in Castellina Scalo

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Top-rated holiday rentals in Castellina Scalo

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

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Top guest favourite
An outdoor patio area features rustic furnishings and is framed by gracefully draping curtains. The space is adorned with comfortable seating and a communal dining table, set against a backdrop of tall cypress trees and a clear blue sky, inviting relaxation in a serene environment.
Home
4.98 out of 5 average rating, 182 reviews

Casa al Gianni - The Simignano Barn

Converted from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit and an outdoor kitchen. Ideal for those seeking a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, with relaxation in the hot tub and al fresco dining. A memorable getaway awaits you in this little slice of paradise!

Top guest favourite
An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.
Cottage
4.99 out of 5 average rating, 153 reviews

Villa di Geggiano – Guesthouse

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

Guest favourite
An aerial view of the historic Monteriggioni Castle showcases its medieval architecture surrounded by lush countryside. The fortified walls encircle the village, which is dotted with trees and buildings, while rolling hills extend into the distance under a sunset sky.
Cottage
4.95 out of 5 average rating, 289 reviews

Monteriggioni Castello, holiday house in Tuscany

Il nostro alloggio è un edificio storico che risale alla costruzione del castello. È stato recentemente restaurato e arredato con cura in tutti i dettagli. È molto accogliente e dispone di tutti i più moderni servizi. I turisti che decideranno di essere nostri ospiti, avranno il vantaggio di vivere nell' ambiente medievale del castello, usufruendo di tutti i confort. Si sentiranno coccolati e avranno l'opportunità di tornare indientro vivendo un' esperienza unica e indimenticabile.

Top guest favourite
An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.
Home
5 out of 5 average rating, 223 reviews

Il Fienile, Luxury Apartment in the Tuscan Hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

Top guest favourite
A lush green garden is framed by a rustic pergola made of wooden beams. Grassy paths lead deeper into the garden, where vibrant flowers and trees provide a natural backdrop. Rolling hills and a clear blue sky are visible in the distance, creating a serene outdoor setting.
Home
4.98 out of 5 average rating, 131 reviews

Private Chianti Cottage, Garden & Vineyard Views

Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

Top guest favourite
A living area is seen with a light-colored sofa facing a flat-screen TV on a wooden unit. A glass coffee table is positioned in front of the sofa, and natural light filters through sheer curtains. A black chair and decorative items are present on shelves.
Apartment
4.98 out of 5 average rating, 120 reviews

Above the Post Office

Apartment located in a village in the municipality of Monteriggioni, on the borders of Chianti. The village is located along the ancient Via Francigena. It is about 10 minutes from Siena, Poggibonsi, and Colle di val d'Elsa. It is about 20 minutes from San Gimignano, 40 minutes from Florence, 60 from Pisa and Arezzo. It is possible to move from the village by bus, train, car, bicycle. It is also possible to reach Monteriggioni via a cycle path (20 minutes on foot).

Guest favourite
Castle
5 out of 5 average rating, 24 reviews

Luxury Medieval Tower • Exclusive Chianti Stay

Benvenuti in una delle residenze più esclusive del Chianti: una torre medievale trasformata in un raffinato luxury retreat con vista sulle colline toscane. Design contemporaneo, arredi iconici, opere d’arte e comfort di lusso si fondono in un’esperienza unica. Un’oasi di quiete con giardino privato, dependance vetrata, Wi-Fi, area smart working. Servizi extra: chef privato, degustazioni in cantina, trattamenti benessere e tour tra i borghi più belli della Toscana.

Top guest favourite
Apartment
5 out of 5 average rating, 15 reviews

Luxury penthouse with a view of Piazza del Campo

There are many houses in Siena. But very few can say they are here. Overlooking the city's most iconic square, this penthouse offers a rare experience: Waking up to the golden light that caresses the Palazzo Pubblico and falling asleep above one of the most beautiful places in the world. The location is quite simply unique. As soon as you step out the door, you find yourself immersed in history, surrounded by restaurants, wine and a timeless atmosphere.

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
4.99 out of 5 average rating, 475 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.

Guest favourite
A compact kitchen includes modern cabinets and a wooden countertop. A gas stove and a sink are positioned against the wall, while a window allows natural light to enter. The floor features tiled patterns, adding a practical touch to the space.
Apartment
4.89 out of 5 average rating, 18 reviews

Da nonna Cri, apartment in Chianti

The apartment with independent entrance is in a strategic position to easily visit all of Tuscany and plan a wonderful trip between nature, art, history and culture. Just minutes from Monteriggioni and Siena, located 1 km from the Siena-Florence highway, it also allows you to easily reach the other beautiful cities of Tuscany. By motorbike, by bike, or by car, it will be the ideal point to visit the beautiful hills of Chianti.

Top guest favourite
A spacious living area features a modern design, with a prominent stone fireplace and minimalist furniture. Large glass doors open to a serene outdoor view, while natural light brightens the room, highlighting the soft tones of the walls and furnishings.
Tower
4.95 out of 5 average rating, 214 reviews

A Big Dream in a Little Tower.

The Tower was created in the late 1800s by an illustrious Englishman, Sir John Temple Leader, in one of the oldest and most important stone quarries belonging to the Medici family. From the same quarry were extracted many important works such as the columns of the Medici chapels, the steps of the Laurenziana library .. all just 5 km from the historic center of Florence.

Top guest favourite
The aerial view captures the historic structure nestled among rolling green hills, framed by tall trees. The stone walls reflect medieval architecture, while a terrace offers an inviting space below. The surrounding landscape showcases farms and cypress trees against a clear blue sky.
Home
4.98 out of 5 average rating, 219 reviews

"La Lambarda" tower Suite

In Val d'Orcia there is a small medieval village called Monticchiello, surrounded by walls and protected by four towers; one of these is the "La Lambarda", which stands at the highest point of the country and enjoys a panoramic view across the valley.

Popular amenities for Castellina Scalo holiday rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Siena
  5. Castellina Scalo