Some info has been automatically translated. Show original language

Holiday houses in Caldana di Sopra

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Caldana di Sopra

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

1 of 1 pages1 / 1
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 in Simignano
4.98 out of 5 average rating, 180 reviews

Casa al Gianni - The Simignano Barn

Transformed from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, and 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, complete with relaxation in the hot tub and al fresco dining. A memorable getaway awaits you in this slice of paradise!

Guest favourite
Home in Barberino Tavarnelle
4.95 out of 5 average rating, 41 reviews

Fabulous farmhouse in Chianti with a panoramic garden

“DIMORA BADIA IN PASSIGNANO” You will experience a wonderful and restorative vacation in the heart of the Chianti Classico region. You will stay in a fully restored, ancient stone barn with a large fenced garden and an old gazebo, suitable for large groups and families. The rooms are comfortable and spacious for 8 people. The renovation was carried out with great care, taking into account every aesthetic detail to allow you to experience the ancient Tuscan tradition mixed with comfortable modernity.

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 in Geggiano
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
The image captures a tranquil outdoor area featuring a swimming pool surrounded by well-maintained grass and foliage. A shaded structure offers seating beside the pool, with steps leading into the water visible. Rolling hills and clear blue skies are seen in the background.
Home in Sovicille
4.93 out of 5 average rating, 133 reviews

Podere Scorno country house with swimming pool

Piccola e accogliente casa di campagna ideale per coppie, su una collina della campagna senese. Edificio in stile toscano in pietra, con una storia secolare. La proprietà è stata comprata e ristrutturata a fine anni '90. Con un ampio giardino con piscina, frutteto, oliveto, vigna e orto, per gli amanti del verde. La piscina è aperta da metà maggio a fine settembre. Non accettiamo animali domestici. Informiamo i nostri ospiti che come host privati non siamo abilitati a fornire colazione.

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 in Gambassi Terme
5 out of 5 average rating, 221 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.

Guest favourite
A lush green facade covered in climbing ivy is depicted, showcasing a stone structure with large arched windows. Stone steps lead up to the entrance, surrounded by neatly arranged flower pots. The area is framed by vibrant greenery and a clear blue sky.
Barn in Siena
4.95 out of 5 average rating, 20 reviews

[Pool and private forest] Former farm la Locaia

Just 15 minutes from the historic center of Siena, our beautiful apartment is located within the Locaia, a former farmhouse that has been completely renovated with no less than 10 hectares of garden at your disposal Our immense courtyard has everything you need to enjoy an unforgettable stay, a beautiful saltwater pool and a dining area where you can enjoy meals in the open air The garden also has a small private forest to enjoy 100% of the nature of the Sienese hills

Guest favourite
Castle in Tignano
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
Villa in Monteroni d'Arbia
4.95 out of 5 average rating, 166 reviews

"Villa Daisy" overlooking Siena

Wonderful villa with independent entrance inside the "Caggiolo" farm, brought to light with careful and thorough renovation that has kept intact the typical features of a Tuscan farm. Beautiful panoramic view of Siena. Located in Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).

Guest favourite
A serene outdoor pool area features a rectangular swimming pool surrounded by wooden decking. Several lounge chairs are positioned nearby, along with a large umbrella for shade. Lush greenery and flowering plants enhance the tranquil atmosphere.
Holiday home in Siena
4.88 out of 5 average rating, 16 reviews

Borgo dei Fondi, Loggia Apartment

Apartment located on the first floor (12 steps) of a typical Tuscan farmhouse, surrounded by greenery, just 15 minutes from the center of Siena. It consists of a large living room with a kitchen, a double bedroom, a bedroom with three single beds (possibility of having a double bed), a bathroom with a shower, and a delightful outdoor loggia where you can eat all your meals.

Guest favourite
A spacious living room is presented with terracotta flooring and wooden beams overhead. A comfortable sofa arrangement surrounds a wooden coffee table, with a flat-screen TV positioned nearby. Natural light filters through the windows, enhancing the inviting ambiance.
Home in Monteriggioni
4.9 out of 5 average rating, 213 reviews

Siena Countryside Colle Ciupi

Countryside Villa apartment. Located in the nearby of Siena (Colle Ciupi, 10 kms away) Ground floor: Kitchen, living room with fireplace, bathroom with shower. First Floor: 3 Double Bedrooms and 2 bathrooms, outdoor with courtyard and huge garden

Guest favourite
An aerial view of the historic ex-convent showcases its rustic architecture surrounded by lush Tuscan countryside. The property is framed by pathways and green fields, revealing manicured gardens and trees. Nearby roads lead into the tranquil landscape, emphasizing the serene setting.
Apartment in Monteriggioni
4.9 out of 5 average rating, 111 reviews

Via Senese, Monteriggioni, Siena

“La Senesina” - Enchanting apartment immersed in the exquisitely beautiful Tuscan countryside, 4 km from Siena and 8 km from Monteriggioni. Ideal location from which to explore the most important towns and cities, rich in history, art and culture.

Top Guest favourite
A shaded outdoor terrace features a wooden pergola draped with green vines. A round table is set with a potted plant at its center, surrounded by several chairs. Stone paths lead to the entrance of the house, framed by blooming flowerbeds.
Home in Siena
4.98 out of 5 average rating, 214 reviews

Secret Garden Siena

A beautiful house located inside the city walls of Siena. The house develops on two floors has three bedrooms and two toilets. The real strong point of this location is the private garden. Walking distance to all the main attractions.

Popular amenities for Caldana di Sopra holiday rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Siena
  5. Caldana di Sopra