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Holiday houses in Caldana di Sopra

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Top-rated holiday rentals in Caldana di Sopra

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

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Top Guest favourite
A charming outdoor dining area features a round table set with delicate dishware and a pink tablecloth. Surrounding the table are intricately designed white chairs. A gazebo provides shade, and lush greenery is visible in the background, creating a serene setting for leisurely meals.
Farm stay in Ruscello
4.99 out of 5 average rating, 498 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 favourite
Home in Asciano
4.96 out of 5 average rating, 131 reviews

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

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, 151 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
4.94 out of 5 average rating, 125 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
The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.
Villa in Montepulciano
4.92 out of 5 average rating, 306 reviews

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

Top Guest favourite
The countryside property is nestled among lush greenery, featuring rustic architecture and terracotta roofs. Surrounded by rolling hills and trees, the natural landscape creates a peaceful setting. A gravel path leads to the house, enhancing the connection to the serene outdoor environment.
Farm stay in Sovicille
4.94 out of 5 average rating, 179 reviews

House at Gianni - Olmo

Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

Top Guest favourite
A welcoming living area features a sofa adorned with a patterned throw, set against a backdrop of wooden beams and a bright window. A coffee table sits on light wooden flooring, while a television is positioned on a stylish cabinet. An artwork depicting a charming pathway adds character.
Apartment in Ancaiano
4.98 out of 5 average rating, 110 reviews

Tower house in the countryside with sensory shower

Take it easy at this unique and tranquil getaway. Designed and built to respect Tuscan tradition, but with unique details to guarantee maximum relaxation and comfort while respecting nature. Fully equipped for short and long stays, with the possibility of using sought-after and exclusive services that you would never expect to find. A place tailored for those who love the well-being and tranquility of the countryside but without missing anything.

Superhost
A spacious bedroom features a double bed dressed in white linens, with a cozy armchair in the corner. Natural light enters through a window, illuminating the stone wall beside wooden beams above. A wooden table displays snacks and additional seating is available.
Condo in Castelnuovo dell’Abate
4.9 out of 5 average rating, 314 reviews

La Casetta di Brunello, very panoramic with terrace

STIAMO LAVORANDO PER VOI! ... WE ARE WORKING FOR YOU! The house is completely renovated and furnished in 2018 with classic-Tuscan style furniture. The colors are warm and enveloping to better rest during your holiday of peace and relaxation. In addition to the two double bedrooms, you have a kitchen with an equipped kitchenette, fridge, induction cooker and a furnished terrace with a beautiful view of the surrounding countryside.

Top Guest favourite
Villa in Monteroni d'Arbia
4.94 out of 5 average rating, 163 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).

Top Guest favourite
A dining table is set with elegant glassware and dinnerware, positioned on a terrace. The view reveals the skyline of Florence, with its historic buildings and rolling hills in the background. Greenery frames the scene, enhancing the outdoor dining experience.
Condo in Santo Spirito
5 out of 5 average rating, 112 reviews

Exclusive Florence Penthouse with city views

The truly Florentine soul of this exquisite apartment and its panoramic terrace sets the stage for an unforgettable stay. From this privileged vantage point above the rooftops, you can almost touch Florence’s monuments as you sip a sunset aperitivo, or greet the morning beneath the pergola with a leisurely breakfast while the city awakens in golden light.

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

Top 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, 110 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.

Popular amenities for Caldana di Sopra holiday rentals

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