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Vacation rentals in Castel Castagnaio

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Top-rated vacation rentals in Castel Castagnaio

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Top guest favorite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Condo in Noce
5 out of 5 average rating, 339 reviews

Podere Vergianoni immerso nelChianti con piscina

Podere Vergianoni is an ancient and historic property dating back to the 17th century, located in the beautiful hills of Chianti in Tuscany, with the possibility of organizing a shuttle service and exclusive experiences tailored to you. The apartment is available for 2 adults, with the possibility of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard, you'll find a saltwater swimming pool with a relaxation area on a panoramic terrace overlooking the castle, hills, and vineyards, with incomparable sunsets.

Top guest favorite
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

Converted from an old 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 looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, including relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!

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

Fabulous farmhouse in Chianti, panoramic garden

"DIMORA BADIA IN PASSIGNANO" You will experience a wonderful and restorative vacation in the heart of the Chianti Classico area. You will stay in a fully restored old 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 combined with comfortable modernity.

Top guest favorite
A spacious terrace is furnished with a large, comfortable sofa and a stylish dining table surrounded by six chairs. Various plants add greenery to the setting. The view over the cityscape, with rooftops and distant landmarks, creates an inviting outdoor living space.
Condo in Centro
4.99 out of 5 average rating, 106 reviews

Acciaiuoli Penthouse Florence Terrace View

Nel cuore del centro storico di Firenze, attico di lusso con terrazza esclusiva ed emozionanti vedute del Duomo,di Palazzo Vecchio e dell’intero panorama della città. Perfetto per famiglie e amici questo appartamento è completamente ristrutturato con finiture di alto pregio, situato al quinto e ultimo piano senza ascensore, si devono salire 106 comodi scalini per arrivare in paradiso ( l’host vi darà una mano a portare le valigie ), tutte le finestre offrono bellissime viste sul centro storico.

Top guest favorite
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.

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, 237 reviews

The Chianti Classico Sunset

Se cercate una location idilliaca nel cuore del Chianti classico, immersi nei vigneti e oliveti delle splendide colline toscane, nel podere di una Villa storica del ‘500, allora venite nel nostro fienile!! Ha una posizione dominante con una vista strepitosa, dove è possibile godersi tramonti mozzafiato. La totale indipendenza della casa, l'accogliente giardino, il grande loggiato permettono di trascorrere soggiorni in totale tranquillità. Le nostre recensioni sono la vostra migliore garanzia.

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, 222 reviews

The Castle of Ferrano - Castle in Tuscany

Try the experience of staying in a real Castle! Il Castello di Ferrano offers to its hosts the chance of living an unforgettable experience: you will be the only guests in the castle, and everything will be for you (private pool from June to September, gardens etc..). 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
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, 427 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 just 35 minutes by car 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.

Top guest favorite
The historic tower-penthouse villa is surrounded by lush greenery and trees. The three-story structure is characterized by its earthy facade and wooden shutters. Well-maintained gardens with various plants create a serene outdoor environment, enhancing the villa's tranquil charm and historical significance.
Castle in Bagno A Ripoli
4.96 out of 5 average rating, 134 reviews

Tower Penthouse in small castle near Florence

900 year old tower-penthouse apartment in Chianti Villa, spacious & super-scenic historical home that combines magical atmosphere with space, light, character, convenience. Painting-like 360° views of Tuscan Hills all the way to Florence; sun-filled, private grounds. Perfect location for an unforgettable family stay. Ample private property (including forest). Walking distance from village shops. Convenient location, Florence in sight.

Top guest favorite
A rustic stone house is illuminated in the evening light, showcasing large windows framed by greenery. Colorful foliage adorns the exterior, complemented by a well-maintained garden area. The structure's classic architectural features highlight its authentic charm.
Villa in Bagno A Ripoli
4.98 out of 5 average rating, 141 reviews

Farmhouse on Florence hill

Two levels 800th rustic country house, on the hills surrounding the town with original forniture and a stunning view of the facing valley, a beautiful patio and large garden. 15 min driving from center, well placed for Chianti area, Siena, San Gimignano. 1hr driving to Pisa, Lucca, Volterra, Arezzo, Cortona and much more! Possible to have cooking class or dinners with my personal chefs Mirella and Stefano!

Top guest favorite
Home in Florence
5 out of 5 average rating, 6 reviews

I Palpiti - Dream Villa in the heart of Florence

Discover the charm of staying in a historic residence nestled in the green hills of Fiesole, just minutes from the center of Florence. This house, once the Tuscan home of painter Elisabeth Chaplin, retains the artistic spirit and tranquility that made it a creative haven and a soulful retreat. You’ll sleep where the artist once painted her works, surrounded by authentic details and a poetic atmosphere.

Top guest favorite
Home in Florence
5 out of 5 average rating, 8 reviews

Villa Carla – Florence View, Tennis & Hot Tub

Escape to a peaceful Tuscan hillside while staying just 15 minutes by car from Piazza del Duomo, in the heart of Florence. Villa Carla combines the tranquillity of the countryside with one of the city’s most spectacular panoramic views. Relax in the spa pool overlooking Florence, enjoy a private tennis court, and dine under the gazebo as the city lights come alive at sunset.

Popular amenities for Castel Castagnaio vacation rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Castel Castagnaio