
Holiday houses in Castel del Bosco
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Top-rated holiday rentals in Castel del Bosco
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Fabulous villa in Chianti with a panoramic garden
"BADIA A PASSIGNANO DWELLING" You will experience a relaxing and restorative holiday in the heart of the Chianti Classico area. 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 little aesthetic detail to allow you to experience the ancient Tuscan tradition mixed with comfortable modernity.

Florence Sunset Hills • Giogoli
Escape to the peaceful hills of Giogoli where authentic Tuscan charm meets breathtaking views of Florence.Just 15 minutes from the city center and the Chianti countryside, this elegant home is the perfect base for exploring Tuscany while enjoying quiet mornings, unforgettable sunsets, and the beauty of the surrounding landscape. Surrounded by nature but close to the region's most iconic spots, it's the ideal retreat for anyone looking for comfort, tranquility, and a genuinely Tuscan experience

Church of the Vaioni
An ancient deconsecrated church dating back to the early 1900s, originally built as a private chapel of Villa Philipson. Chiesino Dei Vaioni has a loft structure with two double bedrooms on two separate mezzanines. Outside, there is a kitchen with a wood-burning oven, private gardens with a tree-lined avenue and an olive grove. The gates and internal stairs were built by the Antica Fonderia Michelucci. Chiesino Dei Vaioni is immersed in the Tuscan countryside just minutes from the city.

Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is a family-run, historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany. Our family can arrange a private shuttle and local experiences directly. The apartment is available for 2 adults with the option of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle and vineyards with unique sunsets.

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.

Historic Tuscan Home - Terrace & Private Garage
Discover the authentic charm of Tuscany by staying in an elegant, recently renovated 200 m² apartment in the heart of the historic center of San Miniato. Equipped with a separate entrance, a private garage connected to the house, a large panoramic terrace overlooking the hills and the sunset, and a private garden, it is the ideal place to experience a stay full of relaxation, comfort, history, and the flavors of the famous white truffle, halfway between Florence and Pisa.

Podere Tignano, 4-bedroom villa in the Chianti!
Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

[SAN LORENZO-DUOMO] Prestigious Historic Residence
Make your stay a unique experience and give yourself an emotion that will last for life. Located in the heart of Florence, this magnificent historic residence is the ideal solution for those looking for an exclusive and prestigious location to combine with a central position, perfect for easily visiting the main sites of interest, reachable in less than 10 minutes on foot. The apartment enjoys exclusive views of the Medici Chapels, offering a unique view.

Villa Lina, Luxury Farmhouse with Pool and Amazing
Lush vegetation invites you to surround to huge stretches of verdant woods. Extensive views towards the city of Lucca and the Tuscan rolling hills on the back are ready to embrace you during lazy summer days. Time can be stopped at Villa Lina, and you will easy forget your busy life left behind. If Stendhal syndrome is known to develop when encountering something overwhelmingly beautiful, then be careful, as you could be subject to it at this magic place.

"La limonaia" - Romantic Suite
Romantic Suite immersed in the enchanting hills of Fiesole. It is the ideal place fot those looking for unique and exclusive experience of its kind characterized by suggestive views and unforgettable sunsets. The accommodation is part of an old 19th century Tuscan farmhouse surrounded by its own olive groves and woods. This is an ideal place for a relaxing holiday and privileged base for visiting the major centers of interest in Tuscany.

Green Dome @ The Land Before Time Retreats
Nestled among Tuscan olive groves between Volterra and San Gimignano, The Land Before Time – Quad & Saddle Retreats offers 4 Green Domes with private jacuzzi, en-suite bathroom, air conditioning and Wi-Fi. Enjoy breakfast each morning in the Cupola Lounge with stunning views. During your stay, experience horseback rides through scenic trails, quad tours to discover hidden Tuscany, or simply relax under the starry sky.

Cercis - La Palmierina
The apartment is part of a completely fenced estate of 60 hectares of unspoiled nature: more than 1000 olive trees, countless cypresses and fragrant forests create an idyllic environment for those seeking tranquility and silence. The Palmierina estate is near Castelfalfi (a true jewel of medieval architecture) and close to Florence (50 Km), Siena (50 Km), and Pisa (50 Km). There are two golf courses nearby.
Popular amenities for Castel del Bosco holiday rentals
Other great holiday rentals in Castel del Bosco

Medieval Tower House in the Historic Center

Villa Due Pini Marti with private pool

AnticaVista, Luxury Apartment with Tower Views

Luxury tent in the countryside

Villa of the Hydrangeas

Villa Montefalcone: Charm, Private Pool, and Chef

Luxury Medieval Tower • Exclusive Chianti Stay

Herons Superior Apartment - Splendid view!
Destinations to explore
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Piazza del Duomo (Pisa)
- Basilica of Santa Maria Novella
- Mugello Circuit
- Stazione Santa Maria Novella
- Pisa Centrale Railway Station
- Mercato Centrale
- Spiagge Bianche
- Uffizi Gallery
- Gulf of Baratti
- Fortezza da Basso
- Parco delle Cascine
- Piazza della Repubblica
- Del Chianti
- Gorgona
- Piazzale Michelangelo
- Piazza della Signoria
- Palazzo Vecchio
- Pitti Palace
- Boboli's Garden
- Parco dell'Orecchiella





