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Holiday houses in Castel del Bosco

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Castel del Bosco

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

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Guest favourite
Townhouse in Scandicci
4.88 out of 5 average rating, 337 reviews

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

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Top Guest favourite
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, 344 reviews

Podere Vergianoni immerso nelChianti con piscina

Podere Vergianoni è un antica proprietà del 1600 a gestione familiare situato nelle splendide colline del Chianti in Toscana con la possibilità di organizzare navetta privata e esperienze locali direttamente con la nostra famiglia . L'appartamento è disponibile per 2 adulti con possibilità aggiunta divano letto per 2 bambini sotto i 12 anni . Nel grande cortile esterno troverete una piscina a sale con area relax su terrazza panoramica con vista su castello e vigneti con tramonti unici.

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Top Guest favourite
A rustic dining area features a long wooden table set with linens and decorative items. The space is illuminated by a chandelier and has large windows offering views of the surrounding landscape, with a stone fireplace and traditional frescoes adorning the walls.
Apartment in Carmignano
4.97 out of 5 average rating, 294 reviews

Giglio Blu Loft di Charme+ Air Conditioning

The accommodation is a portion of a historical noble residence dating back to the 14th century, adorned with frescoes and tastefully restored. It is located on the ground floor of a quiet and safe street, with a private and independent entrance and self check-in. The space is cozy, comfortable, and elegant, perfect for guests seeking an authentic Tuscan experience with modern comfort and technology. It is situated just a few kilometers away from Florence, Pisa, Lucca, Vinci, San Gimignano...

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Top Guest favourite
A spacious bedroom is characterized by exposed brick walls and wooden beams overhead. A large bed with a dark duvet is positioned centrally, accompanied by a rustic wooden table and an antique chair. Soft, natural light filters in, enhancing the authentic medieval ambiance.
Home in Lucca
4.99 out of 5 average rating, 81 reviews

Casa Torre medievale centro storico

Discover the charm of an 11th-century medieval tower, completely original from the period, in the heart of Lucca. Once home to the architects of the Cathedral and later to the bell-ringer, it stands at the foot of the bell tower — but the bells never ring, ensuring peace and restful sleep. Original furnishings, air conditioning, fast Wi-Fi, quality linens, views of the Cathedral and city walls, a small outdoor space, large handcrafted Italian beds, and private parking in front of the house.

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Superhost
Home in Montopoli
4.93 out of 5 average rating, 57 reviews

Villa Due Pini Marti con piscina privata

Villa con piscina tra Pisa e Firenze inserita in un incantevole contesto panoramico, gode di una superlativa vista a 360 gradi sull'incontaminata campagna toscana. Arredata con cura, e' composta da 2 camere matrimoniali di cui una al piano superiore soppalcato, 1 camera doppia al piano terra, bagno soggiorno cucina e sala da pranzo, ampia veranda con un vasto giardino e oliveto con una piscina di 12 metri lontana da sguardi indiscreti. La Piscina e' aperta dal 01 Maggio al 30 Settembre

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Guest favourite
Home in Barberino Tavarnelle
4.95 out of 5 average rating, 44 reviews

favolosa villa nel chianti, giardino panoramico

“DIMORA BADIA A PASSIGNANO” Vivrete una vacanza rilassante e ristorativa nel cuore del chianti classico. soggiornerete in un antico fienile totalmente restaurato in pietra con grande giardino recintato e un antico gazebo, adatto a gruppi numerosi e famiglie. le camere sono comode e spaziose per 8 persone. la ristrutturazione è stata eseguita finemente, tenendo conto di ogni minimo particolare estetico per poter farvi respirare l’antica tradizione toscana mixata con la comoda modernità.

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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, 227 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.

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Top Guest favourite
A spacious living area features exposed brick walls, wooden beams, and warm lighting. A comfortable sofa and a mid-century modern coffee table sit invitingly, while a dining table and chairs are positioned nearby. Large windows enhance the natural light, which complements the earthy tones of the room.
Condo in San Gimignano
5 out of 5 average rating, 62 reviews

AnticaVista, Luxury Apartment with Tower Views

A hidden gem nestled within the ancient walls of a 14th-century tower house, right in the heart of San Gimignano, a UNESCO World Heritage Site. This one-of-a-kind apartment is where history meets contemporary elegance. Look out the window and you’ll feel like you can almost touch the medieval towers. The view is breathtaking: unforgettable glimpses of the majestic Torre Grossa, framed by the iconic skyline that earned San Gimignano its nickname, the “Medieval Manhattan.”

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Top Guest favourite
Villa in Pistoia
5 out of 5 average rating, 84 reviews

Chiesino Dei Vaioni

Antica chiesa sconsacrata risalente ai primi del 900, originariamente costruita come cappella privata di Villa Philipson. Chiesino Dei Vaioni ha una struttura a loft con due camere matrimoniali su due soppalchi distinti. All’esterno cucina con forno a legna, giardini privato con viale alberato ed oliveto. I cancelli e le scale interne furono costruiti dalla Antica Fonderia Michelucci. Chiesino Dei Vaioni è immerso nella campagna toscana a pochi minuti dalla città.

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Luxe
Villa in Lucca
4.94 out of 5 average rating, 32 reviews

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.

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Guest favourite
A spacious freestanding bathtub is filled with water, adorned with floating flowers and candles. A small wooden table beside it holds a bucket of champagne and two glasses. Soft towels and a decorative rose are also visible, contributing to a relaxing ambiance.
Home in Fiesole
4.99 out of 5 average rating, 316 reviews

"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.

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Guest favourite
Dome in Volterra
4.96 out of 5 average rating, 149 reviews

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.

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Popular amenities for Castel del Bosco holiday rentals