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Holiday rentals in Castell'In Villa

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Castell'In Villa

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

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Guest favourite
Flat in Siena
5.0 out of 5 average rating, 18 reviews

Pool Escape Just Outside Siena

Immerso nel cuore delle colline di Siena a soli 6 km dal centro, il nostro agriturismo è un rifugio di pace e bellezza, dove tradizione autenticità e amore per i cavalli si incontrano. Tra queste dolci colline vengono allevati e allenati i cavalli del Palio, simbolo di passione e tradizione senese. Gli ospiti possono avvicinarsi a questo mondo magico, osservando da vicino l’armonia tra uomo, cavallo e natura e la bellezza di un luogo dove l’eccellenza sportiva incontra il rispetto per l’animale.

Guest favourite
Farm stay in Castelnuovo Berardenga
4.92 out of 5 average rating, 356 reviews

Apartment in Tuscan farm house.

Small, cosy apartment with independent access, consisting of charming bedroom with a beautiful view, equipped with ample closet space, a comfortable canopy bed and private bathroom and pretty living room / breakfast area, with sofa-bed. A delicious breakfast is included in the price and from April through October guests also have the option of dining on-site in our traditional farm restaurant. If dates are not available the property includes other rooms in charming cottage also on Airbnb.

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, 155 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
Villa in Castell'In Villa
5.0 out of 5 average rating, 10 reviews

Villa marielena chianti farmhouse with hot tub - v

Villa Marielena is a beautifully restored Tuscan farmhouse located in the prestigious Castel in Villa area of Gaiole in Chianti, one of the most renowned wine regions in Italy. Surrounded by vineyards and olive groves, the villa offers privacy, panoramic views, and direct access to the landscapes that make Chianti famous. The property enjoys a privileged position for exploring Tuscany’s wine country. The vibrant town of Castelnuovo Berardenga is only 8 km away, while Siena and many of ...

Guest favourite
An outdoor terrace is highlighted by a wooden ceiling, featuring a dining table set for six and comfortable seating arrangements. Lush vineyard views extend beyond the railing, complemented by greenery. Subtle outdoor lighting enhances the space, creating an inviting area for relaxation and dining.
Flat in Bossi
4.91 out of 5 average rating, 79 reviews

Villino Ersilia Wine, il fascino del Chianti

Appartamento in fienile ristrutturato, immerso nei vigneti nel Chianti senese, a 15km dal centro storico di Siena. Posto auto, ingresso indipendente, al piano terra cucina, bagno con doccia, soggiorno con camino che affaccia su veranda con panorama meraviglioso, con zona relax e tavolo per godere di tramonti unici. Al piano primo camera matrimoniale con soppalco con ulteriore letto, bagno con doccia e camera con 2 letti a castello. Possibilità di affitto dell’intero villino (2 appartamenti)

Guest favourite
A serene bedroom features a spacious bed with a simple white coverlet. A wooden chair with a striped cushion is placed beside a bench. Natural light filters through the two wooden windows, revealing views of the lush vineyards outside.
Home in Castelnuovo Berardenga
4.9 out of 5 average rating, 133 reviews

La finestra del Chianti

Un luogo meraviglioso dove trascorrere alcuni giorni in piacevole compagnia. Un ampio salone con camino dove rilassarsi al rientro da bellissime passeggiate, giri in bicicletta, ed escursioni. L'appartamento indipendente si trova a 15km da Siena, 20 km dai centri Termali e a 40 minuti dai borghi di san Gimignano e Monteriggioni. Nel complesso è presente un'azienda agricola che produce vini e olio con la possibilità di visite guidate e degustazione dei nostri prodotti con cene a tema.

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
4.97 out of 5 average rating, 192 reviews

Casa al Gianni - Il Fienile di Simignano

Trasformato da un antico fienile, questo rifugio lussuoso offre 5 camere, 4 bagni, grande cucina attrezzata, ampio living, un ampio giardino privato con parcheggio, hot tub, patio con divani, BBQ, fire pit e cucina esterna. Ideale per chi cerca un'esperienza unica, unisce fascino rustico a comfort moderni. Perfetto per famiglie o gruppi, promette serate magiche sotto le stelle, tra relax nell'hot tub e cene all'aperto. Una fuga memorabile vi aspetta in questo angolo di paradiso!

Top guest favourite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Villa in Barberino Tavarnelle
4.98 out of 5 average rating, 105 reviews

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.

Top guest favourite
Apartment in Siena
5.0 out of 5 average rating, 20 reviews

Luxury Penthouse overlooking Piazza del Campo

Ci sono molte case a Siena. Ma pochissime possono dire di essere qui. Affacciato direttamente sulla piazza più iconica della città, questo attico offre un’esperienza rara: svegliarsi con la luce dorata che accarezza il Palazzo Pubblico e addormentarsi sopra uno dei luoghi più belli al mondo. La posizione è semplicemente irripetibile. Appena fuori dalla porta ti trovi immerso nella storia, tra ristoranti, vini e atmosfere senza tempo.

Guest favourite
Villa in Siena
4.89 out of 5 average rating, 307 reviews

Villa Capanna, Private Pool, Breathtaking Views

Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.

Guest favourite
A sparkling swimming pool is surrounded by sun loungers and umbrellas, offering a relaxing space for guests. The rustic farmhouse, with its stone exterior, is visible in the background, amidst lush greenery and trees under a partly cloudy sky.
Holiday home in Castelnuovo Berardenga
4.91 out of 5 average rating, 98 reviews

PIERFANTINI private Chianti house ♿️ 🏊‍♂️ 🐶

Pierfantini is a rustic farmhouse. It is located on a hill in the middle of a natural park. Isolated from the vitta, the nearest town is the medieval village of San Gusmè. The house is renovated and the ground floor adapted for disabled people or wheelchair users There are three apartments but I never rent them separately. The house rent is for all the property

Top guest favourite
A warm living area is presented, featuring a comfortable sofa adorned with soft pillows and a round dining table. The space is illuminated by wall sconces, while an arched entryway leads to another room. Large windows allow natural light to fill the area.
Farm stay in Gaiole in Chianti
4.96 out of 5 average rating, 114 reviews

La Pieve - the house next to the church

To the right of the Argenina church, after which it is named, it has the persuasive look of its 2 small arches facing west. Perhaps it was once the parish priest's house, or the one where cooking was done in the large wood-burning oven, who knows?

Popular amenities for Castell'In Villa holiday rentals