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Vacation rentals in Castell'In Villa

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Top-rated vacation rentals in Castell'In Villa

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Guest favorite
Farm stay in Castelnuovo Berardenga
4.92 out of 5 average rating, 359 reviews

Apartment in a Tuscan farmhouse at Le Pietre Vive

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 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, 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 favorite
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 favorite
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.
Apartment in Bossi
4.91 out of 5 average rating, 81 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)

Superhost
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, 135 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 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
4.97 out of 5 average rating, 198 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 favorite
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, 107 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 favorite
A serene garden area is visible, featuring two wooden lounge chairs positioned on lush green grass. Surrounding plants and flowers add a touch of color. The stone house in the background features multiple windows, framed by greenery and terracotta pots.
Apartment in Villa A Sesta
4.94 out of 5 average rating, 245 reviews

Da Paola nel Chianti

Il mio appartamento è situato nel borgo di Villa a sesta, al pian terreno con accesso diretto al giardino, dispone di due camere, una matrimoniale , l'altra con letti a castello, due bagni, un ampia cucina e un soggiorno. lo spazio esterno è molto grande e il giardino dispone di un grande tavolo e poltrone per il relax, l'auto potrà essere parcheggiata a casa, abbiamo il posto auto privato, arrivati in paese si accede a casa da una piccola strada bianca (30mt).

Superhost
Home in Villa A Sesta
4.86 out of 5 average rating, 157 reviews

Casa Nataly Chianti - Jeky Stay

A typical Tuscan apartment in the heart of Chianti, part of Jeky's Stay. Ideal for bike rides, visits to villages like Siena, Pienza, San Gimignano, Montalcino, and Florence, and for reaching the Rapolano thermal baths. Tastings are available at local wineries or on-site with a sommelier and cooking classes. Private outdoor area, a garden with a view, and a nearby children's playground. There are three restaurants and a wine bar within walking distance.

Guest favorite
Villa in Siena
4.89 out of 5 average rating, 309 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 favorite
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.
Vacation home in Castelnuovo Berardenga
4.91 out of 5 average rating, 100 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 favorite
A welcoming entryway features a mural depicting a serene landscape framed by arches. Built-in shelves display decorative items and books. Natural light illuminates the wood flooring, while a small globe and a vase with dried plants add subtle warmth to the space.
Apartment in San Gusmè
4.98 out of 5 average rating, 129 reviews

Casa Guardiavigna | Chianti Hills Vineyard Retreat

L appartamento Casa Guardiavigna offre la possibilita’ di vivere un esperienza unica e straordinaria, carica di emozioni e di felicita’. Situato a due passi dal piccolo borgo medievale di San Gusme’ e’ circondato da splendide vigne, boschi e prati fioriti. Parcheggio gratuito interno con cancello automatico.

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