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House holiday rentals in Castellina in Chianti

Find and book unique houses on Airbnb

Quick stats about house rentals in Castellina in Chianti

  • Total holiday rentals

    Explore 10 holiday rentals in Castellina in Chianti

  • Nightly prices starting at

    Castellina in Chianti holiday rentals start at $64 SGD per night before taxes and fees

  • Verified guest reviews

    Over 140 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Wifi availability

    10 of Castellina in Chianti holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Castellina in Chianti rentals

  • 4.5 Average rating

    Castellina in Chianti stays receive an average rating of 4.5 out of 5 from guests

Top-rated house rentals in Castellina in Chianti

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

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Guest favourite
A charming pathway leads to the entrance of the house, surrounded by lush greenery. Flower pots are positioned along the stone walkway, with a seating area visible to the side, inviting guests to enjoy the serene landscape of rolling hills in the background.
Home in Greve in Chianti
4.97 out of 5 average rating, 237 reviews

Amore in Chianti

Benvenuti nella deliziosa casetta di Riccardo e Pauline, un piccolo angolo d'amore dove colori e dettagli sono pensati per donare pace e tranquillita'. Vi troverete immersi nel verde delle colline Toscane, dentro un paesaggio mozzafiato dove nasce il rinomato vino Chianti Classico. La zona è ideale per passeggiare a piedi e in bicicletta. Sarete vcino alle città d'arte come Firenze, Siena e Arezzo. Su richiesta e disponibilità offriamo un servizio navetta a pagamento. Vi aspettiamo con gioia ❤️

ValueFamilyWifi

Guest favourite
The kitchen area features wooden cabinetry and modern appliances, including a microwave and coffee maker. A round wooden table with simple chairs is surrounded by natural light from large windows, offering views of the surrounding vineyards.
Home in Greve in Chianti
4.95 out of 5 average rating, 100 reviews

Agriturismo Casa Giulia di Sopra

L'appartamento CASA GIULIA DI SOPRA, ristrutturato nel 2022 e situato al primo piano, è una porzione di un'antica colonica situata nel cuore del Chianti Classico. E' circondato dai vigneti di Villa Calcinaia, tenuta di proprietà dei Conti Capponi dal 1524. L'appartamento si trova a 130 mt. di distanza dalla piscina condivisa, aperta da maggio ad ottobre.L'appartamento dispone di un'area esterna dotata di tavolo e sedie dove gli ospiti potranno desinare e godersi un bicchiere di vino al tramonto.

LocationFamilyCheck-in

Top guest favourite
A stone wall is adorned with vibrant red climbing roses, creating a striking contrast against the rustic texture. A window with a black grid pattern is visible, framed by the lush greenery of surrounding plants, enhancing the inviting character of the setting.
Home in Castellina in Chianti
4.97 out of 5 average rating, 118 reviews

Leonardo - Chianti/Siena, Firenze, San Gimignano.

Ancient stone house from the 15th century in a small renovated medieval hamlet in the heart of the Chianti Classico. Located on top of a hill between Florence, Siena and San Gimignano. TENNIS COURT+ SWIMMING POOL Splendid view over the valley. Independent entrance; On the ground floor: large living room with two sofas, dining area and open kitchen. On the 1st floor: 2 bedrooms and 1 bathroom with shower; Private garden with terrace - table and chairs for eating under the gazebo and sun loungers

LocationFamilyAmenities

Guest favourite
Home in Asciano
4.96 out of 5 average rating, 135 reviews

Palazzo Monaci - Piscina nelle crete Senesi

Benvenuti a Palazzo Monaci ! Un' oasi di natura e bellezza unica, nel cuore delle Crete Senesi, in Toscana. Un residence con piscina e vista mozzafiato sulle crete senesi. Perfetta per coppie o famiglie in cerca di una vacanza rilassante. La posizione è perfetta per esplorare le zone limitrofe. Potrete fare escursioni nella campagna toscana, visitare i borghi medievali caratteristici, assaggiare i vini locali prelibati e immergervi nella cultura e nella storia di questa affascinante regione.

LocationFamilyLong stay

Top guest favourite
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, 239 reviews

Tramonto sul Chianti Classico

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.

ValueFamilyTV

Top guest favourite
The image showcases a refreshing pool surrounded by lounge chairs and umbrellas, enhancing the outdoor relaxation area. The pool is framed by lush greenery and a stone wall, with the charming rustic house visible in the background under a clear blue sky.
Home in San Filippo a Ponzano
5 out of 5 average rating, 136 reviews

Infinity pool in Chianti 1

Sulle colline del Chianti, porzione di antica casa colonica in pietra del 1800, situata a S. Filippo una piccola frazione di Barberino Tavarnelle, a metà strada tra Firenze e Siena, a 30 minuti di macchina dall'aeroporto di Firenze, a 1 ora da quello di Pisa. Tre camere da letto, due bagni, ampia sala con camino, cucina abitabile e sala da pranzo. Vista magnifica sulle colline da ogni finestra! Splendida piscina a sfioro con zona idromassaggio, non riscaldata e aperta da Aprile a Ottobre.

LocationValueCleanliness

Top guest favourite
Home in Greve in Chianti
4.99 out of 5 average rating, 109 reviews

Relax e charme tra le colline del chianti

Bellissima colonica in pietra, indipendente, immersa tra gli olivi e le colline del Chianti, con giardino privato e piscina panoramica. Piano terra con ampi saloni, antico camino e forno a legna, soggiorno luminoso e cucina full optional. Al primo piano tre suites composte da camera, studio e bagno privato. Accesso tramite cancello e strada bianca in proprietà privata a soli 500 metri dal paese di Strada in Chianti. Ideale per quiete e relax. Location strategica per visitare la Toscana.

LocationValueTV

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
4.98 out of 5 average rating, 187 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!

FamilyValueGrill

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.

LocationValueCheck-in

Top guest favourite
A lush green garden is framed by a rustic pergola made of wooden beams. Grassy paths lead deeper into the garden, where vibrant flowers and trees provide a natural backdrop. Rolling hills and a clear blue sky are visible in the distance, creating a serene outdoor setting.
Home in Castellina in Chianti
4.99 out of 5 average rating, 134 reviews

Private Chianti Cottage, Garden & Vineyard Views

Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

LocationFamilySleep quality

Top guest favourite
Home in Il Poggetto
4.93 out of 5 average rating, 150 reviews

La Loggia

Immerse yourself in the authentic Tuscan dream. "La Loggia" is a charming home in the heart of Chianti Classico, just 300 meters on foot from the historic center of Radda. It offers the perfect blend of countryside quietness and village convenience, featuring a large private garden with breathtaking panoramic views over vineyards and a beautiful glass-enclosed loggia. The perfect oasis to relax and enjoy the sunset after exploring Siena, Florence, and nearby wineries.

ValueFamilyCheckout

Superhost
Home in Tavarnelle Val di Pesa
4.86 out of 5 average rating, 212 reviews

La Casa di Nada Home

In my home, you can experience the most authentic side of Tuscany, filled with peace, warmth and family traditions. Surrounded by olive groves and vineyards in the heart of Chianti, you will have a private garden all to yourself, where you can relax in complete tranquillity. On request, you can join a cooking class in the house, preparing our family recipes handed down by Grandma Graziella, or share a special dinner in an intimate and welcoming atmosphere.

ValueFamilyKitchen

Popular amenities for house rentals in Castellina in Chianti