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Apartment vacation rentals in Castellina in Chianti

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Top-rated apartment rentals in Castellina in Chianti

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Top guest favourite
The open-plan living area features wooden beams across the ceiling. Natural light filters through multiple windows, illuminating the cozy seating and dining areas. A rustic stone wall adds character, while a wooden table and light-colored chairs provide a functional dining space.
Apartment in San Gimignano
4.97 out of 5 average rating, 237 reviews

Casa Irene

Casa Irene è un delizioso appartamento in stile Toscano, situato al secondo ed ultimo piano di una palazzina a soli 5 minuti a piedi dal centro,50 mt per porta San Matteo ed altri 50 mt per la via Francigena. Data la posizione defilata si raggiunge facilmente in auto per parcheggiare nell'immediato parcheggio libero. L'appartamento dotato di wifi ed aria condizionata si suddivide in sala/cucina openspace,camera e bagno con doccia ed un terrazzo abitabile con affacci sulle mura di San Gimignano

Top guest favourite
An inviting interior features exposed brick walls and a blend of modern and rustic design elements. A staircase leads to the upper floor, while large doors open to reveal a view of the outdoors. A wooden table and a cozy chair enhance the living space.
Apartment in Montepulciano
4.97 out of 5 average rating, 118 reviews

Under the sunset, Montepulciano

In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting for all the guests of our 4 apartments We can organize barbecue with paired wines after 7 pm. Large free parking area 100 mt away

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
4.96 out of 5 average rating, 226 reviews

Giglio Blu Loft di Charme

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...

Top guest favourite
The rustic exterior of the stone cottage features a traditional red-tiled roof and large arched windows. Lush greenery and flowering plants surround the building, while the rolling hills of Tuscany are visible in the background under a clear sky.
Apartment in Poggibonsi
4.91 out of 5 average rating, 105 reviews

Cottage San Martino con ampia terrazza panoramica

Appartamento di 45 mq a San Martino ai colli, situato lungo la via Cassia e circondato dalla bella campagna toscana. Perfetto per chi ha voglia di visitare le attrazioni della zona: San Gimignano, Monteriggioni, il Chianti, Siena (20 min.), Firenze (30 min.), Volterra (40 min.). A 2 minuti dal raccordo autostradale Firenze-Siena e vicino al centro urbano di Poggibonsi e Barberino-Tavarnelle. La casa è dotata di un'ampia terrazza dove potersi rilassare e ammirare le colline del Chianti.

Top guest favourite
A scenic view captures a lush landscape with rolling hills, vineyards, and olive trees under a colorful sunset. The traditional Tuscan casolare is visible in the background, surrounded by greenery, while the horizon features soft hues of orange and pink.
Apartment in Poggibonsi
4.99 out of 5 average rating, 297 reviews

Laura Chianti Vacanze

Laura Chianti Vacanze è la soluzione ideale per chi cerca pace e tranquillità immerso nelle campagne del Chianti. L'appartamento, a metà strada tra Firenze e Siena, si trova in una posizione strategica per raggiungere velocemente Firenze, Siena, San Gimignano , Volterra, nonché le meravigliose colline del Chianti. L'appartamento dispone di ampio parcheggio privato, due camere, cucina attrezzata, bagno privato, giardino privato, barbecue, ed una stupenda vista sulle colline del Chianti.

Guest favourite
A spacious bedroom features a large bed with a light-colored duvet and striped pillows. Soft lighting is provided by wall sconces on either side. Two windows with sheer curtains allow natural light to fill the room. A small glass table and decorative rug add warmth.
Apartment in Castellina in Chianti
4.84 out of 5 average rating, 320 reviews

Relax Chianti. Appartamento con piscina e giardino

Appartamento immerso nelle colline del Chianti Classico, nel Borgo di Tregole, a 5 km da Castellina in Chianti. Casa Cinzia è un appartamento privato all'interno di un casale tipico Toscano. Adatto a coloro che desiderano passare una vacanza immersi nella natura all'insegna del completo relax e del silenzio. Ideale punto di partenza per visitare i più importanti luoghi della Toscana. L'appartamento è dotato di tutti i comfort. Biancheria inclusa nel prezzo. I bambini sono i benvenuti

Guest favourite
A heated pool is surrounded by lush greenery, offering scenic views of the rolling hills. The pool's clear water reflects the sky, while a fenced area provides safety. Flowering plants are positioned along the edges, enhancing the natural beauty of the setting.
Apartment in Castellina in Chianti
4.95 out of 5 average rating, 185 reviews

Visit Chianti,Siena, Florence, S.Gimignano

Apartment into Borgo Sicelle Residence, in Castellina inChianti area (between Florence, Siena, S.Gimignano). Two people. It has a kitchen, a double bedroom, a bathroom with shower. It's on the first floor. Outside, on the ground floor,there are shared tables. Pool heated up to25 degrees in Spring and Autumn In front of the property there is a restaurant (Osteria Uscio e Bottega), only for dinner, closed on Wed. There is no public transport to reach the property Car is required

Guest favourite
An outdoor seating area features rustic wooden furniture, including a dining table and chairs, under a shaded canopy. Lush greenery surrounds the space, complemented by terracotta planters filled with vibrant plants. The scenic landscape offers a glimpse of the natural beauty of the Chianti region.
Apartment in Barberino Tavarnelle
4.9 out of 5 average rating, 113 reviews

Casa Poggio a Badia & Chianti view

Casa Poggio a Badia it's a typical Chianti's country house, spread in 130 square meters on two floors, the ground floor it's a large living area with a large kitchen full equipped , a sofa in front of the fire place and a bathroom . Up stairs there is two large double bedrooms and one open bedroom with two single bed always attachable and relaxing bath with bathtub Regina of Devon&Devon All the bedroom offer e superb view on the valley and on Badia a Passignano

Guest favourite
A historic villa is situated amidst lush, rolling hills, surrounded by vineyards. The exterior features a traditional stone facade, large windows, and terracotta roof tiles. Manicured gardens with circular patterns enhance the property's charm, complemented by tall cypress trees framing the serene landscape.
Apartment in Castelnuovo Berardenga
4.93 out of 5 average rating, 167 reviews

Villa di Geggiano - Perellino Suite

The 700 years old Villa di Geggiano, surrounded by our working vineyard and lovingly maintained gardens, is located in Chianti in Tuscany which is one of the most beautiful regions of Italy. Our guesthouse is located in one of the original garden pavilions of the villa. PLEASE NOTE THAT WE ARE IN THE COUNTRYSIDE WITH VERY FEW PUBLIC TRANSPORT OTHER THAN TAXI SO THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A RENTAL CAR.

Guest favourite
An aerial view of a beautiful countryside property is shown, featuring a stone farmhouse surrounded by lush greenery, gardens, and vineyards. A shared swimming pool is visible, along with outdoor seating areas and well-maintained landscaping that highlights the tranquil rural setting.
Apartment in Gavignano
4.91 out of 5 average rating, 321 reviews

holidays with swimming pool in Tuscany

Piccolo e confortevole appartamento per 2 persone arredato in stile toscano e con travi a vista,immerso tra le dolci colline della campagna toscana. A disposizione degli ospiti spazio esterno con tavolo,piscina condivisa,forno a legna e barbecue,piccola lavanderia,wi-fi. L'appartamento è stato ricavato da una graziosa casa colonica in pietra del 1800 recentemente ristrutturata secondo la tradizione toscana e suddivisa in tre comodi appartamenti

Guest favourite
A serene outdoor area features a swimming pool surrounded by landscaped gardens. A wooden deck with seating overlooks the pool, while a large umbrella provides shade. The two-story villa is positioned above, framed by vibrant greenery and a clear blue sky.
Apartment in Carpineto
4.94 out of 5 average rating, 183 reviews

Campagna Toscana, pace e relax a 10 min da Siena

Il nostro alloggio è vicino a Siena, quindi alla vita notturna, al centro città ma anche al piccolo aeroporto di Ampugnano, ai parchi, e al trasporto pubblico. Vi piacerà il nostro alloggio per la luce, la comodità del letto, la cucina, l'intimità e i soffitti alti. Il nostro alloggio è adatto a coppie, avventurieri solitari, a chi viaggia per lavoro, alle famiglie (con bambini) e amici pelosi (animali domestici).

Guest favourite
An outdoor dining area is surrounded by lush greenery and flowering plants, featuring a circular table with four elegant wrought iron chairs. A cozy blanket is draped over one chair, and a scenic view of rolling hills extends in the background under a muted sky.
Apartment in Monteroni d'Arbia
4.95 out of 5 average rating, 262 reviews

Appartamento "Red Rose" con vista su Siena.

Caggiolo è un podere completamente ristrutturato composto da più appartamenti, ognuno con ingresso indipendente e giardino privato, con vista panoramica su Siena. Situato alle Ville di Corsano, a soli 14 km dalla città. Luogo ideale per trascorrere giorni in totale relax e godere delle meraviglie che questa zona offre (Chianti, Val d'Orcia, Crete Senesi..).

Popular amenities for Castellina in Chianti apartment rentals

When is the best time to visit Castellina in Chianti?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$175 CAD$179 CAD$185 CAD$234 CAD$235 CAD$249 CAD$204 CAD$220 CAD$228 CAD$211 CAD$178 CAD$181 CAD
Avg. temp7 °C8 °C11 °C14 °C18 °C23 °C25 °C25 °C21 °C16 °C11 °C7 °C

Quick stats about apartment rentals in Castellina in Chianti

  • Total vacation rentals

    Explore 20 vacation rentals in Castellina in Chianti

  • Nightly prices starting at

    Castellina in Chianti vacation rentals start at $98 CAD per night before taxes and fees

  • Verified guest reviews

    Over 500 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Wifi availability

    20 of Castellina in Chianti vacation rentals include wifi access

  • Popular amenities for guests

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

  • 4.8 Average rating

    Castellina in Chianti stays are highly rated by guests—averaging 4.8 out of 5!