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Apartment vacation rentals in Castellina in Chianti

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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 ﺩ.ﺇ 220 per night before taxes and fees

  • Verified guest reviews

    Over 660 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Wi-Fi availability

    20 of Castellina in Chianti vacation rentals include wi-fi 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!

Top-rated apartment rentals in Castellina in Chianti

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

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Top guest favorite
A serene outdoor space features a weathered wooden bench and a round table with a plate, surrounded by lush greenery. Large arched windows provide a view into the brightly lit interior, complemented by colorful flower pots, enhancing the garden-like setting.
Apartment in Greve in Chianti
4.94 out of 5 average rating, 113 reviews

Chianti Patio Apartment

This gem of a Chianti location offers tranquility for its special garden, created by the owners over the last 40 years and is close to Florence and other Tuscan villages such as Siena, Lucca and Pisa for day trips. We also offer a small private pond with deck for those who want to enjoy the vineyard and olive tree views and have a swim. The apartment is very luminous and colorful with a large living and kitchen space, the bedroom and bath are secluded. The patio is right out the door.

Top guest favorite
A spacious piazza is surrounded by elegant medieval architecture, featuring a central hexagonal area with open-air seating. Stone pathways lead to various shaded spots, while umbrellas provide shelter for patrons. Beautiful clouds drift overhead, enhancing the vibrant scene of daily life in the historical center.
Apartment in Arezzo
5 out of 5 average rating, 153 reviews

Piazza Grande Boutique Apartment

Affacciato sulla più bella piazza del centro storico di Arezzo, dove si svolge la rievocazione della Giostra del Saracino, il Piazza Grande Boutique Apartment è situato al secondo piano di un palazzo medievale, con vista sui bellissimi palazzi e le Logge Vasariane ed è una location unica nel suo genere. L'arredamento, opera della contessa Cesaroni Venanzi è stato realizzato con bellissimi mobili antichi reinterpretrati in chiave moderna ed arricchiti da contaminazioni contemporanee.

Top guest favorite
Apartment in Castellina in Chianti
4.85 out of 5 average rating, 348 reviews

Dolce vita in Chianti. Pool and Relaxation

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 favorite
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
4.94 out of 5 average rating, 182 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 favorite
Apartment in Centro
4.92 out of 5 average rating, 104 reviews

Design & Vista Unica {Large Window}

Staying in this apartment means experiencing Florence at its most iconic point: the Ponte Vecchio. The apartment is bright, tastefully maintained and designed to offer an authentic and comfortable experience. Located in a building, with elevator access, rarely available to the public. The interiors combine Italian elegance and modern details: warm colors, refined furnishings and a cozy atmosphere that makes you feel right at home. Unparalleled view!

Top guest favorite
A restored stone mill stands surrounded by trees in a tranquil setting. The building features multi-level architecture with red window accents. A gravel pathway leads to the structure, while a vibrant green lawn and rustic stone borders enhance the natural landscape.
Apartment in Barberino Val d'Elsa
4.99 out of 5 average rating, 149 reviews

Apartment in Chianti at Mulino dell'Argenna

The apartment of the Roses is located inside the Mulino dell'Argenna guest house. The property was completely restored in 2015. It is an ancient stone mill dating back to 1400, built along the course of the Borro dell'Argenna. The Mill is an enchanting place, surrounded by the greenery of the forest, with a beautiful one-hectare park and a large swimming pool. An ideal place to spend your days in Tuscany in maximum privacy, in full contact with nature.

Guest favorite
A heated pool is positioned in a landscaped area, surrounded by greenery. The tranquil setting offers panoramic views of rolling hills and vineyards in the distance, enhancing the peaceful atmosphere.
Apartment in Castellina in Chianti
4.97 out of 5 average rating, 145 reviews

Visit Chianti, Siena, San Gimignano, Florence

Apartment into Borgo Sicelle Residence, in Chianti area, between Florence, Siena, S.Gimignano. The apartment, 2 people, has a kitchen, sat tv, double bedroom, bathroom with shower. It's on the first floor. Outside, there are shared tables and sun umbrellas. Heated pool until 25 degrees in Spring and Autumn In front of the property there is a restaurant, closed on Wednesday. There is no public transport to reach the property Car is required

Top guest favorite
A tranquil landscape is captured at sunrise, with the sun rising above a misty valley. Soft golden light filters through layered clouds, illuminating the distant hills. The scene conveys a sense of peace and natural beauty, set against a backdrop of serene fog.
Apartment in San Gimignano
4.93 out of 5 average rating, 129 reviews

Apartment with panoramic garden in San Gimignano

Located close to the walls of San Gimignano, the apartment is surrounded by nature with every desirable comfort and an amazing panoramic view. The apartment consists of 1 kitchen, 1 double bedroom, 1 living-dining room, panoramic garden and reserved parking next to the house. - 2 minutes' walk from the city center, surrounded by nature - panoramic view - every desirable comfort -private parking - 1 kitchen, 1 bedroom, 1 bathroom, 2 living rooms

Top guest favorite
An aerial view reveals the rustic stone farmhouse surrounded by lush greenery and vineyards. The inviting pool is set within a well-maintained garden, complemented by outdoor seating and barbecue areas, offering a peaceful retreat in the heart of the Tuscan countryside.
Apartment in Gavignano
4.92 out of 5 average rating, 384 reviews

Poggio Massiccioli

Cozy apartment for 4 people furnished in Tuscan style and with exposed beams immersed in the rolling hills of the Tuscan countryside. Guests have access to a furnished garden, free Wi-Fi, a shared swimming pool, a wood-burning oven, a barbecue, and a washing machine. The apartment was converted from a charming 19th-century stone farmhouse recently renovated according to Tuscan tradition and divided into three comfortable apartments.

Top guest favorite
A spacious terrace is shown, featuring comfortable seating arrangements, including lounge chairs and a small dining table. The area is partially shaded by awnings, with a view of the surrounding landscape. A table is set with fresh strawberries and beverages, inviting relaxation.
Apartment in Siena
5 out of 5 average rating, 101 reviews

Terrace on the walls of Siena - Casa Laura

Elegant apartment in the center of Siena with a large terrace, 600 m from the stadium and 1 km from Piazza del Campo. Located on the 4th floor (elevator up to the 3rd), it offers 2 double bedrooms, 2 bathrooms, an equipped kitchen, air conditioning in every room and a beautiful panoramic terrace above the historic walls. In the limited traffic zone. Perfect for experiencing Siena in comfort!

Top guest favorite
A cozy living room features two reclined leather chairs and a wooden table, complemented by a decorative rug. A rustic fireplace is positioned against a wall, and framed artworks adorn the space. Natural light streams through two wooden windows, enhancing the warm ambiance.
Apartment in Poggibonsi
5 out of 5 average rating, 129 reviews

Villa Mocarello "IL LECCIO"

This romantic apartment is located on the second floor of a 19th century Leopoldinian Villa. The independent entrance can be reached walking through the lush garden surrounding the house. The Villa is located in a strategic position in the middle of Tuscany, close to Florence, Siena and San Gimignano. the bus station is about ten minutes on foot, the train station about fifteen minutes,

Guest favorite
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
4.94 out of 5 average rating, 284 reviews

"Red Rose" apartment with view of Siena.

Caggiolo is a completely renovated farm consisting of several apartments, each with an independent entrance and private garden, with a panoramic view of Siena. Located in Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).

Popular amenities for Castellina in Chianti apartment rentals

When is the best time to visit Castellina in Chianti?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 529ﺩ.ﺇ 544ﺩ.ﺇ 595ﺩ.ﺇ 639ﺩ.ﺇ 606ﺩ.ﺇ 632ﺩ.ﺇ 632ﺩ.ﺇ 624ﺩ.ﺇ 624ﺩ.ﺇ 573ﺩ.ﺇ 558ﺩ.ﺇ 518
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