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Apartment holiday rentals in Castellina in Chianti

Find and book unique apartments on Airbnb

Quick stats about apartment rentals in Castellina in Chianti

  • Total holiday rentals

    Explore 20 holiday rentals in Castellina in Chianti

  • Nightly prices starting at

    Castellina in Chianti holiday rentals start at $85 AUD per night before taxes and fees

  • Verified guest reviews

    Over 660 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Wi-Fi availability

    20 of Castellina in Chianti holiday 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 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
4.97 out of 5 average rating, 295 reviews

Giglio Blu Charming Loft + Air Conditioning

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...

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Top Guest favourite
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
5.0 out of 5 average rating, 153 reviews

Piazza Grande Boutique Apartment

Overlooking the most beautiful square in the historic center of Arezzo, where the re-enactment of the Giostra del Saracino takes place, the Piazza Grande Boutique Apartment is located on the second floor of a medieval building, overlooking the beautiful palaces and the Vasari Loggias and is a unique location of its kind. The decor, the work of Countess Cesaroni Venanzi, was created with beautiful antique furniture reinterpreted in a modern way and enriched with contemporary influences.

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Top Guest favourite
A spacious bedroom features a double bed adorned with a yellow bedspread. Natural light floods in from wide glass doors leading to a balcony with views of the valley. A cozy seating area includes two armchairs and a small table, complemented by decorative curtains.
Apartment in Montepulciano
4.98 out of 5 average rating, 165 reviews

Stuart White Tea Central Panoramic & Garden

Offering ample space, the apartment features two double bedrooms, two full bathrooms, and a living room with a kitchen. The bedroom balconies offer stunning views of the valley and natural light. Its proximity to all town amenities ensures convenience, while a delightful café downstairs provides a delectable gourmet breakfast. It has also access to a secluded, terraced backyard garden. It provides a comfortable retreat perfect for long term stays. A public parking is available nearby.

LocationFamilyCheck-in

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
4.94 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.

LocationValueAir conditioning

Top Guest favourite
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, 243 reviews

At Paola's in Chianti

My apartment is located in the village of Villa a Sesta, on the ground floor with direct access to the garden, has two bedrooms, one double, the other with bunk beds, two bathrooms, a large kitchen and a living room. The outdoor space is very large and the garden has a large table and armchairs for relaxation, the car can be parked at home, we have a private parking space, arriving in the village you access the house from a small white road (30mt).

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Top Guest favourite
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

LocationValueLong stay

Top Guest favourite
Apartment in Castellina in Chianti
4.85 out of 5 average rating, 348 reviews

La dolce vita in Chianti. Swimming pool and relaxation

Apartment nestled in the hills of Chianti Classico, in the village of Tregole, 5 km from Castellina in Chianti. Casa Cinzia is a private apartment inside a typical Tuscan farmhouse. Suitable for those who wish to spend a holiday immersed in nature in complete relaxation and silence. Ideal starting point for visiting the most important places in Tuscany. The apartment is equipped with all comforts. Linen included in the price. Children are welcome

FamilyLocationBeach

Top Guest favourite
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 nestled among the rolling hills of the Tuscan countryside. Available to guests is an equipped garden, free Wi-Fi, a shared equipped swimming pool, a wood-burning oven and 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.

LocationFamilyAmenities

Top Guest favourite
The lounge features elegant walls adorned with intricate frescoes and moldings. A large mirror reflects the refined decor. Two white armchairs and a colorful sofa provide seating, while a coffee table rests on a patterned rug before a decorative fireplace.
Apartment in Siena
4.98 out of 5 average rating, 112 reviews

Luxury frescoed apartment in the historical center

The Palazzo Pannilini Superior apartment is composed of a bright entrance enriched by an elegant coffered ceiling, a large fully frescoed lounge, a large foyer, a kitchen equipped with a terrace, a dining room topped with a frescoed vault, four bedrooms, three bathrooms, a wardrobe room, and a panoramic terrace where you can sunbathe and relax. The apartment is located at the second floor with no elevator. The apartment has air conditioning.

FamilyLocationBathroom

Guest favourite
The spacious living area features a decorative ceiling with intricate designs. Soft furnishings, including a light-colored sofa and brown armchairs, are arranged around a neutral area rug. A wooden dining table is visible, complemented by a modern shelving unit housing books and decorative items.
Apartment in Florence
4.96 out of 5 average rating, 102 reviews

Maison San Niccolò Always Florence Collection

Spacious and elegant apt in the San Niccolò district near Ponte Vecchio consists of a living room with kitchen, two bedrooms, 1 double bedroom and 1 twin or queen bedroom. Two bathrooms with shower and a service bathroom with toilet and sink Equipped with washer dryer, smart tv wifi, air conditioning It is located on the 3rd floor with elevator and is very quiet. Late check-in is available from 7:00 PM to 12:00 AM for an additional fee

FamilyLocationWi-Fi

Top Guest favourite
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
5.0 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!

FamilyLocationHospitality

Top Guest favourite
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
5.0 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,

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Popular amenities for Castellina in Chianti apartment rentals

When is the best time to visit Castellina in Chianti?

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