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Apartment holiday rentals in Castellina in Chianti

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Top-rated apartment rentals in Castellina in Chianti

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Top guest favourite
A modern dining area features a large wooden table surrounded by sleek black chairs, with expansive glass walls offering views of the surrounding hills and city. The space is well-lit by hanging pendant lights, creating a bright and inviting environment.
Flat
4.96 out of 5 average rating, 382 reviews

Rooftop with Breathtaking Views. Short Walk to The Duomo.

Climb the white marble staircase to the breathtaking rooftop terrace, boasting unforgettable views of the hills surrounding Florence and the historic center. This apartment has been newly renovated, mixing different kinds of architecture and design. In the flat there is plenty of space for your smart-workstation: internet is fast and reliable, accessible from every corner. We take particular care in sanitizing all the critical areas, in particular the space is sanitized by means of ozone generators. The apartment is newly restyled with a very special taste, mixing different styles in the architecture and design. It is a 2 floors apartment at the last floor of a mid 20th century building right outside the historical city center: at the first floor there are the bedrooms (a Suite and a second bedroom) the bathroom and a wardrobe room. The Suite is introduced by an elegant living area with a separè industry in glass and iron dividing it from the double bedroom with balcony and fireplace. The second bedroom has a big wardrobe with mirrors, a fine couch and twin beds to be disposed at one's will. Through an elegant white marble staircase we have access to the brand new rooftop kitchen and the wide terrace with a view on the hills sorrounding Florence and spots of the old buildings of the historic center. The apartment is entirely reserved to our guests, access to it is by the staircase or by elevator with private access to the floor. The rooftop terrace is only for our guests with sole access from inside the apartment by a staircase. At the same floor in a separate flat live the owners, always ready to help! The owner lives next door and is always available if needed. Chez Geraldine is an apartment just outside the historical center. It’s predominantly a residential district, but the cathedral, Galleria dell'Accademia, and Piazza San Marco are a 15-minute walk away. Food stores, restaurants, and bars are close by. AVAILABLE 4 BIKES (adult size) for our guests, included in the price. Please, use it with care and lock it well each and any time you leave them without custody, thank you. IN CASE OF THEFT OR SEVERE DAMAGE DUE TO NEGLIGENCE YOU WILL BE REQUESTED TO PAY THE VALUE OF THE BIKE OF 160€. Thank you WALKING: the city center is at only 15 mins walking. BY BUS: a few steps away from the building there are buses to the city center and the station.

Guest favourite
A bright and spacious living room features a large marble coffee table and a pair of elegant chaise lounges. A striking painting hangs above a contemporary white sofa adorned with colorful cushions. Antique furnishings and a patterned rug enhance the room's sophisticated ambiance.
Flat
4.94 out of 5 average rating, 363 reviews

Museum Suite - Luxurious unit with a River View -

After 13 wonderful years of hosting on Airbnb, the time has come to close this incredible chapter and embrace the next. These upcoming 7 months will be the final season for MuseumSuite, in Jan 2027, the property will be sold and transformed into a private family residence. It has been an absolute honor and a privilege to welcome guests from all walks of life. Each of you has deeply enriched my journey, and I hope that MuseumSuite has left a beautiful, lasting impression on your lives as well.

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.
Flat
4.97 out of 5 average rating, 283 reviews

Giglio Blu Charming Loft

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
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.
Flat
4.97 out of 5 average rating, 154 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 or barbecue for all the guests of our 4 apartments, after 7pm if booked large in advance Large free parking area 100 mt away

Top 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.
Flat
4.94 out of 5 average rating, 179 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.

Top guest favourite
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.
Flat
4.99 out of 5 average rating, 144 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.

Top guest favourite
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.
Flat
4.93 out of 5 average rating, 127 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 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.
Flat
4.92 out of 5 average rating, 374 reviews

Poggio Massiccioli

Accogliente appartamento per 4 persone arredato in stile toscano e con travi a vista immerso tra le dolci colline della campagna toscana. A disposizione degli ospiti giardino attrezzato,wi-fi gratuita,piscina condivisa attrezzata,forno a legna e barbecue,lavatrice. 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
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.
Flat
4.94 out of 5 average rating, 280 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).

Guest favourite
A large shared pool is set against a backdrop of rolling hills and open skies. Several lounge chairs are arranged around the pool, offering a space for relaxation. The clear turquoise water reflects the surrounding landscape and clouds above.
Flat
4.92 out of 5 average rating, 136 reviews

Chianti, Country house with pool

Peace and relax in the heart of Chianti between Florence and Siena, close to Badia a Passignano (4 km dirt road not too much easy if you drive a sportive car) . In an old farmhouse complex, the apartment "Sangiovese" was recently restored by retrieving the characteristics of the Tuscan rural tradition. Large shared pool (01/05 - 30/09) .

Top guest favourite
A spacious living area is presented, featuring a sleek television mounted on a wooden console. A marble coffee table is centered on a soft rug, with a modern armchair positioned nearby. Natural light filters through large windows adorned with light curtains, highlighting the greenery in the corner.
Flat
4.96 out of 5 average rating, 109 reviews

Cozy design house with view

Recently renovated, this design apartment is located opposite the house of Galileo Galilei, in Pian dei Giullari, a prestigious area of Florence, above Piazzale Michelangelo. Away from the chaos of the city, you will have the opportunity to experience the Tuscan hills while still enjoying city life.

Top guest favourite
An inviting living area features a wooden door, a round table with a potted plant, and a warm-toned rug. Walls are lined with shelves and artwork, while a backdrop displays a modern kitchen and a spacious archway leading to additional living spaces.
Flat
4.93 out of 5 average rating, 109 reviews

La Casina

Recently renovated, a stone's throw from the historic center of Radda in Chianti, with a supermarket and bank 100 m away, 70 sqm apartment with private entrance, large living room with double sofa bed, kitchen, double bedroom, bathroom with shower, outdoor loggia, and adjacent parking.

Popular amenities for Castellina in Chianti apartment rentals

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Quick stats about flat 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 £45 per night before taxes and fees

  • Verified guest reviews

    Over 590 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Wifi availability

    20 of Castellina in Chianti holiday rentals include wifi access

  • Popular amenities for guests

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

  • 4.8 Average rating

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

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