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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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Superhost
The luxurious bedroom features a stunning ceiling adorned with a captivating fresco. A spacious bed is placed in the center, accompanied by a state-of-the-art TV nearby. A hydromassage tub situated at the foot of the bed complements the elegant decor, with soft lighting and decorative elements enhancing the ambiance.
Flat in Florence
4.91 out of 5 average rating, 602 reviews

House of Delights - The Medici private leisure house

La Casa di Delizie, a luxurious retreat nestled in a historic guard tower dating back to the Middle Ages, once cherished by the Medici family. Adorned with the exquisite fresco "Caduta di Icaro," this exclusive apartment seamlessly blends rich history with contemporary luxury. Ideally located on Via Orti Oricellari, just 150 meters from the main train station, it provides effortless access to Florence's treasures. Indulge in bespoke experiences and refined amenities for an unforgettable escape!

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 in Carmignano
4.97 out of 5 average rating, 276 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
A dining area features a round wooden table surrounded by white chairs, with glasses and a bottle set upon it. Large open windows frame a view of the Ponte Vecchio and the Arno River, allowing natural light to brighten the space.
Flat in Centro
5 out of 5 average rating, 370 reviews

[Ponte Vecchio] Charm and Awesome view of Florence

Make your stay unique and treat yourself to an experience that you will carry within you for a lifetime. Located in the heart of Florence, this magnificent apartment is the ideal solution for those looking for an exclusive and prestigious site to combine with a central location, which is perfect for easily visiting the main sites of interest, all reachable in less than 10 minutes by foot. The views are on Ponte Vecchio, and you can enjoy one of the most fascinating panoramas of the city.

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 in Castelnuovo Berardenga
4.94 out of 5 average rating, 177 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
Flat in Castellina in Chianti
4.85 out of 5 average rating, 340 reviews

Relaxation & Pool: an oasis in the heart of Chianti

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

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 in San Gimignano
4.93 out of 5 average rating, 126 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

Superhost
A small wooden table set for two is adorned with fine china cups and a delicate flower vase. The balcony offers a panoramic view of the rolling hills, as the sun sets, casting warm hues over the landscape.
Flat in Montepulciano
4.91 out of 5 average rating, 279 reviews

I Tramonti di Eramo, downtown Montepulciano.

Welcome to Montepulciano, the jewel of the Tuscan hills! Our apartment in the heart of the historic center offers breathtaking views of the surrounding countryside, providing an authentic and unforgettable experience. Step outside and savor the historic atmosphere of Montepulciano. Just a few steps away, you will find the extraordinary Piazza Grande, excellent restaurants, and all kinds of services. Tuscany awaits you for a unique experience.

Guest favourite
A spacious outdoor area is surrounded by greenery and stone buildings. The scenic landscape features a neatly maintained lawn, with a rustic path leading to a wooden door framed by flower pots. Rolling hills can be seen in the distance under a clear blue sky.
Flat in Radda in Chianti
4.85 out of 5 average rating, 115 reviews

💜 "Ilary" Le Fontanelle Farmhouse

Immagina di alloggiare in una piccola casa della campagna toscana, nel bel mezzo della natura del Chianti ma a solo 1km dal centro storico di Radda e di poterti affacciare ogni giorno su un panorama mozzafiato che saprà regalarti incantevoli tramonti. -70m2 -aia esterna panoramica riservata -TV con Google TV -parcheggio privato coperto -piscina condivisa (1 giugno - 15 settembre) -riscaldamento (1 novembre - 1 aprile) -wifi -cucina

Top guest favourite
A spacious terrace features a seating area with comfortable cushions. A bottle of red wine and a glass are placed on a woven table. The view highlights nearby buildings and greenery, framed under a clear blue sky with scattered clouds.
Flat in Panzano in Chianti
5 out of 5 average rating, 110 reviews

Looking at Chianti

"Guardo al Chianti" is a completely new apartment for 4 people, furnished in Tuscan style. It has a beautiful terrace overlooking the famous "Conca d'Oro in Panzano." Panzano is famous for its wines: Chianti Classico and Super Tuscan. There are 22 farms a few kilometers away that offer visits to the cellars and tastings of their wines and oil. The apartment is a short walk from the Coop Supermarket, Pharmacy and town center.

Guest favourite
Flat in Greve in Chianti
4.87 out of 5 average rating, 199 reviews

Apartment Ramerino

Mezzomonte farmhouse is located in one of the most beautiful areas in Chianti, only 33 Km from Firenze and 30 from Siena.We are on the top of the hill ,2km of unmade road from the main street SS222 The farmhouse is immersed in a forest of chestnut and pine trees, surrounded by a completely fenced 6000m2 garden. Our apartments are completaly independent including the private space in the garden.

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 in Monteroni d'Arbia
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).

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 in Radda in Chianti
4.93 out of 5 average rating, 108 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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Avg. price$185 SGD$190 SGD$208 SGD$214 SGD$216 SGD$228 SGD$221 SGD$218 SGD$218 SGD$200 SGD$195 SGD$181 SGD
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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 $77 SGD 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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