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Apartment holiday rentals in Gaiole in Chianti

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Top-rated apartment rentals in Gaiole in Chianti

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

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Top guest favourite
The spacious living area features large windows offering panoramic views of the countryside. A designer sofa and two armchairs provide comfortable seating around a round table. Shelving holds dishes and books, while rustic beams grace the ceiling, enhancing the room's warmth.
Flat
4.96 out of 5 average rating, 314 reviews

A view from the gate, Montepulciano.

The house(castoldi apartments site), renovated in 2019, close to the main street and the Square has AC, 2 double rooms (1 or 2 king ), 2 bathrooms ensuite with shower and a large kitchen-living room with 4 windows and a small terrace, overlooking the hills, wine cellar The apartment offers a spectacular view Available in season a nice garden 50 mt away where to have a wine tasting for all the guests of our 4 apartments or grilled meat always with paired wines. Private parking in our garden.

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
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
Flat
5 out of 5 average rating, 569 reviews

Renaissance Apartment Touch the Dome!

Inspired by the most fascinating artistic era in human history, the Renaissance, each of my homes is a tribute to the elegance, harmony, and craftsmanship that defined that golden age. Step inside and be transported.
You’ll not only see the Renaissance — you’ll feel it in the atmosphere, in the light, and in the soul of each space. Discover also The Renaissance & Baroque apartment: https://www.airbnb.it/rooms/30229178?guests=1&adults=1&s=67&unique_share_id=c0087742-7346-4511-9bcd-198bbe23c1b4

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, 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...

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, 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.

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, 143 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 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.
Flat
4.94 out of 5 average rating, 235 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).

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
4.91 out of 5 average rating, 278 reviews

I Tramonti di Eramo, central 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 tranquil outdoor pool is surrounded by well-maintained gardens and olive trees. Sun loungers are positioned along the poolside, providing space for relaxation. The stone-clad building in the background complements the landscape, contributing to the serene environment.
Flat
4.93 out of 5 average rating, 169 reviews

Countryhouse 9 km to Florence-2+1g,free park, wine

We are a Farmhouse at only 9 km from Florence in the beautiful Chianti hills with gorgeous pool and free private parking We are a small organic farm producing our own wine Chianti Classico and extra virgen olive oil Only 1 hour driving to the most important city of Tuscany such as Pisa, Siena, San Gimignano, Pienza, Monteriggioni, Lucca and Arezzo. Public transportation to Florence and Greve in Chianti (bus stop at only 200 mt from us)

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
4.85 out of 5 average rating, 115 reviews

💜 "Ilary" Le Fontanelle Farmhouse

Imagine staying in a small house in the Tuscan countryside, surrounded by the natural beauty of the Chianti region but only 1 km from the historic centre of Radda, and being able to enjoy a breathtaking view every day, including stunning sunsets. -70m2 -conceived panoramic outdoor patio - TV with Google TV -covered private parking -shared pool (June 1 - September 15) -heating (November 1 - April 1) -wifi -kitchen

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, 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.

Guest favourite
An outdoor terrace offers seating for four, featuring a table and chairs. The view captures the skyline illuminated against a twilight backdrop, showcasing notable landmarks such as the Torre del Mangia and the Duomo in the distance.
Flat
4.89 out of 5 average rating, 181 reviews

Terrace with a view of Siena

A fianco della Basilica di San Domenico, a pochissimi passi dal Duomo e da Piazza del Campo, in questo splendido ed elegante attico potrete godere della splendida vista e della comodità di raggiungere a piedi in pochi minuti tutti i maggiori punti di interesse della città.

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