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Apartment holiday rentals in Gaiole in Chianti

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Top-rated apartment rentals in Gaiole in Chianti

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Top guest favourite
A thoughtfully arranged living area features a spacious blue sectional sofa adorned with neutral pillows. A variety of books are displayed on a wooden coffee table. Artwork and decorative items line the walls, complemented by soft natural light filtering through the windows.
Flat in San Frediano
4.92 out of 5 average rating, 119 reviews

Radiant, Luxury Eclectic Apartment in Oltrarno

Renovated one year ago, this elegant apartment equipped with all necessary comforts is located in Florence's most prestigious neighbourhood. It offers easy access to the historic city center. Plus, parking is very easy as the property is outside the restricted traffic zone. Nestled on a peaceful street in the charming Oltrarno district, the apartment is steps away from many historical sites and museums. There are all kinds of restaurants, shops, cafes, and bars in the immediate surrounding area.

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 in Montepulciano
4.97 out of 5 average rating, 142 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
The elegantly structured Villa di Geggiano is set amidst lush vineyards and well-maintained gardens. Its classic stone facade and terracotta roof harmonize with the surrounding greenery, while neatly manicured pathways and symmetrical garden beds create a picturesque landscape under a partly cloudy sky.
Flat in Siena
4.99 out of 5 average rating, 164 reviews

Villa di Geggiano – Alfieri Suite

The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idilic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa. PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR.

Guest favourite
A well-equipped kitchen area features light cream cabinetry and modern appliances. A wooden dining table is surrounded by white chairs, with a centerpiece of flowers. Natural light filters through the sheer curtains of the window, enhancing the inviting ambiance of the space.
Flat in Gaiole in Chianti
4.88 out of 5 average rating, 134 reviews

Casa Martini in Historic Chianti

Apartment with garden and private parking in Gaiole in Chianti, a stone's throw from the historic center where you will find numerous bars, restaurants and the small supermarket (coop). The accommodation is ideal for holidays with animals because it has a fully fenced garden. Tourist tax is required (€2 per person per night for the first seven nights) minors under 14 years excluded (read the complete regulation on the website of the Municipality of Gaiole in Chianti)

Guest favourite
Flat in La Presura
4.83 out of 5 average rating, 169 reviews

Countryhouse 9 kms to Flor., free park, pool, wine

Farmhouse at only 9 km from Florence in the beautiful Chianti hills with gorgeous pool and free private parking Small organic farm producing our own wine Chianti Classico and extra olive oil 1 hour driving to the most important city of Tuscany :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) possibility to make self check in; security distance in pool.

Top guest favourite
Flat in Villa a Sesta
4.93 out of 5 average rating, 229 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).

Top guest favourite
A serene sleeping area features a spacious bed adorned with soft linens and decorative pillows. Natural light enters through an open window, showcasing views of the surrounding landscape. Two bedside tables hold lamps, and textured wall decor adds a touch of charm.
Flat in Monteroni d'Arbia
4.98 out of 5 average rating, 217 reviews

"Sunflower" apartment with view of Siena

Caggiolo is a completely renovated farm consisting of several apartments, each with a private entrance and exclusive use of the garden, with a panoramic view of Siena. Located 1 km from 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). From the farm, you can hike to the Grotti Castle (6 km) or to our pond (2.5 km)

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, 110 reviews

💜 "Ilary" Le Fontanelle Farmhouse

Imagine staying in a small house in the Tuscan countryside, in the middle of Chianti's nature but only 1 km from the historic center of Radda and being able to overlook a breathtaking view every day that will give you enchanting sunsets. -70m2 - Private outdoor panoramic area - TV with Netflix -private covered parking - shared pool (June 1st - September 15th) - heating (November 1st - April 1st) - wifi - Kitchen

Top guest favourite
The spacious dining area features a rustic wooden table surrounded by chairs, harmonizing with exposed wooden beams above. A white cabinet and a radiator are visible, while the window offers a view of the outside landscape. Light-colored walls create a warm and welcoming ambiance.
Flat in Montepulciano
4.97 out of 5 average rating, 255 reviews

Casa Ricci Apartment in a 14th-century building

Our apartment is located a few meters from Piazza Grande, sleeps up to 4 people and overlooks a beautiful view. It was recently renovated and is located in a historic building from the 1300s. Our apartment is located a few meters from Piazza Grande, it sleeps up to 4 people and overlooks a beautiful view. It was recently renovated and is located in a historic building from the 1300s.

Top guest favourite
A welcoming entryway features a mural depicting a serene landscape framed by arches. Built-in shelves display decorative items and books. Natural light illuminates the wood flooring, while a small globe and a vase with dried plants add subtle warmth to the space.
Flat in San Gusmè
4.98 out of 5 average rating, 111 reviews

Casa Guardiavigna in Chianti, Italy

The Casa Guardiavigna apartment offers the opportunity to enjoy a unique and extraordinary experience, full of emotions and happiness. Located a stone's throw from the small medieval village of San Gusme' and surrounded by beautiful vineyards, woods and flowery meadows. Free indoor parking with an automatic gate.

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
4.92 out of 5 average rating, 100 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.

Top guest favourite
A spacious suite features a comfortable bed with neutral-toned bedding, complemented by wooden beams overhead. A freestanding bathtub is positioned near the entrance. Soft lighting creates a calming ambiance, while the adjoining bathroom is accessible through a glass door, enhancing the airy feel of the space.
Flat in Monticchiello
4.97 out of 5 average rating, 397 reviews

Romantic Tower's dating 1200

The residence "Il Torrino" is a panoramic apartment obtained from the restauration of an ancient tower belonging to the boundaries of the medieval suburb Monticchiello. The apartment has an incredible view on the Val d'Orcia. You can't imagine ...

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