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Apartment holiday rentals in Gaiole in Chianti

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Quick stats about apartment rentals in Gaiole in Chianti

  • Total holiday rentals

    Explore 20 holiday rentals in Gaiole in Chianti

  • Nightly prices starting at

    Gaiole in Chianti holiday rentals start at $101 NZD per night before taxes and fees

  • Verified guest reviews

    Over 570 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Wi-Fi availability

    10 of Gaiole in Chianti holiday rentals include Wi-Fi access

  • Popular amenities for guests

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

  • 4.7 Average rating

    Gaiole in Chianti stays receive an average rating of 4.7 out of 5 from guests

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
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.
Apartment in Florence
4.96 out of 5 average rating, 396 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.

Top Guest favourite
An aerial view captures the agriturismo surrounded by lush green fields and a neatly arranged row of tall cypress trees. The inviting pool reflects the serene landscape, and the winding dirt road leads towards the property, nestled amid the picturesque Crete Senesi.
Apartment in Asciano
4.97 out of 5 average rating, 184 reviews

Loggia 1 in farmhouse with shared pool

Apartment for 2 people in the Santa Lucia farmhouse (farmhouse DIVIDED IN 7 APARTMENTS) in the Crete Senesi, 10 km from Siena. Located on the second floor with a private table in front of the windows of the entrance loggia. It consists of a double bedroom (two single beds joined to form a double bed), a bathroom with shower and a living room with functional kitchen. Outdoor space with table and chairs available on the ground floor. AIR CONDITIONING in the room FOR A FEE according to consumption.

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.
Apartment in Siena
4.99 out of 5 average rating, 168 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.

Top Guest favourite
Apartment in Castellina in Chianti
4.85 out of 5 average rating, 349 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 in a typical Tuscan farmhouse. Suitable for those who want to spend a vacation immersed in nature, enjoying complete relaxation and silence. The 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
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, 385 reviews

Poggio Massiccioli

Cozy apartment for 4 people furnished in Tuscan style with exposed beams, nestled among the rolling hills of the Tuscan countryside. Guests have access to a well-equipped garden, free Wi-Fi, a shared swimming pool with facilities, a wood-fired oven, a barbecue, and a washing machine. The apartment was created from a charming 19th-century stone farmhouse that was recently renovated in the Tuscan tradition and divided into three comfortable apartments.

Superhost
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).

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, 113 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.

Superhost
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.
Apartment in Panzano
4.99 out of 5 average rating, 118 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.

Superhost
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.
Apartment in Monteroni d'Arbia
4.94 out of 5 average rating, 286 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).

Superhost
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.
Apartment in San Gusmè
4.98 out of 5 average rating, 127 reviews

Casa Guardiavigna | Chianti Hills Vineyard Retreat

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.

Guest favourite
A modern kitchen is equipped with stainless steel appliances, including a gas stove and oven. A dining table with metal chairs sits adjacent, adorned with a bright orange tablecloth and a vase of sunflowers. Neutral cabinetry and warm wooden accents create a welcoming ambiance.
Apartment in Gaiole in Chianti
4.81 out of 5 average rating, 331 reviews

Casa Pieralli in the Historic Chianti

Small but cozy two-room apartment in the heart of Gaiole in Chianti. Absolutely quiet and peaceful area in the historic center with free parking nearby. It can comfortably accommodate 2 people, with an equipped kitchen, linen, soap and shampoo.

Guest favourite
A bright and airy seating area features large glass windows that frame an impressive view of the Duomo and the surrounding cityscape. Potted plants and a lamp add subtle touches to the space, while a comfortable chair invites relaxation.
Apartment in San Marco
4.85 out of 5 average rating, 383 reviews

The house of Love

Amazing apartment in the heart of Florence, offering stunning views of the Cathedral and of the whole town. Excellent prices for weekly and monthly stays.

Popular amenities for Gaiole in Chianti apartment rentals