Some info has been automatically translated. Show original language
Airbnb your place

Apartment holiday rentals in Gaiole in Chianti

Find and book unique apartments on Airbnb

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.

1 of 1 pages1 / 1
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

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.

4.99 out of 5 average rating, 168 reviews
Top Guest favourite
A scenic view captures a lush landscape with rolling hills, vineyards, and olive trees under a colorful sunset. The traditional Tuscan casolare is visible in the background, surrounded by greenery, while the horizon features soft hues of orange and pink.
Apartment in Poggibonsi

Laura Chianti Holidays

Laura Chianti Vacanze is the ideal solution for those seeking peace and tranquility in the heart of the Chianti countryside. The apartment is halfway between Florence and Siena, and is in a strategic position for quickly reaching Florence, Siena, San Gimignano, Volterra, as well as the wonderful Chianti hills. The apartment has ample private parking, two bedrooms, an equipped kitchen, a private bathroom, a private garden, a barbecue, and a wonderful view of the Chianti hills.

4.98 out of 5 average rating, 338 reviews
Guest favourite
Apartment in Castellina in Chianti

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

4.85 out of 5 average rating, 350 reviews
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.
Apartment in Villa A Sesta

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).

4.94 out of 5 average rating, 243 reviews
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

Poggio Massiccioli

Cozy apartment for 4 people furnished in Tuscan style and with exposed beams nestled among the rolling hills of the Tuscan countryside. Available to guests is an equipped garden, free Wi-Fi, a shared equipped swimming pool, a wood-burning oven and barbecue, and a washing machine. The apartment was converted from a charming 19th-century stone farmhouse recently renovated according to Tuscan tradition and divided into three comfortable apartments.

4.92 out of 5 average rating, 386 reviews
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

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.

4.98 out of 5 average rating, 113 reviews
Guest favourite
A serene pool area is highlighted by lounge chairs set along a stone terrace. The water reflects a golden sunset, providing a tranquil atmosphere. Surrounding greenery adds to the natural beauty, creating a peaceful environment for relaxation.
Apartment in La Presura

Countryhouse 9 kms to Florence-3+2,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)

4.86 out of 5 average rating, 275 reviews
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.
Apartment in Panzano

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.

4.99 out of 5 average rating, 118 reviews
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.
Apartment in Badia a Passignano

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) .

4.92 out of 5 average rating, 141 reviews
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.
Apartment in San Gusmè

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.

4.98 out of 5 average rating, 128 reviews
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.
Apartment in Siena

Terrace with a view of Siena

Next to the Basilica of San Domenico, a few steps from the Duomo and Piazza del Campo, in this splendid and elegant penthouse you can enjoy the splendid view and the convenience of walking to all the major points of interest in the city in just a few minutes.

4.87 out of 5 average rating, 200 reviews
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

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.

4.81 out of 5 average rating, 332 reviews

Popular amenities for Gaiole in Chianti apartment rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Weekly apartment rentals

Top Guest favourite
A spacious terrace is shown, featuring comfortable seating arrangements, including lounge chairs and a small dining table. The area is partially shaded by awnings, with a view of the surrounding landscape. A table is set with fresh strawberries and beverages, inviting relaxation.
Apartment in Siena

Terrace on the walls of Siena - Casa Laura

5.0 out of 5 average rating, 104 reviews
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

Rooftop with Breathtaking Views. Short Walk to The Duomo.

4.96 out of 5 average rating, 396 reviews
Guest favourite
A serene bedroom features two single beds that can be combined into a double, complemented by soft pillows and warm bedding. Natural light filters through the window, adorned with patterned curtains. Rustic decor includes wooden accents and artwork on the walls, enhancing the inviting atmosphere.
Apartment in Radda in Chianti

The Chianti Cabin

4.97 out of 5 average rating, 63 reviews
Guest favourite
An aerial view of a villa surrounded by lush greenery showcases a spacious pool area nearby. The red-tiled roof of the villa complements the natural landscape with trees framing the property, creating a serene and secluded atmosphere.
Apartment in Gaiole in Chianti

Apartment for 8-9 people in villa with pool

4.85 out of 5 average rating, 52 reviews
Guest favourite
Apartment in Cavriglia

Apartment Comfort | Quiet Escape in Tuscany

4.95 out of 5 average rating, 40 reviews
Top Guest favourite
A panoramic view reveals rolling hills adorned with vineyards and olive groves, stretching under a dramatic sky. The tan-coloured buildings of the property are nestled among lush greenery, while a serene pool reflects the surrounding landscape.
Apartment in Quercegrossa

Tuscany jem: The Chianti Farmer's House

4.98 out of 5 average rating, 84 reviews
Superhost
A sunny terrace garden is visible, surrounded by flowering plants and greenery. A table is set for dining, with chairs arranged nearby, all overlooking the picturesque hills of Tuscany and the town of Gaiole in the distance.
Apartment in Gaiole in Chianti

Casacorvo Maggiore at Borgo Gaiole

5.0 out of 5 average rating, 4 reviews
Guest favourite
Apartment in Siena

Pool Escape Just Outside Siena

5.0 out of 5 average rating, 18 reviews

Private apartment rentals

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

Loggia 1 in farmhouse with shared pool

4.97 out of 5 average rating, 185 reviews
Guest favourite
Apartment in Radda in Chianti

La Terrazza

4.89 out of 5 average rating, 38 reviews
Guest favourite
A shared pool is featured in the foreground, surrounded by stone buildings with a rustic appearance. Guests are seen enjoying the water and sunbathing on the deck. Lush hills are visible in the background, providing a natural and serene setting.
Apartment in Gaiole in Chianti

Idyllic with shared pool in the heart of Chianti

4.82 out of 5 average rating, 28 reviews
Guest favourite
Apartment in Radda in Chianti

Chianti dreaming in Radda in Chianti

5.0 out of 5 average rating, 10 reviews
Top Guest favourite
The living area features a gray sofa adorned with a soft throw, complemented by decorative cushions. A small side table holds a tray with champagne glasses and a bottle. Natural light filters through large glass doors leading to the garden, framed by light curtains.
Apartment in Greve in Chianti

Gilda's house

4.97 out of 5 average rating, 77 reviews
Top Guest favourite
A loggia area features a rustic wooden table set for dining, surrounded by four chairs. Sheer white curtains gently frame the open space, while an expansive view of the green countryside and distant hills is visible through the railing.
Apartment in Rosennano

LATORRE. AN EAGLE NEST ABOVE THE TUSCANY LANDSCAPE

4.93 out of 5 average rating, 97 reviews
Top Guest favourite
A charming stone building is seen surrounded by lush greenery, featuring a terracotta roof. The outdoor area includes a stone patio with wooden chairs and tables, accented by blooming purple flowers and potted plants, with rolling hills visible in the background.
Apartment in Pelago

Barn

5.0 out of 5 average rating, 53 reviews
Superhost
Apartment in Bossi

Villino Ersilia Music, the charm of Chianti

5.0 out of 5 average rating, 3 reviews

Apartment rentals with a hot tub

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.
Apartment in Monteroni d'Arbia

"Red Rose" apartment with view of Siena.

4.94 out of 5 average rating, 287 reviews
Guest favourite
A rectangular swimming pool with a shallow and deep end is surrounded by a stone patio and lush greenery. A villa sits on a hillside in the background, featuring a terrace with windows and shutters. Poolside lights are placed around the pool for evening ambiance.
Apartment in Siena

Villa'Colombaiolo di Marciano', 28

4.9 out of 5 average rating, 146 reviews
Superhost
A sunlit outdoor area features comfortable lounge chairs in vibrant colors beside a hot tub. Olive trees and shrubs surround the space, providing a serene backdrop. A gentle slope of green grass continues toward distant hills, enhancing the tranquil atmosphere.
Apartment in Montevarchi

Apartment with garden in the heart of Tuscany

4.88 out of 5 average rating, 105 reviews
Top Guest favourite
An expansive terrace features a large table surrounded by black chairs, offering a panoramic view of the city. Bright green lounge chairs provide a spot for relaxation. Decorative tiles enhance the visual appeal against a backdrop of historic architecture and blue skies.
Apartment in Florence

At the top faboulous terrace Florence

4.83 out of 5 average rating, 164 reviews
Top Guest favourite
The living area features a stylish design with a dark gray sofa and two deep red armchairs. A round glass table sits on a marble floor, enhanced by natural light from the two windows with light curtains. A decorative mirror and elegant light fixtures adorn the walls.
Apartment in Siena

Domus Nannini - L'Arco di Matteotti Spa

4.98 out of 5 average rating, 107 reviews
Top Guest favourite
A living area is presented with a light-colored sofa and a glass coffee table on a patterned rug. Walls are adorned with framed artwork, and a large television is positioned in a wooden cabinet. Double doors lead to an outdoor space, enhancing natural light.
Apartment in Florence

Fully renovated exclusive apartment in Villa

4.99 out of 5 average rating, 101 reviews
Superhost
Apartment in San Marco

Duomo FillYourHomeWithLove Design Apartment

4.79 out of 5 average rating, 141 reviews
Top Guest favourite
A modern living area features a corner sofa in light tones, paired with a glass coffee table. A chandelier hangs from the ceiling, and large windows allow ample natural light. In the background, a sleek kitchen and dining area are visible, enhancing the space's contemporary feel.
Apartment in Centro

AJ Luxury Duomo View

4.9 out of 5 average rating, 233 reviews

Destinations to explore