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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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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, 611 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
4.97 out of 5 average rating, 284 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 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, 179 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, 145 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
The bedroom features a spacious double bed adorned with soft linens and cushions, complemented by subtle bedside lamps. Exposed wooden beams highlight the ceiling, while natural light filters through a window, adding warmth to the serene, neutral color palette.
Flat
4.97 out of 5 average rating, 414 reviews

Cortona Shabby Chic House - independent & balcony-

Questo è un appartamento curato da una Superhost che vive Cortona ogni giorno. Il mio alloggio è situato in pieno centro storico a soli pochi passi dalle piazze e vie principali. Questo grazioso appartamento è di recente ristrutturazione e può ospitare fino a 3 persone. Appartamento indipendente con entrata singola tutto in un solo piano, con balcone. Arredato con cura, dotato di tutti i comfort per un totale relax

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
4.86 out of 5 average rating, 120 reviews

💜 "Ilary" Le Fontanelle Farmhouse

Imagine staying in a typical stone house in the Tuscan countryside, surrounded by nature, just 1 km from the village of Radda in Chianti, and being able to look out every day on a breathtaking panorama that will offer you enchanting 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
A spacious terrace features a large dining table with ample seating, complemented by an umbrella for shade. A scenic view of the distant church and surrounding architecture is visible, framed by lush greenery and a picturesque sky.
Flat
4.98 out of 5 average rating, 105 reviews

CASA WOW panoramic terrace * . *

Nel cuore di Siena con una terrazza panoramica. La casa offre un sapore sincero, realmente vissuto da una famiglia italiana: con arredi di pregevole antiquariato e moderni confort, cimeli di viaggi, libri e riviste. Ideale per due coppie di amici o una famiglia con bambini. Ammessi gli animali non molesti. Wifi gratuito 24 h. LGBTQ friendly. CIN: IT052032C2EQVX5ICB

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
4.98 out of 5 average rating, 125 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.

Guest favourite
A spacious living area is presented, featuring a sleek television mounted on a wooden console. A marble coffee table is centered on a soft rug, with a modern armchair positioned nearby. Natural light filters through large windows adorned with light curtains, highlighting the greenery in the corner.
Flat
4.96 out of 5 average rating, 109 reviews

Cozy design house with view

Recently renovated, this design apartment is located opposite the house of Galileo Galilei, in Pian dei Giullari, a prestigious area of Florence, above Piazzale Michelangelo. Away from the chaos of the city, you will have the opportunity to experience the Tuscan hills while still enjoying city life.

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, 111 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
A shaded gazebo features comfortable seating with plush cushions surrounding a small table. In the background, a well-maintained pool complements the lush green landscape, framed by colorful trees and distant hills under a clear blue sky.
Flat
4.98 out of 5 average rating, 114 reviews

La Felce Country House

La Felce Country House is a typical Tuscan country house. It is located 15 kilometres from Florence, amidst the Tuscan hills, with extensive private grounds. The beautiful swimming pool and the garden around it are only for the exclusive use of the occupants of the only flat to rent.

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.
Flat
4.81 out of 5 average rating, 326 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.

Popular amenities for Gaiole in Chianti apartment rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Weekly apartment rentals

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
4.94 out of 5 average rating, 280 reviews

"Red Rose" apartment with view of Siena.

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, 188 reviews

Terrace with a view of Siena

Guest favourite
A bright and spacious living room features a large marble coffee table and a pair of elegant chaise lounges. A striking painting hangs above a contemporary white sofa adorned with colorful cushions. Antique furnishings and a patterned rug enhance the room's sophisticated ambiance.
Flat
4.94 out of 5 average rating, 364 reviews

Museum Suite - Luxurious unit with a River View -

Guest favourite
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, 291 reviews

I Tramonti di Eramo, central Montepulciano.

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
4.99 out of 5 average rating, 114 reviews

Looking at Chianti

Top guest favourite
A terrace showcases a small table set with glasses and a bottle, complemented by two chairs. A scenic view of the Tuscan countryside can be seen in the background, revealing rolling hills and traditional rooftops under a bright sky.
Flat
4.99 out of 5 average rating, 167 reviews

San Miniato - Panoramic terrace in the historic center

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.
Flat
4.91 out of 5 average rating, 142 reviews

Villa'Colombaiolo di Marciano', 28

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, 239 reviews

At Paola's in Chianti

Private apartment rentals

Top guest favourite
A serene outdoor space is framed by tall, leafy trees, creating a natural canopy. Within the gravel area, terracotta pots with greenery are visible, offering a sense of tranquility. The expansive view stretches across the hills and valleys of the surrounding landscape.
Flat
4.96 out of 5 average rating, 188 reviews

Casa Le Contesse

Superhost
An outdoor seating area is presented, featuring a large table surrounded by wooden chairs under a shaded umbrella. Two lounge chairs are positioned on the grassy lawn, with a panoramic view of the surrounding hills and a clear blue sky in the background.
Flat
4.77 out of 5 average rating, 117 reviews

Girasole large apartment in a Tuscan village

Guest favourite
The historic villa is surrounded by lush greenery, featuring well-maintained gardens and numerous trees. The architecture reflects centuries of history, with a stone tower visible in the background. The structure incorporates large windows that enhance the natural light entering the home.
Flat
4.96 out of 5 average rating, 72 reviews

Penthouse in small medieval castle near Florence

Top guest favourite
A terrace table is set with two glasses of sparkling wine and a plate of cookies, overlooking the rooftops of the city. The distant bell tower is visible against a clear blue sky, framed by the balcony's railing.
Flat
4.95 out of 5 average rating, 412 reviews

The rooftop terrace

Top guest favourite
A serene outdoor space features a weathered wooden bench and a round table with a plate, surrounded by lush greenery. Large arched windows provide a view into the brightly lit interior, complemented by colorful flower pots, enhancing the garden-like setting.
Flat
4.94 out of 5 average rating, 105 reviews

Chianti Patio Apartment

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.
Flat
4.96 out of 5 average rating, 382 reviews

Rooftop with Breathtaking Views. Short Walk to The Duomo.

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.
Flat
4.96 out of 5 average rating, 57 reviews

The Chianti Cabin

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
4.93 out of 5 average rating, 127 reviews

Apartment with panoramic garden in San Gimignano

Apartment rentals with a hot tub

Guest favourite
A spacious living area features a white leather sofa, a large ottoman, and a decorative chandelier. Exposed stone walls and wooden floors create a warm ambiance. Natural light filters in through two open windows, complemented by a large flat-screen television and decorative shelves.
Flat
4.85 out of 5 average rating, 147 reviews

Executive Apartment City Center

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.
Flat
4.82 out of 5 average rating, 154 reviews

At the top faboulous terrace Florence

Superhost
A private jacuzzi pool is set in a garden surrounded by greenery. A bottle of champagne and two glasses are placed nearby on a table. Comfortable loungers, with soft cushions, are positioned close to the pool, creating a relaxing outdoor space.
Flat
4.81 out of 5 average rating, 306 reviews

Pepi Garden Loft with Jacuzzi Pool

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.
Flat
4.98 out of 5 average rating, 106 reviews

Domus Nannini - L'Arco di Matteotti Spa

Top guest favourite
Flat
4.82 out of 5 average rating, 482 reviews

Nadja's Home with hot tub - perfect for couples

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.
Flat
4.98 out of 5 average rating, 110 reviews

Luxury frescoed apartment in the historical center

Guest favourite
The bathroom features a modern design with a spacious jacuzzi tub and a sleek, dark stone accent wall. A large mirror reflects natural light, while potted greenery adds a touch of freshness. The area is equipped with a bidet and ample storage space beneath the sink.
Flat
4.87 out of 5 average rating, 245 reviews

LUXURY APT IN THE CITY CENTER

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.
Flat
4.9 out of 5 average rating, 226 reviews

AJ Luxury Duomo View

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Siena
  5. Gaiole in Chianti
  6. Flat rentals