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Holiday houses in Gaiole in Chianti

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in Gaiole in Chianti

  • Total holiday rentals

    Explore 30 holiday rentals in Gaiole in Chianti

  • Nightly prices starting at

    Gaiole in Chianti holiday rentals start at $102 NZD per night before taxes and fees

  • Verified guest reviews

    Over 740 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Wi-Fi availability

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

  • Popular amenities for guests

    Guests love Gym, BBQ and Laptop-friendly workspace 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 holiday rentals in Gaiole in Chianti

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

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Superhost
A serene outdoor swimming pool is framed by well-maintained grass and hedges. The pool's surface reflects the sky, while a wooden deck leads to the water's edge. Lush greenery surrounds the area, contributing to a tranquil atmosphere.
Home in Gaiole in Chianti
4.97 out of 5 average rating, 31 reviews

Villa Eroica

On the ground floor, a private entrance welcomes guests, leading to a fully equipped kitchen, a bathroom, and an elegantly furnished living/dining room. The spacious spaces and exposed beams create a warm and welcoming atmosphere. Upstairs, the master bedroom boasts high wooden ceilings and a private terrace with a solarium equipped with a table, loungers, and an outdoor hot-water shower. The second bedroom, with a double and single bed, is perfect for families or groups of friends and includes a study corner. Enjoy a spacious apartment spread over two floors, ideal for a comfortable and relaxing stay. You'll have a large furnished porch at your disposal, perfect for spending pleasant moments outdoors. The loggia, with its comfortable sofa, and the large garden offer an oasis of tranquility. Among the common areas, you can relax by the large 14 x 7 meter swimming pool, equipped with a convenient access staircase suitable for both adults and children. The pool is surrounded by a manicured lawn and a paved solarium perfect for sunbathing. Upstairs, an exclusive panoramic terrace with hot and cold shower awaits you, the perfect spot for tanning during the day or enjoying evening moments under a starry sky. You'll fall in love with this home, whose character will allow you to experience Tuscan style.

Top Guest favourite
A serene outdoor area features a turquoise swimming pool surrounded by chaise lounges. Vibrant pink roses bloom near the edge, while lush greenery provides a natural backdrop. A stone villa with a tiled roof is visible in the distance, highlighting the tranquil setting.
Villa in Gaiole in Chianti
4.99 out of 5 average rating, 74 reviews

Sestuccia

Villa Sestuccia is a lovely Tuscan villa near the popular towns of Gaiole and Radda in Chianti. In this wonderful villa there are 4 bedrooms with private bathrooms.The exterior of the villa is composed by 4 living areas: the "wisteria living", the "panorama living", the "Mondrian living", the "outdoor patio" and a vegetable garden. There is also a swimming pool, a SPA and an outdoor hot tub for 6 people. Inside the fenced property you can find a chicken coop and a beautiful vineyard. Enjoy!

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
4.95 out of 5 average rating, 65 reviews

La Capannina del Chianti

Appartamento rustico in stile toscano situato nel cuore del Chianti, appena fuori dal centro storico di Radda. L'alloggio, recentemente ristrutturato, è dotato di : · 1 camera con due letti singoli o un letto matrimoniale (a scelta dell'ospite) · 1 camera con letto matrimoniale · 1 culla · 1 bagno · Wi-Fi gratuito (fibra ottica) · Cucina accessoriata e macchina del caffè · Lavasciuga · Soggiorno con Smart TV da 43" · Giardino esterno condiviso con tavolo ed ombrellone ad uso esclusivo

Guest favourite
A sunlit sunroom features large windows adorned with sheer curtains, allowing natural light to fill the space. A cozy white sofa is positioned next to a small wooden table with chairs, while indoor plants add a touch of greenery to the inviting atmosphere.
Home in Gaiole in Chianti
4.86 out of 5 average rating, 294 reviews

Charming estate with views. A/C in the bedrooms

The estate finely restored in 2016 is accessorized with all the confort you need for an holiday dedicated to the relax or to excursions The Breathtaking view on the Chianti Classico's vineyards give to the estate a unique feature perfect for a romantic holiday, small group of friend or a little family. The estate is provided of external Jacuzzi, private garden and we can arrange for you bike or hike excursions. The Village of Gaiole in Chianti is just 5 minutes away by 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.
Apartment in Gaiole in Chianti
4.88 out of 5 average rating, 151 reviews

Casa Martini nel Chianti Storico

Appartamento con giardino e parcheggio privato a Gaiole in Chianti, a due passi dal centro storico dove troverete numerosi bar ristoranti ed il piccolo supermercato ( coop). l'alloggio è ideale per vacanze con animali perché è dotato di un giardino tutto recintato. Viene richiesta la tassa di soggiorno ( 2 euro a persona a notte per le prime sette notti) minori di 14 anni esclusi ( leggi regolamento completo nel sito internet del Comune di Gaiole in Chianti)

Guest favourite
Villa in Gaiole in Chianti
5.0 out of 5 average rating, 6 reviews

Villa Il Masseto

Villa Il Masseto is a traditional Tuscan villa, peacefully located on the edge of Gaiole in Chianti, bordered by forest and just a 3-minute walk from the center. Perched on a gentle hill, it offers stunning views over the town’s church tower and rooftops. The distant chimes of the bells add an unmistakably Tuscan ambiance to your stay. It’s a perfect retreat for families or groups of friends looking to relax and enjoy the region’s beauty.

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
4.98 out of 5 average rating, 85 reviews

Tuscany jem: La Casa del Fattore del Chianti

Questo meraviglioso appartamento appena ristrutturato conserva il fascino dei casolari del Chianti e le comodità di un appartamento moderno. La casa è situata all'interno del complesso della Fattoria di Petroio, azienda vitivinicola del Chianti Classico. Potrete godere della bellezza e della tranquillità delle colline del Chianti, mentre vi immergete nella vita dinamica di un'azienda dedita alla produzione di vini di qualità.

Guest favourite
A sparkling swimming pool is surrounded by sun loungers and umbrellas, offering a relaxing space for guests. The rustic farmhouse, with its stone exterior, is visible in the background, amidst lush greenery and trees under a partly cloudy sky.
Holiday home in Castelnuovo Berardenga
4.91 out of 5 average rating, 100 reviews

PIERFANTINI private Chianti house ♿️ 🏊‍♂️ 🐶

Pierfantini is a rustic farmhouse. It is located on a hill in the middle of a natural park. Isolated from the vitta, the nearest town is the medieval village of San Gusmè. The house is renovated and the ground floor adapted for disabled people or wheelchair users There are three apartments but I never rent them separately. The house rent is for all the property

Top Guest favourite
An outdoor dining area is set with a green stone table, featuring neatly arranged plates, silverware, and glassware. A blue ceramic pot and a bottle of wine are included. The background reveals an infinity pool overlooking a lush forest with rolling hills under a partly cloudy sky.
Villa in Gaiole in Chianti
5.0 out of 5 average rating, 34 reviews

Montemarcoli

Immergiti in questo spazio unico nato su una splendida collina a Gaiole in Chianti, una nuovissima villa con piscina situata in un bosco lussureggiante offre un rifugio privato di lusso, stile e amore da cui poter ammirare alba e tramonto. Un progetto realizzato con le ultime tendenze architettoniche, eco sostenibile e con acqua di sorgente naturale.

Guest favourite
A charming stone villa is framed by lush greenery and tall trees. Natural stone pathways lead to the entrance, where wooden shutters are seen beside arched windows. Shadows from the surrounding foliage create a tranquil ambiance, reflecting the serene countryside setting.
Home in Radda in Chianti
4.98 out of 5 average rating, 49 reviews

Villa le Scope 5*

Villa le scope si trova nel cuore del Chianti, in mezzo alla natura e alla tranquillità, pur essendo a pochi passi dal paese. Potrai degustare un ottimo vino Chianti Classico, sulla bellissima terrazza o in totale relax nel nostro grande giardino. La villa le Scope dista un ora circa da Firenze e mezz'ora da Siena.

Top Guest favourite
A warm living area is presented, featuring a comfortable sofa adorned with soft pillows and a round dining table. The space is illuminated by wall sconces, while an arched entryway leads to another room. Large windows allow natural light to fill the area.
Farm stay in Gaiole in Chianti
4.97 out of 5 average rating, 116 reviews

La Pieve - the house next to the church

To the right of the Argenina church, after which it is named, it has the persuasive look of its 2 small arches facing west. Perhaps it was once the parish priest's house, or the one where cooking was done in the large wood-burning oven, who knows?

Superhost
Home in Gaiole in Chianti
4.8 out of 5 average rating, 5 reviews

Fienile House

Nestled in the heart of Chianti, surrounded by rolling vineyards and the timeless beauty of the Tuscan countryside, this charming rustic stone retreat is an intimate hideaway designed for romance, relaxation, and authentic Italian living.

Popular amenities for Gaiole in Chianti holiday rentals

Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Gaiole in Chianti?

    Four-legged friends are welcome in Gaiole in Chianti. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Are there Gaiole in Chianti vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Gaiole in Chianti, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly vacation rentals in Gaiole in Chianti?

    Gaiole in Chianti has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in apartment rentals in Gaiole in Chianti?

    Experience the best of Gaiole in Chianti with our apartment rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do apartment rentals in Gaiole in Chianti have air conditioning?

    Absolutely! We offer over 10 apartment rentals with air conditioning in Gaiole in Chianti. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Gaiole in Chianti have wifi?

    Absolutely! We offer over 10 apartment rentals with wifi in Gaiole in Chianti. Enjoy a tailored experience with all the comforts you desire.