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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 $105 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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Guest favourite
A shaded garden area features a hammock suspended from a tree and a round table with chairs, set against a backdrop of lush greenery and rolling hills. The panoramic view extends under a partly cloudy sky.
Home in Poggio San Marco
4.97 out of 5 average rating, 307 reviews

Charming converted Hayloft overlooking the Chianti Hills

Inspired by the rustic Tuscan style, this gorgeously refurbished hayloft features ceilings with exposed beams and bricks and thoughtful touches for a stylish and comfortable decor. From the relaxing hammock and the stone made barbecue in a panoramic garden to the cozy fireplace, every space feels open and inviting. Immersed in total peace and tranquillity with a breathtaking view over the Chianti hills, halfway between Florence, Arezzo and Siena, the barn is a perfect homebase to visit Tuscany. The accommodation has 2 floors. The upper floor spaces 2 double bedrooms with wonderful views of the olive trees and a bathroom with window and large masonry shower. On the ground floor a cozy and spacious living area with fireplace and a kitchenette with gas stove a large fridge and oven. The barn has ceilings with exposed beams and bricks. Outside there is a panoramic garden set on its own where, in the shade of a walnut trees, you can relax on a hammock or grill your meal (included an authentic local Fiorentina steak :-) on the stone made barbecue. A garden table is there for romantic dinners 'al fresco'. Immersed in total peace and tranquility halfway between Florence, Arezzo and Siena the barn is a perfect homebase to visit Tuscany. To find the exact location of the house type the following code in GMaps: 8FMHGG25+QV The house is in the countryside. The closest towns are Cavriglia and the small Medioeval villages of Moncioni and Montegonzi. In each town you can find great local restaurants and a small grocery shop. Moncioni is 3 km far away. A big supermarket is located in Montevarchi and you can reach it in 8 minutes by car ( exactly 7 km far away). In Montevarchi you can also find one of the best farmer markets in Tuscany! The station of Montevarchi is 8 km away from the barn. From there you can take train to Florence and Arezzo. Siena can be reached in 30 minutes by car. The easy access to the motorway A1/E35 Milan-Florence-Rome (the Valdarno exit is only at 13 km) allows you to reach numerous interesting spots within a short time, both in Tuscany and Umbria, while few kilometres south of Cavriglia you enter the suggestive territory of the Crete Senesi. Out in the countryside, the home offers an authentic experience of Tuscany. Small towns and villages are a short drive away providing acces to exceptional local restaurants and fantastic farmers markets. A big supermarket is located in Montevarchi (7 km far away). The railway station is 8 km away from the barn. From there you can take train to Florence and Arezzo. Cities of interest like Siena, Montepulciano, Pienza and Monteriggioni can be reached in 40 minutes by car The only way to reach the house is by car. A taxi service is active from Montevarchi You will be provided of blankets and towels. The kitchen is equipped with and kind of pots, pans, bowl, plates and silverware. You are welcome to use them. Free Netflix available

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, 75 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 shaded terrace is presented with multiple wooden loungers arranged around a sleek pool. Lush greenery surrounds the space, offering a natural backdrop, while a stone building stands quietly in the distance under a clear sky.
Villa in Gaiole in Chianti
5.0 out of 5 average rating, 31 reviews

Casa Faraona, villa con piscina privata

Imagine the perfect Chianti villa – a secluded house with private pool and fabulous 180-degree views. That’s just what you’ll experience at Casa Faraona.

Set down a lane a few meters away from the "Eroica" road and between the wine towns of Radda and Gaiole, this three-bedroom villa is bound to take your breath away at first sight. Typical Tuscan features include terracotta tiles on the floors and beamed ceilings, while soft pastels and stylish furnishings give a light and modern aspect.

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, 296 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, 153 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)

Top Guest favourite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Villa in Barberino Tavarnelle
4.98 out of 5 average rating, 107 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

Top Guest favourite
A charming stone-crafted villa is set among lush greenery, with terraced levels adorned by landscaped gardens. A private pool with sun loungers is positioned in the lower terrace, while the villa overlooks rolling hills, providing a tranquil backdrop for relaxation.
Villa in Gaiole in Chianti
5.0 out of 5 average rating, 25 reviews

Casanova di Bricciano

Set on the grounds of a family-run organic winery, this stone-built villa offers a harmonious blend of Tuscan charm and modern comfort. Positioned above a tiny hamlet in the rolling Chianti hills, it enjoys panoramic views over vineyards, olive groves and forested slopes. With a spacious interior and generous outdoor areas, the villa is ideal for a memorable stay with family or friends.

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, 50 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, 117 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?

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.