
Holiday houses in Gaiole in Chianti
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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 $84 AUD per night before taxes and fees

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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 grill 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.

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
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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.
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Florence Sunset Hills • Giogoli
Escape to the peaceful hills of Giogoli where authentic Tuscan charm meets breathtaking views of Florence.Just 15 minutes from the city center and the Chianti countryside, this elegant home is the perfect base for exploring Tuscany while enjoying quiet mornings, unforgettable sunsets, and the beauty of the surrounding landscape. Surrounded by nature but close to the region's most iconic spots, it's the ideal retreat for anyone looking for comfort, tranquility, and a genuinely Tuscan experience
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Tuscany Country House, Central Chianti, Pano Views
Tour (no spaces) www. escapetochianti. com/experience Perfect central base in Tuscany! The Farmhouse at Vignale has spectacular views overlooking organic vineyards in the heart of Chianti Classico wine country. Our spacious, historic artist-inspired stone house has 3 bedrooms, 1 bath (add 1bd/1ba extra fee) large living room, massive fireplace & great kitchen. Minutes to top restaurants & Chianti hill towns; easy drive to Florence & Siena; an ideal location for day trips to all parts of Tuscany
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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!
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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.
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Luxury Medieval Tower • Exclusive Chianti Stay
Welcome to one of the most exclusive residences in Chianti: a medieval tower transformed into a refined luxury retreat overlooking the Tuscan hills. Contemporary design, iconic furnishings, works of art and luxury comforts come together in a unique experience. An oasis of tranquility with a private garden, glass annex, Wi-Fi, and smart working area. Extra services: private chef, tastings in the cellar, wellness treatments and tours of the most beautiful villages in Tuscany.
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Independent cottage surrounded by nature
The Cottage is located inside the Tiorcia farm, less than 4 km from Gaiole in Chianti, a village of the Eroica, surrounded by woods and overlooking the hills of Chianti Senese. The property consists of a spacious living room, kitchenette and bathroom with shower. A distinctive feature of the house is the mezzanine with a double bed; there is also the possibility of using a small sofa bed. The accommodation is ideal for a couple or a family with one/two children
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Old hayloft on the Chianti hills
Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.
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Chianti La Pruneta, Raphael Apartment
Stunning apartment in the heart of Tuscany set in the middle of vines and olives trees. The apartment has been totally refurbished keeping the lovely old features, beamed ceilings, marble floors with antique furniture. Patio doors lead to a private terrace with sun loungers for relaxing and space. With table and chairs you can eat 'Al fresco' enjoying the beautiful views.
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A Big Dream in a Little Tower.
The Tower was created in the late 1800s by an illustrious Englishman, Sir John Temple Leader, in one of the oldest and most important stone quarries belonging to the Medici family. From the same quarry were extracted many important works such as the columns of the Medici chapels, the steps of the Laurenziana library .. all just 5 km from the historic center of Florence.
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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?
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Popular amenities for Gaiole in Chianti holiday rentals
Other great holiday rentals in Gaiole in Chianti

Montemarcoli
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Appartamento Holly House
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Villa Il Masseto
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Villa Montemaggio
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Ancient tower w/ private pool Vacavilla Exclusive
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Apartment Comfort | Quiet Escape in Tuscany
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Villa with pool in Chianti - Castellare Petroso
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beautiful farmhouse in the Chianti region with panoramic garden
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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.
Destinations to explore
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Mugello Circuit
- Stazione Santa Maria Novella
- Mercato Centrale
- Uffizi Gallery
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Fortezza da Basso
- Parco delle Cascine
- Piazza della Repubblica
- Del Chianti
- Piazzale Michelangelo
- Piazza della Signoria
- Palazzo Vecchio
- Pitti Palace
- Boboli's Garden
- Mount Amiata
- Basilica of Santa Croce
- Medici Chapel
- Stadio Artemio Franchi





