
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

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.

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.

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!

Casa Faraona, villa with private pool
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.

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.

Casa Martini in Historic Chianti
Apartment with garden and private parking in Gaiole in Chianti, a stone's throw from the historic center where you will find numerous bars, restaurants and the small supermarket (coop). The accommodation is ideal for holidays with animals because it has a fully fenced garden. Tourist tax is required (€2 per person per night for the first seven nights) minors under 14 years excluded (read the complete regulation on the website of the Municipality of Gaiole in Chianti)

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.

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

Villa Montemaggio
Stay in an authentic Tuscan farmhouse set within a working vineyard, surrounded by breathtaking rolling hills. A private property of the estate owners, fully refurbished for modern comfort while preserving its country charm. Far from busy streets, here you’ll hear birdsong and the distant hum of tractors in the fields. Please note: to get to the property you have to drive for about 6 km of unpaved road, part of its secluded countryside setting.

Villa il Balocco
Ancient renovated manor villa with access from the village square and immersed in the green hills of historic Chianti in the back with a large garden and large panoramic terrace with swimming pool and two bersos. The view is magnificent and sweeps from the Chianti mountains to Brolio and Val d'Orcia to Amiata. Easily accessible from the Valdarno exit of the A1, it is ideal for families and couples of friends.

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

Montemarcoli
Immerse yourself in this unique space born on a beautiful hill in Gaiole in Chianti, a brand new villa with swimming pool located in a lush forest offers a private refuge of luxury, style and love from which you can admire sunrise and sunset. A project built with the latest architectural trends, eco-sustainable and with natural spring water.

Villa le Scope 5*
Villa le scope is located in the heart of Chianti, surrounded by nature and tranquility, yet just a short walk from the village. You can taste an excellent Chianti Classico wine on the beautiful terrace or in total relaxation in our large garden. Villa le Scope is about an hour from Florence and half an hour from Siena.
Popular amenities for Gaiole in Chianti holiday rentals
Other great holiday rentals in Gaiole in Chianti

The Chianti Cabin

Villa Le Miccine w/ Pool - Bella Vista Unit for 4

Tuscany jem: The Chianti Farmer's House

Old Chianti chapel-style cottage

Apartment Comfort | Quiet Escape in Tuscany

Ancient tower w/ private pool Vacavilla Exclusive

Apartment for 8-9 people in villa with pool

Appartamento Holly House
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
- Stazione Santa Maria Novella
- Mugello Circuit
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Fortezza da Basso
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden
- Mount Amiata
- Stadio Artemio Franchi
- Medici Chapel
- Basilica of Santa Croce





