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Holiday rentals 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 £45 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Wifi availability

    30 of Gaiole in Chianti holiday rentals include wifi 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.

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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
4.97 out of 5 average rating, 303 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

Guest favourite
The historic farmhouse is surrounded by tall, ancient cypress trees and lush greenery. A gravel patio with outdoor seating is visible in the foreground, leading to an inviting garden area. The sky is clear with scattered clouds, creating a bright and welcoming ambiance.
Holiday home in Radda in Chianti
4.98 out of 5 average rating, 44 reviews

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

Top guest favourite
An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.
Cottage
4.99 out of 5 average rating, 153 reviews

Villa di Geggiano - Guesthouse

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

Top guest favourite
Home
5 out of 5 average rating, 18 reviews

Private House for 4P- La Capanna Di Azzurra

Ideale per famiglie, coppie o amici in cerca di una dimora elegante e accogliente, questa casa è pensata per chi vuole vivere la campagna toscana senza rinunciare alla comodità della città. Immaginate una colazione guardando il profilo di Siena, giornate tra arte, vino e natura, e il rientro al tramonto, quando la luce scalda la pietra e il silenzio restituisce il ritmo autentico di questi luoghi. Un rifugio pratico, con charme e scenografico, perfetto per visitare Siena e i suoi dintorni!

Guest favourite
A sunlit dining area features a rustic wooden table surrounded by chairs, with a view of lush greenery through large windows. The terracotta floor complements the wooden beams of the ceiling, creating a cozy atmosphere for meals.
Guest suite
4.98 out of 5 average rating, 52 reviews

Cottage indipendente immerso nella natura

Il Cottage si trova all'interno del podere Tiorcia, a meno di 4 km da Gaiole in Chianti, paese dell'Eroica, immerso nel bosco e con vista sulle colline del Chianti senese. La struttura si compone di spazioso soggiorno, angolo cottura e bagno con doccia. Tratto distintivo dell'abitazione è il soppalco con letto matrimoniale; vi è inoltre la possibilità di usufruire di un divano letto di ridotte dimensioni. La sistemazione è ideale per una coppia o per una famiglia con uno/due bambini

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
4.86 out of 5 average rating, 290 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
Villa
5 out of 5 average rating, 5 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 charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.
Farm stay
4.99 out of 5 average rating, 475 reviews

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.

Guest favourite
A charming stone exterior reveals a rustic villa surrounded by greenery. The entrance features a wooden door and terracotta roof tiles. Potted plants add color, while seating areas are positioned on a patio, inviting relaxation in the scenic surroundings under a clear blue sky.
Home
4.92 out of 5 average rating, 171 reviews

Casa Dante - Authentic Chianti Stay | Views&Relax

Wake up to breathtaking views over the rolling hills of Chianti and enjoy a glass of wine at sunset from your private terrace. This peaceful home offers the perfect mix of privacy, comfort, and authentic Tuscan charm. Located just minutes from the center of Radda in Chianti, the house is ideally positioned to explore wineries, charming villages, and the surrounding countryside—while still feeling quiet.

Top guest favourite
The stone cottage is set amidst lush greenery, featuring a sloped roof and a large glass door that opens onto a sunlit terrace. Sun loungers are positioned nearby, surrounded by flowering plants, with olive trees visible in the background against a clear blue sky.
Farm stay
4.92 out of 5 average rating, 371 reviews

Chianti La Pruneta, Raffaello 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.

Top guest favourite
An infinity pool reflects the sky, surrounded by lush greenery and cypress trees. The pool's edge seamlessly blends into the landscape, overlooking rolling hills and olive groves. Sun loungers are positioned nearby, providing a serene outdoor setting.
Barn
5 out of 5 average rating, 63 reviews

Cipressini 2 - piscina e vista mozzafiato

Ancient stone farmhouse adjacent to the main farmhouse dating back to the 17. century, located in the heart of the Chianti Classico on the side of a slope with breathtaking views over the Val d'Elsa. Luxuriously renovated and furnished, equipped with every comfort, it is located in such a way as to guarantee absolute privacy.

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
4.98 out of 5 average rating, 45 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.

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.

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