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Holiday houses in Chianni

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in Chianni

  • Total holiday rentals

    Explore 30 holiday rentals in Chianni

  • Nightly prices starting at

    Chianni holiday rentals start at $68 NZD per night before taxes and fees

  • Verified guest reviews

    Over 480 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Chianni holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chianni rentals

  • 4.8 Average rating

    Chianni stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated holiday rentals in Chianni

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

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Top Guest favourite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay in Simignano
4.93 out of 5 average rating, 281 reviews

Casa al Gianni - Hut

Hi, we're Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism facility located in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: There is only the scent of the earth, the song of the birds, and the companionship of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It's not just a vacation; it's a return to our roots. This peaceful haven will stay with you in your heart. We look forward to welcoming you!

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Top Guest favourite
An aerial view captures the sprawling vineyards and olive groves surrounding Podere Vergianoni. The property features a salt-water pool positioned on a terrace, offering panoramic views of the lush Chianti landscape and medieval castle in the distance. Rustic buildings line the garden area.
Condo in Noce
5.0 out of 5 average rating, 213 reviews

Historic 17th-century farmhouse in Chianti, Tuscany

Podere Vergianoni is an ancient and historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany, with the possibility of organizing exclusive services and experiences tailored to you. The apartment is available for 2 adults with the option of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace with a wonderful view of the castle, hills, and vineyards with breathtaking sunsets.

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Guest favourite
A spacious kitchen showcases a large stone fireplace with a wooden mantle as its centerpiece. Light streams through the window, illuminating the wooden beams overhead. A dining table is set for a meal, while traditional utensils adorn the walls, enhancing the inviting ambiance.
Villa in Castellina in Chianti
4.93 out of 5 average rating, 253 reviews

Manor House - IlVillinoFarmhouse

Entire upper floor of the newly renovated Manor House in traditional Tuscan style. High ceilings with exposed beams make the place cozy and perfect for families or groups of friends. In the house, there are two large functional fireplaces (in the living room and kitchen). Private, non-shared accommodation. The house has a large covered terrace, garden with sofas, BBQ, fire pit, private parking. The swimming pool among the olive trees and vineyards is ideal for relaxation and has private access to the shared area

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Guest favourite
Townhouse in Scandicci
4.88 out of 5 average rating, 336 reviews

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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Top Guest favourite
An inviting kitchen area features a glass dining table surrounded by blue chairs. Stone walls complement modern cabinetry and appliances, illuminated by a contemporary circular light fixture. A warm ambiance is created by the rustic elements and soft lighting throughout the space.
Apartment in Rivalto
4.98 out of 5 average rating, 48 reviews

Il Frantoio (Whirlpool + Swimming Pool)

✨ Romantic retreat in the heart of Tuscany — perfect in every season 🍂 Welcome to Palazzo Riccardi, a historic building in the charming village of Rivalto, where Tuscan authenticity meets modern design. Let yourself be won over by the wood-burning fireplace, the bathroom with a whirlpool tub and a warm and enveloping atmosphere. Ideal for couples looking for relaxation and charm, this apartment is a perfect nest in every season, but it is in autumn and winter that it becomes truly magical. 💫

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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 in Geggiano
4.99 out of 5 average rating, 154 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.

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Top Guest favourite
An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.
Home in Gambassi Terme
5.0 out of 5 average rating, 227 reviews

Il Fienile, Luxury Apartment in the Tuscan Hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

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Guest favourite
Castle in Tignano
5.0 out of 5 average rating, 25 reviews

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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Top Guest favourite
The exterior of the castle is showcased at sunset, with vibrant orange and purple skies providing a dramatic backdrop. Stone towers rise from the landscape, surrounded by greenery and colorful flora, reflecting the historic charm of the property.
Castle in Ferrano
4.99 out of 5 average rating, 223 reviews

The Castle of Ferrano - Castle in Tuscany

Try the experience of staying in a real Castle! Il Castello di Ferrano offers to its hosts the chance of living an unforgettable experience: you will be the only guests in the castle, and everything will be for you (private pool from June to September, gardens etc..). Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.

ValueFamilyIndoor spaces

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 in Greve in Chianti
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.

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Top Guest favourite
A spacious living area features a modern design, with a prominent stone fireplace and minimalist furniture. Large glass doors open to a serene outdoor view, while natural light brightens the room, highlighting the soft tones of the walls and furnishings.
Tower in Fiesole
4.95 out of 5 average rating, 218 reviews

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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Guest favourite
Farm stay in Castelfranco di sopra
4.89 out of 5 average rating, 337 reviews

Romantic apartment in the Tuscan village

The house is located in an ancient medieval village that has been completely renovated while maintaining the charm of its history. In the village you will find two swimming pools, a restaurant, many gardens and much more... It is in a strategic position to be able to reach the main attractions such as the Chianti Region, Florence, Arezzo and Siena!

LocationFamilyHot tub

Popular amenities for Chianni holiday rentals

Frequently Asked Questions

  • What are the best places to stay in Chianni?

    Guests often enjoy staying in the historic village center for easy access to cafes and markets, or in countryside homes with views of rolling hills. Both areas have a mix of restored villas and modern apartments.

  • What are the best things to do in Chianni with kids?

    Families with kids can explore local nature paths, visit small farms, or join food experiences like gelato-making workshops. Village playgrounds and relaxed cafes create family-friendly spaces in the town center.

  • What are some of the best things to do in Chianni?

    Popular activities in Chianni include exploring the medieval streets, tasting olive oil or wine at family-run estates, and walking forested trails nearby. Many visitors also enjoy taking part in seasonal village festivals.

  • How is the weather in Chianni?

    Chianni has mild, rainy winters with temperatures around 37–55°F (3–13°C), and warm, dry summers reaching up to 87°F (30°C). Spring and fall are pleasant with moderate rainfall and comfortable temperatures.

  • When is the best time to visit Chianni?

    Spring and early fall are frequently suggested for milder weather and local festivals, with temperatures around 60–73°F (16–23°C). Summer is warmer and lively, while winter is quieter with cooler, rainier days.

  • What are the best places to visit in Chianni?

    The historic village center, traditional churches, and local wineries are often recommended in Chianni. Visitors frequently explore the surrounding countryside and seasonal village markets.

  • What are some hiking trails in Chianni?

    Chianni has countryside paths winding through olive groves, forested hills, and traditional villages. These trails are frequently suggested for gentle hikes and birdwatching, with opportunities to spot local flora.

  • What are some family activities we can do in Chianni?

    Families often explore local parks, join olive oil tastings, or participate in cooking classes rooted in Tuscan traditions. Nearby walking trails and village squares invite relaxed outdoor play and cultural discovery.

  • What are some of the best day trip ideas from Chianni?

    Many visitors plan day trips to nearby hilltop villages, regional thermal baths, or wine-producing estates. Opportunities for exploring local art towns and nature reserves are also frequently suggested.

  • Are there any pet friendly accommodations available in Chianni?

    Many accommodations in and around Chianni welcome pets, with extra amenities like garden access or outdoor patios. Guests often find relaxed stays in traditional stone homes or countryside rentals.

  • What are some local tips for visiting Chianni?

    Pack layers for changing temperatures, especially in spring and autumn. Exploring beyond the main streets reveals small artisan shops and family-run trattorias that highlight Chianni’s local culture.

  • What is Chianni known for?

    Chianni is known for its historic village atmosphere, traditional food festivals, and locally produced olive oil and wine. The area frequently draws visitors seeking authentic Tuscan countryside experiences.

  • What are the best hidden gems to explore in Chianni?

    Hidden gems in Chianni often include tucked-away chapels, small artisanal workshops, and panoramic viewpoints just outside the village. Local markets and lesser-known walking paths invite slower exploration.

  • What are the best foods to try in Chianni?

    Locally inspired foods include wild boar dishes, handmade pasta with truffle sauce, and olive oil–based specialties. Seasonal cheeses and artisanal breads frequently appear in village bakeries and trattorias.

  • What should I bring for a trip to Chianni?

    Bring layers for variable weather, especially a light jacket for cool evenings or rain. Comfortable walking shoes are useful for cobblestone streets and countryside hikes.

  • What is the nightlife in Chianni like?

    Chianni’s nightlife is relaxed, centered on village cafes, wine bars, and seasonal outdoor gatherings. In summer, live music and food stalls sometimes animate the main square.

  • What are the most popular events or festivals in Chianni?

    Chianni is known for an autumn festival celebrating wild boar dishes, along with seasonal food fairs and open-air concerts during summer and early fall. Village celebrations often feature local music and traditional cuisine.

  • Are there family friendly vacation rentals in Chianni?

    Chianni has a variety of family-friendly vacation rentals, including apartments, restored farmhouses, and homes with access to outdoor spaces. Many places include kitchens and flexible sleeping arrangements.