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Holiday rentals 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 £30 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    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

  • Wifi availability

    30 of Chianni holiday rentals include wifi 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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Guest favourite
Home
4.96 out of 5 average rating, 135 reviews

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Guest favourite
Townhouse
4.88 out of 5 average rating, 337 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

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, 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.

Top guest favourite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Apartment
5 out of 5 average rating, 343 reviews

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is a family-run, historic 17th-century property located in the beautiful Chianti hills of Tuscany, with the option of arranging a private shuttle and local experiences directly with our family. The apartment is available for 2 adults with the possibility 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 overlooking the castle and vineyards with unique sunsets.

Top guest favourite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guest house
4.97 out of 5 average rating, 238 reviews

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Top guest favourite
The stone house features a welcoming entrance with large arched windows. A vibrant flower box filled with geraniums complements the lush green lawn. A shaded area with wooden seating offers a place to relax, while the infinity pool and surrounding vineyards are visible in the background.
Cottage
4.98 out of 5 average rating, 212 reviews

Stone House with Exclusive Pool Codilungo in Chianti

Welcome to your Tuscan dream between Florence & Siena. Perfect for families or romantic getaways. • 360° views of iconic Chianti hills. •Huge Exclusive Infinity Pool (17x9m), lit at night (open from May 1st to October 15th) • Total privacy, yet restaurants/shops are 10-15 mins away. • Comfort for 6: 3 bedrooms (2 double, 1 twin) & 3 full baths. • Modern amenities: Fully equipped kitchen area, Smart TV. • Outdoor bliss: Large dining loggia, professional BBQ, poolside porch & bath.

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
4.93 out of 5 average rating, 282 reviews

Casa al Gianni - Hut

Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

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
4.99 out of 5 average rating, 224 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.

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
4.98 out of 5 average rating, 102 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
Farm stay
4.99 out of 5 average rating, 510 reviews

Farmhouse in Chianti with Swimming Pool

Agriturismo Il Colle is located on one of the Chianti hills. The structure has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car The apartment is located on the ground floor of the main farmhouse, with independent access and private space. The care taken in the restoration and furnishing make the house particularly welcoming, respecting the rural style.

Top guest favourite
Home
5 out of 5 average rating, 82 reviews

Breathtaking Views in Our Chianti Country House

An incredible experience between flavor, nature and relax in the heart of Chianti. Situated between Barberino Tavarnelle, San Gimignano, Greve in Chianti, and Florence, Belvedere 27/A overlooks the Santa Maria Novella Castle, amidst vineyards and olive groves with an amazing view. A countryside Tuscan home, surrounded by greenery and olive’s fields, equipped with every comfort. Reconnect in this serene, one-of-a-kind stay, for a relaxing and peaceful holiday.

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
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.

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.