
Holiday houses in Chianni
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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, Wi-Fi 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.

Casa al Gianni - The Simignano Barn
Transformed from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, and a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those seeking a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, complete with relaxation in the hot tub and al fresco dining. A memorable getaway awaits you in this slice of paradise!
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Relaxation and charm in the Chianti hills
Beautiful stone farmhouse, detached, surrounded by olive trees and the Chianti hills, with private garden and panoramic swimming pool. Ground floor with large living rooms, antique fireplace and wood-burning oven, bright living room and fully equipped kitchen. On the first floor, three suites consisting of a bedroom, study and private bathroom. Access via gate and white road on private property just 500 meters from the village of Strada in Chianti. Ideal for peace and relaxation. Convenient location for visiting Tuscany.
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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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Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is a family-run, historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany. Our family can arrange a private shuttle and local experiences directly. 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 overlooking the castle and vineyards with unique sunsets.
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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.
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Belforti Tower
Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.
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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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Casa Giulia di Sopra Farmhouse
The CASA GIULIA DI SOPRA apartment, renovated in 2022 and located on the first floor, is a portion of an ancient farmhouse located in the heart of Chianti Classico. It is surrounded by the vineyards of Villa Calcinaia, an estate owned by the Capponi Counts since 1524. The apartment is 130 meters away from the shared swimming pool, open from May to October. The apartment has an outdoor area with a table and chairs where guests can dine and enjoy a glass of wine at sunset.
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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.
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Relaxing Tuscan Country Home with Beautiful Views
An amazing experience between nature, flavor 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 olive groves and vineyards 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 peaceful and relaxing holiday.
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Nada Home
3 comfortable, fully air-conditioned double bedrooms, each with its own private bathroom, in the heart of Chianti, ideally located between Florence, Siena and San Gimignano. A welcoming, well-kept home in the peaceful Tuscan countryside. Fully equipped kitchen with dishwasher, oven and bar area, plus a laundry room with washing machine and dryer. Private garden for your exclusive use with a private hydromassage pool, heated in winter upon request 🌷
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Tuscany jem: The Chianti Farmer's House
This wonderful newly renovated apartment retains the charm of the Chianti farmhouses and the comforts of a modern apartment. The house is located within the complex of the Fattoria di Petroio, a Chianti Classico winery. You can enjoy the beauty and tranquility of the Chianti hills, while immersing yourself in the dynamic life of a company dedicated to the production of quality wines.
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Popular amenities for Chianni holiday rentals
Other great holiday rentals in Chianni

Cozy Italian stone cottage central Tuscany
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beautiful farmhouse in the Chianti region with panoramic garden
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Villa la scuderia quiet luxury private garden pool
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Cipressini 2 - pool and amazing views
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Villa of the Hydrangeas
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Church of the Vaioni
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Herons Superior Apartment - Splendid view!
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Incredible Views & Pool in the Tuscan Hills
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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.
Destinations to explore
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Piazza del Duomo (Pisa)
- Cala Violina
- Stazione Santa Maria Novella
- Mercato Centrale
- Spiagge Bianche
- Pisa Centrale Railway Station
- Uffizi Gallery
- Gulf of Baratti
- Fortezza da Basso
- Piazza della Repubblica
- Spiaggia Di Sansone
- Parco delle Cascine
- Gorgona
- Del Chianti
- Piazzale Michelangelo
- Palazzo Vecchio
- Piazza della Signoria
- Pitti Palace
- Spiaggia di Capo Bianco





