
Holiday rentals 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 $51 SGD 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.

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
ValueFamilyGetting around

Agriturismo Casa Giulia di Sopra
L'appartamento CASA GIULIA DI SOPRA, ristrutturato nel 2022 e situato al primo piano, è una porzione di un'antica colonica situata nel cuore del Chianti Classico. E' circondato dai vigneti di Villa Calcinaia, tenuta di proprietà dei Conti Capponi dal 1524. L'appartamento si trova a 130 mt. di distanza dalla piscina condivisa, aperta da maggio ad ottobre.L'appartamento dispone di un'area esterna dotata di tavolo e sedie dove gli ospiti potranno desinare e godersi un bicchiere di vino al tramonto.
LocationFamilyHospitality

Podere Vergianoni immerso nelChianti con piscina
Podere Vergianoni è un antica proprietà del 1600 a gestione familiare situato nelle splendide colline del Chianti in Toscana con la possibilità di organizzare navetta privata e esperienze locali direttamente con la nostra famiglia . L'appartamento è disponibile per 2 adulti con possibilità aggiunta divano letto per 2 bambini sotto i 12 anni . Nel grande cortile esterno troverete una piscina a sale con area relax su terrazza panoramica con vista su castello e vigneti con tramonti unici.
FamilyValueOutdoor spaces

Cozy Italian stone cottage central Tuscany
Casa Michelangelo is a beautifully restored stone cottage, in a small gated cluster of houses in the heart of the picturesque town of Chianni. The casa has a lovely view of the neighbouring vineyard and every amenity to feel comfortable during your stay, including AC throughout. Enjoy your evenings either dining on the terrace or out at one of the award winning restaurants near by. Chianni is perfectly situated as a great central base to explore Tuscany's greatest Cities, towns and the coast.
LocationValueComfort

Relax e charme tra le colline del chianti
Bellissima colonica in pietra, indipendente, immersa tra gli olivi e le colline del Chianti, con giardino privato e piscina panoramica. Piano terra con ampi saloni, antico camino e forno a legna, soggiorno luminoso e cucina full optional. Al primo piano tre suites composte da camera, studio e bagno privato. Accesso tramite cancello e strada bianca in proprietà privata a soli 500 metri dal paese di Strada in Chianti. Ideale per quiete e relax. Location strategica per visitare la Toscana.
FamilyLocationOutdoor spaces

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.
FamilyLocationWifi

Casa al Gianni - Il Fienile di Simignano
Trasformato da un antico fienile, questo rifugio lussuoso offre 5 camere, 4 bagni, grande cucina attrezzata, ampio living, un ampio giardino privato con parcheggio, hot tub, patio con divani, BBQ, fire pit e cucina esterna. Ideale per chi cerca un'esperienza unica, unisce fascino rustico a comfort moderni. Perfetto per famiglie o gruppi, promette serate magiche sotto le stelle, tra relax nell'hot tub e cene all'aperto. Una fuga memorabile vi aspetta in questo angolo di paradiso!
LocationFamilyComfort

Torre dei Belforti
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.
LocationValueAir conditioning

Luxury Medieval Tower • Exclusive Chianti Stay
Benvenuti in una delle residenze più esclusive del Chianti: una torre medievale trasformata in un raffinato luxury retreat con vista sulle colline toscane. Design contemporaneo, arredi iconici, opere d’arte e comfort di lusso si fondono in un’esperienza unica. Un’oasi di quiete con giardino privato, dependance vetrata, Wi-Fi, area smart working. Servizi extra: chef privato, degustazioni in cantina, trattamenti benessere e tour tra i borghi più belli della Toscana.
LocationFamilyAmenities

Agriturismo nel Chianti con Piscina
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.
ValueFamilyBathroom

La Casa di 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 🌷
ValueLocationPool

Tuscany jem: La Casa del Fattore del Chianti
Questo meraviglioso appartamento appena ristrutturato conserva il fascino dei casolari del Chianti e le comodità di un appartamento moderno. La casa è situata all'interno del complesso della Fattoria di Petroio, azienda vitivinicola del Chianti Classico. Potrete godere della bellezza e della tranquillità delle colline del Chianti, mentre vi immergete nella vita dinamica di un'azienda dedita alla produzione di vini di qualità.
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Popular amenities for Chianni holiday rentals
Other great holiday rentals in Chianni

Relaxing Tuscan Country Home with Beautiful Views
LocationFamilyAccess

stupenda villa nel chianti, giardino panoramico
FamilyLocationWifi

Villa la scuderia quiet luxury private garden pool
FamilyLocationLaundry

Cipressini 2 - piscina e vista mozzafiato
LocationFamilyCheck-in

Incredible Views & Pool in the Tuscan Hills
LocationValueBreakfast

Villa delle Ortensie
LocationValueComfort

Herons Superior Apartment - Splendid view!
FamilyValueAccess

Villino Isotta (villa privata esclusiva)
ValueLocationWifi
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





