
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 $56 AUD 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.

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
FamilyLocationQuiet
4.97 out of 5 average rating, 305 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
FamilyValueWalkability
4.88 out of 5 average rating, 338 reviews
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.
LocationFamilyPool
4.95 out of 5 average rating, 103 reviews
Antico Podere del 1600 nel Chianti in Toscana
Podere Vergianoni è un antica e storica proprietà risalente al 1600 situato nelle splendide colline del Chianti in Toscana con la possibilità di organizzare servizi ed esperienze esclusive su misura per voi . 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 stupenda vista su castello colline e vigneti con tramonti mozzafiato.
FamilyValueAccess
5.0 out of 5 average rating, 218 reviews
Villa Padronale - IlVillinoFarmhouse
Intero piano superiore della Villa Padronale appena ristrutturata in stile tradizionale toscano.Gli alti soffitti con le travi a vista rendono il posto accogliente e perfetto per famiglie o gruppi di amici.Nella casa si trovano due grandi camini(in salotto e cucina)funzionali.Alloggio privato, non condiviso. La casa ha una ampia terrazza coperta,giardino con divani,bbq,firepit,parking privato. La piscina tra gli ulivi e i vigneti e' ideale per il relax ha un accesso privato alla zona condivisa
LocationValueTV
4.93 out of 5 average rating, 254 reviews
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.
ValueLocationWi-Fi
4.99 out of 5 average rating, 113 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.
ValueFamilyWi-Fi
4.98 out of 5 average rating, 216 reviews
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!
ValueLocationSleep quality
4.97 out of 5 average rating, 194 reviews
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.
FamilyLocationGetting around
5.0 out of 5 average rating, 25 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.
ValueLocationGetting around
4.98 out of 5 average rating, 105 reviews
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.
FamilyLocationComfort
4.99 out of 5 average rating, 510 reviews
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 🌷
ValueFamilyCleanliness
4.87 out of 5 average rating, 215 reviewsPopular amenities for Chianni holiday rentals
Other great holiday rentals in Chianni

Mimosa: Scenic Tuscany Stay, Pool & Walk to town
FamilyValueDecor
4.95 out of 5 average rating, 38 reviews
Cozy Italian stone cottage central Tuscany
LocationValueQuiet
4.94 out of 5 average rating, 71 reviews
Relaxing Tuscan Country Home with Beautiful Views
ValueLocationBreakfast
5.0 out of 5 average rating, 86 reviews
splendida colonica nel chianti giardino panoramico
LocationFamilyAccuracy
4.96 out of 5 average rating, 47 reviews
Tuscany jem: La Casa del Fattore del Chianti
LocationFamilyBreakfast
4.98 out of 5 average rating, 84 reviews
Cipressini 2 - piscina e vista mozzafiato
LocationFamilyBathroom
5.0 out of 5 average rating, 65 reviews
Villa la scuderia quiet luxury private garden pool
LocationFamilyCleanliness
5.0 out of 5 average rating, 23 reviews
Chiesino Dei Vaioni
LocationValueCheck-in
4.99 out of 5 average rating, 86 reviewsFrequently 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





