
Family-friendly holiday rentals in Chianni
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Chianni

Total holiday rentals
Explore 20 holiday rentals in Chianni

Nightly prices starting at
Chianni holiday rentals start at $84 NZD per night before taxes and fees

Verified guest reviews
Over 280 verified reviews to help you choose

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
20 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 family-friendly rentals in Chianni
Guests agree: These family-friendly homes 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

Infinity pool in Chianti 1
Our house is a part of a stone farmhouse completely independent from the rest of the adjacent property. Arranged on three floors, on the ground floor there is a large entrance hall, a large living room with fireplace, a bedroom with 1 double bed and a bathroom with window. On the first floor there are two bedrooms (2 +2 beds) with a bathroom with window. In the basement, at garden level, there is the kitchen and the dining room. From the kitchen you access the outside where you will find an area for outdoor dining with a large dining table under a pergola. You then go down towards the garden with barbecue area.

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!

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.

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

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

Podere La Castellina - No. 1 COTTAGE
Independent stone and brick cottage inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The cottage can comfortably accommodate 5 people and includes: - large living room with TV and fireplace - kitchen with oven - master bedroom - bedroom with three single beds - bathroom with shower Guests have access to a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.

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.

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.

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.

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.

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.
Popular amenities for Chianni family-friendly rentals
Family-friendly home rentals with a hot tub

Le Rondini - where it all began

Palazzo Monaci - Pool in the Crete Senesi

Villa di Geggiano – Guesthouse

A Big Dream in a Little Tower.

Nada Home

Agriturismo PURO - Charming Design House in Tuscany

La Casetta

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
Family- and pet-friendly home rentals

Fienile Santa Teresa

Casa La Misura in the heart of Chianti

Tuscan cottage with an heavenly view

Country Rentals - La Canonica

Hilltop Views From a Historic Tuscan Home

Villa La Doccia, Greve in Chianti

Paluffo Tower House

Agriturismo La Villa - Il Ciliegio, Pool & Garden.
Family-friendly home rentals with a pool

Frontemare house with exclusive sea access

sea view villa with private infinity pool

Villa Isabella

The Castle of Ferrano - Castle in Tuscany

Countryside Dream farm in Tuscany

Farmhouse in Tuscany hills

Private Chianti Cottage, Garden & Vineyard Views

Cercis - La Palmierina
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
- Spiagge Bianche
- Pisa Centrale Railway Station
- Mercato Centrale
- Uffizi Gallery
- Gulf of Baratti
- Fortezza da Basso
- Parco delle Cascine
- Piazza della Repubblica
- Spiaggia Di Sansone
- Del Chianti
- Gorgona
- Piazzale Michelangelo
- Piazza della Signoria
- Palazzo Vecchio
- Pitti Palace
- Boboli's Garden





