
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 $87 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, 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 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
KitchenFamilyView
4.97 out of 5 average rating, 308 reviews
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.
KitchenFamilyAmenities
5.0 out of 5 average rating, 143 reviews
Casa al Gianni - Hut
Hi, we're Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism facility located in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: There is only the scent of the earth, the song of the birds, and the companionship of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It's not just a vacation; it's a return to our roots. This peaceful haven will stay with you in your heart. We look forward to welcoming you!
FamilyKitchenHospitality
4.93 out of 5 average rating, 294 reviews
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.
KitchenIndoor spacesLaundry
5.0 out of 5 average rating, 352 reviews
Villa Gourmet Food, Pizza, Chef, Pool and Nature
Villa Gourmet Typical farmhouse in the heart of Tuscany with 6 bedrooms that can comfortably accommodate up to 14 guests. - Exclusive saltwater infinity pool - Gourmet cuisine - Large garden with private parking - Two Free Charging Station (3,75 KW) - Veranda with table and Weber barbecue by the pool - Children's play area and table tennis - Football pitch - Home Restaurant service available - Cooking class and pizza workshop using a wood-fired oven - Shuttle Services
FamilyIndoor spacesParking
4.98 out of 5 average rating, 127 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.
KitchenFamilyLaundry
4.98 out of 5 average rating, 218 reviews
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.
KitchenIndoor spacesNearby
4.99 out of 5 average rating, 138 reviews
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.
FamilyIndoor spacesLaundry
4.95 out of 5 average rating, 106 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.
FamilyIndoor spacesHospitality
4.99 out of 5 average rating, 227 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.
Indoor spacesKitchenWi-Fi
4.98 out of 5 average rating, 107 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.
FamilyIndoor spacesHot tub
4.99 out of 5 average rating, 516 reviews
Tower Penthouse in small castle near Florence
900 year old Tower-Penthouse apartment in Chianti Villa, spacious & super-scenic historical home that combines magical atmosphere with space, light, history, convenience. (AC throughout). Painting-like 360° views of Tuscan Hills all the way to Florence; sun-filled, private grounds. Perfect location for an unforgettable family stay. Ample private property (including forest). Walking distance from village shops. Convenient location, Florence in sight.
FamilyIndoor spacesHiking
4.96 out of 5 average rating, 139 reviewsPopular amenities for Chianni family-friendly rentals
Family-friendly home rentals with a hot tub

Villa di Geggiano – Guesthouse
KitchenFamilyLayout
4.99 out of 5 average rating, 155 reviews
La Pieve - the house next to the church
Indoor spacesFamilyBarbecue
4.97 out of 5 average rating, 117 reviews
Palazzo Monaci - Pool in the Crete Senesi
Indoor spacesFamilyShared spaces
4.96 out of 5 average rating, 142 reviews
Agriturismo La Villa - L'Olivo, Pool & Hot Tub
FamilyKitchenValue
4.98 out of 5 average rating, 241 reviews
Nada Home
FamilyKitchenAmenities
4.87 out of 5 average rating, 217 reviews
A Big Dream in a Little Tower.
FamilyKitchenCheck-in
4.95 out of 5 average rating, 221 reviews
Wp Relais Borgo Vignalunga
KitchenIndoor spacesQuiet
4.95 out of 5 average rating, 146 reviews
La Casetta
Indoor spacesFamilyAccuracy
4.93 out of 5 average rating, 197 reviewsFamily- and pet-friendly home rentals

Florence Sunset Hills • Giogoli
FamilyKitchenAccess
4.88 out of 5 average rating, 342 reviews
Manor House - IlVillinoFarmhouse
Indoor spacesFamilyView
4.93 out of 5 average rating, 256 reviews
Apartment in a Tuscan farmhouse at Le Pietre Vive
KitchenIndoor spacesHiking
4.92 out of 5 average rating, 359 reviews
Hilltop Views From a Historic Tuscan Home
FamilyKitchenBeach
4.99 out of 5 average rating, 110 reviews
La Dimora del Luca
Indoor spacesKitchenSleep quality
4.98 out of 5 average rating, 171 reviews
Countryhouse 9 kms to Florence-3+2,free park, wine
FamilyIndoor spacesAmenities
4.86 out of 5 average rating, 275 reviews
Poggio Bicchieri Holiday Farm - Memoria apartment
KitchenFamilyAccess
4.92 out of 5 average rating, 626 reviews
Typical Tuscan Country House WITH A/C
KitchenIndoor spacesAccess
4.98 out of 5 average rating, 294 reviewsFamily-friendly home rentals with a pool

Relaxation and charm in the Chianti hills
FamilyKitchenCondition
4.99 out of 5 average rating, 115 reviews
Tenuta Chiudendone in Tuscany
FamilyKitchenEV charging
4.99 out of 5 average rating, 338 reviews
Cercis - La Palmierina
Indoor spacesKitchenBeach
4.96 out of 5 average rating, 147 reviews
Countryside Dream farm in Tuscany
Indoor spacesFamilyQuiet
4.98 out of 5 average rating, 201 reviews
Villa Isabella
FamilyKitchenLayout
4.96 out of 5 average rating, 209 reviews
Charming Farmhouse Suite
Indoor spacesFamilyLocation
4.99 out of 5 average rating, 135 reviews
Frontemare house with exclusive sea access
KitchenFamilyCleanliness
4.96 out of 5 average rating, 112 reviews
sea view villa with private infinity pool
FamilyKitchenQuiet
4.99 out of 5 average rating, 124 reviewsDestinations 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)
- Stazione Santa Maria Novella
- Cala Violina
- Mercato Centrale
- Spiagge Bianche
- Pisa Centrale Railway Station
- Fortezza da Basso
- Gulf of Baratti
- Uffizi Gallery
- Piazza della Repubblica
- Spiaggia Di Sansone
- Gorgona
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria
- Val di Luce
- Pitti Palace





