
Family-friendly holiday rentals in Tuscany
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Tuscany
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Poggio Bicchieri Holiday Farm - Memoria apartment
Relax with the whole family in this accommodation. The holiday farm consists of two independent apartments with a living room, kitchen, bedroom, and bathroom. You won't have to share anything with other guests, as we have taken care to organize everything so that everyone has their own space and everything is separate. Outside there is a barbecue, table with chairs and deck chairs. In the vicinity are Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino, and Bagni San Filippo. To reach us, there is 1.5 km of dirt road!

Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

Tuscan cottage with an heavenly view
Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Tuscan cottages in an ancient villa with a garden
The Cottage is part of a property owned by the Bernocchi family, which was already on maps of the area in the 1500s and is located right on an ancient Roman road that crossed the Calvana Mountains. About 9 km from Prato and 20 km from Florence. The Cottage, open on three sides, is situated in a panoramic position surrounded by a private park, ideal for walking and sports. A real home fitted with kitchen, living room, bedroom and bathroom. Large outdoor spaces, garden, and botanical garden.

House with a view surrounded by nature_ 5
A cozy stone and wood chalet with amazing views of the Apennines, surrounded by nature with a large garden where you can relax and enjoy the spectacular sunsets. We will be happy to host you on the ground floor which is dedicated to the B&B. The warm and welcoming rooms have independent entrances and lead onto the garden. Fantastic location between Bologna and Florence, 10' from the motorway exit and 30' from Bologna airport. Don't miss the sunset, even better with a good glass of wine!

The Cellar (Palazzo Pallotti)
The apartment is two floors below the square, entirely dug into the tuff. Overlooking the valley, it is isolated from the noises of the street, quiet, private, and very welcoming. The tuff walls give it an ancient vibe to transport you to another time. It can be reached on foot, via a footbridge that takes you directly to the square where the property is located. It is perfect for short stays of complete relaxation, but with the fully equipped kitchen you can make the most of it.

Il Fienile, Luxury Apartment in the Tuscan Hills
‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

House at Gianni - Olmo
Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

Il Castello di 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.

House with a breathless view in Tuscany
Halfway between Pisa and Florence, this dreamy Tuscan house is your perfect escape. Lounge on the panoramic terrace with sun-kissed views, sip your morning coffee, or enjoy al fresco dinners under the golden sunset. Nestled in the heart of a charming village turned open-air contemporary art museum, every corner feels like a picture-perfect moment. Peccioli is your gateway to Tuscany’s art cities or a serene hideaway to savor the magic of authentic local life.

The Tower
Ancient Tuscan villa, beautiful, with exclusive private garden, completely renovated, surrounded by the beautiful and gentle Tuscan hills. The villa has a breathtaking view, is very sunny, well furnished and equipped with all amenities, quiet and not isolated. The house is located in Bagnolo, a small hamlet of Impruneta at the gates of Chianti, an area of olive groves, vineyards and peace. The house is about 10 km by car from the center of Florence.

The Enchantment of Civita (The Terrace)
L'Incanto di Civita is located inside the ancient village of Civita di Bagnoregio. After leaving your car at the parking lot, you will need to walk along the bridge, the only way to access our "tufo pearl". L'Incanto di Civita is located in the ancient village of Civita di Bagnoregio. After leaving your car at the parking lot you will need to walk along the bridge, the only way to access our "tufo pearl".
Popular amenities for Tuscany family-friendly rentals
Family-friendly home rentals with a hot tub

A Big Dream in a Little Tower.

Il Fienile, Cottage in the country with Jacuzzi

"Sunflower" apartment with view of Siena

SuiteLouise.pool, Hot Tub,homeGym & private Garden

Captain's House | Monte Grosso, Elba

Old hayloft on the Chianti hills

La Pieve - the house next to the church

La Casetta
Family- and pet-friendly home rentals

Stone farmhouse in Val D'Orcia

Mascagni Farmhouse in Val d'Orcia, Pienza

Private villa/swimming pool in Tuscany

Celeste – The color of the summer sky in Tuscany

Ca' Inua, art, woods, hospitality

Chianti Villa in Tuscany near Siena and Arezzo

Antico Borgo Ripostena – n. 8 Old House

Casa Bonari - a paradise for the eyes
Family-friendly home rentals with a pool

Private Chianti Cottage, Garden & Vineyard Views

Infinity pool in Chianti area

The Eagle and the Olive Tree

Cercis - La Palmierina

Vineyards Paradise

Stone House with Exclusive Pool Codilungo in Chianti

Amazing view, pool and relax, 5 adults

Countryside Dream farm in Tuscany
Destinations to explore
- Rentals with outdoor seating Tuscany
- Rentals with an accessible-height toilet Tuscany
- Waterfront rentals Tuscany
- Serviced apartment rentals Tuscany
- Motorhome rentals Tuscany
- Rentals with a patio Tuscany
- Holiday home rentals Tuscany
- Cabin rentals Tuscany
- Boat rentals Tuscany
- Rentals with a hot tub Tuscany
- Guest house rentals Tuscany
- Tower rentals Tuscany
- Earth house rentals Tuscany
- Villa rentals Tuscany
- Rentals with breakfast Tuscany
- Rentals with an accessible-height bed Tuscany
- Castle rentals Tuscany
- Bungalow rentals Tuscany
- Cottage rentals Tuscany
- Private suite rentals Tuscany
- Fitness-friendly rentals Tuscany
- Luxury rentals Tuscany
- Loft rentals Tuscany
- Hostel rentals Tuscany
- Rentals with a firepit Tuscany
- Apartment rentals Tuscany
- Rentals with a balcony Tuscany
- Rentals with pools Tuscany
- Campsite rentals Tuscany
- Smoking-friendly rentals Tuscany
- Barn rentals Tuscany
- Rentals with beach access Tuscany
- Rentals with lake access Tuscany
- Townhouse rentals Tuscany
- Pet-friendly rentals Tuscany
- Rentals with a washing machine and dryer Tuscany
- House rentals Tuscany
- Tent rentals Tuscany
- Hotel rooms Tuscany
- Rentals with an EV charger Tuscany
- Resort rentals Tuscany
- Flat rentals Tuscany
- Beachfront rentals Tuscany
- Rentals with a sauna Tuscany
- Rentals with a fireplace Tuscany
- Rentals with a kayak Tuscany
- Nature eco lodge rentals Tuscany
- Aparthotel rentals Tuscany
- Lakehouse rentals Tuscany
- Chalet rentals Tuscany
- Tiny house rentals Tuscany
- Ski-in/ski-out rentals Tuscany
- Boutique hotels Tuscany
- Farm stay rentals Tuscany
- Rentals with a cinema Tuscany
- Beach house rentals Tuscany
- Bed and breakfasts Tuscany
- Mansion rentals Tuscany
- Family-friendly rentals Italy
- Things to do Tuscany
- Sightseeing Tuscany
- Art and culture Tuscany
- Entertainment Tuscany
- Tours Tuscany
- Food and drink Tuscany
- Nature and outdoors Tuscany
- Sports activities Tuscany
- Things to do Italy
- Tours Italy
- Food and drink Italy
- Art and culture Italy
- Sightseeing Italy
- Wellness Italy
- Entertainment Italy
- Sports activities Italy
- Nature and outdoors Italy





