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

Farmhouse Fattoria La Parita
Provencal-style apartment nestled between vineyards and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 km from the highway. The song of jays and cuckoos will be the soundtrack to the stay while the roe deer graze among the olive trees. A basic Italian breakfast is included (coffee, tea, milk, biscuits, etc.), but if you prefer a richer breakfast served at the table, the cost is €15 per person (€10 from 5 to 15 years, free under 5 years). EV wallbox available.

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 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!

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.

Experience rustic off-grid life in the wilderness
This ancient rustic farmhouse lies within a national park in one of the largest areas of forests in Europe. Solar power, wood stoves, the bumpy road and the lack of phone signal offer an authentic off-grid experience. A rare privilege to go into the wild and take a break from urban life and modern conveniences. Hike to the monastery of St.Francis and the sacred forests of La Verna...or simply sit and enjoy the peace of this magical remote place.

Il Fienile, Cottage in the country with Jacuzzi
Surrounded by wineyards, close to Florence, a charming accomodation in a cozy cottage with heated jacuzzi at your exclusive use. Perfect starting point to discover Florence and Siena. Kitchen, wide living room, bathroom, two double bedroom (one with an extra single bed). In the living room a sofa bed for other 2 people. Tasteful furniture, Air Conditioning, barbecue, private parking. Partnership for: bike rental, private chef, private driver

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, character, convenience. 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.

Barrel Suite Tuscany • Hot Tub • Vineyard View
Sleep inside a wine barrel in Tuscany — one of the largest in the world (3.5 m × 8 m) — nestled in an olive grove in Reggello, with panoramic views over the hills and vineyard. Private bathroom, kitchenette, veranda, private courtyard and exclusive hot tub: everything for a total escape from the world. 40 min from Florence, with Siena, Arezzo, The Mall Luxury Outlet and Vallombrosa all within easy reach. Free private parking included.

Mafuccio Farmhouse - "Casa di Rigo"
Casa di Rigo is the smallest apartment of Agriturismo Mafuccio, a farmhouse immersed in unspoiled nature in the Sovara Valley, a stone's throw from the Rognosi Mountains nature reserve and nestled at the foot of Monte Castello. A quiet and peaceful place like the streams that cross the valley, where you can find peace, and fully experience nature... in the company of the Valley Kids!

A Big Dream in a Little Tower.
The Tower was created in the late 1800s by an illustrious Englishman, Sir John Temple Leader, in one of the oldest and most important stone quarries belonging to the Medici family. From the same quarry were extracted many important works such as the columns of the Medici chapels, the steps of the Laurenziana library .. all just 5 km from the historic center of Florence.

Chianti, elegant barn among vineyards and pool
Discover a unique sanctuary in Chianti, a historic barn where stone walls meet 80s vintage design. Fall in love with the canopy bedroom, cook in the modern kitchen, and enjoy vineyard views from the living area. Outside, private gazebos and an infinity pool await you in total silence. A perfect blend of Tuscan heritage, sophisticated style, and pure romance."

Romantic apartment in the Tuscan village
The house is located in an ancient medieval village that has been completely renovated while maintaining the charm of its history. In the village you will find two swimming pools, a restaurant, many gardens and much more... It is in a strategic position to be able to reach the main attractions such as the Chianti Region, Florence, Arezzo and Siena!
Popular amenities for Casentino family-friendly rentals
Family-friendly home rentals with a hot tub

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA

Bio-agritourism in the hills of Florence

White lily with a view of Siena

Il Vichiaccio: Accessible Chianti Villa & Jacuzzi

House of Delights - The Medici private leisure house

Villa di Geggiano – Guesthouse

PoggiodoroLoft, Tuscan dream e relax

The Tancherina, a Tuscan heart
Family- and pet-friendly home rentals

Podere La Quercia

Country chill in the heart of a medieval village

Museum Suite - Luxurious unit with a River View -

Beautiful medieval village!!!

Tuscany .Countryhouse on the Florence's hills

Casa Al Poggio & Chianti view

Costalmandorlo, a rustic home in the heart of Tuscany

Casa Luigi Suite with exclusive pool
Family-friendly home rentals with a pool

Farmhouse in Tuscany hills

Infinity pool in Chianti area

Villa with Private Pool in the Tuscan Countryside

Relaxing-unspoiled country place Il Monte...

Stone House with Exclusive Pool Codilungo in Chianti

Podere Tignano, 4-bedroom villa in the Chianti!

Casa San Ripa: Relax Oasis with Private Pool

Relaxation and charm in the Chianti hills
Destinations to explore
- Pet-friendly rentals Casentino
- Bed and breakfasts Casentino
- Rentals with a firepit Casentino
- Fitness-friendly rentals Casentino
- Villa rentals Casentino
- Farm stay rentals Casentino
- Rentals with lake access Casentino
- Rentals with a hot tub Casentino
- Rentals with a patio Casentino
- Cottage rentals Casentino
- Smoking-friendly rentals Casentino
- Flat rentals Casentino
- Rentals with outdoor seating Casentino
- Rentals with an EV charger Casentino
- Rentals with a washing machine and dryer Casentino
- Apartment rentals Casentino
- Rentals with pools Casentino
- Rentals with breakfast Casentino
- House rentals Casentino
- Rentals with a fireplace Casentino
- Holiday home rentals Casentino
- Rentals with a sauna Casentino
- Family-friendly rentals Arezzo
- Family-friendly rentals Tuscany
- Family-friendly rentals Italy
- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Stazione Santa Maria Novella
- Lake Trasimeno
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Fiera Di Rimini
- Mercato Centrale
- Fortezza da Basso
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Piazza della Repubblica
- Uffizi Gallery
- Pinarella Di Cervia
- Mugello Circuit
- Del Chianti
- Misano World Circuit
- Piazzale Michelangelo
- Pitti Palace
- Palazzo Vecchio
- Boboli's Garden
- Palacongressi Della Riviera Di Rimini
- Parco delle Cascine
- Mirabilandia





