
Family-friendly holiday rentals in Casentino
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Top-rated family-friendly rentals in Casentino
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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.
Indoor spacesFamilyBreakfast

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
FamilyIndoor spacesNearby

Villa di Geggiano – Guesthouse
PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.
FamilyKitchenWi-Fi

Tuscan charm of villa - countryside - Villa Senaia
Nell’affascinante campagna Toscana,tra ulivi e vigneti una villa in pietra,in posizione strategica per cogliere i segreti di Toscana e Umbria aria condizionata e piscina con area wellness per il vostro relax e confort Villa Senaia è una grande casa con travi in legno, in una splendida posizione in collina con vista idilliaca che affaccia su uno dei luoghi preferiti della campagna toscana, un ambiente attraente per mangiare all'aperto, bevendo vino toscano e ascoltando i grilli e le cicale
KitchenIndoor spacesHot tub

Casa al Gianni - Hut
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!
FamilyIndoor spacesBreakfast

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.
KitchenFamilyAccuracy

Typical Tuscan country house
Agriturismo Il Colle is located on one of the Chianti hills. The property 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 This apartment is one level, totally independent with private garden. Restored and furnished with great care to make the guest's stay as comfortable and relaxing as possible, in the full respect of the Tuscan rural style.
Indoor spacesKitchenCheck-in

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.
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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.
Indoor spacesKitchenLaundry

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!
Indoor spacesFamilySleep quality

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.
Indoor spacesKitchenNearby

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!
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Popular amenities for Casentino family-friendly rentals
Family-friendly home rentals with a hot tub

Art-Design Fienile in the heart of Tuscany
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Il Fienile, Cottage in the country with Jacuzzi
Indoor spacesFamilyBarbecue

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
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Torretta Apartment
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Il Vichiaccio: Accessible Chianti Villa & Jacuzzi
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Fully renovated exclusive apartment in Villa
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2 ❤️ and 1 Yurt Glamping in Tuscany for adults only
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Le Rondini - where it all began
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Family- and pet-friendly home rentals

Authentic Tuscan Country House WITH A/C
KitchenIndoor spacesWi-Fi

Tuscany .Countryhouse on the Florence's hills
Indoor spacesFamilyBreakfast

Monteriggioni Castello, holiday house in Tuscany
KitchenFamilyTV

Suite in Castello di Valle
KitchenFamilyDecor

At Paola's in Chianti
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Piazza Grande Boutique Apartment
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Cortona’s Rooftop Nest
KitchenIndoor spacesCleanliness

Apartment in Tuscan farm house.
Indoor spacesKitchenCleanliness
Family-friendly home rentals with a pool

Infinity pool in Chianti 1
KitchenIndoor spacesBarbecue

Podere Bocci residence in Casentino - Entire Villa
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Poggelleri the postcard on Poppi and Tuscan hills
CleanlinessComfortAmenities

Relaxation and charm in the Chianti hills
FamilyIndoor spacesValue

La Vignaccia (Farmhouse) - villa w/private pool
FamilyIndoor spacesOutdoor spaces

Il Roseto: your Villa in Tuscan Countryside
KitchenIndoor spacesHiking

Agriturismo I Gelsi
FamilyKitchenLaundry

House Rigomagno Siena
FamilyKitchenHiking
Destinations to explore
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- Cathedral of Santa Maria del Fiore
- Lake Trasimeno
- Santa Maria Novella
- Santa Maria Novella
- Pinarella Di Cervia
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Mirabilandia
- Fiera Di Rimini
- Misano World Circuit
- Stazione Santa Maria Novella
- Mugello Circuit
- Uffizi Gallery
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Fortezza da Basso
- Piazza della Repubblica
- Parco delle Cascine
- Del Chianti
- Autodromo Enzo e Dino Ferrari
- Piazzale Michelangelo
- Pitti Palace
- Palazzo Vecchio
- Piazza della Signoria
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