
Family-friendly vacation rentals in Casentino
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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.
Indoor spacesKitchenSleep quality
4.99 out of 5 average rating, 531 reviews
Stone farmhouse, exclusive private pool
Podere Montebono is located in the hills of Reggello, just 30 kilometers from Florence. Ideal for reaching art cities and natural sites. The farmhouse is isolated on a hill, immersed in nature, surrounded by olive trees, a garden, and woods. The guest house is an independent wing of the large farmhouse on two floors: 3 bedrooms, kitchen, living room, bathroom. The private pool is exclusively for those who rent the house (max 4 people). We do not rent single rooms. Barbecue area. Total privacy.
FamilyIndoor spacesNearby
4.96 out of 5 average rating, 195 reviews
La Vignaccia (Farmhouse) - villa w/private pool
Nestled amidst the rolling hills of Tuscany, La Vignaccia beckons you to experience the true essence of Italian living. This enchanting villa, set within a sprawling estate, offers a haven of tranquility, where you can unwind and immerse yourself in the beauty of the Tuscan countryside. A secluded garden awaits, providing a serene setting for relaxation and alfresco dining. Take a refreshing dip in the sparkling pool, surrounded by breathtaking views of the Tuscan landscape.
Indoor spacesKitchenBackyard
4.96 out of 5 average rating, 102 reviews
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.
Indoor spacesFamilyLong stay
4.99 out of 5 average rating, 227 reviews
Country house with view (NO Jacuzzi)
The house has a private garden of 100 square meters with a tub usable with a depth of 60 cm. Two squares usable for your relaxing and fun, from admire the view, and space for eat outside. WI-FI free. The interior is distributed over two floors: on the first large living room with fireplace, SmartTV, eat area, kitchen and room with pizza oven (there are 2 sofa/bed). On the second floor there are 3 bedrooms, 2 of which are doubles and 1 with a bunk bed and 1 bathroom.
KitchenFamilyDecor
4.87 out of 5 average rating, 124 reviews
Il Roseto: your Villa in Tuscan Countryside
In the heart of Tuscany between Arezzo, Florence and Siena but far away from the bustle of the cities, you will find a pristine landscape where to enjoy nature and relaxing, amazing views and much more for a perfect getaway with your friends or family. A villa of 190 mq with 600 mq garden,where you can enjoy lunch outdoors, have fun making pizza and baking it in the wood- oven, or savour a wonderful barbeque. A comfortable Villa for guests who love being together.
Indoor spacesFamilyComfort
4.99 out of 5 average rating, 124 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 spacesKitchenGrill
4.98 out of 5 average rating, 107 reviews
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.
KitchenFamilySleep quality
4.99 out of 5 average rating, 432 reviews
[SAN LORENZO-DUOMO] Prestigious Historic Residence
Make your stay a unique experience and give yourself an emotion that will last for life. Located in the heart of Florence, this magnificent historic residence is the ideal solution for those looking for an exclusive and prestigious location to combine with a central position, perfect for easily visiting the main sites of interest, reachable in less than 10 minutes on foot. The apartment enjoys exclusive views of the Medici Chapels, offering a unique view.
FamilyIndoor spacesLocation
5.0 out of 5 average rating, 158 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.
Indoor spacesKitchenComfort
4.96 out of 5 average rating, 139 reviews
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.
KitchenIndoor spacesDecor
4.97 out of 5 average rating, 159 reviews
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 spacesKitchenAmenities
4.94 out of 5 average rating, 125 reviewsPopular amenities for Casentino family-friendly rentals
Family-friendly home rentals with a hot tub

Villa Lolù with private heated swimming-pool
Indoor spacesKitchenTV
4.98 out of 5 average rating, 160 reviews
LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
Indoor spacesFamilyValue
4.99 out of 5 average rating, 116 reviews
PIERFANTINI private Chianti house ♿️ 🏊♂️ 🐶
KitchenIndoor spacesPets
4.91 out of 5 average rating, 100 reviews
Tuscan charm of villa - countryside - Villa Senaia
FamilyKitchenNearby
4.9 out of 5 average rating, 241 reviews
Villa di Geggiano - Guesthouse
FamilyIndoor spacesCheck-in
4.99 out of 5 average rating, 155 reviews
Barrel Suite Tuscany • Hot Tub • Vineyard View
FamilyIndoor spacesLocation
4.88 out of 5 average rating, 228 reviews
Torretta Apartment
KitchenFamilyAmenities
4.96 out of 5 average rating, 129 reviews
Ancient Tuscan Rural Residence
FamilyKitchenSleep quality
4.85 out of 5 average rating, 124 reviewsFamily- and pet-friendly home rentals

La Casina Porciano
FamilyKitchenQuiet
4.95 out of 5 average rating, 151 reviews
Casa Rosmarino Eco-Wellness Country Home
FamilyKitchenGetting around
4.99 out of 5 average rating, 274 reviews
Casa Manu
FamilyKitchenHospitality
4.92 out of 5 average rating, 132 reviews
Piazza Grande Boutique Apartment
KitchenIndoor spacesBreakfast
5.0 out of 5 average rating, 155 reviews
Florence Sunset Hills • Giogoli
KitchenIndoor spacesComfort
4.88 out of 5 average rating, 342 reviews
Apartment in a Tuscan farmhouse at Le Pietre Vive
Indoor spacesFamilyCheckout
4.92 out of 5 average rating, 359 reviews
Beautiful medieval village!!!
KitchenIndoor spacesPets
4.99 out of 5 average rating, 474 reviews
Casa Macchia /Florence charming villa private Pool
FamilyKitchenRiver
4.96 out of 5 average rating, 102 reviewsFamily-friendly home rentals with a pool

Relaxation and charm in the Chianti hills
FamilyKitchenWalkability
4.99 out of 5 average rating, 115 reviews
Infinity view
FamilyKitchenAmenities
4.88 out of 5 average rating, 204 reviews
Agriturismo I Gelsi
Indoor spacesKitchenValue
4.96 out of 5 average rating, 171 reviews
Comfort Apartment in the Chianti Vineyards
FamilyIndoor spacesLaundry
4.93 out of 5 average rating, 455 reviews
Tofanello Orange Luxury and Modern Comfort with Outdoor Pool
FamilyIndoor spacesView
4.98 out of 5 average rating, 145 reviews
Villa Montanina - relax in esclusiva in Toscana
KitchenIndoor spacesAccess
4.99 out of 5 average rating, 85 reviews
Podere Bocci residence in Casentino - Entire Villa
FamilyIndoor spacesWifi
5.0 out of 5 average rating, 50 reviews
Cipressino Villa, pool near the historic centre
KitchenIndoor spacesCleanliness
5.0 out of 5 average rating, 13 reviewsDestinations to explore
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- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Pinarella Di Cervia
- Mirabilandia
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Misano World Circuit
- Mugello Circuit
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Fortezza da Basso
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria
- Palacongressi Della Riviera Di Rimini
- Pitti Palace
- Boboli's Garden





