
Holiday Homes in Casentino
Find and book unique holiday homes on Airbnb
Top-rated Holiday Homes in Casentino
Guests agree: These holiday homes are highly rated for location, cleanliness and more.

Holiday Toscany in the Strettoio
Surrounded by the beautiful Tuscan hills, just 30 minutes by train from Florence’s historic city centre, Casale Strettoio is a charming retreat for guests looking for peace, privacy and an authentic Tuscan atmosphere. The apartment is located on the ground floor of one of the oldest homes in Rignano sull’Arno and has recently been carefully renovated, preserving the character and traditional style of the property. The interiors are distinctive, well finished and designed to offer guests a comfortable sense of intimacy and independence. Ideal for 2 adults and 1 child up to 5 years old, the apartment features a cosy 14 m² kitchen-living area with a small one-and-a-half-size sofa bed, refrigerator, electric oven, sink, stovetop, washing machine, dining table and everything needed to prepare and enjoy meals in complete freedom. The bathroom is traditionally built and carefully maintained, with a shower, washbasin and toilet. The sleeping area includes a cosy bedroom with a French bed, a hallway with wardrobe and independent heating, making the apartment suitable for stays during the cooler months as well. One of the most beautiful parts of the property is the swimming pool overlooking the Tuscan hills, next to a relaxing outdoor area where, during the warmer season, guests can enjoy breakfast, lunch or dinner surrounded by peaceful countryside views. The pool may occasionally be shared with members of the owner’s family. Guests also have access to free Wi-Fi, TV, bed linen and towels, sun loungers, a garden and private on-site parking. The location offers the perfect balance between countryside relaxation and easy access to nearby destinations. Rignano sull’Arno is connected by the national railway network, making it easy to reach Florence and explore other beautiful places in Tuscany. Casale Strettoio is an ideal choice for those seeking an authentic, private and peaceful stay in a home full of history and character — a little corner of Tuscany where you can slow down, breathe and enjoy the simple pleasures of life. ...P.S. It 'better to stay at least two nights, thanks!
FamilyLocationGetting around

Casa Manu
Characteristic Tuscan stone house immersed in the hills of the province of Arezzo, Tuscany, just restructured, equipped with every comfort. Solarium with outdoor shower. Barbecue grill. Wi-fi. Bed linen, bathroom, kitchen, solarium. Shops at 2 km. Within 70/100 km you can reach the most important sites of interest such as Siena, Florence, Cortona, Perugia, the sanctuary of Verna with the story of St. Francis of Assisi, Sansepolcro and paintings by Piero Della Francesca. Ideal for trekking, for food and wine tourism (in a few kms some of the best wineries in Tuscany can be found), for art and culture enthusiasts.
ValueLocationGetting around

House of Poggio al Vico
A portion of a farmhouse, cozy, renovated in Tuscan country chic style, in the hills of Pratolino, calm and quiet with private parking. Two double bedrooms, a kitchen, a living room with a fireplace, and a garden. Perfect for 4 people. The apartment is 20 minutes from the center of Florence and can also be reached by bus, with very good connections. Conveniently located, quiet, but close to Florence and safe. In the summer, you can dine in the garden and sleep in a cool environment, thanks in part to the air conditioning.
FamilyValueAccess

[Florence Hills] Tuscan house with parking space
Our B&B offers a peaceful and quiet corner, quick and easy to reach, in a renovated, characteristic Tuscan house just 7 km (25 minutes) from the parking lot in the historic center of Florence. At Borgo Le Palaie, you can immerse yourself in the landscape of the Florentine hills among cypresses and olive trees, enjoy the view, and visit important vineyards and wineries just a short distance away. You can easily get there by car (including a reserved parking space for guests) or by bus, which is 300 meters away.
LocationValueHeating

Tuscan stone farmhouse studio with private terrace
12 km from Arezzo, a delightful studio apartment furnished with care on the ground floor of a typical Tuscan stone farmhouse from the early twentieth century. Surrounded by woods and overlooking a village, the farmhouse is located in a hilly position within a large property of 5 hectares. Through a path immersed in the woods with a pleasant walk you can reach the stream that flows in the valley. Until the end of July approximately (depending on the year) you can take a bath in a small natural pool.
ValueLocationBathroom

Romantic stay at a bio-agritourism in Florence
Escape the crowd and hot of the towns. We are 40 min away from the centre of Florence (consider driving the last 3 km on a narrow winding beautiful countryside road). Be ready for an authentic rural Tuscan lifestyle experience, here the deers graze the fields near the house, you can hear the wild boars grunting and the crickets singing. Healthy food, good wine, a bio sauna and a jacuzzi in the oliveyards; a real re-charge and re-connection in Nature in an eco-friendly and cozy accommodation .
FamilyLocationBathroom

Tuscan Country house with panoramic pool
Old stone Country House located on the top of an uncontaminated hill in a secluded atmosphere, with stunning 360° panoramas over the hills and the Arno river. Surrounded by private olives grooves, the accommodation offers an ideal mix between peaceful relaxation and opportunities for outdoor activities. With easy access to Florence (18 km) and major arts sites of Tuscan region such as Siena, San Gimignano, Pisa, Lucca, the wine Chianti area and many others landscaping or trekking attractions.
ValueFamilyGetting around

Chianti Craft House Badia a Passignano
Ancient house in the historic village of Badia a Passignano, completely and finely restored in 2022. The house is located exactly in the center of the village of Badia a Passignano, overlooking the abbey castle and the Chianti vineyards. The house consists of 2 bedrooms air-conditioned: 1 double bedroom with service bathroom and 1 with 2 single beds and the possibility of a third with sofa chair; a full bathroom with shower, a full kitchen with washing machine and dishwasher, dining area
FamilyValueBiking

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.
ValueLocationOutdoor spaces

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.
LocationFamilyPets

La Loggia. House with pool and stunning view
LA LOGGIA House, renovated in 2015, is a large independent apartment, ideal to be rented by those who love nature, tranquility and peace of these uncontaminated places immersed in nature. The apartment is characterized by a huge window overlooking the valley where you can enjoy one of the most spectacular views in the region. The view that can be admired from LA LOGGIA spans more than 60 km on the Chianti and the Crete Senesi.
FamilyLocationAir conditioning

[Authentic StoneHouse]Jacuzzi & Viewpool Apartment
Nestled in a medieval village in the heart of Chianti, this exclusive historical apartment blends Tuscan charm with refined contemporary design. Enjoy a panoramic pool overlooking the hills, multiple terraces, and a unique hot tub Jacuzzi suite and bathroom carved in travertine. Designed for two, it’s the perfect place to slow down, reconnect, and experience Tuscany in total peace.
LocationFamilyQuiet
Popular amenities for Casentino holiday homes
Family-Friendly holiday homes

"Lisa" apartment with fireplace
ValueFamilyHospitality

Chianti Penthouse with panoramic View & Pool
LocationFamilyParking

"Soffitta" (Loft) 2/3p, pool, pvt garden, view
FamilyLocationWalkability

House in Tuscany with swimming pool "La casetta di Ghiora"
FamilyLocationParking

PIERFANTINI private Chianti house ♿️ 🏊♂️ 🐶
LocationFamilyHeating

Ancient stone farmhouse with park and pool
LocationValueCheck-in

L'orchidea Vacation Home
LocationFamilyCondition

Agriturismo I Moraioli, Cantina apartment
LocationAmenitiesOutdoor spaces
Holiday home rentals with a patio

I Rosai apartment on the Florentine hills
FamilyValueDecor

Il Toscano - New with terrace in downtown Greve
ValueFamilyAccuracy

City Centre Patio - 10 mins to Duomo
ValueLocationLaundry

Tuscany Country House, Central Chianti, Pano Views
ValueLocationQuiet

House in the heart of Tuscany
FamilyValueIndoor spaces

Studio apartment in the hills near Florence
LocationIndoor spacesQuiet

Tuscan country house Monastero
ValueLocationComfort

4BR • Deluxe Palazzo • Private Patio • Santa Croce
LocationFamilyIndoor spaces
Holiday home rentals with a washing machine and dryer

Zen Island downtown Florence, new apartment for 6
LocationFamilyLayout

Melarancio Residence
LocationValueHeating

Duomo Charme – A few steps from the Duomo
FamilyLocationWi-Fi

SMN Luxury Secret Garden View
LocationValueLayout

TOSCANELLA APARTMENT
LocationValueWi-Fi

Historic Center | Duomo • Ponte Vecchio
LocationValueGetting around

Verde, space and relax in historic Florence
FamilyValueAccuracy

Large group house + breackfast + parking Florence
ValueFamilyBreakfast
Destinations to explore
- Pet-friendly rentals Casentino
- Cottage rentals Casentino
- Rentals with lake access Casentino
- Bed and breakfasts Casentino
- Family-friendly rentals Casentino
- Condo rentals Casentino
- House rentals Casentino
- Rentals with pools Casentino
- Villa rentals Casentino
- Rentals with a hot tub Casentino
- Rentals with breakfast Casentino
- Rentals with a sauna Casentino
- Farmstay rentals Casentino
- Apartment rentals Casentino
- Holiday home rentals Arezzo
- Holiday home rentals Tuscany
- Holiday home rentals Italy
- 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
- Mugello Circuit
- Misano World Circuit
- Mercato Centrale
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Uffizi Gallery
- Fortezza da Basso
- Piazza della Repubblica
- Parco delle Cascine
- Del Chianti
- Piazzale Michelangelo
- Palazzo Vecchio
- Palacongressi Della Riviera Di Rimini
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden





