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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.

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Guest favourite
The rustic stone facade of the house features abundant greenery and wisteria blooms cascading from the upper balcony. The entrance is accessible via a stone pathway, and wooden beams frame the windows, enhancing the traditional Tuscan architecture.
Holiday home in San Martino Sopr'Arno
4.94 out of 5 average rating, 129 reviews

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.

Guest favourite
A stone-paved courtyard features a rustic house with weathered yellow walls and green shuttered windows. A small table with chairs is set under the sun, surrounded by potted plants, creating an inviting outdoor space for guests to enjoy the fresh air.
Holiday home in Fiesole
4.91 out of 5 average rating, 139 reviews

[Florence hills] Tuscan house with parking space

Our B&B offers a peaceful and quiet corner, quick and easy to reach, in a characteristic renovated Tuscan house just 7 km (25 minutes) from the parking lot in the historic centre 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 a short distance away. You can easily get there by car (including a reserved parking space for guests) or by bus, which is 300 metres away.

Guest favourite
Holiday home in Chiaveretto
4.95 out of 5 average rating, 131 reviews

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.

Guest favourite
The rustic kitchen area features exposed stone walls and a warm, earthy tone. A small wooden table with two chairs sits adjacent to a red cabinet. A sink with a vintage faucet and decorative items can be seen, complemented by soft lighting from an overhead fixture.
Holiday home in Figline e Incisa Valdarno
4.93 out of 5 average rating, 397 reviews

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 .

Guest favourite
A modern kitchen space features a marble countertop with two wooden stools. Large windows showcase a scenic view of Florence's rooftops, including the iconic dome, while natural light fills the room. A fruit bowl and coffee maker are included on the counter.
Holiday home in Centro
4.95 out of 5 average rating, 480 reviews

Breathtaking view from romantic nest in citycenter

Unique and charming attic in the middle of historic center with amazing breathtaking view on the city center. Perfect for a romantic stay in the heart of Florence. Fully windowed on 3/4 walls. Completely renewed with modern design furniture. Powerful A/C, fast wi-fi, fully equipped kitchen. Going downstairs you will immediately be absorbed in the most beautiful area of city center. Attention! Only for young-soul people: 5th FLOOR, NO LIFT, last 2 flights of stairs in a narrow spiral stair.

Top Guest favourite
An aerial view captures the historic castle surrounded by lush green hills and vineyards. The impressive structure features tall towers and ornate architecture, set amid manicured gardens and tree-lined pathways, reflecting the beauty of the Chianti landscape.
Holiday home in Badia a Passignano
5.0 out of 5 average rating, 121 reviews

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

Guest favourite
An outdoor area features a heated jacuzzi beside a small round table set with four glasses, a bottle of wine, and a potted plant. The space is surrounded by greenery, with a doorway leading into a modern living area.
Holiday home in Florence
4.86 out of 5 average rating, 138 reviews

Courtyard: Jacuzzi and Private Patio

An exclusive wellness oasis in the heart of Florence. Enjoy the luxury of a spacious new apartment with a private heated Jacuzzi on a reserved outdoor patio. Located in a quiet pedestrian area in Borgo la Croce, the accommodation is the perfect starting point: explore the entire city on foot, with Piazza Santa Croce just 8 minutes away and the Duomo 12 minutes away. Experience the authenticity of Florence amidst modern comfort and total tranquility. Book your romantic getaway!

Top Guest favourite
A living area is featured with a plush red sofa positioned across from a marble coffee table. Large windows open to a lush garden, allowing natural light to illuminate the space. Wooden cabinetry is visible in the background, complementing the neutral tones of the decor.
Holiday home in Florence
4.95 out of 5 average rating, 112 reviews

SMN Luxury Secret Garden View

Welcome to the central part of Florentine charm! This extraordinary apartment, located just 50 meters from Piazza Santa Maria Novella, offers you an unparalleled experience in the historic heart of Florence. Imagine crossing the threshold of a Renaissance Palace, a jewel of inestimable artistic and historical value, and being welcomed by an atmosphere that speaks of history and elegance. Two bedrooms, two complete bathrooms, living room with fully equipped kitchen.

Guest favourite
Holiday home in Centro
4.74 out of 5 average rating, 143 reviews

Duomo Charme – A few steps from the Duomo

Experience Florence like a local! Just 100 meters from the Duomo, in a charming 16th-century building, this romantic studio offers a double bed, sofa bed, mini kitchen and bathroom with shower. Typical restaurants, bars and museums are just below the house. A 3-minute walk away, the tram connects directly to the station and airport. Paid parking right in front of the house. Located on the 3rd floor without an elevator: authentic Florentine charm!

Superhost
Holiday home in Reggello
4.88 out of 5 average rating, 218 reviews

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.

Top Guest favourite
An expansive window offers a breathtaking view of rolling hills and valleys, extending into the distant horizon. A small table with a laptop is positioned in front, accompanied by a white chair. Soft light fills the inviting space, emphasizing the serene landscape outside.
Holiday home in Rosennano
4.99 out of 5 average rating, 101 reviews

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.

Superhost
Holiday home in Dimezzano
4.89 out of 5 average rating, 318 reviews

[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.

Popular amenities for Casentino holiday homes