Holiday houses in Casentino

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Top-rated holiday rentals in Casentino

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Guest favourite

An expansive outdoor deck offers a serene view of rolling hills under a clear sky. An infinity pool transitions seamlessly into the landscape, with two soft seating cushions placed nearby, inviting relaxation and contemplation of the stunning panoramic scenery.

Home in Casale

Infinity view

Completely renovated location with breathtaking views of the Valdarno. The ground floor consists of a living room with two windows overlooking the patio, fireplace, sofa bed, bathroom with large shower and modern kitchen with steel island, with three French windows to access the outdoor dining area with BBQ. The second floor consists of two double bedrooms each with its own bathroom with shower. The garden is well-kept, there are various relaxation corners, a sundeck and an infinity pool with hydrolysis

4.88 out of 5 average rating, 204 reviews

Top Guest favourite

A charming outdoor dining area features a round table set with delicate dishware and a pink tablecloth. Surrounding the table are intricately designed white chairs. A gazebo provides shade, and lush greenery is visible in the background, creating a serene setting for leisurely meals.

Farm stay in Ruscello

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.

4.99 out of 5 average rating, 532 reviews

Superhost

Villa in Bibbiena

Tuscan Villa 300m² · 6 Bed 5 Bath · Cool Summers

Managed by Evora Homes — Superhost, 4.96★ across all our homes. A 300 m² villa in the heart of the Casentino, the green Tuscany almost nobody knows. 6 bedrooms and 5 bathrooms: ten people sleep comfortably and nobody queues in the morning. Fenced garden with fruit trees, two balconies over the valley, private parking for 3 cars. Cool air even in August — you sleep with the windows open. Bibbiena 5 min · Casentinesi Forests, La Verna and Camaldoli a few km · Arezzo 40 min.

5.0 out of 5 average rating, 3 reviews

Guest favourite

A spacious outdoor area features a clear swimming pool surrounded by lounge chairs. The stone house is positioned on a green hillside, offering views of the surrounding landscape. Shrubs and potted plants enhance the natural setting, contributing to a serene atmosphere.

Apartment in Subbiano

Ginepro apartment, panoramic view with swimming pool

Apartment in a large hillside house, with a panoramic pool. Immersed in the green of the Casentino hills, Il Rifugio del Moro is located on a hill and is the ideal place for those looking for nature and without sacrificing comfort. The apartment "Ginepro" consists of 3 rooms: kitchen/living room with double sofa bed and 2 double bedrooms, in addition to the bathroom and a private patio. The apartment is arranged entirely on the ground floor, with independent access.

4.9 out of 5 average rating, 30 reviews

Top Guest favourite

The exterior of the castle is showcased at sunset, with vibrant orange and purple skies providing a dramatic backdrop. Stone towers rise from the landscape, surrounded by greenery and colorful flora, reflecting the historic charm of the property.

Castle in Ferrano

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.

4.99 out of 5 average rating, 227 reviews

Top Guest favourite

The exterior of the villa is showcased, featuring stone walls and greenery. A spacious stone patio is visible, furnished with a dining table and chairs, surrounded by neatly trimmed bushes and potted plants, creating an inviting space for outdoor gatherings.

Farm stay in Loro Ciuffenna

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.

4.99 out of 5 average rating, 124 reviews

Top Guest favourite

The image features a serene outdoor area with a spacious swimming pool surrounded by lounge chairs. Lush greenery and flowering plants line the poolside, while a stone wall and distant hills provide a peaceful backdrop under a clear sky.

Villa in Pieve a Socana

Villa Montanina - exclusive relaxation in Tuscany

A typical Tuscan villa exclusively immersed in the views, greenery and peace of the Casentino Valley where you can spend moments of relax, fun and experiences where nature, culture and taste come together. During your stay you can enjoy cooking classes, yoga classes, wine tastings, massages, personalized experiences and relax in the large swimming pool. The Villa with its many large green spaces is also perfect for celebrating your dream wedding in Tuscany.

4.99 out of 5 average rating, 85 reviews

Top Guest favourite

A charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.

Farm stay in Greve in Chianti

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

4.99 out of 5 average rating, 481 reviews

Top Guest favourite

An aerial view of a rustic villa is framed by lush greenery, showcasing a stone exterior and terracotta roof tiles. A salt-water pool is situated nearby, surrounded by outdoor seating. The tranquil landscape of hills is visible in the background under warm evening light.

Home in Poppi

Villa Podere Cerretino

Podere Cerretino is the perfect place to find and discover your own tranquility and relaxation. A corner of paradise surrounded by the picturesque hills of Tuscany in an enchanting landscape, located in a central and strategic position to visit the most interesting places in Tuscany, such as Florence, Siena, Arezzo. The Villa consists of 4 completely independent apartments and an elegant panoramic veranda where you can gather and enjoy a unique vacation.

5.0 out of 5 average rating, 67 reviews

Guest favourite

An ancient stone farmhouse with a rustic red-tiled roof is surrounded by lush greenery. The building sits within a mountainous landscape, framed by trees. The open sky above reveals soft clouds and sunlight, hinting at the serene atmosphere of the rural environment.

Holiday home in Chiusi della Verna

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.

4.97 out of 5 average rating, 159 reviews

Top Guest favourite

A two-story villa is nestled among greenery, featuring a spacious gravel parking area in front. The building showcases a light-colored facade with dark windows and a balcony, while a covered terrace with seating is visible beside the entrance.

Villa in Chitignano

Villa Bruna, entire house in Chitignano

Nestled in the green forests of Casentino, Villa Bruna is an oasis of tranquility in which to enjoy a moment of refreshment in contact with nature. Built in the 1970s by the owners' father to be the home where the family would gather during the holidays, today the two Bennati brothers have decided to open its doors to the world. Structure Identification Code CIR: 051014LTN0009 National Identification Code (CIN): IT051014C2CW2RCQFF

4.94 out of 5 average rating, 80 reviews

Top Guest favourite

A historic tower is visible amidst lush greenery in the garden area. Surrounding plants, including trees and shrubs, create a serene atmosphere. A stone seating area is positioned at the center, providing an inviting spot for relaxation in this tranquil outdoor space.

Apartment in Poppi

Country chill in the heart of a medieval village

Historic structure from the 1600s, located in the center of the medieval village of Poppi, with a large garden available. The apartment offers three double bedrooms, a living room, a kitchen, and a bathroom. We can add one small single bed in one of the bedrooms if necessary. The apartment is part of a larger property that extends in the heart of the town's historic center, yet it is completely surrounded by greenery.

4.97 out of 5 average rating, 32 reviews