Vacation rentals in Casentino

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Casentino

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Top guest favorite

A spacious living room features an archway of exposed brick and stone, with large windows allowing natural light. A comfortable sofa is positioned around a coffee table, while a professional kitchen is visible in the background, complemented by wooden shelves filled with books.

Vacation home in Arezzo

5 out of 5 average rating, 134 reviews

Historic Arched Apartment in the Heart of Arezzo

In the old town centre of Arezzo, next to Casa Vasari, rises up the sixteenth century building, owned in the past by the Ubertini family. A few steps away from all the attractions of the city, the old kitchens of the building have been transformed into an elegant and comfortable guesthouse, rich in charm in every detail. The interior design is well-finished and, making every detail stand out, is finely furnished with traditional carpets and antique pieces. Locanda Bellavita is an apartment for up to 7 people, on the ground floor with an independent entrance. It consists of two master bedrooms, one French bedroom, one restroom with bath and another one with shower, a big living room with a massive fireplace, dining room and professional kitchen. ingresso privato,tutti gli ambienti sono in esclusiva Salvo alcuni giorni della settimana,abito sopra la struttura The apartment is in a building in the old town center of Arezzo next to Casa Vasari. It’s a few steps from all the attractions in the city. a 100mt dalla Chiesa di san Domenico e dal Duomo. Vicinissimo al parcheggio Petri,sotto il Duomo della città. In 5 minuti ovunque a piedi nel centro della città In the middle of the old town centre the guesthouse is a few steps away from every touristic attraction. The apartment is entirely exclusive for you for the period reserved and is provided with every comfort. The kitchen is professionally equipped. The towels and bed linen will be changed every 4 days. To prepare breakfast, there is an area with coffee machine, kettle, toaster and microwave. *The rooms will be naturally chilled thanks to the thick stone walls, so you won’t need any air conditioning.

Top guest favorite

A serene view showcases a rustic guest house surrounded by vibrant autumn foliage and lush greenery. Rolling hills are visible in the background, while the colorful sunset paints the sky in warm hues. An outdoor area features wooden decking and a private hot tub.

Home in Anghiari

4.99 out of 5 average rating, 236 reviews

Casa Rosmarino Eco-Wellness Country Home

Price includes the WELLNESS & COMFORT package as follow: - Wooden fired Hot Tub w/Jacuzzi (1 organic water filling, good for 3/4 days of use) - Infrared Sauna - Wood logs for Fireplace & Hot Tub - Fire starters - House Heating/Air Conditioning - Laundry/Dryer - Shower Gel/Shampoo/Bathrobes - Welcome Appetizers w/Wine - Italian Ground Coffee - Treats during your stay Extra activities (not included) : - Massages, Cooking Classes, Tours & Tasting Please INQUIRE for price & availability.

Top guest favorite

A private swimming pool with clear blue water is surrounded by elegantly arranged lounge chairs. The rustic stone house and lush greenery provide a natural backdrop, while distant hills are visible under a bright blue sky with scattered clouds.

Farm stay in Reggello

4.96 out of 5 average rating, 163 reviews

Stone farmhouse, exclusive private pool

Podere Montebono is located on the hills of Reggello just 30 km from Florence. Ideal for reaching cities of art and naturalistic places. The farmhouse is isolated on a hill, surrounded by nature, olive trees, a garden and woods. The guest house is an independent wing of the large farmhouse on two floors: 3 double bedrooms, kitchen, living room, bathroom. The private pool is exclusively for those who rent the house (max 5 people) We do not rent single rooms. Barbecue area. Total privacy.

Superhost

A natural pool is surrounded by lush greenery, with a small waterfall cascading into the water. The tranquil scene is enhanced by smooth stones lining the pool's edge, creating a serene environment perfect for relaxation.

Condo in Rimbocchi

4.83 out of 5 average rating, 104 reviews

Cozy apartment in stunning National Park forest

This cosy apartment immersed in one of Italy's largest National Parks offers a breath of fresh air. Perfect for hikers - many paths begin direct from the door, ideal for those walking to La Verna. Just a 5min minute walk away are waterfalls and natural pools. In a unique area of the Casentino the tranquil village of Rimbocchi invites you to escape the chaos of urban life. Although remote, it's also a convenient base to visit many historic cultural towns all within an hour by car.

Superhost

An aerial view captures a rustic stone building with red tiled roofs, surrounded by lush greenery, trees, and manicured gardens. The serene landscape showcases a blend of earth tones and foliage, embodying a peaceful atmosphere in a hillside setting.

Condo in Castelfranco di Sopra

4.83 out of 5 average rating, 252 reviews

House between Firenze, Arezzo, chianti e Siena

The House is located in a restored medieval village. There is an atmosphere of peace and tranquility, the gardens are full of flowers and aromatic plants and there is a beautiful panoramic view of the Arno Valley. There is a private terrace outside and two swimming pools to share with other appartraments. Perfect for relaxing and for reaching the main attractions like Florence, Siena, Arezzo, Chianti, Sangimignano. Here you will live a unique experience in the heart of Tuscany ...

Superhost

Aerial view of the villa complex surrounded by lush greenery and olive groves. A spacious pool is centrally located, with well-maintained lawns and trees framing the property. Rolling hills and a clear sky are visible in the distance, enhancing the tranquil countryside setting.

Villa in Rignano sull'Arno

4.95 out of 5 average rating, 138 reviews

Tuscan Dream Villa @ Rustic Elegance Near Florence

🌿Welcome to Villa La Conigliera🌿, an ideal retreat for a romantic getaway or a relaxing stay, just a few kilometers from Florence. 🌟Set in the peaceful Tuscan countryside, overlooking an ancient courtyard, it blends rustic charm with modern comfort. Perfect for couples or families with a newborn, with a crib available upon request 👶. Two adjacent villas for 4 and 6 guests complete the hamlet. 🚗 A car/motorbike is recommended for exploring the beautiful surroundings.

Guest favorite

An outdoor terrace features a stone basin jacuzzi surrounded by lush greenery. Wooden lounge chairs are positioned nearby, providing a serene spot to relax amidst the trees. The setting offers a tranquil connection to nature.

Apartment in Castelnuovo Berardenga

4.93 out of 5 average rating, 161 reviews

Villa di Geggiano - Perellino Suite

The 700 years old Villa di Geggiano, surrounded by our working vineyard and lovingly maintained gardens, is located in Chianti in Tuscany which is one of the most beautiful regions of Italy. Our guesthouse is located in one of the original garden pavilions of the villa. PLEASE NOTE THAT WE ARE IN THE COUNTRYSIDE WITH VERY FEW PUBLIC TRANSPORT OTHER THAN TAXI SO THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A RENTAL CAR.

Top guest favorite

A view through a window showcases rolling hills and green fields under a soft sky. The landscape reveals a peaceful outdoor area, highlighted by a table and chairs nestled amongst the natural scenery, inviting relaxation and contemplation.

Condo in Pienza

5 out of 5 average rating, 112 reviews

Mascagni Farmhouse in Val d'Orcia, Pienza

Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 16th-century barn nestled among olive trees and wheat fields. Relax with a cup of tea, pick rosemary and lavender in the garden with breathtaking views of the Val d'Orcia. Rediscover your true nature among the pristine fields and olive trees: here, walks and bike rides have no limits! Ready to create memories that will last a lifetime?

Guest favorite

A scenic view of rolling hills and lush greenery is visible from a window. Terracotta roofs and a winding path can be seen below, enhancing the historic charm of the medieval surroundings.

Condo in San Gimignano

4.93 out of 5 average rating, 119 reviews

Luxury Medieval Tower - Penthouse

Step into the past... San Gimignano Luxury Medieval Tower is right in the heart of the UNESCO town. You will be caught by the sight of San Gimignano's beautiful landscapes and at the same time you will be able to enjoy the luxury amenities of in-town living: walk downstairs to the cafes, bread shop, butcher, restaurants and local shops. Hear the church bells directly from your windows. Walking distance to all of San Gimignano main attractions.

Top guest favorite

A freestanding, oval-shaped bathtub is filled with water, adorned with floating candles and flowers. Two small wooden side tables hold toiletries and spa essentials. A woven rug lies on the floor alongside a pair of slippers, adding texture to the space.

Home in Fiesole

5 out of 5 average rating, 245 reviews

"La limonaia" - Romantic Suite

Romantic Suite immersed in the enchanting hills of Fiesole. It is the ideal place fot those looking for unique and exclusive experience of its kind characterized by suggestive views and unforgettable sunsets. The accommodation is part of an old 19th century Tuscan farmhouse surrounded by its own olive groves and woods. This is an ideal place for a relaxing holiday and privileged base for visiting the major centers of interest in Tuscany.

Top guest favorite

Farm stay in Greve in Chianti

4.99 out of 5 average rating, 380 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. 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.

Guest favorite

Vacation home in Chiusi della Verna

4.96 out of 5 average rating, 135 reviews

Experience rustic off-grid life in the wilderness

This ancient farmhouse lies within a national park in one of the largest areas of forests in Europe. Solar power, wood stoves and the bumpy road 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.