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Holiday home rentals in Arezzo

Find and book unique holiday home rentals on Airbnb

Top-rated holiday home rentals in Arezzo

Guests agree: these holiday home rentals are highly rated for location, cleanliness and more.

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Top guest favourite
A person interacts with a falcon, demonstrating the connection between humans and raptors. The background features a natural landscape with greenery, and additional animals can be seen grazing in the distance. The setting showcases an engaging outdoor experience in a tranquil environment.
Holiday home
5 out of 5 average rating, 115 reviews

The Eagle and the Olive Tree

At Aquila e l'Ulivo, an ancient renovated farmhouse from the 1200s, you will not only find all the necessary comforts for a wonderful stay, but you will also experience the thrill of feeling free and immersed in the unspoiled nature of Val D'Orcia. Here you'll have the opportunity to walk with the two falcons Ayga and Sayen and interact with the eagles, and why not sip an excellent aperitif by the pool. We are waiting for you in our world, made up of animals, relaxation, nature and even a touch of Magic.

Guest favourite
A window with multiple panes opens to reveal views of the stunning Piazza Signorelli and its historic buildings. Sunlight streams in, highlighting the charming architecture of the opposite structure, which features decorative arches and outdoor seating areas.
Holiday home
4.88 out of 5 average rating, 102 reviews

Theater House

Cozy apartment in the heart of the historic center of Cortona, located on the second floor of an old building, overlooking the beautiful Piazza Signorelli and the theater of the same name. The Casa Teatro is ideal for couples or families with children who want to experience the city, with its enchanting views, typical cuisine and visit the prestigious MAEC museum. Great as a starting point for visiting Montepulciano, Arezzo, Assisi, Perugia, Siena, Pienza or reaching Florence and Rome by train.

Guest favourite
An aerial view captures a charming Tuscan farmhouse nestled within lush green vineyards and rolling hills. The property features a rustic stone exterior and a terracotta roof, complemented by surrounding greenery and a clear blue sky.
Holiday home
4.95 out of 5 average rating, 189 reviews

Vittoria Chianti Vacations 🍇🍷

Vittoria Chianti Vacations is the ideal solution for those seeking peace and tranquility in the heart of Chianti, close to all comforts. Typical Tuscan farmhouse halfway between Florence and Siena, is located in a strategic position to quickly reach Florence, Siena, San Gimignano, Monteriggioni, Volterra and the Chianti hills. Siena Eye Laser Clinic 2 min. Private parking, two bedrooms, equipped kitchen, private bathroom, Wi-Fi, private garden, barbecue, a wonderful view of the Chianti hills.

Guest favourite
Holiday home
4.92 out of 5 average rating, 195 reviews

Stuart Jasmine central, panoramic top location

This abode boasts 1 double and 1 single bedroom, a spacious living room with a fully equipped kitchen, and 1 bathroom with shower. Every window frames a breathtaking view, filling the space with natural light. High-speed Wi-Fi ensures comfort for both work and leisure. Its proximity to all town amenities ensures convenience, while a delightful café downstairs provides a delectable gourmet breakfast. Here, you can unwind and relax, study and learn, discover and explore, or create and dream.

Guest favourite
Holiday home
4.97 out of 5 average rating, 120 reviews

Tuscan stone farmhouse studio with private terrace

A 12 km da Arezzo, delizioso monolocale arredato con cura al piano terra di un casale in pietra tipico toscano di inizio novecento. Circondato dal bosco e con vista su un borgo, il casale si trova in posizione collinare all'interno di un'ampia proprietà di 5 ettari. Attraverso un sentiero immerso nel bosco con una piacevole passeggiata si può raggiungere il torrente che scorre nella valle. Fino a fine luglio circa (a seconda degli anni) si può fare un bagno in una piccola pozza naturale.

Guest favourite
Holiday home
4.89 out of 5 average rating, 169 reviews

Barrel Suite Tuscany • Hot Tub • Vineyard View

Wooden barrel suite in Tuscany, nestled in an olive grove in Reggello: breathtaking views over hills and vineyards, total peace. One of the largest barrels in the world (3.5 m x 8 m) with a private bathroom, kitchenette, veranda and small courtyard. All barrels have a hot tub pool for your relaxation. Strategic location: Florence ~40 min, Siena and Arezzo for day trips. Private parking on the property and a welcome Tuscan cold cuts and cheese board. Close to The Mall Luxury Outlet.

Guest favourite
A stone archway leads into a historic entrance, flanked by rugged walls covered with greenery. The pathway, lined with a metal railing, guides visitors through a tranquil setting enhanced by the natural surroundings.
Holiday home
4.94 out of 5 average rating, 287 reviews

La casina sulle Mura with garden

La Casina è situata nella parte alta di Cortona, nella zona denominata "il Poggio". Si puo' giungere in auto fino al suo ingresso. Il Centro citta' e' raggiungibile a piedi in pochi minuti, percorrendo strade e vicoli caratteristici. Gode di una splendida vista su Cortona e la Valdichiana. E' facile parcheggiare nelle vicinanze. Gli ospiti che giungono in treno in una delle stazioni vicine, su richiesta, possono essere prelevati e accompagnati a destinazione.

Top guest favourite
Holiday home
4.98 out of 5 average rating, 132 reviews

Fontarcella, H&R- mediterranean home with jacuzzi

Located in the hills between Montepulciano, Castiglione del Lago, and Cortona, Fontarcella is a detached villa surrounded by greenery, offering a private jacuzzi and parking. You'll discover a timeless place to share precious moments. The property, furnished in Mediterranean style, features air conditioning and free Wi-Fi. The fully fenced garden offers a variety of amenities. Just minutes from the highways, Fontarcella is easily accessible for travelers.

Top guest favourite
An outdoor seating area features a small table surrounded by two chairs, adorned with a light breakfast setup. The stone facade of the house is complemented by climbing vines and a bright flower arrangement, inviting guests to enjoy the fresh air.
Holiday home
4.97 out of 5 average rating, 120 reviews

In Tuscany Rooms

**Your Dream Retreat in the Heart of Val d'Orcia** Welcome to In Toscana Camere, a charming holiday home located in the historic center of Monticchiello, a Tuscan village full of charm and authenticity. Surrounded by stone walls and enhanced by modern, comfortable interiors, this home offers the perfect balance between tradition and contemporary style. Wake up every morning to a breathtaking view of the stunning Val d'Orcia.

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
4.94 out of 5 average rating, 121 reviews

Casa Manu

CHARACTERISTIC TUSCAN HOUSE in stone nestled in the hills of the province of Arezzo. Close to Siena, Florence, Cortona, Perugia, Sansepolcro and the Casentino Forests. Ideal for trekking, food and wine tourism (some of the best wineries in Tuscany are just a few kilometers away), for art and culture enthusiasts. A large, very private panoramic terrace is available exclusively for guests. We will welcome you with a welcome gift.

Top guest favourite
Holiday home
4.95 out of 5 average rating, 172 reviews

Chianti, elegant barn among vineyards and pool

Discover a unique sanctuary in Chianti, a historic barn where stone walls meet 80s vintage design. Fall in love with the canopy bedroom, cook in the modern kitchen, and enjoy vineyard views from the living area. Outside, private gazebos and an infinity pool await you in total silence. A perfect blend of Tuscan heritage, sophisticated style, and pure romance."

Guest favourite
The exterior of a two-story terraced apartment features warm, rustic brickwork, a private terrace adorned with potted plants, and a wooden dining table surrounded by seating. Lush greenery and scenic hills are visible in the background under a clear blue sky.
Holiday home
4.89 out of 5 average rating, 117 reviews

Charming home Crete Senesi

Less than 15 kilometers from Siena, the terratetto apartment is located in a characteristic Tuscan village on the hill that leads to the suggestive "Site Transitoire". The property is completed by a nice garden overlooking Siena and a comfortable pool.

Popular amenities for holiday home rentals in Arezzo

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