Cottage vacation rentals in Arezzo

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Top-rated cottage rentals in Arezzo

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Guest favorite

An outdoor terrace features a rustic wooden ceiling supported by brick columns. Comfortable seating is provided by a light-colored couch and benches, alongside a dining table with chairs. The surrounding greenery and pathways lead to additional buildings, creating a serene and inviting space.

Cottage in Pergine Valdarno

Tuscan countryside vacation home with pool

Exclusive independent house, surrounded by the greenery of the Tuscan countryside near Pergine Valdarno, in the hills of Chianti Aretino between woods, olive trees and vineyards, in the middle of the triangle formed by Arezzo Siena and Florence, on the left bank of the Arno river. Large swimming pool with super panoramic view shared with another apartment. Large fully fenced park. Covered and uncovered panoramic terraces for exclusive use, perfect for lunch and dinner. Large garden. Possibility of trekking bikes.

LocationFamilyLaundry

4.78 out of 5 average rating, 67 reviews

Superhost

A charming stone house is surrounded by lush greenery and a trellis adorned with climbing vines. The structure features rustic wooden doors and a sloped, tiled roof, while the outdoor area includes a shaded seating space. The landscape is serene, highlighting the natural beauty of the countryside.

Cottage in Sogna

House in Sogna

We would like to offer out romantic house in the heart of Tuscany. Our house is small restored stone house in a walking-only community in the country. It has 1 bedroom and 1 bathroom on two levels with a fully equipped kitchen and comfortable living spaces with a sofa bed . The home has old-style terra-cotta tiles, stucco walls, a fireplace, chestnut wood beams making for a very charming Tuscan get-away. We really hope you will enjoy the nature and a very quiet athmosphere. It is pure relax.

LocationComfortSleep quality

4.71 out of 5 average rating, 34 reviews

Superhost

A rustic stone house is surrounded by a well-maintained garden featuring flowering plants. A shaded umbrella provides outdoor seating, while lounge chairs are arranged nearby. A swimming pool is visible in the background, set against a clear blue sky.

Cottage in Pergine Valdarno

Collina: country house, garden and private pool

La Collina is a beautiful large independent house with panoramic views and furnished in typical Tuscan country style. It is set over two floors and has an annexed building with a loggia equipped with barbecue, table and chairs to eat outdoors as well as ping pong and laundry rooms. The main house has: 4 bedrooms, 3 bathrooms, kitchen, and a large living room. The large garden and the swimming pool are for your exclusive use. Heating excluded: cost according to consumption WE LOVE DOGS!

FamilyLocationKitchen

4.7 out of 5 average rating, 44 reviews

Superhost

An exterior view of a rustic stone structure is presented, featuring a covered porch with a wooden table and benches. Olive trees surround the area, providing shade. A barbecue station is visible nearby, with a pathway leading through the outdoor space.

Cottage in Sinalunga

Stunning cottage on the Tuscan hills

An amazing renovated Tuscan cottage set in one hectare of olive grove with around 200 trees, in a panoramic hillside location overlooking the Valdichiana countryside. The house offers two double bedrooms with air conditioning and TV, two bathrooms, a spacious living area with fully equipped kitchen and dishwasher, plus an extra room with washing machine and sofa. Outside, a rustic covered patio with dining table and built-in barbecue is ideal for outdoor meals in total peace.

ValueFamilyCleanliness

4.85 out of 5 average rating, 98 reviews

Guest favorite

A spacious living area features a large arched window offering views of the garden. A modern fireplace is centered within the room, complementing a comfortable seating arrangement. Natural light fills the space, enhancing the rustic wooden beams overhead.

Cottage in San Martino in Grania

Crete Senesi - Asciano Cavoni Hut

Available from April to October, Capanna Cavoni returns after a major renovation, enriched with air conditioning and Wi-Fi. Immersed in the rainbow of colors of the Crete Senesi, the carefully furnished property covers over 130 square meters: large master bedroom, bedroom, two bathrooms, kitchen, living room and large living room with fireplace from which you can access the loft relaxation area and possible additional bed outside a large garden with veranda.

FamilyLocationHeating

5.0 out of 5 average rating, 57 reviews

Top guest favorite

A charming stone house showcases a rustic design with wooden shutters and a balcony. The front porch features seating areas, surrounded by lush greenery and well-maintained gardens. An elegant pathway leads to the house, enhancing its countryside appeal.

Cottage in Villa A Sesta

CASA MARIA

Beautiful country house located on the hills of the famous Chianti Classico region 20 km from Siena. Casa Maria guarantees privacy and comfort; a beautiful swimming pool in the middle of the vineyards will make you have precious moments of relaxation with family and friends. A large garden with a barbecue area will make your spring and summer holiday unique. A gorgeous fireplace in the tavern will make evenings spent in cold periods warmer.

LocationFamilyComfort

5.0 out of 5 average rating, 20 reviews

Guest favorite

The exterior features a spacious garden surrounded by greenery, showcasing a variety of plants. A shaded area provides seating with lounge chairs and a large tree offers additional shade. The house structure is visible in the background, with large windows reflecting the landscape.

Cottage in Castelfranco Piandiscò

Villetta Belvedere

The villa is finely renovated, surrounded by greenery, with a large courtyard, garden and woods bordering the property, and with a wide panoramic view of the typical Tuscan landscape. Its strategic location, at the end of a residential cul-de-sac, while surrounded by greenery, allows you to reach, on foot, all the necessary services (market, bars, historic center, pizzeria & restaurants) for a relaxing and comfortable stay.

FamilyLocationAccess

4.91 out of 5 average rating, 88 reviews

Guest favorite

A spacious bedroom features a comfortable bed, with natural light flowing in through a window that offers a glimpse of the surrounding greenery. Soft linens and a minimalist decor contribute to a serene and relaxing environment.

Cottage in Massa Sabbioni

Private Country House with swimming pool -Chianti

In the heart of Tuscany, at the gateway to Chianti Classico, Amoliv is a private retreat with 5 bedrooms, each featuring en-suite bathrooms and separate entrances. A professional kitchen and living room open onto a panoramic terrace with stunning views of Valdarno and Pratomagno. Surrounded by olive groves and woodlands, the property offers a private pool and BBQ area, ideal for families and groups seeking Tuscany's beauty.

FamilyLocationNearby

4.95 out of 5 average rating, 57 reviews

Top guest favorite

The charming cottage is constructed with warm-toned brick, featuring a staircase leading to a small balcony. Lush greenery surrounds the building, while the well-maintained gravel pathway guides to the entrance, complemented by vibrant flower pots adding a touch of color.

Cottage in Castiglion Fiorentino

Charming Cottage with Pool

This charming cottage with pool is nestled in the heart of the beautiful Val di Chiana, a few minutes’ drive from the picturesque hilltop town of Castiglion Fiorentino and 15 minutes from Cortona. Here you can enjoy the peace of the Tuscan countryside. The large swimming pool (12.00 x 6.00 m) is for exclusive use of the guests. During summer 2026 the pool is open May 16th - October 3th

LocationFamilyNearby

4.98 out of 5 average rating, 46 reviews

Guest favorite

A charming cottage is surrounded by lush green grass and decorative plants. The rustic brick exterior features large windows framed with climbing vines. A cozy seating area on a tiled porch offers a relaxing view of the garden and the inviting countryside.

Cottage in Montagnano

Charming cottage in Tuscany

Charming cottage located on a hill with 360-degree views. An oasis of peace and quiet. Surrounded by greenery. Large swimming pool BBQ Area Inside there is a bedroom with a French bed, a living room with a sofa bed, a bathroom, a kitchenette and an indoor and outdoor dining area. Ideal for couples and families with one/two children. Crib available

LocationFamilyIndoor spaces

4.94 out of 5 average rating, 141 reviews

Superhost

Cottage in Cortona

Casale Cantalena | Farmhouse with private pool

Casale Cantalena is located on the top of Sant'Egidio, the hill on which the tuscan town of Cortona is built. It is a small, completely detached, country house with a private swimming pool and soccer field. This location is extremely quiet, so it is especially suitable for those who are looking for peace, nature and relax.

LocationFamilyDecor

4.91 out of 5 average rating, 22 reviews

Superhost

A glass-enclosed veranda offers a view of the private garden and pool area. A round dining table with decorative tiles is surrounded by iron chairs. Light filters through the glass, enhancing the rustic charm of the exposed stone walls.

Cottage in Trequanda

"Rosso Poggiolo" farmhouse with swimming pool.

Ideal for families, groups of friends or a luxurious and exclusive romantic getaway. Entire independent farmhouse on 3 floors with parking and private garden. Dishwasher, Microwave, Bimby, Gas and wood ovens, Fireplace, Veranda, Independent heating, BBQ, deckchairs.

ValueFamilyAccuracy

4.75 out of 5 average rating, 144 reviews