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Castle holiday rentals in Arezzo

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Top-rated castle rentals in Arezzo

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

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Top guest favourite
The historic stone building is illuminated at dusk, enhancing its architectural features. A tranquil swimming pool reflects the soft light, surrounded by landscaped olive trees and a stone wall, creating a serene outdoor space.
Flat in Montone
4.98 out of 5 average rating, 42 reviews

Annex in the Cardaneto Castle

Studio apartment in the Cardaneto Castle (8th century) with swimming pool, private parking and 4,000 sqm of garden. 2 km from one of the most beautiful villages in Italy, Montone, famous for the tourist attractions and events that make it a unique place. The studio of about 50 sqm has a separate entrance overlooking the garden, a living room entrance, a double bedroom and a bathroom. ADSI historic residence. Panoramic swimming pool overlooking Montone. Also available apartment with kitchens and private balcony.

A swimming pool is surrounded by a spacious grassy area with two lounge chairs positioned for relaxation. The background features a rustic stone building set among lush greenery, offering a serene outdoor environment.
Flat in Bossi in Chianti
4.86 out of 5 average rating, 28 reviews

Rosa - Bossi di Sopra - Bossi Castle

Beautiful complex consisting of 5 apartments located within a large farm in the heart of Chianti Classico with production of excellent red wines. The property has an outdoor space and a swimming pool whose use is shared among the guests. The decor is simple in rustic style. Appartamento Rosa is a 35 m2 two-room apartment, located on the ground floor with a living/dining room with a kitchenette and fireplace, a double bedroom, and a bathroom with a shower. Private outdoor space. Renovated in 2018

Guest favourite
Villa in Siena
4.79 out of 5 average rating, 288 reviews

XIII Century Tower with Private Panoramic Pool

Ancient country tower property with 5 airconditioned bedrooms for up to 10 guests at the heart of the peaceful Montechiaro organic wine estate. From your private pool, soak in the Tuscan sun and enjoy unforgettable views of the Chianti rolling hills and the medieval towers of Siena. The property also boasts access to the endless olive grove, a large patio area for outside dining in the shade, ping pong table for fun family matches, WIFI & free parking. Silence and time are the real luxury here.

Superhost
The manor house, featuring a stone facade and towers, is partially obscured by lush greenery. A statue stands prominently in the foreground, framed by trees, creating a serene atmosphere. Balconies with wooden shutters adorn the upper levels, contributing to the picturesque setting.
Home in Badia Agnano

Ancient manor house with garden&pool by Vacavilla

Splendid manor house of 600 square meters that hosts 10 people in 5 double bedrooms, 4 bathrooms (1 with bath), lounges with a balcony, Sat TV and a fireplace, a large equipped kitchen and dining room. Outside there is a reserved area with fountains and secular trees, where it is possible to enjoy al fresco dining and barbecues. A swimming pool with view (possibly shared), Internet WI-FI and parking are included in the price. 2 extra beds, maid service and cooking classes available on request.

Superhost
The property is situated on a hillside, surrounded by greenery and rolling vineyards. The building features a combination of stone and yellow facades, with terracotta roofs and tree-lined paths leading to it. The expansive landscape offers a panoramic view of the Tuscan countryside.
Villa in Gaiole in Chianti

Castle wing with pool&Jacuzzi, Vacavilla Exclusive

Property for exclusive use Independent part of the castle with private swimming pool and Jacuzzi, holding up to 7 persons with 2 double bedrooms with bathroom with bathtub and shower, one bedroom with two beds, one single bedroom, one bathroom with shower and one bathroom with hydromassage tub and shower. The property has an internet connection, air conditioning and midweek cleaning service (for weekly stays). Guests will also find a garden with panoramic, furnished terraces, bbq and parking.

An aerial view reveals a fortified village surrounded by lush green hills. The medieval tower stands prominently, complemented by rustic stone buildings with terracotta roofs. Tall cypress trees frame the property, while cultivated gardens and pathways invite exploration through this historic landscape.
Castle in Gargonza

Sleep in a 14th-century tower

The thrill of staying in a newly restored 14th-century tower. You will be accommodated on the third floor with windows overlooking the valley and the red roofs of the fortified village of Gargonza. The thrill of living in history and imagining life in the fortified village in the Middle Ages when it was disputed between Siena and Arezzo, where Dante Alighieri found refuge in 1304. Prudent restorations have given us a restored village with its Tower finally ready to welcome you.

Bed and Breakfasts in Trequanda
4.74 out of 5 average rating, 175 reviews

Abbadia Sicille - Junior Suite with sauna

The Junior Suite with Sauna of Abbadia Sicille Relais, located in the eighteenth-century complex Le Piazze, offers 60 square meters of comfort and intimacy. Equipped with a private sauna in the living room, a kitchenette, a king-size bed, a modern bathroom with shower and an exclusive outdoor area, it is perfect for relaxing in the Sienese countryside. Complete with air conditioning, TV, minibar and coffee machine, it guarantees a regenerating stay in the heart of Tuscany.

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
4.99 out of 5 average rating, 216 reviews

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.

Guest favourite
The exterior of the castle features intricate stonework and several arched windows. Palm trees frame the entrance, which is approached via a paved pathway. A turret rises above the main structure, contributing to the historic charm of the building.
Villa in Passignano sul Trasimeno
4.77 out of 5 average rating, 22 reviews

Borgia Castle at the border of Umbria Tuscany

3 to 7 bedrooms available with airconditioning, 6 bathrooms, but can be rented with the use of less room, than there are toilets, kitchen, dining room, biliard room, lounge room, patio with tables and chairs, porch with tables and chairs, swimming pool, fenced off park. All the interiors and pictures external parts of the garden described and pictured are of EXCLUSIVE USE OF OUR GUESTS. There is a part of the castle that is closed to the public.

Superhost
An aerial view of a medieval castle, showcasing its stone facade surrounded by lush greenery. A sparkling blue swimming pool is situated in the foreground, bordered by loungers. The landscape features rolling hills and trees, enhancing the serene atmosphere of the property.
Villa in Pontassieve
4.79 out of 5 average rating, 42 reviews

[CASTELLO DI CASALTA POOL ✭✭✭✭✭] 15 min from FLORENCE

Castello di Casalta is an authentic medieval stone castle, fully refurbished and surrounded by the lush nature of Tuscany, at only 15 minutes distance from Florence outskirt. Located in a unique position with a spectacular view of the surrounding hills, Castello di Casalta will allow you to live an unforgettable experience, combining history, comfort, nature and privacy.

Top guest favourite
An aerial view showcases a scenic outdoor area featuring a rectangular swimming pool surrounded by stone tiles. Towering cypress trees and well-maintained gardens create a lush atmosphere, while a historic tower and rustic buildings are visible in the background, framed by rolling Tuscan hills.
Castle in Serre di Rapolano
4.96 out of 5 average rating, 25 reviews

Castello delle Serre – Private Villa

Our Private Villa is located on the grounds of Castello delle Serre, owned and operated by Italian-American family and staff. Castello delle Serre sits at the top of Serre di Rapolano, an unspoiled Tuscan village with the easiest access to all of the major points of interest. Siena, Chianti, Montepulciano, Montalcino, Cortona and Arezzo are only a short drive away.

Guest favourite
A cozy bedroom features a spacious bed dressed in soft linens, complemented by an elegant armchair. Natural light enters through a window adorned with a flowing curtain, highlighting the simplicity and charm of the space.
Private room in Monteroni d'Arbia
4.93 out of 5 average rating, 42 reviews

B&B - Suite in Castle near Siena

The "Guardiacaccia's" Suite is an elegant apartment with two bedrooms and a cosy living room, located at the 3rd floor of the Castello di San Fabiano 15 km from Siena and 1 km from the nearest village, in the "Crete Senesi" area. Homemade Breakfast, WiFi, parking and daily cleaning are included in the price.

Popular amenities for castle rentals in Arezzo

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