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Castle holiday rentals in Arezzo

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Top-rated castle rentals in Arezzo

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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.

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.

Bed and Breakfasts in Trequanda
4.71 out of 5 average rating, 49 reviews

Abbadia Sicille Relais, Executive Suite with a view

Executive Suite with Jacuzzi overlooking Abbadia Sicille Relais, in the eighteenth-century village of Le Piazze. 60 square meters of elegance with a king-size bed, bathroom with shower and private Jacuzzi for two. Air conditioning, TV, minibar, coffee machine and panoramic outdoor area. Adjacent to the pool, it combines modern comforts and Provençal charm.

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.

A serene outdoor seating area is positioned near a pool, featuring white cushioned chairs and a loveseat. The backdrop showcases rolling green hills and distant mountains, with a cloudy sky enhancing the tranquil atmosphere.
Holiday home in Monte Santa Maria Tiberina

Stunning lux House (lower 2 floors) Pool in marble

Stunning views & recently renovated with sophisticated interiors mixed within medieval walls; a truly fabulous home with unique green marble pool. Its adjoining medieval hamlet has its own family run restaurant, yet is nestled away & is totally private & peaceful paradise set in the Umbrian green hills.

Aerial view of a charming independent house surrounded by lush olive groves in the Tuscan countryside. The area features a mix of buildings, greenery, and a distant tower, showcasing the serene landscape and the inviting proximity to nature.
Farm stay in Figline e Incisa Valdarno
4.33 out of 5 average rating, 3 reviews

barn house - Pratelli Castle

nice detached house surrounded by typical Tuscan countryside, surrounded by olive groves, spacious and comfortable, well furnished and equipped, with private garden and barbecue, beautiful view of the Arno valley, shared pool

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