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Castle holiday rentals in Tuscany

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Top-rated castle rentals in Tuscany

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Top guest favourite
A cozy living area features a historic stone fireplace, radiating warmth. Comfortable seating arrangements include two armchairs and a central coffee table. Large windows offer a view of the surrounding countryside, allowing natural light to fill the space. Textured ceiling beams add character to the room.
Flat in Proceno
4.98 out of 5 average rating, 53 reviews

Proceno Castle, Apartamento Loggia

Apartment of 65 square meters for 2 people, inside the medieval courtyard of the Castle of Proceno, with private entrance, large living room with working historic fireplace and kitchenette, 1 double bedroom placed on a mezzanine from which you dominate the living room, bathroom with shower box, veranda with porch in stone and wood, in typical medieval style, which through the stone stairs leads to the internal courtyard of the Castle, from which guests have access to the village and the rest of the accommodations of the courtyard.

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.

Guest favourite
Villa in Siena
4.8 out of 5 average rating, 280 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.

Guest favourite
Aerial view of the surrounding landscape featuring the historic structure of the abbey nestled among ancient olive groves. The serene waters of Lake Trasimeno are visible in the background, alongside cultivated fields and a glimpse of the swimming pool amid lush greenery.
Flat in Sant'Arcangelo
4.78 out of 5 average rating, 97 reviews

Trasimeno Lake - "The Convent"

On top of a hill of centuries-old olive trees on the southern shore of the Trasimeno stands LA BADIA DI S.ARCANGELO. In this unique and precious place is the apartment "Il Convento" which will welcome you with its warm atmosphere and a welcome gift with local products. It can accommodate up to 5 people and consists of a dining kitchen, a living room with a comfortable sofa bed, a double bedroom, a single bedroom and a special bathroom created in what used to be the bell tower of the Abbey.

Guest favourite
A light-filled living area is framed by large windows that showcase sweeping views of the surrounding hills. A staircase with a sleek design leads to the upper levels. A comfortable white sofa with green accent pillows invites relaxation.
Flat in San Gimignano
4.9 out of 5 average rating, 20 reviews

Zafferano Rooftop Terrace Tower House 4 pax

Zafferano is a luxurious apartment set in the very heart of San Gimignano, characterized by an elegant mixture of ancient and modern. The wide open spaces of this medieval tower are shaped by perfectly preserved squared stones dating back to the XIIth century and they are wisely combined with modern, comfortable furnishings. A special mention is deserved by the breathtaking vistas over the wonderful Piazza della Cisterna and the Tuscan countryside enjoyable from Zafferano's windows.

Top guest favourite
Home in Palaia
4.95 out of 5 average rating, 220 reviews

at the castle of montacchita stunning view

REGISTRATION NO. 50024LTN0077 Unique and romantic cottage with a magical atmosphere and breathtaking views of the valley, with large garden and private access, renovated in rustic style within an ancient medieval fortress. Unique place, great starting point for visiting Pisa, Lucca, Florence San Gimignano and only 40 minutes from the sea and located in the truffle area. Remember before booking: those who are not named in the reservation will not be allowed to enter the property.

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, 210 reviews

The Castle of Ferrano - Castle in Tuscany

Try the experience to stay in a real Castle! Il Castello di Ferrano offers to his hosts the chance of doing an unforgettable experiece:you will be the only guests in the castle and everythig will be for you (private pool from June to September, gardens ecc.)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.

Top guest favourite
The historic tower-penthouse villa is surrounded by lush greenery and trees. The three-story structure is characterized by its earthy facade and wooden shutters. Well-maintained gardens with various plants create a serene outdoor environment, enhancing the villa's tranquil charm and historical significance.
Castle in Bagno A Ripoli
4.96 out of 5 average rating, 122 reviews

Tower Penthouse in small castle near Florence

900 year old tower-penthouse apartment in Chianti Villa, spacious & super-scenic historical home that combines magical atmosphere with space, light, character, convenience. Painting-like 360° views of Tuscan Hills all the way to Florence; sun-filled, private grounds. Perfect location for an unforgettable family stay. Ample private property (including forest). Walking distance from village shops. Convenient location, Florence in sight.

Top guest favourite
A cozy living area showcases a comfortable sofa adorned with decorative cushions. A television is positioned on a modern unit, while textured stone walls highlight the space's architectural features. Warm light fixtures enhance the inviting atmosphere of the room.
Flat in Tognazza
5 out of 5 average rating, 16 reviews

La Piccola Badia

Unique place just a few minutes drive to Siena. Apartment with garden located in an old 12th-century Abbey and transformed into a castle fortified by a noble Sienese family in the 16th century. The apartment located on the ground floor is complete with kitchen, living room with sofa bed, double bedroom and bathroom. Tiled outdoor space with gazebo and outdoor living area and an enchanting garden with olive trees and flowers.

Superhost
The image features a historic brick facade of a building, showcasing a large wooden door framed by stone archways. Tall walls topped with battlements rise above, while small windows add character. A clear blue sky enhances the sense of history and architectural significance.
Flat in Certaldo
4.73 out of 5 average rating, 187 reviews

TOWER HOUSE TUSCANY - CASA TORRE

Wooden beams, red bricks and typical Tuscan style: Casa Torre is an elegant, newly renovated apartment, located in the Castle Palazzo Stiozzi Ridolfi, dated 1200! It has 3 double rooms, a bathroom, a laundry room/second bathroom, a spacious living room/kitchen. The main feature is absolutely the wonderful private tower with amazing view of the town and the surround countryside! Ideal also for no-car travellers!

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.

Top guest favourite
An elegant medieval castle is surrounded by lush olive trees, showcasing its stone façade and characteristic towers. Soft lighting emanates from the windows, creating a warm ambiance as dusk approaches. The castle is set against a backdrop of gently rolling hills, enhancing its historic charm.
Castle in Barberino Tavarnelle
4.88 out of 5 average rating, 119 reviews

Suite in Castello di Valle

A unique experience in a historical dwelling located in the Chianti region. This medieval castle is situated in a strategic position, surrounded by the major Tuscan touristic attractions. The suite is at the entrance floor level: double bedroom with bathroom, sofa bed for two people, kitchenette, fireplace.

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