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Castle holiday rentals in Siena

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Top-rated castle rentals in Siena

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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 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 of a historic neo-gothic castle reveals its textured stone exterior and distinctive tower, surrounded by lush greenery. Neatly trimmed hedges and tall trees enhance the natural landscape, while a vineyard can be seen in the distance, providing a picturesque backdrop.
Castle in Sarteano
4.84 out of 5 average rating, 19 reviews

DreamCastleinAncientFarmOfTuscany.4Holiday&Events

You rent the castle in exclusive,no other guests.Min 9pp max 24pp(In winter max12pp in 6 bedrooms).Self-catering unit.If u rent also the farmhouses we can accommodate 56+pp.A/C in 4 bedrooms and 1 living room,most the other rooms have fans.Big pool 10X20 mt to shared (can be rented in exclusive for you when still possible).Historical big garden in exclusive.Perfect dream wedding or holiday.We can help organizing your event,great tuscan meals,activities.We produceORGANIC NATURALwines&OliveOil.

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.

Guest favourite
Flat in Seggiano
5 out of 5 average rating, 7 reviews

Castle of Potentino- Nobile Apartment, Tuscany

Set on Mount Amiata in the south of Tuscany, Castello Di Potentino is a working organic farm that produces award-winning wines and olive oil. Its grounds include a private chapel and beautiful garden and a beautiful swimming pool set amongst thousand year old olive trees. Charlotte makes award-winning wines and olive oil and Alexander makes gin from botanicals from the valley. The castle also has a large vegetable garden and fruit vegetables can be bought from us, fresh from the garden.

A crystal-clear pool is surrounded by a spacious patio area, furnished with several lounge chairs for relaxation. Lush greenery and trees provide a serene backdrop, enhancing the open and inviting atmosphere of the outdoor space.
Flat in Sovicille, Siena
4.71 out of 5 average rating, 35 reviews

Agriturismo at Poggiarello (II)

At Poggiarello you won't find marble bathrooms and wall-sized televisions. Our luxuries are of a different sort: here, you will discover an atmosphere untouched by time, where you can savor the serenity and tranquility of the countryside and immerse yourself in the castle's rich, centuries-old history. And why not, surrender to slumber, embraced by the fragrance of freshly laundered linens, and awaken to the chirping of birds or the aromas of must.

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, 21 reviews

La Piccola Badia

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

Guest favourite
An inviting outdoor area features a stone building with wooden shutters, complementing the lush green lawn. A round table with chairs is positioned under a white umbrella, surrounded by colorful flower beds and a stone planter.
Holiday home in San Gimignano
4.89 out of 5 average rating, 9 reviews

Private garden overlooking the Via Francigena

Only 6 km from the medieval historic center of San Gimignano and near the Via Francigena is the Agriturismo, a small village surrounded by greenery and composed of the manor house and farmhouses partly renovated and transformed into comfortable homes, each with independent access. Enchanting view of the Tuscan countryside and large green outdoor area with panoramic swimming pool of 7x14 meters. shared with three other apartments.

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
4.72 out of 5 average rating, 191 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
4.89 out of 5 average rating, 123 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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