Castle vacation rentals in Siena

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Top-rated castle rentals in Siena

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Superhost

An outdoor dining event takes place at sunset, surrounded by a historic stone building and a prominent tower. The area is illuminated with string lights, and guests are seated at long tables, enjoying a meal in a picturesque garden setting with lush greenery.

Villa in Siena

4.8 out of 5 average rating, 275 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.

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.

Apartment 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.

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.

Apartment in Bossi in Chianti

4.81 out of 5 average rating, 21 reviews

Rosa - Bossi di Sopra - Bossi Castle

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

A medieval castle stands surrounded by lush green vineyards and rolling hills. Olive trees and other vegetation fill the landscape, creating a serene backdrop. The castle's stone facade is visible, reflecting the historical architecture of the area.

Apartment in Seggiano

4.75 out of 5 average rating, 8 reviews

Castello di Potentino- Granary Apartment

This self-catering apartment at the rear of the castle, has one double room and two single rooms with a shared bathroom. The apartment in the old tower behind the castle has a fully equipped kitchen/living room with exposed beams and high ceilings (the room is roughly 15m by 6m) has a wood burning fireplace. The master bedroom has a king sized double bed and a fully functional wood-burning bread oven. The other two bedrooms are single rooms with beautiful vaulted ceilings.

Superhost

An ancient stone farmhouse is surrounded by lush gardens filled with colorful flowers. Stone steps lead to the entrance, flanked by vibrant red and pink blooms. Open wooden doors invite guests to explore the rustic charm of the residence under a partly cloudy sky.

Apartment in Castelnuovo di Val di Cecina

4.83 out of 5 average rating, 12 reviews

The Red House of "Poderepiandicava"

Immersed in the Tuscan countryside, within the natural park of the Pavone stream, is the ancient rural residence Pian di Cava. The house has three independent apartments, the Green House, Red and Blue. Pian di Cava is an excellent base for cultural, food and wine trails, and for spending days relaxing. The farm is carbon free and allows electric vehicles to be recharged Casa Rossa is located on the first floor and consists of two bedrooms, living room, kitchen and bathroom.

The outdoor area features a serene swimming pool surrounded by a well-maintained lawn. Lounge chairs are positioned along the poolside, while lush trees and potted plants provide natural shade. A historic stone tower is visible in the background, contributing to the peaceful ambiance.

Apartment in Sovicille

4.57 out of 5 average rating, 199 reviews

Agriturismo at Poggiarello (I)

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.

Superhost

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.

Vacation 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.

Guest favorite

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.

Apartment in Tognazza

5 out of 5 average rating, 10 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.

Apartment in Certaldo

4.72 out of 5 average rating, 185 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!

The exterior of the rustic stone house is showcased, featuring arched doorways and a mixture of natural stone textures. Lush green plants and colorful flowers enhance the garden area in front. A clear blue sky is visible above, adding to the serene countryside atmosphere.

Home in Panzano

4.92 out of 5 average rating, 12 reviews

Reggine by Interhome

All discounts are already included, please go ahead and book the property if your travel dates are available. Below please see all the listing details "Reggine", 5-room house 140 m2 on 1st floor. Object suitable for 8 adults. Renovated, rustic and cosy furnishings: living room with open-hearth fireplace, dining table, kitchen corner and satellite TV. 2 double bedrooms. 2 rooms, each room with 2 beds (80 cm).

Guest favorite

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, 24 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 favorite

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, 113 reviews

Suite in Castle of 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.