Castle holiday rentals in Siena

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Top-rated castle rentals in Siena

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Superhost

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.

Villa in Castiglione del Lago

4.58 out of 5 average rating, 38 reviews

Huge Private Umbrian Villa,Garden, Panoramic Views

🏡 Exclusive use of a huge Umbrian villa with modern facilities 🛌 6bedrooms 🎯 Games room 📡 Speedy free Wi-Fi 🏓 Ping pong 🍝 2 Kitchens 🍽️ 2 Dining rooms 🚿 3.5 bathrooms 🛋️ 2 living rooms 🌬️Aircon 🔥Fireplace+wood, electric heaters. 📺 Smart TVs 🌅 Sunset views 🚙 Free 🧻 Bedsheets + towels 🌲 Private garden, olive grove 🛝Playground, football next door 🔥 BBQ, outdoor dining 🐕 OK 🍇 Villages+vineyards 🚗 Lake Trasimeno 🍷Local village Bar| pizzaria 🍕 grocery, PO+ pharmacy

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.

Flat in Bossi in Chianti

4.8 out of 5 average rating, 20 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 between guests.Thefurnishings are simple in rustic style. Apartment Rosa is a two-room apartment of 35 m2, located on the ground floor with living/dining room with kitchenette and fireplace, double bedroom, bathroom with shower. Private outdoor space. Renovated 2018

Flat 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

Flat in Castelnuovo di Val di Cecina

4.83 out of 5 average rating, 12 reviews

The Red House of "Poderepiandicava"

Nestled in the Tuscan countryside, within the natural park of the Pavone stream, is the ancient rural house 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 The Red House is located on the first floor and consists of two bedrooms, living room, kitchen and bathroom.

Flat in Sovicille

4.57 out of 5 average rating, 198 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

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.

Guest favourite

Flat 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

Flat 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!

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 favourite

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.