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Castle holiday rentals in Siena

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Top-rated Castle Accommodation in Siena

Guests agree: These castle accommodation options are highly rated for location, cleanliness and more.

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A charming outdoor space features a grassy area surrounded by stone walls. Colorful seating options include two turquoise lounge chairs, two white loungers, and several red and pink chairs. Potted plants and a small blue scooter are also visible, contributing to a relaxed ambiance.
Farm stay in Castiglione della Pescaia
4.88 out of 5 average rating, 25 reviews

Castiglione della Pescaia-in FATTORIA MEDIEVALE

a pochi minuti da castiglione della pescaia sorge le case di vetulonia, borgo in pietra risalente all'anno mille. a sinistra della torre c'è l'appartamento "mezzano". è un ampio monolocale a pianta quadrata di circa 45 mq con angolo cottura, tavolo rettangolare toscano dell'800 con sedie di design contemporaneo, un letto matrimoniale ed un letto singolo largo 120 cm. nel bagno, molto grande, il lavabo è ricavato da un'antica acquasantiera. SIAMO PUBBLICATI SULLA GUIDA LONELY PLANET (VEDI FOTO)

Superhost
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
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
4.84 out of 5 average rating, 25 reviews

Rosa - Bossi di Sopra - Castello di Bossi

Bel complesso composto da 5 appartamenti situato all'interno di una vasta azienda agricola nel cuore del Chianti Classico con produzione di ottimi vini rossi. La proprietà dispone di uno spazio esterno e di una piscina il cui utilizzo è in comune tra gli ospiti.L’arredamento è semplice in stile rustico. Appartamento Rosa è un bilocale di 35 m2, situato al piano terra con soggiorno/pranzo con angolo cottura e camino, camera matrimoniale, bagno con doccia. Spazio esterno privato. Rinnovato 2018

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 Il Bindaccio is an 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 is cleaned weekly. Guests will also find a garden with panoramic, furnished terraces, barbecue 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

Dormire in una torre trecentesca

L'emozione di soggiornare all'interno di una torre trecentesca appena restaurata. Sarete alloggiati al terzo piano con finestre che si affacciano sulla vallata e sui i tetti rossi del borgo fortificato di Gargonza. L'emozione di Abitare la Storia ed immaginare la vita del borgo fortificato nel Medioevo quando era conteso tra Siena ed Arezzo, dove Dante Alighieri trovò rifugio nel 1304. Prudenti restauri ci consegnano un borgo restaurato con la sua Torre finalmente pronta ad accogliervi.

Superhost
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.

Villa in Castiglione del Lago
4.58 out of 5 average rating, 38 reviews

Magical Umbrian Villa + Garden, Stunning Views

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

Guest favourite
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.

A well-maintained garden features neatly trimmed hedges and decorative planters. The landscape is dotted with cypress trees, complementing the open Tuscan countryside in the background. A charming stone building is seen in the distance, surrounded by lush greenery under a cloudy sky.
Farm stay in San Rocco a Pilli
4.29 out of 5 average rating, 7 reviews

Prestigious apt typical farm breath-taking views

At FATTORIA DI CAVAGLIONI, the whole top floor in exclusive;16th century ancient fortress.Big working farm,natural pool,Siena 10minutes drive or25 minutes by bus.Town within walking distance.Breath-taking views on typical tuscan landscape&open countryside, huge outdoor, bbq. Rooms decorated with original frescos and original furniture. No elevator. 3 bedrooms w air conditioning. In the property there is our restaurant Ocio Giulivo open at dinner from wednesdays to saturdays.

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.
Apartment 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.
Apartment in Tognazza
5 out of 5 average rating, 16 reviews

La Piccola Badia

Posto unico a pochi minuti di auto da Siena. Appartamento con giardino situato in una vecchia Abbazia del XII secolo e trasformato inun castello fortificato da una nobile famiglia Senese nel XVI secolo. L'appartamento situato a piano terra è completo con cucina, soggiorno con divano letto, camera matrimoniale e bagno. Spazio esterno piastrellato con gazebo e zona living esterna ed un incantevole giardino con alberi di ulivo e fiori.

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.
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.

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