Castle vacation rentals in Province of Siena

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Top-rated castle rentals in Province of Siena

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Villa in Castiglione del lago

4.63 out of 5 average rating, 35 reviews

Huge Magical Villa, Stunning Views, Private Garden

🏡 Huge private villa/modern comfort 🛌 6bedrooms 😴13ppl 🎯 Games room: foosball, darts 🏓 Ping pong ⚽️ playground/football next door 🍝 2 full kitchens 🍽️ large dining room 🚿 3.5 bathrooms 🛋️ 2 living rooms 📺 Smart 🌅 Stunning sunset views 🚙 Free parking 🧻 Linen/towels included 🌲 Private garden, olive grove 🌬️Portable Aircon 🛝Playground, football next door 🔥 BBQ, outdoor dining 💻 Fast freeWi-Fi 🐕 OK 🍇 Villages+vineyards 🚗 Lake Trasimeno 🍷Centre of village: bar/pizzaria 🍕 Local store, PO+ pharmacy

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Villa in Siena

4.8 out of 5 average rating, 263 reviews

XIII Century Tower with Private Panoramic Pool

Ancient country tower property with 5 airconditioned bedrooms for up to 12 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 Barberino Tavarnelle

5 out of 5 average rating, 3 reviews

Villa Paneretta - Historical vacation villa with

300 m2 Ground floor: entrance, large bedroom with 2 single beds (the fireplace in the room cannot be used) and private bathroom with shower (without window and accessible by going down 3 steps). 4 steps down: large living area with living room with fireplace and dining area, kitchen (oven, fridge, freezer, dishwasher, microwave, espresso machine, toaster, kettle, juicer), double bedroom (air conditioning) with private bathroom with shower (without window), second living room with direct...

Rental unit in San Gimignano

4.88 out of 5 average rating, 17 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.

Rental unit in Bossi in Chianti

4.67 out of 5 average rating, 12 reviews

Rosa - Bossi di Sopra - Castello di Bossi

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

Rental unit in Seggiano

4.6 out of 5 average rating, 5 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.

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Rental unit in Castelnuovo di Val di Cecina

4.83 out of 5 average rating, 12 reviews

La Casa Rossa del "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.

Condo in Sovicille

4.56 out of 5 average rating, 192 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.

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Home in Gaiole In Chianti

4.9 out of 5 average rating, 49 reviews

Charming House Chianti Siena | 2-4 p | Casinetta

Jolie maison typique de Toscane à 15km de Sienne avec joli jardin, terrasse ensoleillée, rénovée avec goût . Au milieu des vignes du Chianti près de Brolio. C'est un endroit idéal comme base pour visiter la région. La 2e chambre est plus petite et convient par ex pour des enfants. Elle est équipée d'un lavabo. La salle de bain est attenante à la grande chambre. Il faut donc passer par cette chambre pour accéder à la salle de bain.

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Vacation home in San Gimignano

4.86 out of 5 average rating, 7 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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Rental unit in Certaldo

4.72 out of 5 average rating, 179 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!

Guest favorite

Castle in Serre di Rapolano

4.94 out of 5 average rating, 17 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.