
Castle holiday rentals in Siena
Find and book unique castle rentals on Airbnb
Top-rated castle rentals in Siena
Guests agree: these castle rentals are highly rated for location, cleanliness and more.

Castiglione della Pescaia-in MEDIEVAL FARM
a few minutes from Castellione della Pescaia is located in Vetulonia houses, a stone village dating back to the year one thousand. To the left of the tower is the "mezzano" apartment. It is a large square studio apartment of about 45 square meters with kitchenette, Tuscan rectangular table of the 19th century with chairs of contemporary design, a double bed and a single bed 120 cm wide. in the very large bathroom, the sink is from an old watering space. WE ARE POSTED ON THE LONELY PLANET GUIDE (SEE PHOTO)

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.

Huge Private 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 🍽️ 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

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.

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.

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

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.

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.

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.

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.

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.

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!
Popular amenities for castle rentals in Siena
Family-friendly castle rentals

Double bedroom in Tuscan Castle with breakfast

Suite in a Castle | Breakfast & Swimmingpool

Suite Executive with Jacuzzi at Abbadia Sicille

Charming studio in a Castle & Farm w shared pool

Superior Room in Abbadia Sicille Relais

B&B in a Charming Castle near Siena

Suite in the Tower, with Homemade Hearty Breakfast

Castello delle Serre B&B: Pool Cottage/Standard
Other castle holiday rentals

Next to castle of Villa-Siena. heart Francigena

Private garden overlooking the Via Francigena

Castle wing with pool&Jacuzzi, Vacavilla Exclusive

Castello delle Serre – Private Villa

TOWER HOUSE TUSCANY - CASA TORRE

The Red House of "Poderepiandicava"

Rosa - Bossi di Sopra - Bossi Castle

Suite in Castello di Valle
Destinations to explore
- Rentals with a fireplace Siena
- Tent rentals Siena
- Townhouse rentals Siena
- Apartment rentals Siena
- Smoking-friendly rentals Siena
- Villa rentals Siena
- Tiny house rentals Siena
- Hotel rentals Siena
- Rentals with a cinema Siena
- Luxury rentals Siena
- Family-friendly rentals Siena
- Flat rentals Siena
- Cottage rentals Siena
- Rentals with an EV charger Siena
- Rentals with an accessible-height bed Siena
- Rentals with beach access Siena
- Rentals with pools Siena
- Boutique hotel rentals Siena
- Private suite rentals Siena
- Serviced apartment rentals Siena
- Rentals with a firepit Siena
- Rentals with a patio Siena
- House rentals Siena
- Rentals with outdoor seating Siena
- Rentals with a washing machine and dryer Siena
- Rentals with a sauna Siena
- Fitness-friendly rentals Siena
- Holiday home rentals Siena
- Rentals with a balcony Siena
- Nature eco lodge rentals Siena
- Rentals with a hot tub Siena
- Farm stay rentals Siena
- Guest house rentals Siena
- Loft rentals Siena
- Rentals with breakfast Siena
- Pet-friendly rentals Siena
- Waterfront rentals Siena
- Barn rentals Siena
- Bed and breakfasts Siena
- Rentals with lake access Siena
- Castle rentals Tuscany
- Castle rentals Italy
- Santa Maria Novella
- Duomo di Firenze
- Lake Trasimeno
- Basilica of Santa Maria Novella
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Ponte Vecchio
- Cala Violina
- Uffizi Gallery
- Mugello Circuit
- Mercato Centrale
- Piazzale Michelangelo
- Fortezza da Basso
- Parco delle Cascine
- Pitti Palace
- Piazza della Repubblica
- Careggi University Hospital
- Kite Beach Fiumara
- The Boboli Gardens
- Avignonesi Winery Fattoria Le Capezzine
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Spiaggia Marina di Cecina
- Stadio Artemio Franchi
- Cala Di Forno
- Medici Chapels
- Things to do Siena
- Sightseeing Siena
- Nature and outdoors Siena
- Art and culture Siena
- Food and drink Siena
- Tours Siena
- Things to do Tuscany
- Tours Tuscany
- Food and drink Tuscany
- Nature and outdoors Tuscany
- Art and culture Tuscany
- Entertainment Tuscany
- Sightseeing Tuscany
- Wellness Tuscany
- Sports activities Tuscany
- Things to do Italy
- Sports activities Italy
- Nature and outdoors Italy
- Art and culture Italy
- Sightseeing Italy
- Entertainment Italy
- Wellness Italy
- Tours Italy
- Food and drink Italy