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Smoking friendly vacation rentals near Siena Cathedral

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Top-rated smoking friendly rentals near Siena Cathedral

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Top guest favorite
A medieval stone tower stands tall against a clear blue sky, showcasing its historic architecture. The narrow road lined with greenery leads to the entrance, with the texture of the stonework and windows highlighted, inviting guests to explore its unique charm.
Tower in San Quirico d'Orcia
5 out of 5 average rating, 103 reviews

Luxurious Medieval Tower & Private Concierge

It’s rare to find a place that’s not only romantic but also historic & truly one of a kind. La Torretta is part of Toscana a Due—a medieval tower with a huge garden & olive trees, right in the heart of San Quirico, overlooking the Val d’Orcia. The 1000-year-old building has been redesigned as a blend of heritage & antique luxury. With our unique tailored concierge service and a warm welcome into our family’s life, we share our traditions, history, and Tuscany’s hidden treasures with you.

Top guest favorite
A spacious balcony is lined with arches, providing a panoramic view of the rooftops and distant cathedral of Siena. Terracotta tiles cover the floor, while potted plants add a touch of greenery. Sunlight floods the area, enhancing the architectural features and scenic outlook.
Condo in Siena
4.88 out of 5 average rating, 178 reviews

Panoramic attic in old town of Siena

We are pleased to propose a top floor apartment in a historic building located in front of the Cathedral of San Domenico, in the heart of the historic center of Siena, a few steps from Piazza del Campo and the Duomo. The area is equipped with every service: shops, cafes, bars, restaurants. Composed of a large living room, kitchen, two double bedrooms, bathroom and terrace with panoramic views of the city. Very bright, it is equipped with every service to make your holiday enjoyable

Top guest favorite
An aerial view of the historic Monteriggioni Castle showcases its medieval architecture surrounded by lush countryside. The fortified walls encircle the village, which is dotted with trees and buildings, while rolling hills extend into the distance under a sunset sky.
Cottage in Monteriggioni
4.95 out of 5 average rating, 273 reviews

Monteriggioni Castello, holiday house in Tuscany

Il nostro alloggio è un edificio storico che risale alla costruzione del castello. È stato recentemente restaurato e arredato con cura in tutti i dettagli. È molto accogliente e dispone di tutti i più moderni servizi. I turisti che decideranno di essere nostri ospiti, avranno il vantaggio di vivere nell' ambiente medievale del castello, usufruendo di tutti i confort. Si sentiranno coccolati e avranno l'opportunità di tornare indientro vivendo un' esperienza unica e indimenticabile.

Guest favorite
A warm and inviting open space features a wooden dining table surrounded by chairs, illuminated by natural light from several windows. A red sofa is positioned nearby, while a television and kitchen appliances, including a stove and oven, are visible in the background.
Apartment in Montepulciano
4.94 out of 5 average rating, 106 reviews

Casa Crociani - Amazing Pool & Free Parking

Just 4.7 km from Montepulciano (7 minutes by car), this house is located in a quiet position surrounded by greenery, with a splendid view of the Tuscan hills. The property is equipped with all the necessary amenities to ensure a pleasant stay, perfect for relaxing weekends or vacations. You can relax on the private patio, in the outdoor gardens, or spend unforgettable moments by the pool, enjoying the peace and beauty of the surrounding landscape.

Guest favorite
Villa in Siena
4.89 out of 5 average rating, 294 reviews

Villa Capanna, Private Pool, Breathtaking Views

Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.

Top guest favorite
The rustic building features a warm ochre facade and a classic tiled roof. An expansive oak tree provides shade to the outdoor seating area, which includes wooden chairs and a small table. Lush greenery surrounds the property, contributing to the tranquil rural setting.
Farm stay in Simignano
4.92 out of 5 average rating, 253 reviews

Casa al Gianni - Fig

Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

Top guest favorite
The exterior of the country house is framed by tall, narrow cypress trees and well-maintained gardens featuring various plants. A terracotta pot stands prominently, and gravel pathways lead to the entrance, which is characterized by stone walls and an arched doorway.
Home in Tavarnelle Val di Pesa
4.96 out of 5 average rating, 318 reviews

Casa Al Poggio & Chianti view

Casa al Poggio is a typical country house of Chianti area is spread in 145 square meters on two floors, the ground floor is a large living area, with kitchen and sofa ,fireplace ,up stairs there is 2 large double bedrooms and a sofa bed in the middle open room , always setable as 2 singles or a double bed bed and a relaxing bathroom with shower and bath with Chianti view.

Guest favorite
Farm stay in Castelfranco di sopra
4.88 out of 5 average rating, 309 reviews

Romantic apartment in the Tuscan village

The house is located in an ancient medieval village that has been completely renovated while maintaining the charm of its history. In the village you will find two swimming pools, a restaurant, many gardens and much more... It is in a strategic position to be able to reach the main attractions such as the Chianti Region, Florence, Arezzo and Siena!

Top guest favorite
A welcoming entryway features a mural depicting a serene landscape framed by arches. Built-in shelves display decorative items and books. Natural light illuminates the wood flooring, while a small globe and a vase with dried plants add subtle warmth to the space.
Apartment in San Gusmè
4.98 out of 5 average rating, 111 reviews

Casa Guardiavigna in Chianti, Italy

The Casa Guardiavigna apartment offers the opportunity to enjoy a unique and extraordinary experience, full of emotions and happiness. Located a stone's throw from the small medieval village of San Gusme' and surrounded by beautiful vineyards, woods and flowery meadows. Free indoor parking with an automatic gate.

Top 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, 119 reviews

Suite in Castello di 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.

Guest favorite
Aerial view of a countryside villa surrounded by lush green hills and vineyards. The outdoor swimming pool is visible alongside a well-kept garden. Olive trees and various plants create a natural landscape, reflecting the serene environment of the property.
Apartment in Greve in Chianti
4.83 out of 5 average rating, 115 reviews

Beautiful medieval tower in Chianti

This is a lovely flat in an ancient farm, restored, in the heart of Chianti Classico , with an amazing panoramic view on the hills, surrounded by our vineyards as well as olive trees, where you will have an unforgettable holiday discovering Tuscany. CINIT048021B5LTBDVFE3

Guest favorite
An open-plan living and dining area features a comfortable red couch and a wooden dining table surrounded by chairs. Natural light enters through large windows adorned with green curtains, illuminating the space. A piano and a wooden cabinet are positioned along the walls, complemented by wooden beams on the ceiling.
Condo in Siena
4.92 out of 5 average rating, 135 reviews

The most ancient part of the city

Inside the medieval walls of Siena, in the most ancient part of the city you will find your home away from home at Buonsignori Apart built in the 1300s. Your opportunity to enjoy living like a native as you experience life in a small Tuscan city.

Popular amenities for smoking friendly rentals near Siena Cathedral