Smoking friendly vacation rentals in Castiglion Fiorentino

A cozy outdoor loggia features two wicker chairs and a round table, framed by rustic stone walls. Breathtaking views of rolling hills and olive trees are visible in the distance, enhancing the serene atmosphere of the space.

4.94 out of 5 average rating, 82 reviews

The small tower

The proposed farmhouse is a typical townhouse made of characteristic Tuscan stone, ideal for those who want to spend relaxing vacations surrounded by the green hills of Castiglione that surround the small valley of Chio. The turreted accommodation is on three levels: the usable portion of the building is on the first floor with a living/dining room and an equipped kitchen and on the second floor with a double bedroom, a twin bedroom and a bathroom with shower, all furnished with period furniture.

A rustic stone building is surrounded by green grass and vibrant flower pots filled with white and purple blooms. Tall cypress trees are visible in the background, under a clear blue sky, enhancing the peaceful Tuscan landscape.

4.91 out of 5 average rating, 202 reviews

Bed and Breakfast CASA CERNANO

- 5 Double or Triple rooms each with its own bathroom/WC, with individual entrance from the outside aerea - Rooms are also individually rented -The price of your stay is based on 1 double room each 2 guests ( also with separate beds ) - Garden - Large car park - Free Wi-Fi in the rooms and common aerea - Barn with sitting aerea, games for children, coffee machine, ping ong table - Breakfast sweet or savory upon request ( 5 or 7 euro a person/day ) - Dogs are welcome ( 15 euro the entire stay )

4.99 out of 5 average rating, 158 reviews

A small balcony is featured with two black woven chairs flanking a round table. On the table, a bottle and two glasses are set against a backdrop of panoramic views of rolling hills and terracotta rooftops under a partly cloudy sky.

Apartment

Cortona’s Rooftop Nest

L’appartamento è sito in pieno centro storico proprio di fronte alla meravigliosa chiesa di San Francesco e a pochi passi dalla piazza principale.Arredato in stile country chic e dotato di tutti i comfort.Ospita 4 persone.Ventilatori nelle camer The apartment is located in the historic center right in front of the wonderful church of San Francesco and a few steps from the main square. Furnished in a country chic style and equipped with all comforts. It can host up to 4 people. Fan in the rooms.

4.91 out of 5 average rating, 118 reviews

A well-maintained outdoor pool is surrounded by sun loungers and patio umbrellas, providing a tranquil setting. Lush greenery and colorful flowers frame the area, with a backdrop of a historic villa nestled among trees, capturing the essence of the serene countryside.

Apartment

Unique location farmhouse

Farmhouse Santa Margherita is a splendidly restored 18th century house that sits on a hilltop on the Tuscan-Umbrian border in sight of Montepulciano.The farmhouse has been recently renovated in order to offer to its guests eightvacation apartments. The rooms are very spacious and comfortable. The furnishings are luxurious and include wooden furniture, wrought iron beds and elegant lamps. The kitchens are well equipped so that all your culinary skills can be exercised.

4.99 out of 5 average rating, 78 reviews

The pool is illuminated with soft lighting, creating a calming ambiance during the evening. Surrounding greenery provides privacy, and seating areas are visible. The smooth water surface reflects the gentle glow, inviting relaxation in a serene outdoor setting.

Villa

CHARMING TUSCANY VILLA PRIVATE POOL

Antico casale rurale, situato sulle colline Toscane con vista sulla campagna circostante . Isolato e ideale per chi desidera rilassarsi ma vicino alle principali città turistiche italiane. Ogni camera è dotata di condizionatori con tecnologia windfree, nel salotto è presente una TV 82" ULTRA HD con SKY e canali internazionali. La piscina è dotata di illuminazione Philips Hue per creare l'atmosfera giusta in ogni momento e di impianto audio Bose Soundtouch bluetooth

4.92 out of 5 average rating, 66 reviews

The living area features a spacious sectional sofa, a modern television on a low cabinet, and a round dining table surrounded by four chairs. A map artwork adorns the wall, complemented by shelf plants, enhancing the open feel of the apartment.

Apartment

Modern apartment in the heart of Tuscany

A few steps from Castiglion Fiorentino train station. Ideal for exploring not only this charming medieval city but also other beautiful Tuscan cities, such as Arezzo, Cortona and Siena. The apartment has 1 bathroom and 5 beds, ideal for families or groups of friends. There is also an additional sofa bed for extra guests. It also has a small loggia for relaxing. Its central location allows you to easily find services such as shops, restaurants and bars nearby.

4.92 out of 5 average rating, 59 reviews

A modern kitchen area is presented with a sleek design, featuring a gas stove and minimalist cabinetry. A dining table with four black chairs is set with tableware, while ambient lighting from a nearby lamp creates a soft glow. The space reflects a comfortable and functional dining environment.

Condo

Life is beautiful

Cozy apartment of very recent construction, in class "A". Underfloor heating and air conditioning system. Located in the beautiful setting of the Tuscan hills of Valdichiana. Private parking in front of the property It is located about 1 km from the center of Castiglion Fiorentino, in a quiet area with private parking, supermarket and shops can be reached on foot in 3 min. A few kilometers from Cortona, and Arezzo, easily accessible by Equestrian Center

5 out of 5 average rating, 9 reviews

The image captures a serene Tuscan landscape at sunset, with rolling vineyards and a charming estate visible. The brick building is surrounded by lush greenery, and the soft orange and blue tones of the sky enhance the tranquil setting.

Farm stay

Podere Il Belvedere Farmhouse - La Stalla

Podere Il Belvedere is a charming estate located in Castiglion Fiorentino, just 15 minutes from Cortona. The property features seven well-equipped apartments, each with a living room and kitchenette. Guests can enjoy a pool area with gazebos and sunbeds, a barbecue area, and free parking. With its stunning views, proximity to Tuscany’s art cities, and activities like wine tastings or cooking classes, it’s perfect for a memorable holiday.

4.89 out of 5 average rating, 286 reviews

A serene outdoor pool is set against a panoramic view of rolling hills and vineyards. Six lounge chairs are arranged along the pool's edge, with manicured bushes providing greenery. The sky is dotted with clouds, and a flock of birds can be seen in the distance.

Villa

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.

Superhost

A spacious farmhouse with a rustic tiled roof is surrounded by lush green landscapes and rolling hills. The scenic view includes distant mountains and a clear blue sky, creating a tranquil atmosphere in the natural setting.

Farm stay

4.89 out of 5 average rating, 232 reviews

il poderuccio farmhouse studio apartment

From the careful renovation of an old farmhouse from 1619, various apartments have been obtained for a total of 11 beds, including: - a studio with double bedroom, private bathroom with shower, and a small kitchenette with fridge, electric hot plate and everything you need for a quick breakfast or meal. Possibility of using the sweet and savory BREAKFAST service, served, at an additional cost of €12 per person per day.

The image captures a vibrant town square in Cortona, featuring a historic clock tower and a series of stone steps leading to a large building. Outdoor seating is visible, with visitors enjoying the sunny day, and nearby buildings display a range of architectural styles.

4.94 out of 5 average rating, 202 reviews

Casa del Passerino

Apartment located inside a historic building in Cortona, dating back to the 1500s, overlooking the city's main square... Our property, while condemning the war, dissociates itself from all racist behavior towards the Russian and Belarusian population. At Casa del Passerino, people of these nationalities are welcome and will be treated the same as everyone else. We look forward to seeing you in Tuscany!

A rustic stone house is surrounded by lush greenery, featuring wooden shutters and a tiled roof. A shaded outdoor dining area is visible, complemented by potted plants. The serene garden setting invites relaxation and enjoyment of the natural landscape.