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Holiday houses in Chiassa Superiore

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Top-rated holiday rentals in Chiassa Superiore

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
The outdoor area features a large swimming pool surrounded by lush greenery, including trees and shrubs. Sun loungers are positioned nearby for relaxation. The rustic farmhouse is visible in the background, showcasing traditional Tuscan architecture with terracotta accents.
Guesthouse in Antria
4.92 out of 5 average rating, 138 reviews

A charming Tuscan retreat

Villa Pianelli is a traditional farmhouse dating from the 1500's and consists of 2 structures. The main house where I live, always available to ensure your stay runs smoothly and the Garden apartment. Both are completely independant with separate entrances. The Garden apartment is composed of 5 rooms on ground level, the interiors have retained the Tuscan characteristics with brick ceilings and chestnut beams and terracotta floors. There are 2 double bedrooms, 1 bathroom with shower, 1 lounge with a wood burning stove and open plan kitchen - dining area. The kitchen is equipped with fridge,oven and ceramic hob. From the lounge you access the spa room with sauna and from there onto a terraced garden complete with b.b.q. The swimming pool is 8mx16m and is open May through September, furnished with sun loungers,a b.b.q area and a large covered pergola with dining tables and chairs. Villa Pianelli is secluded in a quiet corner of the Tuscan countryside, nestled in the hills of Arezzo, surrounded by vineyards, olive groves and oak forests.We can offer our guests a dimension of peace and quiet whilst ensuring various possibilities of entertainment in wineries, restaurants,shopping etc just a few kilometres away in Arezzo. Please note that the house has two bedrooms but if the booking is for two people only one bedroom will be provided.If required there is an additional cost of 50 euro per night for the second bedroom.

Top Guest favourite
An outdoor patio area features rustic furnishings and is framed by gracefully draping curtains. The space is adorned with comfortable seating and a communal dining table, set against a backdrop of tall cypress trees and a clear blue sky, inviting relaxation in a serene environment.
Home in Simignano
4.98 out of 5 average rating, 176 reviews

Casa al Gianni - The Simignano Barn

Transformed from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, and a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those seeking a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, complete with relaxation in the hot tub and al fresco dining. A memorable getaway awaits you in this slice of paradise!

Top Guest favourite
Farm stay in Ruscello
4.99 out of 5 average rating, 499 reviews

Farmhouse Fattoria La Parita

Provencal-style apartment nestled between vineyards and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 km from the highway. The song of jays and cuckoos will be the soundtrack to the stay while the roe deer graze among the olive trees. A basic Italian breakfast is included (coffee, tea, milk, biscuits, etc.), but if you prefer a richer breakfast served at the table, the cost is €15 per person (€10 from 5 to 15 years, free under 5 years). EV wallbox available.

Guest favourite
Home in Asciano
4.96 out of 5 average rating, 132 reviews

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Guest favourite
A bright and spacious living room features a large marble coffee table and a pair of elegant chaise lounges. A striking painting hangs above a contemporary white sofa adorned with colorful cushions. Antique furnishings and a patterned rug enhance the room's sophisticated ambiance.
Apartment in Centro
4.94 out of 5 average rating, 363 reviews

Museum Suite - Luxurious unit with a River View -

After 13 wonderful years of hosting on Airbnb, the time has come to close this incredible chapter and embrace the next. These upcoming 7 months will be the final season for MuseumSuite, in Jan 2027, the property will be sold and transformed into a private family residence. It has been an absolute honor and a privilege to welcome guests from all walks of life. Each of you has deeply enriched my journey, and I hope that MuseumSuite has left a beautiful, lasting impression on your lives as well.

Top Guest favourite
The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.
Villa in Montepulciano
4.93 out of 5 average rating, 309 reviews

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

Top Guest favourite
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, 111 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 favourite
A natural swimming pool features a sandy beach area, surrounded by lush greenery and plants. Soft, clear water reflects the blue sky, creating a serene environment for relaxation.
Villa in Tavarnelle Val di Pesa
5 out of 5 average rating, 25 reviews

Tuscan Luxury Villa • Natural Pool & Privacy

Immagina di svegliarti in totale privacy, circondato dalle colline del Chianti, con la tua piscina naturale, la spiaggia e il chiringuito. Non è solo un soggiorno, ma una vera “private luxury experience” toscana. Tenuta Virgilio nel Chianti è una villa immersa nella natura, perfetta per chi cerca relax, silenzio ed esclusività in Toscana. Oltre 3 ettari di uliveto e totale privacy: nessuno spazio condiviso, solo la tua esperienza in Toscana.

Top Guest favourite
An outdoor seating area features a small table surrounded by two chairs, adorned with a light breakfast setup. The stone facade of the house is complemented by climbing vines and a bright flower arrangement, inviting guests to enjoy the fresh air.
Holiday home in Monticchiello
4.97 out of 5 average rating, 130 reviews

In Tuscany Rooms

**Your Dream Retreat in the Heart of Val d'Orcia** Welcome to In Toscana Camere, a charming holiday home located in the historic center of Monticchiello, a Tuscan village full of charm and authenticity. Surrounded by stone walls and enhanced by modern, comfortable interiors, this home offers the perfect balance between tradition and contemporary style. Wake up every morning to a breathtaking view of the stunning Val d'Orcia.

Top Guest favourite
Casa particular in Florence
5 out of 5 average rating, 44 reviews

Palazzina Maresa - Loft 4

Palazzina Maresa is a 1920s building carefully restored to host eight independent apartments, each shaped by the vision of a different young local designer. The project reflects on early 20th-century aesthetics through a contemporary lens, blending architecture, design, and artistic research. Located in a quiet residential area with private and shared gardens, the building is just a short walk from Florence’s historic center.

Top Guest favourite
A stone wall encloses a charming property, featuring a large iron gate surrounded by blooming flowers. The entrance is framed by a well-maintained garden with potted plants, showcasing the rustic architecture of the building, which has multiple windows and a welcoming facade.
Villa in Marcena
4.96 out of 5 average rating, 71 reviews

VILLA LAMA - A window overlooking the river

The villa is located within a complex dating back to the 11th century, of which some ruins remain. The building, built as a monastery of the Olivetan monks around 1400, saw various owners until 1878. It was renovated by the current owners who made it their country home. Villa Lama, nestled in the countryside and surrounded by the Casentino hills, is located on the banks of the Arno River, accessible via a short path.

Superhost
Home in Muciafora
5 out of 5 average rating, 3 reviews

The Court of Muciafora

Welcome to our structure in Muciafora (AR), immersed in the heart of the Tuscan countryside. Consisting of three apartments located in the same condominium, this solution offers ample space to accommodate up to 8 people. Surrounded by centuries-old olive trees and unspoiled nature, our structure represents an oasis of tranquility. Each apartment is cared for in detail and offers modern amenities.

Popular amenities for Chiassa Superiore holiday rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Chiassa Superiore