
Holiday houses in Sasso di Simone
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Top-rated holiday rentals in Sasso di Simone
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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.

Tuscan charm of villa - countryside - Villa Senaia
In the charming Tuscan countryside, among olive trees and vineyards, a stone villa, in a strategic position to grasp the secrets of Tuscany and Umbria air conditioning and swimming pool with wellness area for your relaxation and comfort Villa Senaia is a large house with wooden beams, in a beautiful hillside location with idyllic views overlooking one of the favorite places in the Tuscan countryside, an attractive setting for outdoor dining, drinking Tuscan wine and listening to crickets and cicadas

Tuscany Villa Mammi
Large, renovated stone villa in the woods of Castiglion Fiorentino, close to Cortona, Arezzo and Siena. A haven of privacy featuring a swimming pool, a panoramic hot tub with breathtaking views of the valley, and table tennis. Enjoy magical evenings under the stars, thanks to the authentic stone barbecue and the wood-fired pizza oven. The ideal getaway for those seeking relaxation, nature and comfort in the heart of Tuscany, perfect for families or groups dreaming of a truly unforgettable holiday.

House "Independent" close to the Historic Center
This independent house, located a few steps from the walls surrounding the historic center of the Republic of San Marino, is the top place for those seeking relax, privacy and a breathtaking view of the surrounding mountains. The house, modern and with attention to detail, is perfect for families, couples or small groups who want to live an unforgettable experience. Large and well-organized spaces are designed for your every comfort. Free parking a few steps from the front door. Pets are welcome

Palazzo: a little house in the woods – peace and quiet
Independent apartment surrounded by greenery in the Tuscan Apennines, on the edge of the Alpe della Luna nature reserve. Perfect for single hikers, couples or families and lovers of nature and tranquility. The house is a few minutes' walk from two taverns in the hamlet of Montagna, where you can taste typical local products and enjoy the hospitality of the people of Montagna. Every day you come across fallow deer, roe deer, badgers, porcupines and wild boars... and the wolf that hunts them!

Dimora Virgili - Urbino - (Full Historic Centre)
Dimora Virgili is a large 80 sqm apartment located in the heart of Urbino's historic centre, inside one of the oldest buildings in the city. The spaces are generous and equipped with all comforts, designed for a comfortable and relaxed stay. Set in a historical context of great value, the residence combines well-kept and functional rooms with a quiet and elegant atmosphere. Ideal for those who want to experience Urbino at a leisurely pace, soaking up its history without sacrificing comfort.

Piazza Grande Boutique Apartment
Overlooking the most beautiful square in the historic center of Arezzo, where the re-enactment of the Giostra del Saracino takes place, the Piazza Grande Boutique Apartment is located on the second floor of a medieval building, overlooking the beautiful palaces and the Vasari Loggias and is a unique location of its kind. The decor, the work of Countess Cesaroni Venanzi, was created with beautiful antique furniture reinterpreted in a modern way and enriched with contemporary influences.

[Bridgerton atmosphere] Historic residence in the village
Welcome to my beautiful new home in Sansepolcro! It has just been completely renovated and is as fresh as a daisy, but with a touch of Bridgerton style, making it historic, themed and classic 😃 🌿 An oasis of natural coolness: Located in a historic building in the centre of Sansepolcro, the apartment boasts thick original stone walls. This traditional insulation keeps the house beautifully cool and pleasant (around 24°C) even on the hottest summer days.

Tofanello Turquoise Luxury with Outdoor Pool
Escape to the rolling hills of Umbria in this updated farmhouse (90 m2 over 2 floors) that retains its original charm. The home features classic beamed vaulted ceilings, original stone finishes, an indoor wood-burning fireplace, private entrance and a private garden terrace. The shared pool has a large sun lounge area. If your favourite dates aren't available anymore take a look at our orange apartment. Orange: https://www.airbnb.com/rooms/plus/9429730

Nature Retreat | Peace & Relax in the Hills
A stone house immersed in nature, in the heart of Romagna, between the Apennines and historic villages. A peaceful and quiet place for those seeking slow living, intimacy and relaxation, with a private hot tub. La Cappelletta holds generations of memories and is now a space to live slowly: sleep, cook, taste, meditate and enjoy the silence. Perfect for romantic stays, escapes from the city, retreats with friends or weekends away from the noise.

Mafuccio Farmhouse - "Casa di Rigo"
Casa di Rigo is the smallest apartment of Agriturismo Mafuccio, a farmhouse immersed in unspoiled nature in the Sovara Valley, a stone's throw from the Rognosi Mountains nature reserve and nestled at the foot of Monte Castello. A quiet and peaceful place like the streams that cross the valley, where you can find peace, and fully experience nature... in the company of the Valley Kids!

Explore nature in the heart of the Chianti vineyards
Feel close to the land in a rustic building on a Tuscan farm. Old stone walls, ceilings with exposed beams and terracotta floors are the backdrop to a characteristic apartment with fireplace. Plunge into an infinity pool for a unique view of the surrounding landscape. Dine outdoors, with the fresh air caressing you, sit and relax admiring the sunset under the ancient cypresses.
Popular amenities for Sasso di Simone holiday rentals
Other great holiday rentals in Sasso di Simone

Ciurelli Room - Urbino - [Full Historic Center]

Coaching House

Glamping Pandaland - Sisley

Fonte del Leone - Exclusive suite

Camelia Loft - Apartment in the historic center

Villa with Private Pool for 12 guests: Urbania

Galasterna, at the foot of the mountain

Historic Arched Apartment in the Heart of Arezzo
Destinations to explore
- Lake Trasimeno
- Pinarella Di Cervia
- Mirabilandia
- Mugello Circuit
- Fiera Di Rimini
- Misano World Circuit
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Senigallia Beach
- Frasassi Caves
- Basilica of St Francis
- Autodromo Enzo e Dino Ferrari
- Palacongressi Della Riviera Di Rimini
- Italia in Miniatura
- Oltremare
- Avignonesi Winery Fattoria Le Capezzine
- Fiabilandia
- Furlo Gorge Nature Reserve
- Eremo Di Camaldoli
- Papeete Beach
- Parco Naturale del Monte San Bartolo
- Ugolino Golf Club
- Val di Chiana
- Valdichiana Outlet Village
- Gola del Furlo





