
Vacation rentals in Sasso di Simone
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Top-rated vacation rentals in Sasso di Simone
Guests agree: these stays are highly rated for location, cleanliness, and more.

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.
ValueFamilySleep quality
4.99 out of 5 average rating, 531 reviews
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
ValueFamilyPool
4.9 out of 5 average rating, 241 reviews
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
LocationValueWifi
4.98 out of 5 average rating, 203 reviews
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.
LocationFamilyHospitality
5.0 out of 5 average rating, 155 reviews
Dimora Virgili - Urbino - (Full Historic Center)
Dimora Virgili is a large 80-square-meter apartment located in the heart of Urbino's historic center, in one of the city's oldest buildings. 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 environments with a quiet and elegant atmosphere. Ideal for those who want to experience Urbino calmly, living its history without sacrificing comfort.
LocationConditionIndoor spaces
5.0 out of 5 average rating, 19 reviews
Tofanello Orange Luxury and Modern Comfort 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 turquoise apartment. Turquoise: https://www.airbnb.com/rooms/plus/9430389.
FamilyValueBathroom
4.98 out of 5 average rating, 145 reviews
Villa Montanina - relax in esclusiva in Toscana
A typical Tuscan villa exclusively immersed in the views, greenery and peace of the Casentino Valley where you can spend moments of relax, fun and experiences where nature, culture and taste come together. During your stay you can enjoy cooking classes, yoga classes, wine tastings, massages, personalized experiences and relax in the large swimming pool. The Villa with its many large green spaces is also perfect for celebrating your dream wedding in Tuscany.
LocationValueAmenities
4.99 out of 5 average rating, 85 reviews
Villa del Duca - Private villa with pool
Surrounded by the harmonious landscape of Le Marche region, Villa del Duca is a private villa with a swimming pool, located just a few kilometers from Urbania, a peaceful and welcoming town offering all the services needed for a comfortable stay. Set in the countryside, the villa features an infinity pool with panoramic views, accessible via a scenic path lined with aromatic herbs, plants, and flowers, making the walk a true delight for all the senses.
LocationFamilyEV charging
4.94 out of 5 average rating, 18 reviews
PoggiodoroLoft, Tuscan dream e relax
Welcome to Poggiodoro Loft, 16th century stones' villa located in the countryside of Anghiari. Stunning views, charming and furnished interiors providing all type of comforts, the relaxing sauna, the private garden where you can enjoy the open air and lunch under the pergola, BBQ, fantastic in the warm seasons, lounge with brazier a panoramic swimming pool to spend great moments with friends, to be shared with the hamlet guests.
ValueLocationGetting around
4.87 out of 5 average rating, 167 reviews
Casa Rosmarino Eco-Wellness Country Home
Price includes: - Infrared Sauna - Wood for Fireplace - Heating/Air Conditioning - Laundry/Dryer - Shower Gel/Shampoo/Bathrobes - Welcome Appetizer w/Wine - Treats during your stay The house is located inside a Borgo (small group of houses) Pool & parking lot are shared areas. We have 6 units for rent Extra activities (not included) : - Massages, Cooking Classes, Tours & Tasting Please INQUIRE for price & availability.
ValueLocationTV
4.99 out of 5 average rating, 274 reviews
Tuscan dream lux 2-bed, pool, private balcony
Explore Tuscany in a beautifully decorated 2-bedroom, 2 bathroom apartment with all amenities & a log fire. Welcome to your luxurious home in the heart of Tuscany, Italy, where every moment will be a new adventure. This beautifully designed and well-furnished apartment is located in a restored farmhouse, surrounded by olive groves, vineyards, and rolling hills, offering you the best of Italian living.
ValueLocationPets
5.0 out of 5 average rating, 56 reviews
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!
LocationFamilyAccess
4.94 out of 5 average rating, 125 reviewsPopular amenities for Sasso di Simone vacation rentals
Other great vacation rentals in Sasso di Simone

The house on the bridge
LocationValueParks
4.95 out of 5 average rating, 59 reviews
[Bridgerton atmosphere] Historic residence in the village
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5.0 out of 5 average rating, 10 reviews
Apartment with two parks
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Villa Cerfoglio, peace in the Romagna hills
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La Malvina ~5* historic center~ Private garden
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4.93 out of 5 average rating, 76 reviews
Historic Arched Apartment in the Heart of Arezzo
LocationValueParking
5.0 out of 5 average rating, 153 reviews
Casa Flavia, Umbria’s New Secret
LocationFamilyOutdoor spaces
5.0 out of 5 average rating, 12 reviews
Agriturismo Montefiorentino with Private Pool
LocationHospitalityHiking
5.0 out of 5 average rating, 6 reviewsDestinations to explore
- Lake Trasimeno
- Pinarella Di Cervia
- Mirabilandia
- Misano World Circuit
- Mugello Circuit
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Senigallia Beach
- Palacongressi Della Riviera Di Rimini
- Basilica of St Francis
- Frasassi Caves
- Autodromo Enzo e Dino Ferrari
- Italia in Miniatura
- Furlo Gorge Nature Reserve
- Eremo Di Camaldoli
- Fiabilandia
- Oltremare
- Parco Naturale del Monte San Bartolo
- Avignonesi Winery Fattoria Le Capezzine
- Val di Chiana
- Papeete Beach
- Valdichiana Outlet Village
- Gola del Furlo
- Basilica di Sant'Apollinare in Classe
- Castello di Gradara





