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Holiday houses in Sasso di Simone

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Top-rated holiday rentals in Sasso di Simone

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

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Superhost
A tranquil scene featuring a swimming pool reflecting the morning sun, surrounded by lush greenery. Soft clouds linger below, creating a serene atmosphere. The distant hills are barely visible beneath a gentle mist, with the clear blue sky overhead enhancing the peaceful ambiance.
Villa in Poppi
5 out of 5 average rating, 4 reviews

Poggelleri the postcard on Poppi and Tuscan hills

Imagine waking up with the golden light of Tuscany filtering through the windows, the intoxicating scent of the countryside and the feeling of absolute peace. This villa awaits you for an unforgettable experience. Located in an exclusive and private location, it offers breathtaking views of rolling hills within walking distance of the most beautiful cities of art. If you are looking for a refuge where time seems to stand still, where beauty is everywhere and exclusivity is the watchword, you have found your ideal destination.

Top Guest favourite
A charming outdoor dining area features a round table set with delicate dishware and a pink tablecloth. Surrounding the table are intricately designed white chairs. A gazebo provides shade, and lush greenery is visible in the background, creating a serene setting for leisurely meals.
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.

Top Guest favourite
Apartment in San Marino
5 out of 5 average rating, 70 reviews

Camelia Loft - Apartment in the historic center

New and beautiful apartment in the historic center of San Marino. Thanks to its location, you will be in the heart of this beautiful Republic and a stone's throw from the main attractions, museums, shops and clubs. You'll have a large living area, modern kitchen, Smart TV, beautiful double bedroom, bathroom, Wi-Fi and more! Possibility of parking at a discounted price reserved for our guests! Ideal accommodation for families or groups of friends. Perfect for vacation, leisure or work.

Top Guest favourite
Home in Caprile
4.97 out of 5 average rating, 39 reviews

Montana House in Stone-Garden-Panorama-Jacuzzi

House on two levels connected by an internal staircase, with independent entrances. On the ground floor there is a fully equipped kitchen, a living area, and a bathroom with a whirlpool bathtub. Upstairs you’ll find two bedrooms, including one with a double bed, a versatile room that can be used as a living room or bedroom, and a second bathroom. Three satellite TVs. Spacious, well-kept and comfortable interiors, ideal for couples, families or small groups looking to relax.

Top Guest favourite
The exterior of a rustic stone building is captured, showcasing a two-story structure with multiple shuttered windows. A small balcony is visible on the upper level. Lush green grass and a few decorative plants frame the entrance, while a vehicle is parked nearby.
Apartment in Urbino
4.96 out of 5 average rating, 204 reviews

Apartment in an old farmhouse 4 km from Urbino

Charming 45 sqm apartment in a finely renovated old farmhouse. On the hills, a 5-minute drive from Urbino, the accommodation is equipped with a kitchen and living room, private bathroom with shower and double bed. Third bed on the mezzanine. Wi-Fi, TV, free on-site parking, mosquito nets, fan, library, informational material for discovering the area. Breakfast is offered for the first 2 days of the stay, after which it will be the customer's responsibility to provide it.

Top Guest favourite
A spacious bedroom features a king-size bed with neutral bedding, complemented by decorative pillows. Soft lighting is provided by wall sconces, while natural stone walls add texture. A small bedside table and an armchair enhance the inviting ambiance.
Home in Sarsina
4.98 out of 5 average rating, 59 reviews

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.

Guest favourite
Chalet in San Leo Bastia
4.79 out of 5 average rating, 47 reviews

Casa Isabella - Villa with pool and sauna

Welcome to beautiful Tuscany. The detached Casa Isabella is located on a picturesque hill between Cortona and Città di Castello. Nestled in 20,000 m² of forests and meadows, a stay invites you to long walks, bike rides and saunas. The sunny orientation of the terrace area with a large pool offers plenty of space for sunbathing. Around the Casa there are several cozy seating areas. The wonderful panoramic view is a constant companion.

Superhost
A rustic dining area features a long wooden table set for eight, with simple tableware and napkins. A large window allows natural light to fill the space, offering a view of the vibrant garden outside, where a hammock is visible in the background.
Home in Anghiari
4.86 out of 5 average rating, 155 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.

Guest favourite
Tower in Santarcangelo di Romagna
4.92 out of 5 average rating, 13 reviews

Torre dei Battagli-Dormi in a medieval tower

On the bike path that leads from Rimini to Valmarecchia, there is a medieval tower dating back to the 14th century. Done erected from a wealthy Raminese Fusso de’ Battagli. Once on the watchtower of an extensive fortified farm, guarded wheat and produce from the land. People came here to cook bread. Today this no longer happens but the tower maintains its charm as a fortress place to relax and feel protected .

Top Guest favourite
The outdoor pool area is surrounded by neatly trimmed cypress trees and colorful gardens. A gentle slope leads to the pool, with views of the rolling green hills in the background. Sun loungers and umbrellas are placed around the pool, creating a serene atmosphere.
Farm stay in Anghiari
5 out of 5 average rating, 46 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.&

Top Guest favourite
Condo in Arezzo
4.95 out of 5 average rating, 174 reviews

Chianti, elegant barn among vineyards and pool

Discover a unique sanctuary in Chianti, a historic barn where stone walls meet 80s vintage design. Fall in love with the canopy bedroom, cook in the modern kitchen, and enjoy vineyard views from the living area. Outside, private gazebos and an infinity pool await you in total silence. A perfect blend of Tuscan heritage, sophisticated style, and pure romance."

Superhost
An oval-shaped swimming pool is surrounded by a spacious sunbathing area with lounge chairs and deck chairs. The rustic two-story house, with brown shutters, sits amidst lush greenery, offering a peaceful retreat. Natural stone features are placed around the pool area, enhancing the outdoor setting.
Villa in Capoville
4.75 out of 5 average rating, 8 reviews

Casa Melograno 11+2, Emma Villas.

Set in the rolling hills of Montefelcino, in the Marche region, is Casa Melograno, a 19th century barn carefully restored by the owners in 2015. From the old barn, where once the animals sought shelter from the sun, has sprung a house with six bedrooms, designer kitchens, large living rooms and a beautiful swimming pool surrounded by a spectacular panorama.

Popular amenities for Sasso di Simone holiday rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Sasso di Simone