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Holiday houses in Sestino

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Top-rated holiday rentals in Sestino

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Guest favourite
A rustic stone structure is featured with a terracotta roof and detailed stonework. An outdoor area showcases a barbecue grill and a table, surrounded by lush greenery and distant mountainous views.
Home in Pietrarubbia
4.95 out of 5 average rating, 40 reviews

Galasterna; at the foot of the mountain

Recently renovated farmhouse that maintains original architectural features. The farmhouse is located in the Municipality of Pietrarubbia in the heart of Montefeltro and is surrounded by meadows and woods of evocative and pristine beauty. Recently renovated farmhouse that maintains all the architectural features of a rural agricultural building. Located in the Municipality of Pietrarubbia in the heart of Montefeltro on the north side with respect to the centre of the capital, in a wonderful panoramic position 700 m above sea level, it enjoys a cool and ideal climate to escape the summer aphids. From this position you can see the most beautiful mountains of the Apennine ridge to the south until you reach Monte Conero, and some typical towns of Montefeltro such as Sassocorvaro and Urbino. To the northwest is Mount Carpegna with its picturesque Ripa known as the "coast of jumps" that highlights the sandstone stratification of Mount Carpegna. It is possible to reach in a few kilometres small and important ancient villages such as San Leo, Montecerignone, Cavoleto, Frontino and many others that offer, especially in the summer, local festivals and medieval revisions for a dip in the past. The house is surrounded by meadows and woods of evocative beauty and a still pristine environment, inhabited in every corner by nature, a privileged guest and always present, offers an ideal place to rest your mind and body. Guests can access the entire structure using all the services provided Guests will be assisted by the staff of the structure for any eventuality or need. In addition, the staff will be happy to illustrate nature trails and itineraries and suggest popular events in the surrounding area. Pietrarubbia is a hilly town of medieval origins. The town is dominated by the majestic summit of Mount Carpegna, which shows steep slopes on this side, with thick beeches alternating with bare rock; allaround there is a varied mosaic of crops, forests and, here and there, sharp rocky spurs dominated by ancient fortresses. The ancient village is just steps away and deserves your attention. The vast territory around the house is magnificent to visit on horseback or with a beautiful walk. Horseback riding in the green lands of Montefeltro! Enjoy the wonderful views of the area on the saddle of a horse along the itineraries proposed by us.

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, 473 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
A spacious bedroom is presented featuring two beds, one being convertible, and artwork depicting a mountain landscape. Natural light enters through a nearby window, enhancing the modern decor. A small bedside table and decorative elements, including a plant, add warmth to the space.
Home in San Marino
4.99 out of 5 average rating, 146 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

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
4.87 out of 5 average rating, 151 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: a beautiful fireplace that will keep the ambient warm in winter, 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
An expansive outdoor deck offers a serene view of rolling hills under a clear sky. An infinity pool transitions seamlessly into the landscape, with two soft seating cushions placed nearby, inviting relaxation and contemplation of the stunning panoramic scenery.
Home in Casale
4.88 out of 5 average rating, 189 reviews

Infinity view

Completamente ristrutturata posizione con vista mozzafiato sul Valdarno. Il piano terra è composto da soggiorno con due vetrate che danno sul patio, camino, divano letto, bagno con grande doccia e cucina moderna con isola in acciaio, con tre porte finestre per accedere alla zona pranzo esterna con bbq. Il primo piano è composto da due camere matrimoniali ognuna dotata del proprio bagno con doccia. Giardino è moto curato,ci sono vari angoli relax, prendisole è una piscina infinity ad idrolisi

Top Guest favourite
A stone house with a rustic exterior is highlighted by a greenery-adorned entrance. The two-story structure features multiple windows and a staircase leading to an upper level. A cozy patio area is visible, surrounded by a lawn and natural landscape.
Home in Sansepolcro
4.97 out of 5 average rating, 59 reviews

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!

Guest favourite
The villa is surrounded by lush greenery, showcasing an inviting infinity pool that reflects the sky. The stone exterior of the house features warm wooden shutters, with outdoor seating visible on the terrace. Nearby, lavender plants create a serene ambiance against the landscape.
Villa in Lisciano Niccone
4.88 out of 5 average rating, 50 reviews

Villa San Martino, on the Tuscany/ Umbria border

Villa San Martino is not just another holiday in Tuscany or Umbria - this is a really special place. With spectacular views across the world famous Niccone Valley towards Mercatale di Cortona, relax in the infinity pool, or dine alfresco on the terrace. From the villa you can easily access the enchanting towns of Cortona, Pienza, Montepulciano, Siena, Perugia, Assisi and Florence. The Niccone valley is home to delightful restaurants and you can sample great local Tuscan & Umbrian cuisine.

Top Guest favourite
A cozy kitchen area is seen featuring wooden cabinetry and a rustic dining table with chairs. Natural light fills the space, highlighting the stove and oven built into the cabinetry. A kettle and various kitchen items are arranged on the countertops.
Holiday home in Auditore
4.98 out of 5 average rating, 84 reviews

Villa Ca’ Doccio - Ca’ Doccio Holiday

A private cottage (by Villa Ca Doccio Holiday) nestled in nature, with spectacular views of the Montefeltro. It has 4 comfortable beds, with an optional extra bed or a cot for your baby, and a Biodesign Natural Pool – shared with Villa Ida – with a secluded sunbathing area, so you can enjoy the pool in complete privacy. You’ll find everything you need for an authentic, relaxing holiday where time slows down: you can hear the animals, see the fields, and breathe in the magic of rural life.

Top Guest favourite
A rustic living area features a wooden table surrounded by two elegant armchairs and a beige sofa. A stone fireplace, stocked with logs, stands as a focal point, while wooden beams adorn the ceiling. An inviting atmosphere is created by warm, natural colors and soft furnishings.
Home in Anghiari
4.99 out of 5 average rating, 258 reviews

Casa Rosmarino Eco-Wellness Country Home

Summer 2026 villas w/private pool available : airbnb.com/h/casaflavia10 airbnb.com/h/villaflaviaarezzo Price includes: - Infrared Sauna - Wood for Fireplace - Fire starters - Heating/Air Conditioning - Laundry/Dryer - Shower Gel/Shampoo/Bathrobes - Welcome Appetizer w/Wine - Treats during your stay 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.

Top Guest favourite
The farmhouse entrance is framed by two potted plants and orange pumpkins. A stone facade features a wooden door with gray shutters, complemented by a tiled roof. Natural surroundings are visible in the background, emphasizing the peaceful rural setting.
Home in Prato
4.98 out of 5 average rating, 140 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.

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, 39 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.&

Guest favourite
The rustic stone building is illuminated softly in the evening, revealing warm lights from the windows. A spacious courtyard is visible, featuring a planted area and paths leading to the entrance. Nearby trees and greenery frame the serene outdoor space.
Holiday home in Sestino
4.88 out of 5 average rating, 8 reviews

The Three Sources

This enchanting vacation home is housed inside a stone farmhouse with a rustic profile cared for in every detail nestled in the Tuscan countryside in an unspoiled environment overlooking the rows of vines placed at the foot of the Sasso Simone massif. A haven of peace and tranquility for those who wish to get away from the hustle and bustle of daily life.

Popular amenities for Sestino holiday rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Arezzo
  5. Sestino