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Holiday houses in Montecastelli

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Top-rated holiday rentals in Montecastelli

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

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Top Guest favourite
A historic stone building rises against a clear blue sky, surrounded by olive trees. The inviting pool stretches alongside the structure, enhanced by a smooth stone edge, creating a serene outdoor space for relaxation.
Apartment in Montone
4.98 out of 5 average rating, 53 reviews

Annex in the Cardaneto Castle

Studio apartment in the Castello del Cardaneto (8th century) with a swimming pool, private parking, and a 4,000 square meter garden. 2 km from one of the most beautiful villages in Italy, Montone, famous for its tourist attractions and events that make it a unique place. The studio apartment of about 50 square meters has a separate entrance overlooking the garden, an entrance hall, a living room, a double bedroom, and a bathroom. Panoramic swimming pool with a view of Montone for all guests. Another apartment with a kitchen and a private balcony is available.

Top Guest favourite
Villa in Colombella
5.0 out of 5 average rating, 113 reviews

Torre Villa Belvedere Luxury & Relax with pool

"TORRE VILLA BELVEDERE" Wonderful 260 square meter apartment in a villa with a 12th century tower. Private swimming pool (15 meters long and 5 meters wide), billiards, darts, large garden, 80 square meter porch, barbecue, gym, and relaxation area inside the tower. Convenient private parking within the property. Located in a strategic position, 12 km from Perugia and 4 km from the highway, it can comfortably accommodate up to 8 guests with 3 double bedrooms with private bathrooms, TV, and a safe.

Guest favourite
An aerial view captures a large hilltop property surrounded by lush greenery, with a spacious pool at its center. Two rustic buildings, with traditional tiled roofs, sit amidst olive trees, and expansive hills stretch into the distance under a clear blue sky.
Villa in Umbertide
5.0 out of 5 average rating, 8 reviews

Il Posto Umbria - full property with large pool

Il POSTO UMBRIA is large hilltop property with an olive grove in the middle of the Umbrian nature. It's quiet and peaceful yet not isolated. It has a large pool (10x15m) and lots of sunny areas as well as shaded spots under the trees. There are options to book culinary experiences and activities: truffle hunting, wine tastings and cooking classes. Il Posto is the perfect place to stay with a large family, multiple families or a group of friends. Come and live ‘la dolce vita’ at IL POSTO

Guest favourite
A large heated swimming pool is surrounded by a stone patio, featuring a wooden gazebo with seating and sun loungers. Lush greenery and trees frame the pool area, providing natural shade, while expansive views of rolling hills and valleys stretch out in the background.
Home in Umbertide
4.96 out of 5 average rating, 23 reviews

Casa Maestra, Umbria hills, AC, large heated pool

High above the beautiful Niccone Valley, with extensive views over the green hills and valleys of Umbria and Tuscany. In a secluded and quiet position and not over-looked. 10 minutes drive down to the valley where there is a small village with grocery store, good restaurants and a vineyard. The historic and stunning towns of Umbria and Tuscany, including Cortona, Assisi, Siena, Todi, Gubbio, and Perugia are within easy driving distance. Air conditioning in bedrooms and a large scenic heated pool

Superhost
A saltwater swimming pool is framed by lush greenery, with sunbeds positioned on the grass nearby. A natural fence enhances the privacy of the outdoor area, which is surrounded by trees that provide shade and a serene environment.
Villa in Pierle
4.89 out of 5 average rating, 45 reviews

Historic Villa Getaway with 6BR/9BA, Pool, Views

This six-bedroom villa complex, set in atop a hill, overlooks a panorama of surrounding hills, fully immersed in nature. Villa was estored in 2020, with the rustic flair preserved to maintain its unique charm. The authentic stonework, the open fireplace in the entrance hall, and the exposed beams are in harmony with wooden floors. The villa is within 30min drive of Cortona. Also near Siena, Gubbio, Assisi, Lake Trasimeno, Arezzo, Montepulciano, Spoleto, and Perugia. (Read other details to note)

Guest favourite
The image captures a tranquil outdoor area featuring a private swimming pool with clear blue water. Surrounding the pool are several lounge chairs and umbrellas, providing shaded seating. In the background, a rustic stone villa is framed by lush greenery, enhancing the serene atmosphere.
Villa in San Pietro A Monte
4.95 out of 5 average rating, 20 reviews

Villa Casanova - Private Pool & Garden in Umbria

Countryhouse Casanova is a typical Umbrian farmhouse framed in the peaceful environment of its surrounding olive grove and centuries-old trees and the breathtaking view of the valley below. The villa features 3 independent apartments and, on the ground floor, a common lounge perfect for pleasant convivial moments. The villa is 15 km from Città Castello and 30 km from Cortona. The entire villa is fenced and the large park with private swimming pool is perfect for an holiday in total relaxation.

Guest favourite
Villa in Umbertide
5.0 out of 5 average rating, 26 reviews

Stunning house with pool, final summer discounts

40 mins from Perugia airport and Terontola railway station Charming and tastefully restored farmhouse with panoramic views. Large heated private swimming pool. Outdoor terraces with pergolas for shade. BBQ and pizza oven Security gate and cameras Four bedrooms with air-conditioning, three bathrooms. Two sitting rooms. Full equipped kitchen. Parking up to four cars. Wi-fi throughout. Weekly cleaning included. Washing Machine and Dishwasher Table tennis, Sky TV, indoor and outdoor games.

Top Guest favourite
The rustic stone building is set amidst lush gardens, framed by tall cypress trees. A winding pathway leads through the greenery, guiding towards the entrance. The structure showcases rustic charm with climbing vines and an inviting, well-maintained outdoor space. A small dog is seen wandering nearby.
Home in Città di Castello
5.0 out of 5 average rating, 24 reviews

Due Torri, Umbrian elegance

Due Torri oozes rustic Italian elegance and charm amongst the rolling hills of the Umbrian/Tuscan border. A private estate with vineyard, immersed in nature, Due Torri is the perfect place to relax and unwind. Comprising two original watch towers dating back to the 13th century, the property has been painstakingly renovated in a way which preserves the character and features of this historic building, whilst providing a modern level of comfort, style and convenience (air-con throughout).

Superhost
An infinity pool is framed by stone decking and wooden lounge chairs, inviting relaxation. Umbrellas provide shade, while terraced gardens with olive trees rise in the background. The surrounding landscape features gently rolling hills and clear blue skies, enhancing the serene outdoor setting.
Villa in Cortona
5.0 out of 5 average rating, 96 reviews

Stunning Tuscan Villa & Panoramic Infinity Pool

Stunning Tuscan hilltop Villa, with infinity edge swimming pool, has sweeping 180° panoramic views to Cortona, Lake Trasimeno and the entire Val Di Chiana. The perfect family retreat within ancient sun-drenched olive groves. 5 Double bedrooms; 4 bathrooms; new fully integrated kitchen & dining living space; living room with fireplace; TV snug; stone BBQ & outdoor kitchen within dining terraces and gardens; covered breakfast porch; parking; private infinity pool with sunset views.

Superhost
Apartment in Umbertide
5.0 out of 5 average rating, 25 reviews

B&B Lavinia

In the heart of the historic center of Umbertide, B&B Lavinia offers a cozy apartment with convenient access on the ground floor. Renovated and with attention to the smallest details, it consists of a spacious double bedroom, a bathroom with a shower and bidet, a large living area with a sofa bed, and a kitchen. The location is strategic not only for visiting the charming town, but also for easily reaching the most famous places in the region, such as Perugia, Assisi, and Gubbio.

Top Guest favourite
Home in Umbertide
5.0 out of 5 average rating, 11 reviews

Farmhouse with incredible view with pool

Ancient stone farmhouse from 1418 located just 4 km from Umbertide, immersed in a landscape of incomparable beauty. In Scarione you can enjoy a unique view of the surrounding valleys. Ideal for those seeking peace and tranquility, walks and trekking in the countryside among olive groves and castles. Also ideal for those who want to explore the Umbrian cities all within a short distance

Guest favourite
A swimming pool is framed by natural stone walls and surrounded by lounge chairs. Water features create gentle splashes as they flow into the pool. A patio area is located above, showcasing outdoor seating and shaded spaces under a fabric canopy.
Apartment in Umbertide
4.95 out of 5 average rating, 22 reviews

Montecastelli House - Terra

Casa Montecastelli is located in Umbertide in the Umbria region, 6 km from beautiful Montone. It features free Wi-Fi, barbecue facilities, a private swimming pool (2027), trampoline and free private parking. The apartment has a seating area, a smart TV, a kitchen and a private bathroom. For added convenience, the property has towels and bed linen.

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