
Vacation rentals in Montecastelli
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Top-rated vacation rentals in Montecastelli
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Historic 8th-century residence with panoramic pool
Experience the thrill of sleeping in a real 8th-century castle in the heart of Umbria. The Dependance, in the historic part of the Castello del Cardaneto, is a 50-square-meter studio apartment with a separate entrance, a double bedroom, a living room, and a bathroom. Nestled in a 4,000-square-meter park, the Castle offers a panoramic swimming pool with a spectacular view of Montone, one of the most beautiful historic towns in Italy. An authentic historic residence, where history, nature, and relaxation meet (no kitchen but a well-stocked bar area)
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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
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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
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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.
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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).
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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.
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Torre Villa Belvedere Luxury & Relax with pool
"TORRE VILLA BELVEDERE" Wonderful 260-square-meter apartment in a villa with a 12th-century tower. Private 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. Strategically located, 12 km from Perugia, 4 km from the highway, it can comfortably accommodate up to 8 guests. 3 double bedrooms with private bathroom, TV, safe.
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B&B Lavinia
In the heart of the historic center of Umbertide, B&B Lavinia offers a cozy apartment, with convenient access to the ground floor, renovated and cared for in detail, consisting of a spacious double bedroom, bathroom with shower and bidet, large living area with sofa bed and kitchen. The location is strategic not only to visit the characteristic town, but also to easily reach the most famous places in the region such as Perugia, Assisi and Gubbio.
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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
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Casa Montecastelli - 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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Relaxing-unspoiled country place Il Monte...
The Il Monte apartment, on the first floor, takes its name from its garden side entrance, which is accessed via an external staircase that leads to a small covered terrace that can accommodate two comfortable seats for reading and relaxing and the table with private wrought iron chairs in the garden with a small gazebo.
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Tower House
Have fun with the whole family at this stylish place. Kick back and relax in this calm, stylish space. 16th-century village in the greenest heart of Italy. You have the space and time, we'll be there for you. Located on the border between Umbria and Tuscany, discover, visit, explore and book now!
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Popular amenities for Montecastelli vacation rentals
Other great vacation rentals in Montecastelli

Villa San Martino, on the Tuscany/ Umbria border
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Fantastic vieuw House
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Casa Isabella - private pool sauna and views
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Hamlet San Biagio a Colle - Casa di Venere
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Acadirospi
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La Querciola
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Villa Montecastelli By MMega
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Ancient Mill on the Tiber - Alte Mühle am Tiber
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Destinations to explore
- Lake Trasimeno
- Misano World Circuit
- Basilica of St Francis
- Frasassi Caves
- Mount Amiata
- Centro Storico Orvieto
- Furlo Gorge Nature Reserve
- Eremo Di Camaldoli
- La Scarzuola
- Oltremare
- Avignonesi Winery Fattoria Le Capezzine
- Siena Cathedral
- Parco Naturale del Monte San Bartolo
- Val di Chiana
- Mount Subasio
- Palazzo Pubblico
- Valdichiana Outlet Village
- Terme San Filippo
- Gola del Furlo
- Abbey of Sant'Antimo
- Abbey of Monte Oliveto Maggiore
- Castello di Gradara
- Fonti Del Clitunno
- Rocca Maggiore





