Holiday rentals in Montecastrilli

Poggio Bicchieri Holiday Farm - Memoria apartment

Relax with the whole family in this accommodation. The holiday farm consists of two independent apartments with a living room, kitchen, bedroom, and bathroom. You won't have to share anything with other guests, as we have taken care to organize everything so that everyone has their own space and everything is separate. Outside there is a barbecue, table with chairs and deck chairs. In the vicinity are Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino, and Bagni San Filippo. To reach us, there is 1.5 km of dirt road!

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Chef’s Retreat

Beautiful hillside home, the perfect space for relaxation and fun. Enjoy the spectacular sunset across the pool overlooking the ancient Tiber valley. Umbria rich history and culture surround you and its centuries of culinary and artisanal tradition are at your doorstep. The Etruscan towns of Orvieto, Todi, Amelia are easily reached by car, or take the local train to Rome or Florence. A 3-minute drive away is Guardea with a supermarket, butchers, cafés, shops and an outdoor market on Sundays.

Exclusive 10 Acre Estate w/ Pool & Olive Grove!

Enchanting, exclusive 10acres estate on a hill, memorable sunsets; large pool framed by lavender&rosemary, open year-round. New air conditioning, Starlink internet. Very private&peaceful 2 floors, 4bedrooms, 4baths, jacuzzibathtub, 55inch smartTV, well-equipped kitchen, porch & pergola for alfresco dining, Weber barbecue, pizza oven, olive grove, fireplace; 20 min. to Orvieto,Todi,Amelia; 10 minutes drive to train station to Rome/Florence, 5min drive to shops in town. Grounds/pool caretaker

Stylish Umbrian farmhouse in stunning countryside

Welcome to Casale Amerina, an idyllic place to rest, rebalance and revitalise. This is a much-loved Umbrian farmhouse, with stylish contemporary interior, set in wonderful Umbrian countryside. There are two bedrooms with king size beds, a comfy sitting room with a balcony, and a gorgeous kitchen-dining room with Tuscan oak beams and a fireplace. Soak up the sun on our grass lawn, relax in the shade of our olive, walnut and fig trees, or explore the local area with its wonderful hilltop towns.

The Lost Stone paradise with pool, views and AC

The Old Stone is a 2025 fully refurbished 200 yrs old stone house in the hills of Todi, Umbria. It features a magnificent new pool, AC, high speed Wi-Fi and it is immersed in beautiful nature. It has a large garden, 3 patios, two kitchens, 3 bedrooms, 2.5 bath and a spectacular living room. Designed for comfort and entertaining, every detail has been thoughtfully curated to blend rustic charm (wood beams, cotto floors and stone walls) with moder luxury in a peaceful, panoramic setting.

The Cellar (Palazzo Pallotti)

The apartment is two floors below the square, entirely dug into the tuff. Overlooking the valley, it is isolated from the noises of the street, quiet, private, and very welcoming. The tuff walls give it an ancient vibe to transport you to another time. It can be reached on foot, via a footbridge that takes you directly to the square where the property is located. It is perfect for short stays of complete relaxation, but with the fully equipped kitchen you can make the most of it.

La Piazzetta - Cozy open space in the historic center of Montepulciano

Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, stone walls. Then go outside and admire the magnificent view of the Valdichiana. Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, and stone walls. Enjoy yourself and relax! Then go out and admire the magnificent view of the Valdichiana Valley.

Rural Umbria | countryside accommodation with pool

Tenuta Capitolini is an enchanting stone and brick farmhouse set in nature, surrounded by olive trees and a privileged and suggestive panorama in Umbria. It stands at the foot of the medieval village of Collelungo (twelfth century) with a splendid view overlooking the middle Tiber valley. Precisely because of its central location, is an excellent starting point to continue with cultural excursions in the nearby cities of Perugia, Todi, Orvieto, Assisi, Spoleto, Gubbio.

Mascagni Farmhouse in Val d'Orcia, Pienza

Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 16th-century barn nestled among olive trees and wheat fields. Relax with a cup of tea, pick rosemary and lavender in the garden with breathtaking views of the Val d'Orcia. Rediscover your true nature among the pristine fields and olive trees: here, walks and bike rides have no limits! Ready to create memories that will last a lifetime?

The Enchantment of Civita (The Terrace)

L'Incanto di Civita is located inside the ancient village of Civita di Bagnoregio. After leaving your car at the parking lot, you will need to walk along the bridge, the only way to access our "tufo pearl". L'Incanto di Civita is located in the ancient village of Civita di Bagnoregio. After leaving your car at the parking lot you will need to walk along the bridge, the only way to access our "tufo pearl".

Country Chalet and mini spa

A welcoming and comfortable nest, immersed in the bright colors of the Umbrian countryside, among roses and lavender, in the silent garden that frames it... Live a romantic dream: let yourself be enveloped by the warmth of the hot tub, under a starry sky and in the heart of the magic of our chalet. An oasis of tranquility, but well connected to all the major attractions of the region...