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Vacation rentals in Montecastelli

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Top-rated vacation rentals in Montecastelli

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Top guest favorite
An inviting interior features exposed brick walls and a blend of modern and rustic design elements. A staircase leads to the upper floor, while large doors open to reveal a view of the outdoors. A wooden table and a cozy chair enhance the living space.
Apartment in Montepulciano
4.97 out of 5 average rating, 130 reviews

Under the sunset, Montepulciano

In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting for all the guests of our 4 apartments We can organize barbecue with paired wines after 7 pm. Large free parking area 100 mt away

Top guest favorite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guesthouse in Macciano
4.97 out of 5 average rating, 204 reviews

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Top guest favorite
A spacious exterior view reveals a charming stone house complemented by vibrant sunset lighting. The image showcases an inviting outdoor seating area with two chairs, set against a backdrop of lush hills and the distant glimmer of the lake.
Home in Perugia
4.98 out of 5 average rating, 172 reviews

La Perla del Lago Holiday home on Lake Trasimeno

Forget all your worries in this oasis of serenity. Let yourself be soothed by our amazing views and the sunsets that the lake offers us every evening. The La Perla del Lago Vacation Home overlooks Lake Trasimeno. 8 minutes away is the highway from which you can easily reach Florence, Perugia, Gubbio, Spoleto, Norcia, and many others. In the town, there are cafés, restaurants, grocery stores, a pharmacy, an ATM, a small playground, and a beautiful pool for the hottest days just 2 km away.

Guest favorite
A scenic view showcases rolling green hills beneath a partly cloudy sky. The ancient stone farmhouse sits among lush trees, with several chimneys visible on the roof. The natural landscape offers a serene backdrop, enhancing the peaceful ambiance of the surrounding countryside.
Apartment in Citta di Castello
4.86 out of 5 average rating, 109 reviews

Two-room apartment in the woods

Charming two-room apartment in a beautiful, ancient stone farmhouse surrounded by the green Umbrian countryside, ideal for relaxing in the midst of nature and enjoying pleasant walks in the woods. Just a five-minute drive to the center of Città di Castello. IG: @bilocalenelbosco NB: From July 1, 2024, it is mandatory to pay the tourist tax for the Municipality of Città di Castello. The tax is equivalent to 1.5 euros per night per person for a maximum of three nights, to be paid on site.

Guest favorite
A stone building with rustic charm is seen behind a sparkling swimming pool. Olive trees and lush greenery are positioned throughout the grounds, complementing the serene atmosphere. The pool area is accompanied by a well-maintained stone wall, creating a private outdoor space.
Condo in Montone
5 out of 5 average rating, 8 reviews

Apartment in Cardaneto Castle

Immerse yourself in the history of this 8th-century castle. An apartment with a kitchen, bathroom, bedroom, and private terrace is available. It is located in the oldest part of the castle with a dining room embellished with a rustic fireplace and a rustic kitchen full of history. From the private terrace you can enjoy an enchanting view. Large park with swimming pool, waterfall, whirlpool and bar area. Large wine shop for tasting Fresh pasta on request. Historic residence ADSI

Top guest favorite
A charming stone cottage is set within lush greenery, featuring a covered porch with outdoor seating. Olive trees surround the area, enhancing the natural beauty. A bicycle leans against the wall, inviting exploration of the peaceful countryside.
Cottage in Osteria delle Noci
5 out of 5 average rating, 103 reviews

Your Tuscan oak tree house, enchanting Val d'Orcia

The house enjoys a rare and enchanting view of the Val d’Orcia and Monte Amiata, ensuring maximum privacy. The interiors mirror the charm of the Tuscan style, with antique furniture and finishes made by local artisans. It is equipped with a double bedroom, a large living room with a big table, a fully equipped kitchenette, a double sofa bed in front of the fireplace, in the living room. Outside, the patio will allow you to eat with the colors of the sunset as a backdrop.

Top guest favorite
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.

Guest favorite
An inviting bedroom is highlighted by exposed wooden beams and warm lighting. A spacious bed with neutral bedding occupies the center, accompanied by patterned wall art. A dark wardrobe stands against one wall, while a modern floor lamp adds a touch of style.
Apartment in Umbertide
5 out of 5 average rating, 14 reviews

Civico14

Welcome to our cozy and charming home, located in the heart of the village! Don't be fooled by its small size: this house is a real gem of comfort and practicality. The cozy and intimate environment will make you feel right at home, you will find everything you need to feel comfortable. Thanks to its central location, you will have easy access to all attractions and services. Discover the pleasure of living in a typical house. Have a great stay!

Top guest favorite
The exterior of the stone annexe is showcased, surrounded by lush greenery. A shaded seating area is highlighted in front, with a small table and chairs beneath an umbrella. A pathway leads up to the entrance, nestled in a serene natural landscape.
Guesthouse in Perugia
4.99 out of 5 average rating, 138 reviews

Ethical house in Umbria

It is a 60 sqm annex suitable for couples who want to visit our region. We don't have a swimming pool but we have the truffle ground, the stream, the roe deer, porcupines, wild boars, our cats and the little dog Moti. In the garden, you will find herbs, fruit, and garden produce. Inside the cottage we rent, you will have our olive oil and helichrysum liqueur that we produce. We also produce saffron, but we sell it! Of course, pets are welcome!

Top guest favorite
An outdoor dining area is set under a wooden pergola, featuring a large wooden table surrounded by chairs. View of lush greenery and rolling hills is visible in the background. Wine bottles and glassware are arranged on the table, ready for a meal.
Guesthouse in Molino Vitelli
4.99 out of 5 average rating, 82 reviews

The dryer

The house is in a good location for country walks, wildlife, sun, and sightseeing. It's in a nature filled valley with easy routes to interesting places like Siena or smaller towns such as Montone. The house is desirable because of the location, the people, the ambiance, the outdoors space, and the neighborhood. This small place is good for couples and solo adventurers. Wi-fi access has recently been improved in the house.

Guest favorite
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, 20 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 swimming pool, 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.

Top guest favorite
A rustic cottage with a stone facade is set against a backdrop of rolling hills and a dramatic sunset sky. Surrounding greenery includes manicured shrubs and olive trees. A red umbrella stands at the entrance, providing a spot of color against the serene landscape.
Farm stay in Pierantonio
4.97 out of 5 average rating, 112 reviews

La Stalla - San Gabriel House

1 bedroom cottage located on the property of Casa San Gabriel, set in the stunning Umbrian countryside, it has access to the large gardens and swimming pool. The cottage is a full self catering studio cottage with 1 double or twin bed and air-conditioning.

Popular amenities for Montecastelli vacation rentals

  1. Airbnb
  2. Italy
  3. Umbria
  4. Perugia
  5. Montecastelli