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Holiday rentals in Montecastelli

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Top-rated holiday rentals in Montecastelli

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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, 464 reviews

Farmhouse Fattoria La Parita

Provencal style apartment surrounded by vineyard and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 from the highway. The singing of the acorn and cuckoo will be the soundtrack to the living room while the roe deer burn among the olive trees. An Italian basic breakfast (coffee, tea, milk, cookies, etc.) is included, if you prefer a richer and served breakfast at the table, the cost is €15 per person (€10 from 5 to 15 years, free less than 5 years old). Wallbox EV available.

Superhost
A private swimming pool is bordered by tiling, with two lounge chairs positioned nearby. The stone building features multiple windows with wooden shutters. A shaded seating area with a canopy can be seen on the upper terrace, creating an inviting space for relaxation.
Home in Umbertide
5 out of 5 average rating, 4 reviews

House for two family’s of 4

Bring the whole family to this great place with lots of room for fun. The house consists of two apartments with there own kitchen and bathroom. Each apartment has two bedrooms with two single beds and a dubbel bed. There are two swimming pools on the property. The one in front of the apartments is private if the two apartments are booked together. The larger pool is shared. Casa Montecastelli is located in Umbertide in the Umbria region, 6 km from beautiful Montone. It features free Wi-Fi, bar

Top guest favourite
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.
Flat in Montepulciano
4.97 out of 5 average rating, 119 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 favourite
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.
Guest house in Macciano
4.97 out of 5 average rating, 200 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.

Guest favourite
A stone villa surrounded by greenery is featured under a clear blue sky. A large swimming pool reflects the sunlight, complemented by sun loungers and colorful potted flowers along the edges. The outdoor area is perfect for relaxation with scenic views of the Tuscan hills.
Villa in Castiglion Fiorentino
4.91 out of 5 average rating, 222 reviews

Tuscan charm of villa - countryside

Nell’affascinante campagna Toscana,tra ulivi e vigneti una villa in pietra,in posizione strategica per cogliere i segreti di Toscana e Umbria aria condizionata e piscina con area wellness per il vostro relax e confort Villa Senaia è una grande casa con travi in ​​legno, in una splendida posizione in collina con vista idilliaca che affaccia su uno dei luoghi preferiti della campagna toscana, un ambiente attraente per mangiare all'aperto, bevendo vino toscano e ascoltando i grilli e le cicale

Guest favourite
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, 160 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 La Perla del Lago Holiday 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 village there are bars, restaurants, food restaurants, ATM pharmacy,a small playground, 2 km away, a beautiful pool for the hottest days.

Top guest favourite
A stone exterior is showcased, with a staircase leading up to the entrance. A shaded area features outdoor seating, including a table and chairs. Potted plants line the pathway, and greenery provides a serene backdrop, enhancing the outdoor living space.
Home in Prato
4.99 out of 5 average rating, 130 reviews

Tofanello Turquoise Luxury 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 orange apartment. Orange: https://www.airbnb.com/rooms/plus/9429730

Top guest favourite
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.
Guest house in Perugia
4.99 out of 5 average rating, 137 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 favourite
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.
Guest house 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.

Top guest favourite
A serene bedroom space features a spacious bed adorned with soft, neutral-toned linens. Sheer white drapes create a cozy atmosphere, while the open doors offer a view of the lush outdoors, inviting natural light into the room.
Farm stay in Arezzo
4.98 out of 5 average rating, 244 reviews

Explore nature in the center of Vigneti Chianti

Feel close to the land in a rustic building on a Tuscan farm. Old stone walls, ceilings with exposed beams and terracotta floors are the backdrop to a characteristic apartment with fireplace. Plunge into an infinity pool for a unique view of the surrounding landscape. Dine outdoors, with the fresh air caressing you, sit and relax admiring the sunset under the ancient cypresses.

Top guest favourite
Farm stay in Campiglia D'orcia
4.94 out of 5 average rating, 467 reviews

Poggio Bicchieri Holiday Farm - Poesia apartment

Overlooking the Val d 'Orcia, our holiday farm consists of 2 apartments each with a kitchen, bedroom, and bathroom. Large equipped garden. Surrounded by silence, close to Pienza, Montalcino, Bagno Vignoni, and the natural thermal baths of Bagno San Filippo. Getting here is very easy; the last km of the road is unpaved but accessible for all.

Top guest favourite
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, 110 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 holiday rentals

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