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Holiday houses in Montepennino

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Top-rated holiday rentals in Montepennino

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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.
Guesthouse in Macciano
4.97 out of 5 average rating, 221 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 favourite
A serene landscape features rolling green hills under a vibrant sunset sky, casting soft colors across the horizon. A stone wall is adorned with lush greenery and flowers, providing a tranquil viewpoint for someone contemplating the picturesque view of the valley and distant hills.
Home in Cetona
4.99 out of 5 average rating, 159 reviews

Casa Dolce Toscana | Panoramic Suite with View

CASA DOLCE TOSCANA 🖼️ Hi! I'm Jolanta 😊 Welcome to our beloved Tuscan accommodation, with panoramic views, nestled in the hills of Tuscany. A perfect oasis of peace for those who want to relax and enjoy an authentic experience. Located a few kilometers from Siena and Florence, our accommodation combines rustic charm with all modern comforts. It is located in the heart of the historic center of the famous village of Cetona, below the castle, overlooking the valley and the scent of Tuscany.

Top Guest favourite
An outdoor spa area is featured beneath a wooden pergola, surrounded by lush greenery. A hot tub sits on a wooden deck, accompanied by two small tables and a lantern. Comfortable lounge chairs can be seen in the background, inviting relaxation.
Villa in Montepulciano
4.92 out of 5 average rating, 302 reviews

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

Top Guest favourite
Aerial view of the villa surrounded by lush vineyards and olive groves. The spacious garden features manicured landscaping and a private pool. The villa, with a terracotta roof and warm exterior, is situated amidst tranquil countryside, offering scenic views of the surrounding hills.
Villa in Bevagna
5 out of 5 average rating, 30 reviews

Escape to Umbria, Mevania Villa

The villa is surrounded by the Sagrantino hills, a few steps from the medieval village of Bevagna, located in the center of Umbria, few miles away to Assisi. The strategic location allows you to easily reach the most enchanting locations such as Perugia, Spoleto, Montefalco, Foligno, Gubbio, Spello, Trevi, Campello Sul Clitunno, Rasiglia, Norcia, Todi, Rome, Florence and many others. You will find yourself in a unique place, immersed in an enchanting paradise of peace and tranquility.

Guest favourite
A stone farmhouse is depicted, surrounded by lush greenery and blooming pink roses in the foreground. The gravel path leads to the entrance, framed by olive trees casting gentle shadows in the sunlight. The tranquil setting showcases the natural beauty of the surroundings.
Villa in Montepennino
4.83 out of 5 average rating, 42 reviews

The "Capanna" among the olive trees, a special vacation

The "Capanna" among the olive trees is an ancient farmhouse restored in 1978 with an airy view of Mount Subasio, Assisi, Spello. You can enjoy the house, large green space and swimming pool in absolute privacy. Inside, thanks to the family furnishings and local handicrafts, you can live in a unique atmosphere, while not having to give up modern comforts. It is convenient to reach the delightful Umbrian towns and villages, but Rome and Florence are also a couple of hours' drive away.

Top Guest favourite
An ancient stone building is showcased, featuring arched doorways and multiple windows. The façade is adorned with climbing greenery, creating a blend of natural and architectural beauty. Cobblestones form the ground, contributing to a rustic and historic ambiance.
Apartment in Civita
4.94 out of 5 average rating, 275 reviews

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.

Guest favourite
An arched window frames a picturesque view of Assisi, featuring the Church of Santa Chiara and surrounding terracotta pots with greenery. Sunlight illuminates the scene, creating a serene atmosphere amidst the historical architecture of the city.
Home in Assisi
4.84 out of 5 average rating, 348 reviews

Casa Spagnoli

Following the recent implementation of the Limited Traffic Zone (ZTL), it is not possible to access our car park during closed hours. Historic residence right in the heart of Assisi's old town, convenient for getting around on foot, with free on-site parking. The house features a spacious dining room overlooking the Basilica of Santa Chiara, a kitchen, and two bedrooms with two en suite bathrooms equipped with a bathtub and shower. Equipped with Wi-Fi, television and heating.

Top Guest favourite
An open kitchen area features a large window that offers a panoramic view of the surrounding landscape. A dining table is set for two, with modern chairs and colorful decor elements. Light reflects off the terracotta floor, highlighting the wooden beams overhead.
Loft in Montepulciano
5 out of 5 average rating, 502 reviews

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.

Top Guest favourite
A spacious terrace is shown with two lounge chairs featuring patterned cushions. A small table and two folding chairs are visible, alongside an open door leading into the apartment. The stone wall texture of the building complements the warm sunset light.
Condo in Spello
4.96 out of 5 average rating, 265 reviews

"Al Belvedere" Charme & View Tourist Lease

In a XII century building, the property, with a suggestive access, is valorized by a large, furnished terrace overlooking the wide valley facing Assisi, Spoleto, Bastia Umbra, Bevagna, Castel Ritaldi , Trevi, Montefalco and Perugia. My accommodation is suitable for couples, nature fans, families (max 2 children) and 'hairy' friends (pets). We are eco-friendly ... At Belvedere Electricity is 100% from renewable sources! :-)

Top Guest favourite
A small stone alcove features a wooden table with a potted flower and two red folding chairs. The background reveals a serene view of lush hills, creating a quiet space for relaxation.
Apartment in Civita
4.98 out of 5 average rating, 490 reviews

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".

Guest favourite
A quaint outdoor terrace is framed by stone walls and lush greenery. A small table and two chairs offer a cozy space to enjoy views of the Umbrian Valley, with trees and rolling hills visible in the distance under a partly cloudy sky.
Apartment in Spello
4.97 out of 5 average rating, 218 reviews

Sognando Spello - a luxury 1 bedroom with views

Originally a farmhouse, this medieval building is located in the quiet upper part of the historical centre of Spello. Our apartment is perfect for couples looking for a romantic base to explore Spello and the delights of Umbria. Also consider our nearby properties (separate entrance) at https://www.airbnb.com/h/amiciefamiglia or https://www.airbnb.com/h/ilmuretto if you need additional rooms for guests.

Top Guest favourite
A charming stone cottage is set within a lush green landscape. The building features a rustic tiled roof and wooden shutters. Surrounding plants include flowering vines and a cactus in the foreground, creating a serene outdoor atmosphere.
Cabin in Massa Martana
4.95 out of 5 average rating, 231 reviews

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...

Popular amenities for Montepennino holiday rentals

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