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Vacation rentals in Monticchiello

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Top-rated vacation rentals in Monticchiello

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Top guest favorite
The bedroom features a spacious bed adorned with floral bedding. Exposed wooden beams highlight the ceiling, while a decorative bicycle hangs on the wall. A contemporary fireplace adds to the room's character. Natural light filters through the open doorway, enhancing the inviting ambiance.
Home
4.97 out of 5 average rating, 218 reviews

Il Focolare - Superior Tuscany Apartment

The "Il Focolare" apartment is located in the small medieval village of Monticchiello, inside the historic center, between the ancient walls. Immersed in the classic and enchanting landscapes of Tuscany with cypresses, rolling hills as far as the eye can see and winding white roads. Newly renovated (2019), it perfectly blends its historical soul with modern furnishings, giving the environment personality and charm, while the fireplace in the bedroom adds that extra touch of romance. Total 52 sqm

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
4.97 out of 5 average rating, 124 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
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.

Superhost
The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.
Villa
4.92 out of 5 average rating, 262 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 favorite
A spacious bedroom features a double bed adorned with a yellow bedspread. Natural light floods in from wide glass doors leading to a balcony with views of the valley. A cozy seating area includes two armchairs and a small table, complemented by decorative curtains.
Apartment
4.98 out of 5 average rating, 134 reviews

Stuart White Tea Central Panoramic & Garden

Offering ample space, the apartment features two double bedrooms, two full bathrooms, and a living room with a kitchen. The bedroom balconies offer stunning views of the valley and natural light. Its proximity to all town amenities ensures convenience, while a delightful café downstairs provides a delectable gourmet breakfast. It has also access to a secluded, terraced backyard garden. It provides a comfortable retreat perfect for long term stays. A public parking is available nearby.

Top guest favorite
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
5 out of 5 average rating, 483 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 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
5 out of 5 average rating, 102 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
Two comfortable chairs are positioned on a lush green lawn, complemented by a small wooden table. A basket of vibrant yellow flowers is nearby, set against a backdrop of rolling hills and cypress trees under a clear blue sky.
Apartment
4.97 out of 5 average rating, 171 reviews

Casa Bonari - a paradise for the eyes

Casa Bonari is a single-level independent apartment inside a villa at the foot of Monticchiello. It consists of 3 bedrooms, 2 bathrooms, an equipped kitchen and a living room. The rooms are bright and furnished in Tuscan style, with old restored family furniture combined with contemporary elements. The kitchen is fully equipped and the apartment is surrounded on all sides by a large garden, so that all rooms boast a beautiful view of the countryside.

Guest favorite
A small wooden table set for two is adorned with fine china cups and a delicate flower vase. The balcony offers a panoramic view of the rolling hills, as the sun sets, casting warm hues over the landscape.
Apartment
4.93 out of 5 average rating, 245 reviews

I Tramonti di Eramo, Montepulciano city center.

Welcome to Montepulciano, the jewel of the Tuscan hills! Our apartment in the heart of the historic center offers breathtaking views of the surrounding countryside, providing an authentic and unforgettable experience. Step outside and savor the historic atmosphere of Montepulciano. Just a few steps away, you will find the extraordinary Piazza Grande, excellent restaurants, and all kinds of services. Tuscany awaits you for a unique experience.

Top guest favorite
An outdoor seating area features a small table surrounded by two chairs, adorned with a light breakfast setup. The stone facade of the house is complemented by climbing vines and a bright flower arrangement, inviting guests to enjoy the fresh air.
Vacation home
4.97 out of 5 average rating, 119 reviews

In Tuscany Rooms

**Your Dream Retreat in the Heart of Val d'Orcia** Welcome to In Toscana Camere, a charming holiday home located in the historic center of Monticchiello, a Tuscan village full of charm and authenticity. Surrounded by stone walls and enhanced by modern, comfortable interiors, this home offers the perfect balance between tradition and contemporary style. Wake up every morning to a breathtaking view of the stunning Val d'Orcia.

Guest favorite
A dining area features a round wooden table surrounded by four green chairs. A modern kitchen is visible in the background, equipped with light cabinetry and appliances. The room showcases an elegant wall fresco, adding historical character to the space.
Apartment
4.87 out of 5 average rating, 165 reviews

Panoramic Apaertment Val d'Orcia

Nel centro storico. In prestigioso palazzo del ‘700, appartamento restaurato in ogni sua componente, nel massimo rispetto delle caratteristiche originarie con pavimenti in parquet. Gode di un'ottima vista sulla campagna fra Radicofani e Pienza. Sulla parete a nord del soggiorno ampio affresco detto “del fagiano” con tempio ed altri motivi architettonici.

Top guest favorite
Farm stay
4.95 out of 5 average rating, 473 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.

Popular amenities for Monticchiello vacation rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Siena
  5. Monticchiello