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Apartment holiday rentals in Montalcino

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Top-rated apartment rentals in Montalcino

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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, 140 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 or barbecue for all the guests of our 4 apartments, after 7pm if booked large in advance Large free parking area 100 mt away

Top guest favourite
A spacious bedroom features a large, inviting bed adorned with a light blanket. Natural light floods through sheer curtains draped over a large window, revealing views of the lush valley outside. The rustic walls, made of tufo, add a unique character to the room.
Flat in Civita di Bagnoregio
4.94 out of 5 average rating, 257 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
A spacious open-plan living area is displayed, featuring a modern kitchen with sleek cabinetry and an island. The dining table is set for meals, and a comfortable sofa is positioned in the background. Natural light fills the room, highlighting the wooden beams overhead.
Flat in Montalcino
4.91 out of 5 average rating, 106 reviews

Bruna's House

LA CASA DI BRUNA A finely renovated apartment, furnished with love and attention to detail, is located inside a historic building The entrance opens onto a living room with a very comfortable sofa connected to a large and comfortable kitchen From the living room, we access the terrace overlooking the fortress where you can enjoy wonderful sunsets On the same floor, there is a bathroom and a bright double bedroom Upstairs is the second bathroom and another comfortable bedroom

Top guest favourite
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.
Flat in Monticchiello
4.97 out of 5 average rating, 173 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.

Top guest favourite
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.
Flat in Montepulciano
4.93 out of 5 average rating, 263 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.

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.
Flat in Bagnoregio
4.98 out of 5 average rating, 480 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".

Top guest favourite
A panoramic view of San Quirico d'Orcia showcases the picturesque village rooftops with their warm, terracotta tiles. In the background, rolling hills extend towards the horizon, framed by a clear blue sky. Stone buildings reflect the region's architectural charm.
Flat in San Quirico d'Orcia
4.96 out of 5 average rating, 105 reviews

La Violetta di San Quirico, Historic Center.

Welcome to the heart of Tuscany, in San Quirico d'Orcia, where your stay will be an unforgettable experience in our apartment, offering the perfect combination of comfort and authentic Tuscan beauty. You'll enjoy the apartment's true magic as you look out the windows and be captivated by the 360-degree views of the majestic Val d'Orcia, its hills, vineyards, olive groves, and rooftops.

Top guest favourite
The outdoor pool area features a light blue water surface complemented by three tiered fountains. A small white table with a glass is placed on the wooden deck, surrounded by two white chairs. The rustic stone buildings create a charming backdrop, adorned with greenery.
Flat in Montalcino
4.99 out of 5 average rating, 114 reviews

Castel Brunello - 2 doublebed rooms + terrace

Located in amidst the Tuscan countryside, Castel Brunello is offers an outdoor swimming pool and a garden. This self-catering accommodation features rustic-style furnishings, air condioning and free Wi-Fi. They also offer a satellite TV, and a fully equipped kitchenette with a refrigerator and a dining table. Each apartment has a terrace with an outdoor seating area.

Top guest favourite
The image showcases a sprawling rural landscape viewed from above, featuring a rustic stone building with a terracotta roof. Surrounding areas include lush green fields, trees, and hills in the distance, under a bright blue sky accented by soft, fluffy clouds.
Flat in Castiglione d'Orcia
4.9 out of 5 average rating, 120 reviews

agriturismo il poderuccio "sweet apartment"

The IL PODERUCCIO farmhouse has several apartments, including: -A romantic apartment inaugurated in 2019 consisting of a private bathroom and a single room with a double bed, single sofa bed and equipped kitchen. Independent entrance, private loggia equipped for outdoor dining and a magical window overlooking a breathtaking view.

Guest favourite
Aerial view of a countryside villa surrounded by lush green hills and vineyards. The outdoor swimming pool is visible alongside a well-kept garden. Olive trees and various plants create a natural landscape, reflecting the serene environment of the property.
Flat in Greve in Chianti
4.83 out of 5 average rating, 115 reviews

Beautiful medieval tower in Chianti

This is a lovely flat in an ancient farm, restored, in the heart of Chianti Classico , with an amazing panoramic view on the hills, surrounded by our vineyards as well as olive trees, where you will have an unforgettable holiday discovering Tuscany. CINIT048021B5LTBDVFE3

Guest favourite
A scenic view of the Tuscan hills is framed by clusters of pink roses in the foreground. The rolling landscape features layers of green and gold fields, softly fading into the horizon under a clear sky.
Flat in Montalcino
4.89 out of 5 average rating, 381 reviews

Panoramic Country Suite Montalcino

Fonte Aulente is a Tuscan farmhouse from the 12th century recently restored surrounded by beautiful garden-park, 2 km from Montalcino with amazing views on Tuscan hills. We offer a beautifully furnished apartment with independent entrance and all facilities.

Top guest favourite
A scenic rural landscape captures rolling hills and expansive fields bathed in warm sunset hues. The silhouette of a rustic villa, surrounded by trees and olive groves, is positioned in the foreground, while distant mountain outlines are visible on the horizon.
Flat in Pienza
4.99 out of 5 average rating, 101 reviews

Unplug at a 17th-Century Farmhouse Enveloped by Olive Groves

Pick figs and rosemary in secluded, extensive gardens and soak up the peace and quiet of this beautiful rural setting with spectacular panoramic views. Whitewashed walls, terracotta-tiled floors, and ceiling beams reflect the space's rich history.

Popular amenities for Montalcino apartment rentals

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Avg. price$147 SGD$160 SGD$167 SGD$181 SGD$187 SGD$191 SGD$194 SGD$194 SGD$185 SGD$178 SGD$187 SGD$180 SGD
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Quick stats about flat rentals in Montalcino

  • Total holiday rentals

    Explore 370 holiday rentals in Montalcino

  • Nightly prices starting at

    Montalcino holiday rentals start at $77 SGD per night before taxes and fees

  • Verified guest reviews

    Over 10,300 verified reviews to help you choose

  • Family-friendly holiday rentals

    190 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 200 rentals that welcome pets

  • Holiday rentals with a pool

    140 properties feature pools

  • Rentals with dedicated workspaces

    120 properties have a dedicated workspace

  • Wifi availability

    340 of Montalcino holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Montalcino rentals

  • 4.8 Average rating

    Montalcino stays are highly rated by guests – averaging 4.8 out of 5!

Destinations to explore

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  2. Italy
  3. Tuscany
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  5. Montalcino
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