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Condo holiday rentals in Montalcino

Find and book unique condos on Airbnb

Top-rated condo rentals in Montalcino

Guests agree: These condos are highly rated for location, cleanliness and more.

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Top Guest favourite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Condo in Noce
5 out of 5 average rating, 321 reviews

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

Top Guest favourite
A charming terrace features a small round table and two white chairs, offering expansive views of the surrounding hills and distant landscape. A walnut tree stands nearby, enhancing the tranquil outdoor space bathed in natural light from the setting sun.
Condo in Montepulciano
5 out of 5 average rating, 103 reviews

The walnut tree view, Montepulciano

The walnut tree view ( castoldi apartments site) is our new apartment in the most peaceful part of Montepulciano. The house with Ac is 250 metres from the piazza and the main street, and has 1 double rooms (king ) 1 bathroom with large shower and a large kitchen-living room with a nice terrace overlooking the hills. From summer 26 a wine tasting will be available in the new garden for all the guests from 7 pm Old private wine cellar available Guests will park close the apartment

Guest favourite
A private terrace is visible, adorned with vibrant flowers and a small table set for two. A bottle of wine and two glasses are elegantly placed, inviting relaxation with a view of the terracotta rooftops and the distant landscape under a pastel sky.
Condo in Montepulciano
4.93 out of 5 average rating, 166 reviews

Amazing Apartment near Piazza Grande w/ Terrace

Benvenuti nel cuore di Montepulciano, uno dei borghi più iconici, affascinanti e storici della Toscana, celebre per i suoi palazzi rinascimentali, le antiche cantine e l’atmosfera senza tempo che conquista ogni viaggiatore. Il nostro appartamento si trova in una posizione incredible nel pieno centro storico, a pochi passi da Piazza Grande, ottimi ristoranti, botteghe locali e dalle meraviglie più autentiche del paese. Che siate qui per degustare vini straordinari, vivere una fuga romantica.

Top Guest favourite
An aerial view captures the property nestled in a scenic landscape, surrounded by rolling hills and cultivated fields. Olive groves line the winding road, with cypress trees dotting the surroundings, showcasing the natural beauty of the Tuscan countryside.
Condo in Asciano
4.96 out of 5 average rating, 338 reviews

Green – The meadows in Tuscany

Apartment consisting of 1 double bedroom, fully equipped kitchen, large living room, and bathroom. TV, BBQ, (we provide the washing machine from 9 a.m. to 8 p.m. which is in our laundry room to those who request it). We recommend a car as we live in the countryside, both to be independent and to visit the magnificent Tuscany. You will like the outdoor environment because it is magical by day and at night Free parking and WiFi Convenient location to visit both Tuscany and Umbria.

Guest favourite
A spacious bedroom features warm brick walls and a wooden beamed ceiling. A large bed with a striped blanket is positioned next to a cozy seating area. A desk and chair setup is visible, along with a Smart TV mounted above, completing the functional space.
Condo in Torrenieri
4.97 out of 5 average rating, 295 reviews

[9 minutes from Montalcino] Elegant House Mafalda

Comfortable apartment located in the heart of Orcia valley (val d’Orcia); strategic location for visiting the sought-after medieval villages of Montalcino, Castiglione d’Orcia, Pienza, Montepulciano and San Quirico d’Orcia. In addition, Torrenieri (Montalcino) has always been considered an excellent starting point for various trekking itineraries. The balcony in one of the suites overlooks the splendid surrounding Sienese hills!! Finally, there is free parking near the house.

Top Guest favourite
A spacious terrace is showcased with two comfortable armchairs positioned around a glass table. Potted red flowers adorn the railing, overlooking a panoramic view of the rolling hills of the Tuscan countryside under a partly cloudy sky.
Condo in Montalcino
4.98 out of 5 average rating, 131 reviews

"Landscape Notes" Suite

The 80 sqm Suite "Note di paesaggio" is located on the second floor of a historic building where it meets the landscape of the Val d'Orcia. It is divided into several rooms including a furnished double bedroom with air conditioning overlooking the terrace, a living room with a panoramic view, a study with a desk, a marble bathroom with shower, and another double bedroom without air conditioning . You can enjoy a 30sqm terrace and its suggestive view of the countryside.

Top Guest favourite
A spacious living area is adorned with a vintage-style sofa and a decorative wooden armchair. Natural light floods the space through large windows covered with light curtains. A brick fireplace adds warmth, and a patterned rug enhances the room's character.
Condo in Tuoro sul Trasimeno
4.97 out of 5 average rating, 110 reviews

Foscolo's Apartment

The apartment is on the second floor of a two-story single-family home, surrounded by land, children's playground and lots of greenery, It is very comfortable, quiet and the rooster of the house wakes you up. Apartment near many strategic points, two km from the Siena-Perugia junction, 30 km from Perugia and 40 km from Siena, 20 from nearby Cortona and also very convenient to reach islands and beautiful Assisi. Relax with the whole family in this quiet accommodation.

Top Guest favourite
A light-filled living space features a comfortable sofa and a dining table set for four. A large TV is mounted on a white cabinet, while a door leads to the bedroom area, which appears partially visible in the background. Wooden beams enhance the ceiling's charm.
Condo in Cortona
4.99 out of 5 average rating, 202 reviews

Chicca: Cortona's historic centre

Bright, delightful and welcoming apartment located right in the heart of the historic center of Cortona with an unforgettable view: the town hall on one side and Lake Trasimeno and the Valdichiana on the other. The apartment has been recently renovated and consists of a living room with sofa bed, a small kitchen, a double bedroom and two bathrooms. The apartment has WiFi, heating and air conditioning, a washing machine, oven, microwave, hairdryer and flat iron.

Top Guest favourite
A spacious outdoor area features lounge chairs arranged on a concrete patio. Lush green hills stretch into the distance, bordered by tall, slender cypress trees. The sky is filled with dramatic clouds, enhancing the serene landscape.
Condo in Pienza
5 out of 5 average rating, 139 reviews

Mascagni Farmhouse in Val d'Orcia, Pienza

Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 16th-century barn nestled among olive trees and wheat fields. Relax with a cup of tea, pick rosemary and lavender in the garden with breathtaking views of the Val d'Orcia. Rediscover your true nature among the pristine fields and olive trees: here, walks and bike rides have no limits! Ready to create memories that will last a lifetime?

Superhost
A welcoming living area showcases wooden beams across the ceiling and a charming fireplace, adding warmth to the space. A television is mounted on the wall, while a stylish white cabinet and comfortable armchairs are arranged around the central hearth, inviting relaxation.
Condo in Castelnuovo dell’Abate
4.9 out of 5 average rating, 315 reviews

Il Borghetto: Alice's House, charm and relaxation

Alice's House is located in the central area for the visit of Valdorcia and Montalcino with its Brunello wineries. All renovated and very bright, it can sleep 2 to 4 people. Entirely covered by Wifi, it has two double bedrooms, each with a private bathroom, a kitchen equipped with a relaxing living room with LED TV, armchairs, wood-burning fireplace for the cold evenings in winter. Heated with clean energy and restored with eco-friendly materials.

Guest favourite
A cozy bedroom features a spacious bed with neutral-toned linens and decorative pillows. The warm yellow walls are adorned with framed photographs, while shelves hold books and small decorative items. Soft lighting enhances the inviting atmosphere, creating a comfortable space for relaxation.
Condo in Pienza
4.92 out of 5 average rating, 118 reviews

Casa Gioia

My place is located in the historic center of Pienza, on the second floor without an elevator. It overlooks the main street of Pienza. The nearest paid parking lots are 150m away, the free ones 300m, loading/unloading area 50m. You'll love my place because of the comfort of the bed, the intimacy, the wooden-beam ceilings, and the typical terracotta floor. My place is good for couples, business travelers, and families (with kids)

Guest favourite
The spacious kitchen and living area features a central island counter with a wine bottle and glasses. Natural light floods the space through multiple windows, illuminating the dining table and a cozy seating area with a sofa. A rustic ceiling enhances the homey ambiance.
Condo in Pienza
4.91 out of 5 average rating, 113 reviews

Amazing view of Val d'Orcia Pienza

Beautiful 75-square-meter apartment located on the ground floor of the “Podere Colombaio,” a historic farmhouse named after its 15th-century tower. The property features a lovely pergola and a garden overlooking the Val d’Orcia Park, just a 10-minute walk from Pienza.

Popular amenities for Montalcino condo rentals

When is the best time to visit Montalcino?

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Avg. price$133 AUD$133 AUD$154 AUD$163 AUD$177 AUD$177 AUD$178 AUD$191 AUD$184 AUD$185 AUD$147 AUD$153 AUD
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Quick stats about condo rentals in Montalcino

  • Total holiday rentals

    Explore 70 holiday rentals in Montalcino

  • Nightly prices starting at

    Montalcino holiday rentals start at $70 AUD per night before taxes and fees

  • Verified guest reviews

    Over 3,690 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Montalcino holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Montalcino rentals

  • 4.9 Average rating

    Montalcino stays are highly rated by guests—averaging 4.9 out of 5!

Destinations to explore

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