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Condo holiday rentals in Montalcino

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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, 309 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.

Guest favourite
A serene bedroom features a spacious bed adorned with neatly arranged towels and light bedding. A wooden accent wall complements a stone wall, while natural light floods through a window with light blue shutters. A small desk and decorative plants add a touch of warmth to the room.
Condo in Castelnuovo dell’Abate
4.96 out of 5 average rating, 111 reviews

La Casetta di Nise, Private Spa in the Hamlet

Private apartment in the heart of the medieval village of Castelnuovo dell'Abate, a few kilometers from Montalcino and the Abbey of Sant'Antimo. The apartment is a real gem of the village: kitchen and living room with terrace on the square, the private spa inside the room and the tranquility of the village are the elements that distinguish the accommodation. We are ready to make you enjoy the genuine experience of an Italian village without filters. Air conditioning Free Wifi Sauna and hot tub

Top Guest favourite
Aerial view of a charming countryside villa surrounded by rolling hills and vineyards. Olive trees are visible lining the roads, which lead to the home nestled within a serene natural landscape. The colors and textures reflect the characteristic beauty of the Tuscan countryside.
Condo in Asciano
4.98 out of 5 average rating, 295 reviews

Celeste – The color of the summer sky in Tuscany

The apartment is located on the 2nd floor and consists of 2 bedrooms (possibility of making single or double beds on request), a bathroom, a living room, and a kitchen equipped for cooking. (Washing machine available from 9 a.m. to 8 p.m. in the laundry room) Free parking and wifi. Convenient location for visiting Tuscany's tourist centers. We are in the countryside, in the heart of the Crete Senesi, a car is recommended to be independent and visit the magnificent Tuscan countryside

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, 286 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.

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
4.92 out of 5 average rating, 159 reviews

"Dimora Valinda" Montepulciano Piazza Grande + A/C

Welcome to Montepulciano, a historical gem! Our apartment, located in the heart of the historic center, offers the perfect location to experience the authenticity of this unique place: just a few steps from Piazza Grande, excellent restaurants, shops, and all the main attractions. Whether you come to explore the wineries, for a romantic getaway, or to learn about the history and culture of Montepulciano, here you will find the perfect place for an unforgettable experience.

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, 130 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 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
4.98 out of 5 average rating, 198 reviews

Chicca: Cortona's historic center

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 charming outdoor seating area is set against a backdrop of rolling green hills. Two green metal chairs and a matching table are surrounded by flowering plants, with cypress trees rising in the distance under a partly cloudy sky.
Condo in Pienza
5 out of 5 average rating, 137 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?

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, 113 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
Condo in Monteriggioni
4.86 out of 5 average rating, 140 reviews

Lornano Winery Farm - Villa ''Trebbiano''

4 villas with private garden, private parking, large swimming pool (OPEN FROM 1ST MAY TO 15TH OCTOBER) and park, located within the historic complex of the Fattoria Lornano, immersed in the Chianti hills. Trebbiano is an apartment for two within one of the houses, accessed either from the main piazza or its private garden patio. It is a lovely retreat for a couple wishing to enjoy the wine estate with a touch more privacy.

Top Guest favourite
The bedroom features a wrought iron bed adorned with an orange coverlet. A wooden desk and chair are positioned beside a round mirror, providing a functional space. Natural light filters through the window, while rustic walls and high ceilings enhance the classic charm of the room.
Condo in Castiglione del Lago
4.94 out of 5 average rating, 199 reviews

AURA Garbino apartment in the historic center

-Aura Appartamenti- The Garbino apartment is located along the main street of the historic center of Castiglione del Lago. Furnished in a classic style with high ceilings and exposed beams, it is spacious, quiet and relaxing, an oasis of tranquility during your stay. On the ground floor and managed by us is the Ristorante L'Acquario, a traditional Slow Food and Michelin Bib Gourmand restaurant.

Top Guest favourite
An outdoor terrace features a glass dining table set for four, complemented by green chairs. A bottle of wine and glasses rest on the table, with vibrant red flowers adding a pop of color. A scenic valley view showcases rolling hills and a distant mountain.
Condo in Chiusi
4.95 out of 5 average rating, 154 reviews

La Terrazza su Chiusi - panoramic apartment

Large and spacious apartment in the historic center, comfortable, well finished, comfortable living room and large terrace with barbecue. Equipped with every appliance, well ventilated, perfect for relaxing stays, close and well connected to the best known tourist destinations such as Siena, Rome, Florence, Perugia, Arezzo and others.

Popular amenities for Montalcino condo rentals

When is the best time to visit Montalcino?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$161 NZD$161 NZD$187 NZD$197 NZD$214 NZD$214 NZD$215 NZD$231 NZD$222 NZD$224 NZD$178 NZD$185 NZD
Avg. temp8°C8°C11°C13°C18°C22°C25°C25°C21°C17°C12°C9°C

Quick stats about condo rentals in Montalcino

  • Total holiday rentals

    Explore 60 holiday rentals in Montalcino

  • Nightly prices starting at

    Montalcino holiday rentals start at $85 NZD per night before taxes and fees

  • Verified guest reviews

    Over 3,630 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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