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Holiday houses in Montalcino

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Quick stats about holiday rentals in Montalcino

  • Total holiday rentals

    Explore 120 holiday rentals in Montalcino

  • Nightly prices starting at

    Montalcino holiday rentals start at $103 NZD per night before taxes and fees

  • Verified guest reviews

    Over 3,160 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    120 of Montalcino holiday rentals include Wi-Fi 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!

Top-rated holiday rentals in Montalcino

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Home in Asciano
4.96 out of 5 average rating, 134 reviews

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Top Guest favourite
The exterior of a charming stone villa is surrounded by a lush garden featuring vibrant lavender plants. Stairs lead to a welcoming entrance adorned with potted flowers and a shaded seating area. The rustic façade reflects traditional Tuscan architecture against a clear blue sky.
Villa in Chianciano Terme
4.97 out of 5 average rating, 126 reviews

Charming Tuscan Villa with View forFamily&Friends

Huge and charming top floor apt in Tuscan Villa with breathtaking view! Visit Montepulciano, Pienza, Siena, explore country side, vineyards and hot springs, hiking or e-biking, strolling or driving! Two roomy suites with top quality beds and bathroom ensuite. Windows walled living room, comfy sofas, professional kitchen at your own use. We can set Winery visits & tasting, Cooking classes and private dinners. NEW Hot tub facing green hilltop! ExperienceTuscany as a local, with your local Host!

Top Guest favourite
An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.
Cottage in Geggiano
4.99 out of 5 average rating, 153 reviews

Villa di Geggiano – Guesthouse

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

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
5.0 out of 5 average rating, 127 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

Top Guest favourite
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 in Montepulciano
4.93 out of 5 average rating, 318 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
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
5.0 out of 5 average rating, 508 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.

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
4.97 out of 5 average rating, 140 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 rustic stone farmhouse is embraced by mature olive trees and lush greenery. The building features traditional window shutters and is set against a clear blue sky, with a gravel pathway leading up to the entrance, enhancing the tranquil countryside ambiance.
Farm stay in San Quirico d'Orcia
4.98 out of 5 average rating, 115 reviews

Podere Pereti Nuovi – Modern Tuscan Villa

Podere I Pereti was entirely build by our grandfather Remo in the 1970's. My siblings and I spent most of our summers on the porch with our grandparents watching sunsets and admiring the view of the Val d'Orcia. Entirely surrounded by vineyards and olive groves. Nonno Remo, besides having a building company, proudly produced Orcia red wine that was consumed by the family. From the 150 olive trees, every November we filled our tanks with green gold olive oil.

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
5.0 out of 5 average rating, 155 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 spacious bedroom features a double bed dressed in white linens, with a cozy armchair in the corner. Natural light enters through a window, illuminating the stone wall beside wooden beams above. A wooden table displays snacks and additional seating is available.
Condo in Castelnuovo dell'Abate
4.9 out of 5 average rating, 322 reviews

La Casetta di Brunello, very panoramic with terrace

STIAMO LAVORANDO PER VOI! ... WE ARE WORKING FOR YOU! The house is completely renovated and furnished in 2018 with classic-Tuscan style furniture. The colors are warm and enveloping to better rest during your holiday of peace and relaxation. In addition to the two double bedrooms, you have a kitchen with an equipped kitchenette, fridge, induction cooker and a furnished terrace with a beautiful view of the surrounding countryside.

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.
Apartment in Montalcino
4.99 out of 5 average rating, 117 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
Farm stay in Campiglia D'orcia
4.94 out of 5 average rating, 557 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 Montalcino holiday rentals

Frequently Asked Questions

  • What are the best places to stay in Montalcino?

    Stays near the medieval town center are frequently chosen for walkable access to shops, cafes, and historic sites. For a quieter escape, countryside villas and rural estates around Montalcino immerse guests in scenic vineyards and olive groves.

  • What are the best things to do in Montalcino with kids?

    Families often explore the medieval Fortress of Montalcino, wander local markets, and visit interactive museums around town. Outdoor picnics and guided nature walks in the Tuscan countryside are frequently suggested activities.

  • What are some of the best things to do in Montalcino?

    Explore the Fortress of Montalcino, sample Brunello wine, and discover the town's artisan shops and historic churches. Walking through local markets and scenic countryside paths is frequently suggested for visitors.

  • How is the weather in Montalcino?

    Montalcino has a temperate climate with warm summers and cooler winters, typical of inland Tuscany. It is helpful to pack layers, as evening breezes can feel cooler even in warmer months.

  • When is the best time to visit Montalcino?

    Late spring and early fall are often recommended for comfortable temperatures and vibrant landscapes. Harvest season draws visitors for wine-related activities, while summer highlights outdoor events and festivities.

  • What are the best places to visit in Montalcino?

    Many visitors explore the Fortress of Montalcino, stroll through the old town, and take in the views from Piazza del Popolo. The Museo Civico and nearby historic churches are frequently suggested spots.

  • What are some hiking trails in Montalcino?

    Montalcino has gentle countryside paths winding through vineyards, oak groves, and rolling hills. Many guests enjoy walking trails that start near the town center and offer panoramic views of the Tuscan landscape.

  • What are some family activities we can do in Montalcino?

    Montalcino has relaxed piazzas, scenic fortress walks, and local museums that often welcome families. Exploring nearby farms, sampling gelato in the historic center, or joining a gentle countryside tour can be enjoyable for all ages.

  • What are some of the best day trip ideas from Montalcino?

    Many guests explore nearby villages known for historic architecture, visit regional thermal baths, or tour scenic vineyards in the Tuscan countryside. Montepulciano and Pienza are often recommended for cultural and culinary discoveries.

  • Are there any pet friendly accommodations available in Montalcino?

    Pet-friendly rentals can be found in and around Montalcino, from townhouses to country villas. Many hosts welcome travelers with pets; always confirm amenities in advance.

  • What are some local tips for visiting Montalcino?

    Wear comfortable shoes for strolling hilly streets, and plan visits to both the town center and surrounding countryside for a fuller experience. Join a regional wine tasting and inquire about seasonal festivals for unique local activities.

  • What is Montalcino known for?

    Montalcino is known for its locally crafted Brunello wine, medieval architecture, and hilltop views of Tuscany. The historic village draws visitors with its culinary traditions and scenic landscapes.

  • What are the best hidden gems to explore in Montalcino?

    Montalcino has small artisan shops, lesser-known vineyards, and quiet hillside chapels that invite discovery. Wandering cobbled side streets or visiting local olive oil producers provides a deeper look into community traditions.

  • What are the best foods to try in Montalcino?

    Try locally made pecorino cheese, hearty Tuscan soups, and handmade pasta such as pici. Brunello di Montalcino wine pairs well with traditional stews, wild boar dishes, and seasonal produce.

  • What should I bring for a trip to Montalcino?

    Pack layered clothing for changeable weather, comfortable walking shoes for cobbled streets, and a light jacket for cool evenings. Bringing a reusable water bottle and a small daypack helps with town explorations and countryside excursions.

  • What is the nightlife in Montalcino like?

    Nightlife in Montalcino centers on cozy wine bars, relaxed cafés, and occasional live music venues around the town center. Evening gatherings often celebrate local wines and regional fare in a casual, welcoming atmosphere.

  • What are the most popular events or festivals in Montalcino?

    The Sagra del Tordo archery festival and seasonal wine celebrations like Benvenuto Brunello are often highlighted by locals. Summer music concerts and regional harvest events around Tuscany are also frequently suggested.

  • Are there family friendly vacation rentals in Montalcino?

    Montalcino has family-friendly stays, including country homes and apartments near the town center. Many accommodations provide space for groups and amenities suited to travelers with children.

Destinations to explore