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Holiday houses in Montalcino

Find and book unique accommodation on Airbnb

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 $84 AUD 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, Wi-Fi 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

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.

LocationValueOutdoor spaces

4.96 out of 5 average rating, 142 reviews
Top Guest favourite
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 in Macciano

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.

FamilyValueIndoor spaces

4.97 out of 5 average rating, 251 reviews
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.
Apartment in Montepulciano

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

LocationFamilyWalkability

4.98 out of 5 average rating, 165 reviews
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

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

ValueFamilyNearby

4.93 out of 5 average rating, 335 reviews
Top Guest favourite
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 in Osteria delle Noci

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.

ValueLocationParking

5.0 out of 5 average rating, 116 reviews
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

"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.

LocationValueHeating

4.95 out of 5 average rating, 144 reviews
Top Guest favourite
A view from the window reveals a serene landscape of rolling hills and valleys bathed in soft morning light. The garden below is adorned with colorful flowers and greenery, enhancing the tranquil atmosphere of the Tuscan countryside.
Home in San Quirico d'Orcia

Alma Vignoni - Vignoni Val d 'Orcia - Bagno Vignoni

Alma Vignoni is an elegant and exclusive holiday house in Vignoni Alto that recalls Tuscan style and is enriched by unusual and personal details. The house consists of an open-space with fireplace in the center. On the one hand the room with stunning views over the surrounding hills (Pienza, Monticchiello and Montepulciano) on the other the kitchen area. Two cozy rooms overlook the ancient Via Francigena and the Orcia river valley. The bathroom has a large shower.

FamilyValueNearby

4.99 out of 5 average rating, 232 reviews
Top Guest favourite
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.
Holiday home in Monticchiello

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.

ValueLocationQuiet

4.96 out of 5 average rating, 137 reviews
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

La Casetta di Brunello, very panoramic with terrace

WE'RE WORKING FOR YOU. ... 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.

FamilyValueHiking

4.9 out of 5 average rating, 324 reviews
Top Guest favourite
An outdoor terrace features a glass dining table surrounded by four metal chairs, shaded by a large umbrella. Lush greenery and colorful flowers enhance the view, while decorative planters filled with plants add vibrancy to the space.
Home in Montalcino

Panoramic nest in Montalcino

A completely independent accommodation recently refurbished - from the design to the furnishings - directly by the host. It is composed of a living room with a fully equipped kitchen and a bedroom with bathroom. The peculiarity of the property is the extremely favorable location in the historic center, with a splendid terrace with panoramic garden on the Val d'Orcia, with barbecue, hammock, sink and outdoor shower.

ValueLocationDecor

4.98 out of 5 average rating, 163 reviews
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

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.

ValueLocationBreakfast

4.99 out of 5 average rating, 118 reviews
Top Guest favourite
Farm stay in Campiglia D'orcia

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.

FamilyLocationAccuracy

4.95 out of 5 average rating, 579 reviews

Popular amenities for Montalcino holiday rentals

When is the best time to visit Montalcino?

MonthJune
Avg. price$254 AUD
Avg. temp22°C

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