Montalcino holiday lettings

We found 1,895 holiday rentals — enter your dates for availability

Discover a selection of 28 homes, 49 apartments and other holiday rentals in Montalcino that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll find the amenities that you need and want, which might include parking and a pool. Whatever you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Montalcino

  • Rich Historical Culture: Discover Montalcino's charming piazzas, historic monasteries, and beautiful churches, showcasing the region's vibrant heritage.
  • Scenic Landscapes: Enjoy breathtaking views of the Tuscan hills and vineyards, perfect for outdoor enthusiasts and photographers alike.
  • Local Cuisine and Wine: Savour delectable Tuscan dishes and the famous Brunello di Montalcino wine in delightful local eateries.
  • Romantic Atmosphere: Experience the enchanting ambiance, ideal for couples seeking a romantic escape.
  • Diverse Accommodation: Choose from a variety of charming villas and holiday rentals that offer comfort and local charm.

Popular types of accommodation in Montalcino

You've chosen Montalcino for your next getaway, and now it's time to find the perfect place to stay. Explore a range of holiday rentals, from charming villas and houses to comfortable apartments. With a variety of options available, you're sure to discover the ideal villa rental or house rental that offers both relaxation and local charm. Start your adventure in this stunning Tuscan town today!

  • Villas: The top choice for visitors to Montalcino, offering luxurious stays with stunning views and ample space for relaxation.
  • Houses: A popular option for families or groups, these homes provide a homely atmosphere with all the amenities you need.
  • Apartments: Ideal for couples or solo travellers, apartments offer a convenient and comfortable base for exploring the area.
  • Cottages: Quaint and cosy, cottages provide a charming retreat in the heart of the Tuscan countryside.
  • Caravan Parks: A unique and budget-friendly option, perfect for those who enjoy a more adventurous stay in nature.**

Top attractions in and around Montalcino

Montalcino, nestled in the heart of Tuscany, is an idyllic destination for romantic and outdoor getaways. Explore charming piazzas, historic monasteries, and beautiful churches that reflect the region's rich culture. Whether you're seeking a romantic escape or cultural experiences, Montalcino offers a delightful array of attractions. Don't miss the opportunity for sightseeing in both Italy and Tuscany, ensuring a memorable holiday in this enchanting locale.

  • Fortress of Montalcino: This historic fort offers a glimpse into the past with its impressive stone walls and panoramic views of the surrounding vineyards. The fortress is a perfect spot for those interested in culture and history, providing a serene atmosphere to explore.
  • Pienza Cathedral: Located 6.2km from Montalcino, this stunning cathedral is a masterpiece of Renaissance architecture. Its intricate details and tranquil ambiance make it a must-visit for culture enthusiasts and admirers of art.
  • Abbazia di Sant'Antimo: Nestled within Montalcino, this enchanting monastery boasts beautiful Romanesque architecture. Visitors can experience a peaceful atmosphere and the chance to attend Gregorian chant services, immersing themselves in its rich cultural heritage.

Things to do recommended for couples

For a romantic getaway in Montalcino, visit Castello Banfi for a delightful wine experience. Explore the luxurious Chapel of our Lady of Vitaleta, only 4.3km away, and unwind at the serene Terme di Chianciano spa, located 14.3km from Montalcino, perfect for relaxation and wellness.

Things to do recommended for families

Families will love the Parco Piscine Capenti Outdoor Pool, an aquatic centre 8.1km from Montalcino, perfect for splashing about together. For a dash of adventure, the Siena Circuit karting experience, located 11.2km away, promises thrills for all ages, making it a memorable day out.

Things to do recommended for groups

Groups visiting Montalcino can enjoy a unique shopping experience at RI Crea RE, indulge in retail therapy at Valdichiana Outlet Village, and embark on an exhilarating adventure at Saltalbero Adventure Park, which offers thrilling zipline courses amidst the beautiful Tuscan landscape.

What do I need to keep in mind when booking a vacation in 'Montalcino

When travelling with a group, family, pets, or seeking longer stays, it's essential to apply the right filters according to your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Montalcino with a group: Think about how many bedrooms you require, along with features like a fully-equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all of these options and much more on Vrbo.
  • Traveling to Montalcino with young kids: Travelling with young children can be quite demanding. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that are suitable for families.
  • Taking your pets with you to Montalcino: For many, a family holiday isn't truly fulfilling without their furry companion by their side. If this resonates with you, take a look at Vrbo accommodations that welcome pets. Most pet-friendly properties offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Montalcino: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay near Montalcino

Montalcino, nestled in the breathtaking hills of Tuscany, offers a delightful blend of romance and adventure for every traveller. Explore its charming streets, revel in the rich historical culture, and enjoy the serene atmosphere of nearby secluded villages. Whether you're seeking a relaxing family holiday or an entertaining escape, Montalcino is the perfect base to discover the enchanting landscapes and vineyards of this idyllic region.

  • Montepulciano: Situated 9.3km from Montalcino, Montepulciano is a charming hilltop town celebrated for its rich culture and stunning views of the surrounding countryside. This city offers visitors a romantic atmosphere, perfect for leisurely strolls through its historic streets. Attractions include historic monuments and a serene lake, ideal for a picturesque day out. Montepulciano is also renowned for its spa and body treatment venues, alongside a vibrant shopping area, making it a delightful destination for relaxation and indulgence.
  • Pienza: Located 6.2km from Montalcino, Pienza is a UNESCO World Heritage Site known for its Renaissance architecture and breathtaking landscapes. This small city draws visitors with its outdoor experiences and cultural charm, offering a wonderful backdrop for romantic getaways. Highlights include historic places and places of worship, as well as rejuvenating hot springs. The local shopping scene and spa offerings ensure that you can unwind while exploring the beauty of the region.
  • San Quirico d'Orcia: Just 3.7km from Montalcino, San Quirico d'Orcia is a quaint town that captures the essence of Tuscany's rustic charm. Visitors are lured by its outdoor experiences and romantic vibe, complemented by entertaining attractions. Enjoy the soothing hot springs, historical sites, and tranquil lakes that surround the town. With a focus on relaxation, the area boasts spa and body treatment facilities, as well as a country private club, making it an ideal spot for a leisurely escape.

Best time to go to Montalcino

If you're planning a trip to Montalcino, it's a good idea to check both the weather and property rates. The warmest months are July and August. Peak season runs in March to April and September, while off-peak times, like November to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January39.4°F (4.1°C)Light RainMostly SunnyAverageSlightly Low
February40.6°F (4.8°C)Light RainMostly SunnyAverageSlightly Low
March45.0°F (7.2°C)Light RainMostly SunnyModerately HighSlightly Low
April50.9°F (10.5°C)Light RainMostly SunnyModerately HighAverage
May57.4°F (14.1°C)Light RainMostly SunnyAverageAverage
June66.7°F (19.3°C)Light RainSunnyAverageSlightly High
July73.0°F (22.8°C)No Rain (Dry)SunnyAverageSlightly High
August73.0°F (22.8°C)No Rain (Dry)SunnyAverageSlightly High
September64.8°F (18.2°C)Light RainMostly SunnyModerately HighAverage
October56.7°F (13.7°C)Light RainMostly SunnyAverageAverage
November48.6°F (9.2°C)Light RainMostly SunnyModerately LowAverage
December42.1°F (5.6°C)Light RainMostly SunnyModerately LowAverage

Booking with Vrbo is simple

Are you hoping to cut costs on your upcoming journey? It may be beneficial to remain adaptable with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo accommodation that fits your budget, utilise our filters to organise by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform to plan new journeys, continue from where you last stopped, or review and arrange your travel itineraries. You can easily access your saved or booked properties, which are sorted into categories: Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Explore the picturesque setting in Montalcino

Come and experience Montalcino and its wineries, history and monuments. This city is well-known for its spas and local tours. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in Montalcino

Are you hoping to discover things to do while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Montalcino a one-of-a-kind holiday spot. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Tenuta Greppo Franco Biondi Santi (1 mi / 1.6 km)
  • Torrenieri Montalcino Station (3.9 mi / 6.2 km)
  • Castiglion del Bosco Winery (4.1 mi / 6.5 km)
  • Castello Banfi (6.9 mi / 11.1 km)
  • Terme Petriolo (9.8 mi / 15.7 km)
  • Baths of San Filippo (13.8 mi / 22.2 km)

Exploring the natural features in Montalcino

Whether you're an active traveller or just want to spend some time taking in the scenery, Montalcino is a great place to get out in nature. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Horti Leonini (5.8 mi / 9.4 km)
  • Historic Centre of Pienza (9.7 mi / 15.6 km)
  • Mount Amiata Fauna Park (12.9 mi / 20.7 km)
  • Monte Amiata (13.4 mi / 21.6 km)
  • Val di Merse (15.7 mi / 25.2 km)
  • I Canaloni del Torrente Farma (15.8 mi / 25.5 km)

Frequently asked questions

What is the best area to stay in Montalcino when booking a holiday rental?
When considering a holiday rental in Montalcino, Tuscany, a popular area to stay is the historic centre. This charming part of town is characterised by its medieval architecture and offers a delightful atmosphere that truly captures the essence of Tuscany. Here, you can find a variety of properties ranging from rustic villas to quaint apartments, allowing for a pleasant selection to suit different preferences.

Staying in the historic centre places you within walking distance of several top attractions. The stunning Fortress of Montalcino, with its panoramic views of the surrounding vineyards and countryside, is a must-visit. Additionally, the beautiful Abbey of Sant'Antimo, located just a short drive away, offers a serene experience and showcases the region's rich history.

Another appealing area is the countryside surrounding Montalcino, where you can immerse yourself in the breathtaking landscapes of vineyards and olive groves. This area features a selection of villas that provide a more secluded retreat while still being a short drive from the town's amenities and attractions. Here, you can enjoy wine tours and tastings, particularly of the renowned Brunello di Montalcino, making it an ideal choice for wine enthusiasts.
How much does it cost to rent a holiday home in Montalcino?
Prices for holiday rentals in Montalcino vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Montalcino to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Montalcino holiday house rentals?
You can find great discounts on house rentals in Montalcino on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of holiday rental accomodation in Montalcino?
In Montalcino, villas are the most popular type of holiday rental, with around 244 available throughout the picturesque Tuscan countryside. These villas often feature luxurious amenities, including private pools, expansive gardens, and stunning views of the surrounding vineyards and rolling hills. Many come with fully equipped kitchens, spacious living areas, and outdoor dining spaces, great for enjoying the mild Italian climate.

Apartments are also a popular choice, with approximately 212 options in the town centre, providing easy access to local attractions like the historic fortress and charming piazzas. These typically include essential amenities such as kitchen facilities and comfortable living areas, ideal for couples or small groups.

For those looking for a homier feel, there are about 128 holiday houses available, which often offer multiple bedrooms and private outdoor spaces, making them suitable for families or groups. Several cottages can also be found, providing a quaint and rustic option for travellers seeking a great experience in the heart of Tuscany.
Are there any family house rentals in Montalcino?
In Montalcino, Tuscany, there is a wealth of family-friendly house rentals available, with around 94 properties to choose from. This picturesque town, renowned for its vineyards and stunning landscapes, offers a variety of homes suitable for families. Many of these rentals feature spacious living areas, fully equipped kitchens for preparing hearty Italian meals, and outdoor terraces or gardens where children can play in a safe environment.

Visitors can enjoy amenities such as swimming pools, BBQ facilities, and sometimes even game rooms, ensuring that both relaxation and entertainment are at hand. The charming town centre is just a short distance away, where families can explore local shops, enjoy the vibrant market scene, and sample the famous Brunello di Montalcino wine.

Moreover, the surrounding countryside invites outdoor activities like hiking and cycling, making it a fantastic destination for families looking to immerse themselves in the natural beauty and culture of Tuscany.
Can I rent a holiday home with a pool or hot tub in Montalcino?
In Montalcino, Tuscany, there are plenty of holiday homes available for rent that come with pools or hot tubs, with around 84 options to choose from. This picturesque medieval town, renowned for its wine and stunning landscapes, offers a variety of properties located among the rolling hills of the Val d'Orcia. Travellers can find charming villas and rustic farmhouses, many featuring private pools, outdoor terraces, and hot tubs, ideal for relaxing after a day of exploring the beautiful countryside.

Amenities in these rentals often include fully equipped kitchens for preparing local Tuscan cuisine, spacious living areas for family gatherings, and sometimes even outdoor dining spaces with breathtaking views of the vineyards. The region is also known for its wine tours and local culinary experiences, making it a superb destination for those looking to indulge in the flavours of Tuscany while enjoying a luxurious stay.
Can I find long-stay holiday rentals in Montalcino?
A long-stay holiday rental in Montalcino is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Montalcino?
In Montalcino, there are numerous pet-friendly house rentals available, offering travellers the chance to enjoy the beautiful Tuscan countryside alongside their furry companions. Many of these properties are situated amidst picturesque vineyards and olive groves, providing a serene backdrop for a relaxing getaway.

Holiday rentals in this area typically feature amenities such as spacious outdoor terraces, private gardens, and fully equipped kitchens, which are ideal for those looking to self-cater and enjoy al fresco dining. Additionally, some properties may include swimming pools, barbecue areas, and comfortable living spaces, making them superb for families or groups.

Montalcino itself is renowned for its wine production, particularly the famous Brunello di Montalcino, and visitors can explore local wineries that often welcome pets. The charming medieval town centre offers quaint shops and restaurants, where dogs are generally welcomed, allowing for a delightful experience for pet owners.
Are there any remote work holiday rentals in Montalcino?
In Montalcino, Tuscany, there are numerous remote work-friendly holiday rentals available, with around 516 properties suiting this need. The area is renowned for its stunning landscapes, rolling hills, and famous vineyards, providing an inspiring backdrop for those looking to blend work and leisure. Many of the rentals offer essential amenities such as free Wi-Fi, dedicated workspaces, and comfortable seating arrangements, ensuring that remote workers can maintain productivity while enjoying the tranquillity of the Tuscan countryside.

Travellers can find a variety of accommodation types, from charming villas to rustic farmhouses, often equipped with modern conveniences like kitchens and outdoor spaces for relaxation. The town itself is steeped in history, with delightful restaurants and local shops offering a taste of authentic Tuscan culture. Additionally, the nearby vineyards and olive groves present opportunities for exploration and unwinding after a productive workday. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Montalcino holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Montalcino with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Montalcino?
In Montalcino, popular rental amenities include well-equipped kitchens, allowing guests to prepare local Tuscan dishes with ease. Many properties also offer onsite parking, which is a convenient feature for those exploring the stunning countryside by car. The presence of fireplaces adds a touch of charm and warmth, superb for the cooler evenings. Outdoor spaces such as decks or patios are common, providing lovely spots to relax and enjoy the breathtaking views of the surrounding vineyards. Additionally, some rentals are pet-friendly, accommodating those who wish to travel with their furry companions.
When is the best time to visit Montalcino for a holiday rental?
September is the most popular time to visit Montalcino, as this month captures the essence of the grape harvest season in Tuscany. The landscape is adorned with vibrant colours, and the pleasant weather, typically ranging from 15 to 25 degrees Celsius, makes it ideal for exploring the picturesque vineyards and historic sites. This period attracts wine enthusiasts and those who enjoy the outdoor charm of the Tuscan countryside, with plenty of opportunities for sightseeing and leisurely strolls through the quaint streets of Montalcino.

The peak tourist season spans from March to May, when visitors flock to experience the blooming landscapes and participate in various local festivals. During these months, the atmosphere is bustling, with many events celebrating the region's rich winemaking heritage. If you relish a lively environment brimming with activities, this is the time for you.

For those seeking a quieter escape with excellent value, consider visiting in December. Although this is the low season, Montalcino offers a unique charm during this time, with fewer crowds and a chance to enjoy the tranquillity of the region. You can savour the peaceful winter landscape and perhaps indulge in some local culinary delights without the hustle and bustle.
How early should I book a Montalcino holiday rental?
Book your Montalcino holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Montalcino?
In Montalcino, visitors can experience firsthand the rich cultural and historical tapestry of this charming hilltop town. The stunning Fortress of Montalcino stands as a prominent landmark, offering panoramic views of the surrounding vineyards and countryside. Nearby, the historic centre features narrow cobblestone streets lined with quaint shops and local eateries, superb for sampling the renowned Brunello di Montalcino wine.

Another must-visit is the Abbey of Sant'Antimo, a beautiful Romanesque church located just a short drive from the town, surrounded by picturesque landscapes and serene grounds. For those interested in local history, the Civic and Diocesan Museum of Montalcino showcases a collection of art and artefacts that reflect the region's heritage.

Wine enthusiasts will appreciate the many vineyards and wineries in the area, where guided tours and tastings provide insight into the winemaking process.
Can I change or cancel my Montalcino home rental booking on Vrbo?
To find Montalcino holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Montalcino holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

More holiday ideas