Montalcino holiday lettings

We found 1,800 holiday rentals — enter your dates for availability

Discover a selection of 27 homes, 46 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.

Holiday rentals with weekly discounts - Montalcino

Showing deals for:24 Apr - 1 May

Image gallery for Tuscany romance. Rural charm between Montalcino and sea. Relax pur

Pool
9.6 out of 10, Exceptional, (40 reviews)
Exceptional
(40 reviews)

Tuscany romance. Rural charm between Montalcino and sea. Relax pur

Cinigiano

8% off
Price is £2,954
for 7 nights, 1 villa
£422 per night
includes taxes & fees
Tuscany romance. Rural charm between Montalcino and sea. Relax pur

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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:

  • Historic Centre of Pienza (9.7 mi / 15.6 km)
  • Garden of Daniel Spoerri (10 mi / 16 km)
  • Mount Amiata Fauna Park (12.9 mi / 20.7 km)
  • Monte Amiata (13.4 mi / 21.6 km)
  • La Foce (14.8 mi / 23.8 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 planning a holiday rental in Montalcino, Tuscany, one of the best areas to consider is the historic centre, known as the Centro Storico. This charming neighbourhood is characterised by its medieval architecture and narrow cobbled streets, making it a picturesque base for your stay. The central area is convenient for exploring local attractions such as the stunning Fortress of Montalcino, which offers breathtaking views of the surrounding countryside, and the renowned Abbazia di Sant'Antimo, a beautiful Romanesque abbey located just a short drive away.

Another appealing option is the surrounding countryside, particularly the areas of Castelnuovo dell'Abate and the hillsides near the vineyards. This region is great for those looking to immerse themselves in the famous Brunello wine culture, with numerous wineries and vineyards at your doorstep. Staying here allows for a peaceful retreat while still being within easy reach of the historic centre.
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 61 available throughout this picturesque Tuscan town. These villas typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and private outdoor spaces ideal for enjoying the stunning views of the surrounding vineyards and rolling hills. Many of these properties are located near attractions like the historic centre of Montalcino and the renowned wineries that produce Brunello di Montalcino.

Apartments are also a common choice, with approximately 42 options scattered throughout the town, providing a more intimate setting for travellers. Most apartments come with amenities like kitchen facilities, comfortable living areas, and some even have balconies to enjoy the charming streetscape.
Are there any family house rentals in Montalcino?
In Montalcino, Tuscany, there is an impressive selection of family-friendly holiday rentals, with around 87 options available. This charming region is renowned for its stunning landscapes and world-class vineyards, making it an ideal destination for families looking to explore the beauty of Italy. Many of these homes feature spacious living areas, well-equipped kitchens great for preparing meals together, and outdoor terraces where families can enjoy al fresco dining against a picturesque backdrop.

Visitors can find properties in areas close to the historical town centre, which is known for its medieval architecture, or in the surrounding countryside, where traditional Tuscan farmhouses provide a rustic charm. Amenities such as private gardens, swimming pools, and even game rooms in some cases ensure that there's plenty to keep the whole family entertained.
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 feature pools or hot tubs, with around 85 options to choose from. This picturesque town, renowned for its stunning landscapes and world-famous Brunello wine, offers a variety of properties located among rolling hills and vineyards. Many rentals come with private swimming pools, expansive outdoor terraces, and hot tubs, providing the great setting for relaxation amidst the breathtaking Tuscan scenery. Find your rental in Montalcino with a pool or a hot tub.
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 a delightful experience for both travellers and their furry companions. Many of these properties are set amidst the picturesque Tuscan countryside, often featuring traditional architectural elements such as terracotta tiles and wooden beams. Travellers can expect amenities including fully equipped kitchens, spacious living areas, and private outdoor spaces, which are great for relaxing after a day of exploring.
Are there any remote work holiday rentals in Montalcino?
In Montalcino, Tuscany, there are numerous remote work holiday rentals available, with around 120 options to choose from. This picturesque town, famous for its Brunello wine, offers a superb blend of work and leisure. Many of the properties are equipped with essential amenities for remote work, including Wi-Fi, dedicated desks, and comfortable desk chairs, ensuring a productive environment while enjoying the serene Tuscan countryside. Additionally, some accommodations feature safes for securing valuables, providing peace of mind during your stay. 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 fully equipped kitchens, allowing guests to prepare their own meals with ease. Most accommodations feature essential appliances such as refrigerators, ovens, and stovetops. Additionally, complimentary Wi-Fi is commonly available, ensuring that travellers can stay connected during their stay.
When is the best time to visit Montalcino for a holiday rental?
September is the most popular time to visit Montalcino, as the grape harvest season brings a vibrant energy to this charming Tuscan town. During this month, the landscape is adorned with lush vineyards, and the mild weather (averaging around 20°C) creates the superb backdrop for outdoor activities and sightseeing.

The peak season in Montalcino typically runs from March to May, when visitors flock to enjoy the blooming countryside and partake in various cultural events. This is an ideal time for those who appreciate quality experiences, as the region offers guided vineyard tours, wine tastings, and opportunities to savour the renowned Brunello wines in their birthplace.

If you're looking for a more budget-friendly option, consider visiting in December. While this month falls into the low season, it presents a unique charm with fewer tourists, allowing for a more intimate experience of Montalcino's historic streets and rustic cuisine. The festive atmosphere during the holiday season enhances the appeal, making it a delightful time to explore local traditions.
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 engage in a rich tapestry of attractions that highlight the region's famed wine culture and stunning landscapes. The historic centre, characterised by its medieval architecture, is home to the impressive Fortezza di Montalcino, which offers panoramic views of the surrounding vineyards and hills. Holiday rentals in this area often provide a charming rustic atmosphere, great for those wishing to experience the local lifestyle.

The nearby vineyards, particularly those producing the renowned Brunello di Montalcino, are a must-visit for wine enthusiasts. Many properties are within easy reach of these wineries, allowing for convenient wine tours and tastings. Additionally, the picturesque countryside surrounding Montalcino invites exploration, with opportunities for hiking and cycling amidst the beautiful landscapes.
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.

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