Montalcino vacation rentals

We found 1,887 vacation rentals — enter your dates for availability
Discover a selection of 31 homes, 58 apartments, and other vacation rentals in Montalcino that are perfect for your trip. Whether you’re staying in a vacation home with your kids or with friends, you'll find the amenities you need and want, which might include a fireplace and a washer and dryer. Whatever you're looking for, you're sure to find a rental that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Montalcino

Showing deals for:Nov 13 - Nov 20

Image gallery for Recently restored Villa in Tuscany, sleeps 12, sw.pool, gym, big garden.

Pool
10 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)

Recently restored Villa in Tuscany, sleeps 12, sw.pool, gym, big garden.

Montalcino

10% off
Price is CA $3,553
CA $26,043 total
includes taxes & fees
Recently restored Villa in Tuscany, sleeps 12, sw.pool, gym, big garden.

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Find out more about Montalcino

Why visit Montalcino

  • Rich wine heritage: Indulge in exquisite Brunello wine tastings and tours at local wineries, immersing yourself in Montalcino's renowned viticulture.
  • Historical charm: Explore the town's enchanting piazzas, historic monasteries, and beautiful churches that showcase its rich history.
  • Cultural experiences: Visit the Montalcino Museum and the Museum of Wine for a deeper understanding of the region's cultural heritage.
  • Stunning landscapes: Enjoy picturesque views and serene surroundings that make for perfect outdoor adventures.
  • Diverse accommodations: Choose from spacious villas, cozy apartments, and inviting holiday homes to suit your travel needs.

Popular types of accommodation in Montalcino

If you're exploring accommodation options in Montalcino, you're in for a treat. The most popular types of holiday rentals in this charming Italian town include spacious villas, inviting private holiday homes, and cozy apartments. Whether you're seeking a romantic getaway or a family retreat, Montalcino offers a variety of Italy holiday rentals that cater to your needs, ensuring a memorable stay filled with comfort and local charm.

  • Villas: Luxurious and spacious residences offering stunning views, ideal for families or groups seeking comfort and elegance during their stay in Montalcino.
  • Private Holiday Homes: Cozy and well-equipped homes that provide a personal touch, perfect for travellers wanting a homely atmosphere while exploring the region.
  • Apartments: Conveniently located units that offer a blend of comfort and independence, suitable for couples or individuals enjoying a city-like experience.
  • Cottages: Charming and rustic retreats nestled in nature, great for those looking to unwind in a peaceful setting.
  • Agritourism: Unique stays on working farms, allowing guests to immerse themselves in local culture and enjoy authentic culinary experiences.**

Top attractions in and around Montalcino

Montalcino, Tuscany, is perfect for a romantic outdoor holiday filled with culture and entertainment. Visitors can explore charming piazzas, historic monasteries, and beautiful churches, while indulging in wine tours and tastings at local wineries. Don't miss the Montalcino Museum and the Museum of Wine for a deeper understanding of the region's rich heritage. With friendly activities and picturesque landscapes, Montalcino offers an unforgettable experience for all types of travellers.

  • Abbazia di Sant'Antimo: This stunning monastery, nestled in the heart of Montalcino, offers a serene atmosphere and breathtaking Romanesque architecture, making it a perfect spot for reflection and tranquility.
  • Civic and Diocesan Museum of Sacred Art of Montalcino: Housing an impressive collection of religious artworks, this museum provides insight into the region's rich artistic heritage and deep spiritual history.
  • Historic Centre of Pienza: Just 16km from Montalcino, this UNESCO World Heritage site showcases elegant Renaissance architecture and charming streets, ideal for leisurely exploration.

Things to do recommended for couples

Experience the charm of Montalcino with your partner by wandering through the picturesque vineyards, indulging in wine tastings, and enjoying a romantic dinner at a local trattoria. Don't miss the breathtaking sunset views from the fortress, perfect for creating unforgettable memories together.

Things to do recommended for families

Families will love exploring the charming streets of Montalcino, tasting local gelato, or visiting a nearby vineyard for a fun grape juice tasting. Children can enjoy the beautiful parks and playgrounds, while adults can appreciate the stunning views of the Tuscan countryside.

Things to do recommended for groups

Experience the thrill of ziplining at Saltalbero Adventure Park, located 27km from Montalcino. This ropes course offers an exhilarating outdoor adventure, perfect for groups seeking excitement and bonding in the beautiful Tuscan landscape.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're planning a trip with a group, family, or pets, or if you're considering an extended stay, it's important to refine your search according to your key priorities. Here are some helpful booking tips for Vrbo to assist you.

  • Traveling to Montalcino with a group: Think about how many bedrooms you require, along with amenities like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Montalcino with young kids: Travelling with young children can present its difficulties. It's important to prioritize 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 family-friendly attractions.
  • Taking your pets with you to Montalcino: For many, a family vacation isn't truly fulfilling without their furry companions by their side. If that resonates with you, explore Vrbo listings that welcome pets. Many of these 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 vacation 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 a private pool in your search as well.

Where to stay near Montalcino

Montalcino, Tuscany, is a captivating destination perfect for romantic getaways and outdoor adventures. Visitors can immerse themselves in its rich history, explore the stunning landscapes, and savour the local culture. The surrounding regions offer a tranquil atmosphere with picturesque scenery and charming towns. Whether you’re enjoying the renowned Brunello wine or wandering through historic streets, Montalcino promises a memorable holiday experience filled with adventure and relaxation.

  • Montepulciano: Nestled about 24km from Montalcino, Montepulciano is a charming hilltop city renowned for its romantic ambiance and rich cultural heritage. Visitors can indulge in outdoor activities while exploring its picturesque streets lined with historic architecture. Notable attractions include the lively piazza, stunning historic sites, and serene lakes perfect for a day of relaxation. The city is also famous for its local spas and body treatment offerings, making it an ideal retreat for those seeking wellness and rejuvenation, alongside delightful shopping experiences.
  • Pienza: Located approximately 16km from Montalcino, Pienza is a UNESCO World Heritage site that captivates visitors with its enchanting outdoor settings and romantic allure. This quaint city is known for its stunning landscapes and historical significance, making it a delightful stop for those keen on entertainment and culture. Explore the charming streets, relax in nearby hot springs, and enjoy the serene lake views. Pienza also features various spas and private clubs for a unique leisure experience, ensuring every traveller finds something to cherish.
  • San Quirico d'Orcia: Just 10km from Montalcino, San Quirico d'Orcia is a picturesque town that offers a blend of romance and outdoor adventure. Visitors are drawn to its tranquil atmosphere and the scenic beauty of the surrounding countryside. The town boasts historic landmarks, inviting hot springs, and a beautiful lake, making it perfect for leisurely strolls and exploration. For those looking to unwind, the local spas and body treatment facilities provide a relaxing escape. Golf enthusiasts will also find opportunities to enjoy the sport amidst stunning landscapes.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Plus, opting for a longer stay often results in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to narrow down your search by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers a user-friendly area to plan new journeys, resume your previous activities, or manage your travel arrangements. You can easily find your saved or booked accommodations organized into sections for Potential, Upcoming, or Current Trips. To begin using Trip Boards, please head over to: https://www.vrbo.com/en-ca/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 accommodations with space to entertain friends and family, Vrbo 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

Do you want to discover attractions to visit in the city? Venture out of your vacation home and experience everything that makes Montalcino a fun spot to vacation. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Tenuta Greppo Franco Biondi Santi (1 mi / 1.6 km)
  • Poggio Antico (2.7 mi / 4.3 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)
  • Parco Piscine Capenti Outdoor Pool (13.5 mi / 21.7 km)

Exploring the natural features in Montalcino

Whether you're an active traveler or just want to take in the scenery, Montalcino is a great place to spend some time outside. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Val di Merse (15.7 mi / 25.2 km)

Frequently asked questions

What is the best area to stay in Montalcino when booking a vacation rental?
When considering a vacation 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 vacation home in Montalcino?
Prices for vacation 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 travelling 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.
Are there any discounts for Montalcino vacation 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 vacation rental accomodation in Montalcino?
In Montalcino, villas are the most popular type of vacation 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 vacation 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 vacation home with a pool or hot tub in Montalcino?
In Montalcino, Tuscany, there are plenty of vacation 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 vacation rentals in Montalcino?
A long-stay vacation 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.

Vacation 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 vacation rentals in Montalcino?
In Montalcino, Tuscany, there are numerous remote work-friendly vacation 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 vacation rentals with parking?
Vrbo offers a wide selection of vacation 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 vacation 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 vacation rental?
Book your Montalcino vacation 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 vacation 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 vacation 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 vacation 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.

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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