Montepulciano holiday lettings

We found 2,745 holiday rentals — enter your dates for availability

Find the perfect place for you stay in Montepulciano by choosing from 50 houses, 184 apartments and other holiday rentals. Holiday homes offer the amenities that you expect for your family, friends or furry companion, such as a garden and pool. Whatever you're looking for, you're sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Montepulciano

Showing deals for:27 Feb - 6 Mar

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

Pool
10 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)

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

San Giovanni d'Asso, Provincia di Siena

9% off
Price is £15,138
for 7 nights, 1 villa
£2,163 per night
includes taxes & fees
Recently restored Villa in Tuscany, sleeps 12, sw.pool, gym, big garden.

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Why visit Montepulciano

  • Cultural immersion: Discover Montepulciano's rich heritage through its charming piazzas and stunning churches.
  • Scenic beauty: Enjoy breathtaking views of the Tuscan countryside and picturesque vineyards.
  • Relaxing hot springs: Unwind in natural hot springs, perfect for a soothing retreat.
  • Quaint villages: Explore nearby villages that offer a warm, family-friendly atmosphere.
  • Diverse accommodation: Choose from luxurious villas, cosy cottages, or modern apartments for a tailored stay.

Popular types of accommodation in Montepulciano

Discover the charm of Montepulciano with an array of holiday rentals tailored to your needs. Whether you prefer a luxurious villa, a cosy cottage, or a modern apartment, our selection offers something for everyone. Ideal for families, couples, or solo adventurers, these holiday rentals in Tuscany provide the perfect base to explore Italy's stunning landscapes and rich culture. Let us help you find the ideal accommodation for your unforgettable getaway.

  • Villas: The top choice for holiday accommodation in Montepulciano, offering luxurious living spaces and beautiful surroundings.
  • Houses: A popular option for those seeking a home-away-from-home experience, ideal for families and groups.
  • Apartments: A convenient choice for couples or solo travellers, providing a blend of comfort and local charm.
  • Cottages: Quaint and rustic, these charming retreats offer a peaceful getaway amidst the Tuscan countryside.
  • Agritourism: Experience authentic Italian rural life with stays on working farms, complete with local produce and traditions.**

Top attractions in Montepulciano

Montepulciano is ideal for those seeking a cultural, outdoor, or romantic getaway. Visitors can explore charming piazzas, stunning churches, and relaxing hot springs, all set against the picturesque Tuscan backdrop. This enchanting town offers a rich blend of experiences for travellers looking to immerse themselves in local culture and enjoy the beauty of the countryside.

  • Terme di Montepulciano Spa: Experience the rejuvenating powers of this natural hot spring, set in a serene environment. Enjoy outdoor wellness facilities and relaxation treatments that harness the healing properties of the thermal waters, making it a perfect retreat to unwind.
  • Dome of Montepulciano: Visit this stunning place of worship that boasts magnificent architecture and rich cultural history. The dome is an emblem of Montepulciano, offering a peaceful atmosphere and a glimpse into the town's artistic heritage.
  • Piazza Grande: This vibrant square is the heart of Montepulciano, surrounded by charming buildings and lively cafés. Immerse yourself in the local culture, enjoy open-air events, and take in the splendid views that characterise this bustling hub.

Things to do recommended for couples

For a romantic getaway in Montepulciano, indulge in wellness at Terme di Chianciano, just 2.5km away. Explore the intimate ambiance of Cantina Contucci and Cantina del Redi, where you can enjoy fine wines amidst captivating outdoor settings, perfect for couples seeking romance and entertainment.

Things to do recommended for families

Families visiting Montepulciano can have a splashing good time at Tavernelle Aquatic Park, located 11.2km away. With its thrilling slides and pools, it's perfect for adventure-seeking families looking to enjoy a fun-filled day together.

Things to do recommended for groups

In Montepulciano, groups can indulge in retail therapy at the Valdichiana Outlet Village, enjoy a unique shopping experience at RI Crea RE, or tee off at the scenic Golf Club Valdichiana, perfect for those seeking outdoor sports activities.

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

When planning your trip, whether you're travelling with friends, family, pets, or seeking extended stays, it’s important to apply the right filters to suit your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Montepulciano with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Montepulciano with young kids: Travelling with young children can present certain challenges. It’s essential to prioritise their comfort and safety, alongside suitable facilities like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that are enjoyable for families.
  • Taking your pets with you to Montepulciano: For many, a family holiday isn’t truly fulfilling without the companionship of their four-legged friend. If this resonates with you, take a look at Vrbo properties that welcome pets. The majority of pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels completely at home.
  • Planning for a long term stay visiting Montepulciano: If you're searching for holiday rentals with 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 consider adding amenities like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay near Montepulciano

Montepulciano offers a delightful blend of culture and relaxation, making it a perfect getaway in Tuscany. Explore its charming streets, historic architecture, and picturesque vineyards. Nearby, you can enjoy the welcoming atmosphere of quaint villages, perfect for a family-friendly escape or a romantic retreat. Whether you seek a tranquil holiday or an immersive cultural experience, Montepulciano and its surroundings promise a memorable adventure in the heart of Italy.

  • Pienza: Situated a mere 3.7km from Montepulciano, Pienza is a charming town renowned for its Renaissance architecture and breathtaking landscapes. Visitors flock here for a delightful blend of outdoor activities, cultural experiences, and romantic settings. The town is home to various spas and body treatment centres, making it a perfect spot for relaxation. Notable attractions include its historic churches and the picturesque hotsprings that attract wellness enthusiasts. Pienza's quaint shopping areas offer local crafts and delicacies, making it a delightful place to explore and unwind.
  • San Quirico d'Orcia: Located 6.2km from Montepulciano, San Quirico d'Orcia is an idyllic destination for those seeking outdoor adventures and a romantic atmosphere. The town is well-known for its entertainment options, including private country clubs and rejuvenating spas. Visitors can immerse themselves in the stunning landscapes, with local landmarks such as historic sites and serene lakes enhancing the experience. The hotsprings here are particularly popular, providing a perfect backdrop for relaxation after a day of exploration.
  • Chianciano Terme: Just 2.5km from Montepulciano, Chianciano Terme is famed for its wellness offerings and enchanting natural beauty. This spa town is perfect for tourists looking to indulge in outdoor activities while enjoying a romantic getaway. Chianciano Terme boasts numerous spas and body treatment facilities, along with vibrant shopping areas. The nearby hotsprings and historic sites provide a unique blend of relaxation and cultural immersion, making it a must-visit location during your Tuscan adventure.

Best time to go to Montepulciano

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

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

Booking with Vrbo is a breeze

Are you hoping to cut costs on your next getaway? It might be worth being flexible 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 property that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly area to plan new journeys, resume your previous efforts, or review and arrange your travel plans. You'll discover the properties you've saved or booked sorted into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

The culturally rich city of Montepulciano awaits you

Enjoy the area's wineries, culture and history with a rental holiday home in Montepulciano. This city's sightseeing, festivals and local tours draw many visitors. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Montepulciano

Do you want to find attractions to visit in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Montepulciano a one-of-a-kind holiday spot. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Cantina del Redi (0.5 mi / 0.8 km)
  • Cantina Contucci (0.5 mi / 0.8 km)
  • Consorzio del Vino Nobile di Montepulciano (0.5 mi / 0.8 km)
  • Piscine Termali Theia (4 mi / 6.5 km)
  • Terme di Chianciano (4.2 mi / 6.8 km)
  • Torrenieri Montalcino Station (11.9 mi / 19.1 km)

Exploring the natural landscape of Montepulciano

Whether you're looking for adventure or just want to take in the scenery, Montepulciano is a great place to get out in nature. Here are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Terme di Montepulciano Spa (1.9 mi / 3.1 km)
  • Val di Chiana (1.9 mi / 3.1 km)
  • Piscine Termali Theia (4 mi / 6.5 km)
  • La Foce (5.1 mi / 8.3 km)
  • Historic Centre of Pienza (5.7 mi / 9.1 km)
  • Horti Leonini (9.6 mi / 15.5 km)

Transport to and around Montepulciano

The nearest airport is in Perugia San Francesco d'Assisi – Umbria Intl. Airport (PEG), located 36.1 mi (58.1 km) from the city centre.

If you prefer train travel, the main station serving the city is Montepulciano Station.

Frequently asked questions

What is the best area to stay in Montepulciano when booking a holiday rental?
When considering a holiday rental in Montepulciano, the historic centre is the best area to stay. This picturesque neighbourhood is characterised by its charming medieval architecture, narrow cobblestone streets, and stunning views of the surrounding Tuscan countryside. Staying here puts you right at the heart of the town, making it easy to explore local attractions such as the magnificent Piazza Grande, where you can admire the impressive Palazzo Comunale and the beautiful Santa Maria Assunta Cathedral.

Another appealing area is the area surrounding Via di Gracciano nel Corso, which offers a blend of local shops, delightful cafés, and authentic restaurants, superb for experiencing the vibrant local culture. Here, you can enjoy the renowned Vino Nobile di Montepulciano at one of the many wine cellars nearby, which provide a wonderful opportunity for tastings and tours.

For those seeking a quieter stay, the outskirts of Montepulciano offer a selection of charming rural properties set amongst vineyards and olive groves. This area allows for a peaceful retreat while still providing easy access to the town's main attractions.
How much does it cost to rent a holiday home in Montepulciano?
Prices for holiday rentals in Montepulciano 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 Montepulciano 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 Montepulciano holiday house rentals?
You can find great discounts on house rentals in Montepulciano 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 Montepulciano?
In Montepulciano, apartments are the most popular type of holiday rental, with around 134 available throughout the charming town. These apartments are often situated in picturesque neighbourhoods with stunning views of the surrounding Tuscan countryside, providing a great base for exploring local attractions such as the Piazza Grande and the famous Vino Nobile wineries. Most apartments come equipped with fully fitted kitchens, comfortable living areas, and some even feature private balconies or terraces to enjoy the scenic vistas.
Are there any family house rentals in Montepulciano?
In Montepulciano, Tuscany, there are numerous family-friendly house rentals available—around 120 options throughout the area. This charming town is renowned for its stunning landscapes and historical significance, making it a wonderful choice for families seeking a memorable getaway. Many of these properties feature spacious living areas, fully equipped kitchens ideal for preparing family meals, and outdoor terraces where children can play while adults relax with a glass of local wine.
Can I rent a holiday home with a pool or hot tub in Montepulciano?
In Montepulciano, Tuscany, there are plenty of holiday homes available for rent featuring pools and hot tubs, with around 144 options to choose from. This enchanting hilltop town is renowned for its stunning landscapes and historical charm, making it a fantastic destination for travellers seeking relaxation and luxury. Many of the properties come equipped with private swimming pools, hot tubs, and spacious outdoor areas great for al fresco dining and enjoying the picturesque views of the Tuscan countryside. Find your rental in Montepulciano with a pool or a hot tub.
Can I find long-stay holiday rentals in Montepulciano?
A long-stay holiday rental in Montepulciano 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 Montepulciano?
In Montepulciano, travellers can find a variety of pet-friendly house rentals that cater to both comfort and convenience. With over a hundred options available, visitors can choose from charming rustic villas to modern apartments, many of which include amenities such as fully equipped kitchens, private gardens, and outdoor dining areas, superb for enjoying the stunning views of the Tuscan countryside.
Are there any remote work holiday rentals in Montepulciano?
In Montepulciano, Tuscany, there are numerous remote work holiday rentals available, with around 210 options to choose from. This picturesque town, known for its stunning landscapes and historic architecture, provides the great backdrop for a productive workation. Many properties offer amenities tailored for remote workers, including high-speed Wi-Fi, dedicated workspaces with desks and chairs, and some even feature office setups with computer monitors. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Montepulciano holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Montepulciano 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 Montepulciano?
In Montepulciano, popular rental amenities include fully equipped kitchens, which allow guests to prepare their own meals, and refrigerators for storing fresh produce and local delicacies. Many properties also feature pools, offering a refreshing escape during the warm Tuscan days. Additionally, rentals often come with essential cookware, dishware, and utensils to facilitate a comfortable dining experience. Coffeemakers are also commonly found, enabling travellers to enjoy a nice cup of coffee while taking in the stunning views of the surrounding countryside.
When is the best time to visit Montepulciano for a holiday rental?
April is one of the most popular months to visit Montepulciano, as the region bursts into life with vibrant spring blooms and pleasant temperatures. This time of year is ideal for travellers seeking to explore the picturesque vineyards and historic architecture that define this beautiful Tuscan town. With average temperatures in the low to mid-teens Celsius, outdoor activities such as wine tours and leisurely strolls through the charming streets become all the more enjoyable.

The peak season runs from July to September, attracting a multitude of tourists eager to experience the summer festivities, including local festivals and outdoor dining. While the atmosphere is lively and filled with energy, the warm summer months can be busy, and accommodation prices may reflect that popularity.

If you're looking for more affordable options, consider visiting in January, when the town is quieter and you can enjoy a more intimate experience of Montepulciano. This low season offers a different charm, where you can savour the tranquillity of the Tuscan countryside without the hustle and bustle of peak tourist traffic.
How early should I book a Montepulciano holiday rental?
Book your Montepulciano 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 Montepulciano?
In Montepulciano, visitors can immerse themselves in the rich history and stunning architecture that define this charming hilltop town. The Piazza Grande serves as the heart of Montepulciano, surrounded by beautiful Renaissance buildings, including the Palazzo Comunale, which offers breathtaking views of the surrounding countryside.

For those interested in wine, the town is renowned for its Vino Nobile di Montepulciano, and many holiday rentals are conveniently located near local vineyards where tastings and tours are available.

The Church of San Biagio, situated just outside the town walls, is another must-see, known for its striking architecture and serene setting, making it a superb spot for relaxation and photography.
Can I change or cancel my Montepulciano home rental booking on Vrbo?
To find Montepulciano 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 Montepulciano 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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