Pienza holiday lettings

We found 1,737 holiday rentals — enter your dates for availability
Select from 34 houses, 38 apartments and other holiday rentals to find the perfect place for your stay in Pienza. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll have the best amenities for spending time at your home away from home, which might include a pool and a washer and dryer. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

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Why visit Pienza

  • Renaissance Architecture: Discover Pienza's stunning Renaissance buildings and charming streets that reflect its rich history.
  • Historic Churches: Visit the impressive cathedral and serene monastery, both steeped in cultural significance.
  • Pecorino Cheese: Savour the delightful local pecorino cheese, a culinary highlight of the region.
  • Picturesque Landscapes: Enjoy breathtaking views of the surrounding Tuscan countryside, perfect for leisurely strolls.
  • Relaxing Atmosphere: Experience the warm hospitality of locals in a tranquil setting, ideal for a romantic getaway.

Popular types of accommodation in Pienza

Welcome to Pienza, a charming gem in Tuscany, Italy, renowned for its stunning Renaissance architecture and breathtaking landscapes. Explore its delightful piazzas, historic churches, and the famous Pecorino cheese. As you plan your stay, consider the best vacation rentals in Pienza, ranging from elegant villas to cosy apartments, ensuring you find the perfect summer residence for your Tuscan adventure.

  • Villas: Elegant and spacious, villas offer a luxurious retreat with stunning views and ample amenities, making them the top choice for visitors to Pienza.
  • Houses: Ideal for families or groups, these homes provide a comfortable and private atmosphere, perfect for a relaxing holiday.
  • Apartments: Conveniently located, apartments are a popular choice for those seeking a blend of comfort and accessibility in the heart of Pienza.
  • Cottages: Charming and quaint, cottages offer a rustic escape surrounded by the beautiful Tuscan countryside.
  • Agritourism: Experience authentic rural life with agritourism stays, combining accommodation with local produce and farming activities.**

Top attractions in Pienza

Pienza, nestled in the heart of Tuscany, offers a charming blend of romance and culture, perfect for outdoor enthusiasts and couples alike. Explore the stunning piazza, visit the impressive cathedral, and wander through the serene monastery. Each attraction is steeped in history and invites you to immerse yourself in the local ambiance. Don't miss the chance to savour the beautiful landscapes and delightful Tuscan cuisine while enjoying this picturesque city.

  • Pienza Cathedral: This stunning cathedral, with its elegant façade and beautiful interior, embodies the Renaissance spirit. Visitors can admire exquisite artwork and experience the tranquil atmosphere that reflects the rich cultural heritage of Pienza.
  • Historic Centre of Pienza: A UNESCO World Heritage Site, the historic centre showcases charming streets, picturesque squares, and well-preserved architecture. Strolling through this vibrant area offers a glimpse into the town's fascinating history and culture.
  • Palazzo Piccolomini: This magnificent palace features beautiful gardens and impressive Renaissance architecture. Visitors can explore its grand rooms and enjoy panoramic views of the surrounding countryside from its terrace.

Things to do recommended for couples

Seeking a romantic getaway in Pienza? Explore the charming streets hand-in-hand, savour exquisite local cheeses at a quaint agriturismo, and enjoy a sunset picnic overlooking the stunning Val d'Orcia. For a truly memorable experience, indulge in a wine tasting at a nearby vineyard.

Things to do recommended for families

Families will delight in exploring the charming streets of Pienza, sampling delicious pecorino cheese at local farms, and taking part in cooking classes that celebrate Tuscan cuisine. The stunning views of the Val d'Orcia will make for memorable family photos.

Things to do recommended for groups

Experience the thrill of the Saltalbero Adventure Park, a zipline and ropes course located 24km from Pienza. Embrace the outdoors with your group as you tackle exciting challenges amidst stunning scenery in Tuscany.

*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 Pienza

If you're planning a trip with friends, family, or pets, or if you're seeking longer stays, be sure to refine your search according to your key preferences. Here are some helpful tips for booking on Vrbo.

  • Traveling to Pienza with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can refine your search for all of these options and more on Vrbo.
  • Traveling to Pienza with young kids: Traveling with young children can present its own set of challenges. It's essential to prioritise their comfort and safety, along with access to suitable amenities, like a private swimming pool. Additionally, it’s wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Pienza: For many, a family holiday feels incomplete without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Pienza: If you're seeking holiday rentals with special offers 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 accommodations. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Pienza

Pienza, nestled in the heart of Tuscany, offers a delightful blend of romance and scenic beauty. Known for its stunning Renaissance architecture, visitors can explore charming streets adorned with historic landmarks. Don't miss the chance to savour local pecorino cheese, a delicious highlight of the region. The town's relaxing atmosphere and friendly locals provide an inviting escape, making Pienza a worthy destination for those seeking culture, history, and exquisite Tuscan flavours.

  • Montepulciano: Nestled approximately 10km from Pienza, Montepulciano is a charming hilltop town renowned for its romantic atmosphere and rich cultural heritage. Visitors can indulge in outdoor activities while exploring its historic streets, exquisite piazza, and scenic landscapes. The town is famous for its local wines, particularly Vino Nobile, and offers numerous opportunities for spa treatments and body care. Don't miss visiting the historic landmarks, including ancient churches and the picturesque lake that enhances the town's beauty. Montepulciano is a perfect blend of relaxation and cultural exploration.
  • Montalcino: Located about 16km from Pienza, Montalcino is celebrated for its enchanting views and vibrant entertainment scene. This city invites travellers to experience its outdoor charm and indulge in local spas and body treatments. Montalcino is synonymous with Brunello wine, making it a must-visit for wine enthusiasts. Key attractions include the imposing fortress and several historical sites, alongside delightful theatres that showcase local performances. The nearby hot springs provide a unique relaxation experience, ensuring that Montalcino offers both excitement and tranquility.
  • San Quirico d'Orcia: Just 6km from Pienza, San Quirico d'Orcia is a picturesque town that captivates visitors with its romantic vibe and outdoor activities. It is an ideal destination for those seeking entertainment, with local spas, body treatments, and even golf courses to enjoy. The town is rich in history, featuring several significant landmarks, including hot springs and a serene lake. San Quirico d'Orcia's charm lies in its ability to combine leisure with cultural exploration, making it a delightful stop on your Tuscan journey.

Best time to go to Pienza

If you're planning a trip to Pienza, 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 August to September, while off-peak times, like November to January 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 SunnySlightly LowSlightly Low
February40.6°F (4.8°C)Light RainMostly SunnyAverageSlightly 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)SunnyAverageSlightly High
August73.0°F (22.8°C)No Rain (Dry)SunnySlightly HighSlightly High
September64.8°F (18.2°C)Light RainMostly SunnySlightly HighAverage
October56.7°F (13.7°C)Light RainMostly SunnyAverageAverage
November48.6°F (9.2°C)Light RainMostly SunnySlightly LowAverage
December42.1°F (5.6°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Are you aiming to make your next getaway more affordable? Consider being flexible with your travel dates, as prices often fluctuate. Additionally, you could enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a handy platform for you to plan new journeys, continue from where you last stopped, or manage your travel arrangements. Here, you can easily access properties you’ve saved or reserved, sorted into categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Rustic Pienza will entice you

The area's churches and wineries are just some of the reasons to come on holiday to Pienza. This scenic city has many special qualities. 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 Pienza

Do you want to find attractions to visit while you're in town? Venture out of your holiday home and check out everything that makes Pienza a one-of-a-kind holiday spot. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Consorzio del Vino Nobile di Montepulciano (5.3 mi / 8.5 km)
  • Cantina Contucci (5.3 mi / 8.5 km)
  • Piscine Termali Theia (7 mi / 11.2 km)
  • Terme di Chianciano (7.4 mi / 11.9 km)
  • Tenuta Greppo Franco Biondi Santi (9.2 mi / 14.8 km)
  • Baths of San Filippo (10.2 mi / 16.5 km)

Exploring the natural landscape of Pienza

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Pienza is a great place to get outside. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Historic Centre of Pienza (0.1 mi / 0.1 km)
  • La Foce (6.2 mi / 10 km)
  • Terme di Montepulciano Spa (6.2 mi / 10 km)
  • Piscine Termali Theia (7 mi / 11.2 km)
  • Val di Chiana (7.1 mi / 11.4 km)
  • Garden of Daniel Spoerri (11.9 mi / 19.2 km)

Frequently asked questions

What is the best area to stay in Pienza when booking a holiday rental?
When considering a holiday rental in Pienza, Tuscany, the historic centre is the best area to stay. This charming neighbourhood is renowned for its stunning Renaissance architecture and picturesque streets, making it an ideal base for exploring the town's rich history. Within the historic centre, visitors can easily access great attractions such as the Palazzo Piccolomini, with its beautiful gardens offering breathtaking views of the surrounding Val d'Orcia countryside, and the stunning Cathedral of Pienza, a masterpiece of Renaissance design.The area boasts a variety of properties, ranging from quaint apartments to elegant villas, providing something for every preference and budget. Staying in this central location allows for easy strolls to local shops, cafes, and restaurants, where you can indulge in the region's famous pecorino cheese and delightful Tuscan cuisine. Additionally, the nearby countryside offers opportunities for scenic walks and bike rides, showcasing the beautiful rolling hills and vineyards that define this part of Tuscany.
How much does it cost to rent a holiday home in Pienza?
Prices for holiday rentals in Pienza 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 Pienza 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 Pienza holiday house rentals?
You can find great discounts on house rentals in Pienza 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.
Where are the best areas for renting a beach house in Pienza?
For renting a beach house in Pienza, the nearby coastal area of Castiglione della Pescaia is a fantastic option. This charming seaside town along the Tuscan coast offers a selection of beach houses that provide easy access to beautiful sandy beaches and crystal-clear waters. Many of these properties come equipped with amenities such as private terraces, outdoor dining areas, and fully equipped kitchens, making them great for families or groups looking to enjoy a relaxing beach holiday.Just a short drive away from Pienza, you can also explore the stunning beaches at Punta Ala, where holiday rentals often feature modern furnishings, swimming pools, and proximity to local shops and restaurants. The area is known for its elegant beach clubs and vibrant seaside atmosphere, ensuring you have everything you need at hand for a delightful stay.Additionally, the natural beauty of the Maremma region surrounding Pienza offers opportunities for outdoor activities, from hiking in the nearby hills to exploring the picturesque countryside. Rentals in this area frequently boast amenities like gardens, barbecues, and even access to local vineyards, allowing guests to immerse themselves in the delightful Tuscan lifestyle.
What is the most popular type of holiday rental accomodation in Pienza?
In Pienza, apartments are the most popular type of holiday rental, with approximately 188 available in charming locations throughout the town. These apartments often feature traditional Tuscan decor, fully equipped kitchens, and spacious living areas, allowing guests to immerse themselves in the local culture while enjoying the comforts of home. Many also come with balconies or terraces that provide stunning views of the surrounding countryside.Villas follow closely behind, with around 164 options offering more luxurious accommodations. These villas typically provide multiple bedrooms, private gardens, and swimming pools, making them ideal for larger groups or families seeking a more upscale experience. Additionally, there are about 92 holiday houses and several cottages that provide a quaint and rustic feel, great for those wanting a peaceful retreat in the heart of Tuscany.
Are there any family house rentals in Pienza?
In Pienza, Tuscany, there is a great selection of family-friendly house rentals, with around 64 options available. This charming town, known for its stunning Renaissance architecture and picturesque landscapes, offers a variety of accommodations suitable for families. Many properties feature spacious living areas, fully equipped kitchens ideal for preparing family meals, and outdoor spaces where children can play and adults can relax while enjoying the beautiful Tuscan countryside.Nearby attractions include the iconic Pienza Cathedral and the scenic Val d'Orcia, superb for family outings and exploration. Visitors can also discover local markets where traditional Tuscan delicacies are sold, providing a delightful experience for all ages.
Can I rent a holiday home with a pool or hot tub in Pienza?
In Pienza, Tuscany, there are numerous holiday homes available for rent that feature pools and hot tubs, with around 69 options to choose from. This picturesque town, famed for its Renaissance architecture and stunning views of the Val d'Orcia, offers a delightful escape for travellers. Many of the rental properties come equipped with private pools, ideal for soaking up the Tuscan sun, as well as hot tubs for ultimate relaxation after a day of exploring.Travellers can expect amenities such as spacious outdoor terraces, well-appointed kitchens, and comfortable living areas, making them superb for families or groups. Additionally, some properties may include outdoor dining areas with barbecues, allowing guests to enjoy al fresco meals amidst the beautiful landscape.
Can I find long-stay holiday rentals in Pienza?
A long-stay holiday rental in Pienza 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 Pienza?
In Pienza, there are several pet-friendly house rentals available, offering a charming base for exploring this beautiful Tuscan town. Many of these properties come equipped with essential amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air.The historic centre of Pienza is a UNESCO World Heritage Site and provides a picturesque backdrop for pet owners, with its lovely streets and stunning views of the surrounding countryside. Nearby, the Val d'Orcia region offers plenty of opportunities for outdoor activities, including scenic walks and vineyard visits, where pets are often welcome.Additionally, the local area is dotted with quaint cafes and restaurants that may accommodate pets, enhancing the overall experience for travellers with furry companions.
Are there any remote work holiday rentals in Pienza?
In Pienza, Tuscany, there are numerous remote work-friendly holiday rentals available, with around 400 options to choose from. This enchanting town, known for its stunning Renaissance architecture and picturesque landscapes, is an ideal setting for those looking to blend work and leisure. Many properties come equipped with essential amenities for remote work, including free Wi-Fi in rooms and public areas, dedicated laptop workspaces, and comfortable living spaces that allow for a productive environment.The charming streets of Pienza offer not only a serene atmosphere but also the allure of local attractions such as the Palazzo Piccolomini and the beautiful Val d'Orcia, making it easy to take breaks and explore the surrounding countryside. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Pienza holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Pienza 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 Pienza?
In Pienza, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals with ease. Many properties also offer onsite parking, which is a convenient feature for those exploring the beautiful Tuscany region by car. For added comfort, numerous rentals come with fireplaces, superb for cosy evenings after a day of sightseeing. Additionally, some accommodations are pet-friendly, suiting travellers who wish to bring their furry companions along. Lastly, amenities such as coffee and tea makers are commonly found, providing a nice touch for guests to enjoy their morning brews while taking in the stunning views of the surrounding countryside.
When is the best time to visit Pienza for a holiday rental?
The best time to visit Pienza for a holiday rental is in September, when the region begins to transition from the bustling summer peak. This month offers a superb blend of pleasant weather and fewer crowds, allowing for a more relaxed exploration of this beautiful Tuscan town. With average temperatures ranging from 15 to 25 degrees Celsius, September provides ideal conditions for outdoor activities such as leisurely walks through the scenic vineyards and olive groves that characterise the area.During the peak season from July to September, Pienza attracts a vibrant mix of tourists eager to experience its rich history, stunning architecture, and delicious cuisine. While July is the busiest month, September strikes a harmonious balance, as visitors can still enjoy local festivals and markets without the overwhelming hustle and bustle.For those seeking a more budget-friendly option, visiting in January can be quite appealing. Although this is the low season, it offers a unique opportunity to experience Pienza's charm in a quieter atmosphere. This time of year allows for intimate explorations of the town's quaint streets and the chance to savour winter delicacies at local trattorias.Ultimately, the best time to book a holiday rental in Pienza hinges on your preferences for vibrant summer energy or the tranquillity of the winter months.
How early should I book a Pienza holiday rental?
Book your Pienza 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 Pienza?
In Pienza, visitors can take part in the enchanting Renaissance architecture and picturesque landscapes that define this charming town. The Piazza Pio II is a central attraction, featuring the stunning Pienza Cathedral and the Palazzo Piccolomini, where you can enjoy breathtaking views of the Val d'Orcia.Wander through the quaint streets lined with local shops selling artisanal cheese, particularly the famous pecorino, offering a true taste of the region. Nearby, the beautiful gardens of the Palazzo Piccolomini provide a serene spot for relaxation and scenic vistas.For those interested in art and history, the town is also close to the historic sites of Montepulciano and Montalcino, where you can explore additional cultural treasures and sample exquisite wines.
Can I change or cancel my Pienza home rental booking on Vrbo?
To find Pienza 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 Pienza 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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