Pienza vacation rentals

We found 1,745 vacation rentals — enter your dates for availability

Select from 28 houses, 42 apartments, and other vacation rentals to find the perfect place for your stay in Pienza. Whether you’re staying in a vacation home with a group or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a garden. Whatever you're looking for, you'll be able to choose a rental to meet everyone's needs, including accessible or non-smoking choices.

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Find out more about Pienza

Why visit Pienza

  • Stunning architecture: Explore the beautiful Pienza Cathedral and other historic buildings that showcase the town's rich heritage.
  • Charming piazzas: Wander through picturesque squares filled with vibrant local life and inviting cafes.
  • Outdoor adventures: Enjoy the breathtaking landscapes of southern Tuscany, perfect for hiking and exploring.
  • Relaxing hot springs: Unwind in soothing thermal baths that offer a serene escape from daily life.
  • Diverse accommodations: Choose from luxurious villas to cozy apartments that cater to every traveler's style and budget.

Popular types of accommodation in Pienza

Planning a getaway to Pienza? You're in for a treat. Discover the charm of this beautiful destination by choosing from a variety of vacation rentals. Whether you're looking for luxurious villas, cozy apartments, or private holiday homes, Pienza has something for everyone. Dive into the options and find the perfect villa rental that suits your style and budget. Enjoy your stay in this enchanting Tuscan town.

  • Villas: The top choice for vacation rentals in Pienza, offering luxurious spaces and stunning views for a memorable getaway.
  • Apartments: A popular option for those seeking convenience and comfort, ideal for couples and solo travelers.
  • Houses: Great for families or groups, these homes provide a cozy and personal atmosphere.
  • Cottages: Charming and quaint, perfect for a romantic retreat or a peaceful escape.
  • Caravan Parks: A unique option for adventurous travelers looking to explore the outdoors while enjoying basic amenities.**

Top attractions in and around Pienza

Pienza, nestled in Tuscany, is perfect for outdoor adventures, cultural experiences, and romantic getaways. Visitors can explore charming piazzas, historic monasteries, and soothing hot springs. Key attractions include the stunning Pienza Cathedral, offering a glimpse into the region's rich heritage. Whether you're seeking a cultural immersion or a relaxing escape, Pienza caters to all types of travelers looking to enjoy the beauty of Italy.

  • Pienza Cathedral: This stunning cathedral, located in the heart of Pienza, showcases beautiful Renaissance architecture and offers a serene atmosphere filled with cultural significance.
  • Historic Centre of Pienza: A UNESCO World Heritage site, this charming historic village features picturesque streets, artful buildings, and a rich cultural vibe that immerses you in Tuscan history.
  • Piazza Grande: Just 5 miles from Pienza, this lively square serves as a vibrant hub for locals and tourists alike, surrounded by cafes and shops that embody the essence of city life.

Things to do recommended for couples

For a romantic getaway in Pienza, explore the luxurious Chapel of Our Lady of Vitaleta just 2 miles away. Indulge in wellness at the Terme di Chianciano spa, 7 miles away, and savor delightful wines at Cantina Contucci, 5 miles away, perfect for an unforgettable experience together.

Things to do recommended for families

Families can have a thrilling time at the Siena Circuit, a karting venue located 19 miles from Pienza, perfect for adventure seekers. With exciting races and a lively atmosphere, it's a fantastic activity for kids and adults alike to enjoy together.

Things to do recommended for groups

Explore the Valdichiana Outlet Village for shopping and entertainment, just a short drive from Pienza. Enjoy a round of golf at the scenic Golf Club Valdichiana, or visit RI Crea RE for unique local finds. Perfect activities for bonding with your group.

*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 traveling with friends, family, pets, or planning an extended stay, be sure to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Pienza with a group: Think about how many bedrooms you'll require, as well as any amenities like a full kitchen or outdoor area for group gatherings. The good news is that you can easily filter for all these options and more on Vrbo.
  • Traveling to Pienza with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, as well as look for age-appropriate amenities like a private pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Pienza: For many, a family vacation wouldn’t feel complete without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Pienza: If you're in search of vacation rentals that offer great discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider additional features like a parking space, a well-equipped kitchen, or a private pool while you search.

Where to stay near Pienza

Pienza, a charming gem in Tuscany, offers an enchanting blend of outdoor adventures and rich cultural experiences. Just a stone's throw away, explore the idyllic landscapes of southern Tuscany, where scenic views and historical towns await. Whether you're seeking a romantic getaway or a relaxing retreat, the friendly atmosphere and luxurious vacation homes make Pienza the perfect base. Discover the beauty of Italian towns nearby and immerse yourself in the tranquil vibes of this stunning region.

  • Montepulciano: Located a mere 6 miles from Pienza, Montepulciano is a charming hilltop city known for its rich cultural heritage and stunning landscapes. This picturesque destination offers a romantic experience with its medieval architecture and scenic vineyards. Visitors can indulge in spa treatments, explore local shops, and enjoy outdoor activities amidst breathtaking views. Don't miss the chance to visit historic landmarks, including the impressive Piazza Grande and the ancient walls that encircle the city. The nearby lake provides a serene setting for relaxation and reflection, making Montepulciano an ideal getaway for those seeking both adventure and tranquility.
  • Montalcino: Situated 10 miles away from Pienza, Montalcino is famous for its wine, particularly the renowned Brunello di Montalcino. This enchanting city offers a blend of romantic and entertainment-themed experiences set against a backdrop of rolling hills and vineyards. Visitors can enjoy spa services and outdoor activities while exploring the historic sites that dot the landscape. Notable attractions include the majestic Fortress of Montalcino and the quaint tourist precinct, where you can savor local delicacies and discover artisanal products. Montalcino is perfect for those looking to immerse themselves in Tuscany's vibrant culture and culinary delights.
  • San Quirico d'Orcia: Just 4 miles from Pienza, San Quirico d'Orcia is a quaint town that offers a wonderful mix of outdoor activities and romantic charm. Visitors will find beautiful gardens and historic places, along with a serene lake and refreshing hot springs ideal for relaxation. The town features inviting spa facilities and opportunities for outdoor adventures, including nearby hiking trails. Its picturesque streets are lined with charming shops and eateries, making it a delightful spot for discovering local cuisine and culture. San Quirico d'Orcia is a hidden gem that promises an unforgettable Tuscan experience.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 hoping to save money on your upcoming trip? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that meets your budget, feel free to utilize our filters to narrow down options by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Planning made easy

Vrbo's Trip Board is designed to help you easily plan your travels, whether you're starting a new trip, refining your existing plans, or managing your bookings. Your saved or reserved properties are conveniently categorized into Potential, Upcoming, or Current Trips for your ease of access. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Rustic Pienza will entice you

The area's churches and wineries are just a few of the reasons to vacation in Pienza. This scenic city has many special qualities. 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 Pienza

Are you looking for attractions to visit while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Pienza a fun place to get away. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Consorzio del Vino Nobile di Montepulciano (5.3 mi / 8.5 km)
  • Cantina del Redi (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 appreciate the scenery, Pienza is a great place to get out in nature. These are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • Historic Centre of Pienza (0.1 mi / 0.1 km)
  • Horti Leonini (3.9 mi / 6.4 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)
  • Terme Sant'Elena (7.4 mi / 11.8 km)

Frequently asked questions

What is the best area to stay in Pienza, Tuscany, Italy when booking a vacation rental?
When considering a vacation rental in Pienza, Tuscany, a popular area to stay is the historic center, which is renowned for its stunning Renaissance architecture and charming streets. This area offers a delightful atmosphere where you can easily explore iconic sites such as the Palazzo Piccolomini, a beautiful palace with incredible gardens, and the stunning views from the town's viewpoints that overlook the picturesque Val d'Orcia landscape.

Staying in the historic center allows you to immerse yourself in the local culture, with quaint shops, artisanal food markets, and traditional restaurants just a short walk away. You can also enjoy the famous Pienza cheese, known as Pecorino, at local cheese shops. The concentration of properties in this area tends to be quite favorable, offering a range of options from cozy apartments to more luxurious accommodations, ensuring you can find something that suits your preferences.

Another delightful option is the outskirts of Pienza, where you'll find beautiful countryside views and a more tranquil setting. This area is great for those who enjoy outdoor activities like hiking and biking, with easy access to scenic trails that wind through the rolling hills of Tuscany. Additionally, you'll be close to the stunning landscapes of the Val d'Orcia, a UNESCO World Heritage site, which is great for day trips and exploring the natural beauty of the region.
How much does it cost to rent a vacation home in Pienza?
Prices for vacation 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 vacation 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, travelers might consider the nearby coastal areas along the Tuscan coastline, particularly in towns like Castiglione della Pescaia or Punta Ala. These charming seaside locations offer a variety of vacation rentals that typically include amenities such as private terraces with sea views, outdoor dining areas, and access to sandy beaches. Many properties in these areas have modern features like air conditioning and fully equipped kitchens, great for preparing meals after a day spent by the water.

In Castiglione della Pescaia, you'll find beautiful beach houses just a short walk from the shoreline, often equipped with outdoor showers and barbecues, allowing for a seamless transition from beach fun to evening relaxation. The local area is also home to vibrant markets and seaside restaurants, enhancing the overall experience for visitors looking to enjoy fresh seafood and local cuisine.

Further south, Punta Ala provides additional options with upscale rentals that may include amenities such as private pools or direct beach access, making them ideal for families or groups seeking a more luxurious beach holiday. The region is also dotted with nature trails and scenic viewpoints, providing opportunities for hiking and exploration.
What is the most popular type of vacation rental accomodation in Pienza?
In Pienza, apartments are the most popular type of vacation rental, with around 47 available in the charming town and its surrounding countryside. These apartments often feature fully equipped kitchens, cozy living spaces, and some even offer stunning views of the picturesque Tuscan landscape.

Additionally, there are about 41 villas that provide a more luxurious option, typically boasting multiple bedrooms, private gardens, and outdoor terraces superb for enjoying al fresco dining. For those seeking a more rustic experience, there are also several vacation houses and cottages that offer a quaint and tranquil retreat, often located among the rolling hills.
Are there any family house rentals in Pienza?
In Pienza, Tuscany, there are numerous family-friendly house rentals available—around 64 in total. This charming town, known for its stunning Renaissance architecture and beautiful landscapes, offers a variety of properties suitable for families. Many of these homes feature spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces where children can play and enjoy the fresh air.

Visitors can explore the nearby Val d'Orcia, a UNESCO World Heritage site, known for its rolling hills and picturesque vineyards. Additionally, Pienza is famous for its delicious pecorino cheese, with local markets and shops where families can sample and purchase regional delicacies.
Can I rent a vacation home with a pool or hot tub in Pienza?
In Pienza, Tuscany, there are many vacation homes available for rent that feature pools and hot tubs, with around 69 options to choose from. This picturesque town, known for its stunning Renaissance architecture and beautiful countryside views, offers a range of properties equipped with luxurious amenities. Many of these rentals include private pools, inviting hot tubs, and spacious outdoor areas superb for relaxation and enjoying the scenic surroundings.

Travelers can expect fully equipped kitchens, comfortable living spaces, and some properties may even feature outdoor dining areas or terraces with spectacular views of the Tuscan landscape.
Can I find long-stay vacation rentals in Pienza?
A long-stay vacation rental in Pienza is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Pienza?
In Pienza, Tuscany, travelers can find a variety of pet-friendly house rentals, with around 54 options available. Many of these charming rentals feature traditional Tuscan architecture, offering amenities such as fully equipped kitchens, outdoor terraces with stunning views of the surrounding countryside, and cozy living spaces great for relaxation after a day of exploring.

The town itself is known for its picturesque streets and historical sites, making it a delightful destination for both pets and their owners. Nearby, the Val d'Orcia region provides ample opportunities for outdoor activities, including hiking and exploring scenic trails. Many properties are conveniently located near pet-friendly parks and nature spots, allowing guests to enjoy the beautiful landscapes of Tuscany with their furry companions. See all pet-friendly rentals in Pienza.
Are there any remote work vacation rentals in Pienza?
In Pienza, Tuscany, there are numerous vacation rentals suitable for remote work, with around 100 options available. Many of these properties offer essential amenities for a productive stay, such as free Wi-Fi, both in public areas and in individual rooms, ensuring that guests can stay connected while enjoying the stunning Tuscan landscape.

Travelers can expect a variety of accommodations, from charming apartments in the historic center to more spacious villas on the outskirts, often equipped with comfortable workspaces and serene environments conducive to focus. The picturesque town itself, a UNESCO World Heritage Site, provides a beautiful backdrop for breaks from work, with its stunning Renaissance architecture and nearby attractions like the Val d'Orcia landscape, which is great for leisurely strolls or cycling during downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Pienza vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Pienza with parking available—perfect for families or travelers 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 vacation rental amenities cater to travelers seeking comfort and convenience. Most rentals come equipped with kitchens, allowing guests to prepare their own meals using fresh local ingredients. Onsite parking is typically available, which is a great benefit for those exploring the scenic Tuscan countryside. Many properties also feature cozy fireplaces, creating a warm and inviting atmosphere, especially during the cooler months. Additionally, some rentals are pet-friendly, enabling guests to bring their furry companions along for the stay. Lastly, having a coffee or tea maker in the rental allows guests to enjoy a warm beverage while taking in the stunning views of the surrounding landscape.
When is the best time to visit Pienza for a vacation rental?
The best time to visit Pienza for a vacation rental is during September, when the summer crowds begin to dwindle yet the beautiful Tuscan landscape remains alive with color. This month is particularly appealing for travelers who appreciate mild temperatures and the opportunity to enjoy outdoor activities without the hustle and bustle of peak tourist season.

From July to September, Pienza experiences its peak season, attracting visitors eager to explore its charming streets, historic architecture, and stunning countryside. With daytime temperatures typically ranging from the mid-60s to mid-80s Fahrenheit, September offers a comfortable climate ideal for leisurely strolls through the town or savoring local cuisine at outdoor cafes.

For those looking to save on their travel budget, January presents a wonderful chance to experience Pienza's tranquility. While this is considered the low season, travelers can enjoy the serene beauty of the region, often with fewer tourists around. It's a superb time for cozying up in a vacation rental and immersing oneself in the local culture at a leisurely pace.
How early should I book a Pienza vacation rental?
Book your Pienza 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 Pienza, Tuscany, Italy?
In Pienza, travelers can engage in the charm of this UNESCO World Heritage site known for its Renaissance architecture and stunning landscapes. The historic center, with its picturesque streets, features attractions like the Pienza Cathedral, which boasts impressive frescoes and beautiful views from its exterior. Visitors can also explore the Palazzo Piccolomini, a stunning palace with gardens that offer panoramic views of the Val d'Orcia countryside.

For those interested in local culture, the town is famous for its pecorino cheese, and the numerous shops offer tastings and local delicacies. The surrounding countryside is dotted with scenic vineyards and olive groves, providing ample opportunities for leisurely walks and photography.
Can I change or cancel my Pienza home rental booking on Vrbo?
To find Pienza 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 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 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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