Pienza holiday rentals

We found 1,648 holiday rentals — enter your dates for availability
Select from 33 houses, 40 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.

Holiday rentals with weekly discounts – Pienza

Showing deals for:18 Dec - 25 Dec

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 AU$26,244
for 7 nights, 1 villa
AU$3,749 per night
includes taxes & fees
Recently restored Villa in Tuscany, sleeps 12, sw.pool, gym, big garden.

Find spaces that suit your style

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Why visit Pienza

  • Cultural heritage: Pienza captivates with its Renaissance architecture, historic cathedral, and ancient monastery, embodying timeless Italian charm.
  • Scenic vistas: Experience breathtaking views of rolling Tuscan landscapes, blending natural beauty with historic allure.
  • Piazza ambience: Wander through picturesque piazzas, where vibrant local life meets traditional Italian hospitality.
  • Local gastronomy: Savour authentic Tuscan cuisine and fine wines, reflecting the region’s rich culinary traditions.
  • Artistic legacy: Immerse in a rich tapestry of art and history, with charming streets that echo Pienza’s Renaissance past.

Popular types of accommodation in Pienza

Discover the charm of Pienza, Tuscany, Italy, where breathtaking landscapes meet timeless art and history. Explore its renowned villas, private holiday homes, and apartments for a memorable stay. Uncover local attractions, savour authentic cuisine, and immerse yourself in the Renaissance heritage that makes Pienza a quintessential Italian destination. Experience the best in Italy holiday rentals and holiday homes, with properties in Pienza offering a unique blend of comfort and cultural enrichment.

  • Villas: Experience the charm of Tuscany in spacious and luxurious villas, perfect for a memorable getaway.
  • Private Holiday Homes: Enjoy the comforts of home in private residences, ideal for families and groups seeking privacy.
  • Apartments: Discover well-appointed apartments that offer a cosy and convenient base for exploring Pienza.
  • Cottages: Stay in quaint cottages that provide a rustic and intimate setting amidst picturesque landscapes.
  • Agritourism: Immerse yourself in rural life with agritourism stays that offer authentic food and farm experiences.**

Top attractions in and around Pienza

Pienza, Tuscany, Italy enchants visitors with its delightful blend of culture and outdoor charm. Explore its quaint piazza squares, historic monastery, and magnificent cathedral, all offering a romantic and entertaining backdrop for a memorable holiday. The city invites travellers to immerse themselves in its rich heritage and vibrant local experiences, making it a perfect destination for those seeking both relaxation and cultural discovery.

  • Historic Centre of Pienza: Wander through this charming historic village steeped in culture, where every cobbled street sings tales of Renaissance splendour.
  • Palazzo Piccolomini: Step into this elegant historic palace, an emblem of Pienza's rich heritage and artistic legacy, perfect for history enthusiasts.
  • Piazza Grande: Discover this vibrant piazza square, located 8km from Pienza, offering a lively blend of urban and cultural experiences.

Things to do recommended for couples

Enjoy a romantic getaway in Pienza, with its charming streets and stunning views. Savour exquisite local cheese at a quaint trattoria, explore the picturesque countryside on a leisurely bike ride, or indulge in a sunset wine tasting at a nearby vineyard for an unforgettable experience.

Things to do recommended for families

Families will delight in exploring the picturesque streets of Pienza, tasting delicious local cheeses, or visiting the nearby stunning landscapes of the Val d'Orcia. Enjoy a leisurely bike ride through the scenic countryside or participate in a cooking class to learn traditional Tuscan recipes together.

Things to do recommended for groups

Experience the thrill of the Saltalbero Adventure Park, a zipline ropes course located 24km from Pienza. Enjoy an exhilarating day of adventure amidst stunning outdoor scenery, perfect for group bonding and unforgettable memories.

*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

Whether you're journeying with a group, travelling as a family, accompanied by your pets, or seeking extended stays, ensure you filter by the appropriate priorities. Here are some Stayz booking tips for you.

  • Traveling to Pienza with a group: Consider how many bedrooms you'll require, along with facilities like a fully equipped kitchen or an outdoor area for group events. Fortunately, you can use Stayz to filter for all these features, and much more.
  • Traveling to Pienza with young kids: Travelling with young children can present its challenges. It’s important to prioritise their comfort and safety, along with suitable amenities, like a private swimming pool. Additionally, it’s wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Pienza: For some, a family holiday isn’t complete without the company of their four-legged companion. If this resonates with you, explore Stayz properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels right 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 place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features such as a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Pienza

Pienza, nestled in the heart of Tuscany, is a delightful blend of romance and history, offering stunning views and serene landscapes. Visitors can explore its charming centre, with picturesque streets and Renaissance architecture, while indulging in local delicacies and fine wines. Just a short drive away, the lush vineyards provide a perfect backdrop for leisurely wine tastings. Pienza's inviting atmosphere and friendly locals make it an ideal destination for a relaxing holiday.

  • Montepulciano: Nestled 10km away from Pienza, Montepulciano offers an enchanting blend of romance, culture and outdoor leisure. Wander through historic piazza squares and explore the ancient landmarks that speak of rich heritage. Enjoy rejuvenating spa experiences and indulgent body treatments, while exploring charming shopping areas. The city’s scenic lake and storied historical sites provide an ideal backdrop for a leisurely day out, perfect for travellers seeking a mix of cultural immersion and outdoor delight.
  • Montalcino: Located 16km from Pienza, Montalcino is celebrated for its romantic ambience and a blend of entertainment and outdoor activities. This historic city invites visitors to experience the allure of its ancient castle and hotsprings, alongside vibrant theatre scenes. Indulge in relaxing spa treatments and body therapies, while the nearby historic sites enrich your journey through time. Montalcino is an inviting destination for those in search of both cultural enrichment and leisurely pursuits amidst a scenic landscape.
  • San Quirico d'Orcia: Situated 6km from Pienza, San Quirico d'Orcia charms with a delightful mix of romance, outdoor adventures and entertainment. Explore the town's historic places and enjoy the rejuvenating effects of nearby hotsprings. Whether you are indulging in spa experiences, body treatments or a round of golf, this locale offers a vibrant mix of activities. The picturesque lake and scenic surroundings enhance the experience, making it a perfect stop for travellers eager to immerse themselves in both culture and nature.

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 Stayz is a breeze

Are you keen to make savings on your next adventure? Being flexible with your travel dates can be advantageous, as prices often fluctuate. Additionally, opting for a longer stay can lead to substantial savings. To discover a Stayz property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental. We're here to help you find the ideal accommodation for your needs.

Stayz Trips: Planning made easy

Stayz’s pioneering Trip Board offers you a dedicated area to devise new journeys, pick up where you last left off, or review and organise your plans. Properties that you have previously saved or booked are now conveniently located under Potential, Upcoming, or Current Trips. To access Trip Boards, please visit: https://www.stayz.com.au/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)
  • 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)
  • Castiglion del Bosco Winery (13.2 mi / 21.3 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)
  • Terme Sant'Elena (7.4 mi / 11.8 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.
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.
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 Stayz.
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.
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.
Are all fees included in the Pienza holiday homes prices shown on Stayz?
Stayz 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.
Are there any Pienza holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Pienza holiday homes?
You can find great discounts on holiday homes in Pienza on Stayz, 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.
Can I change or cancel my Pienza holiday home booking on Stayz?
To find Pienza holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Pienza?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Pienza holiday home?
Book your Pienza holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Pienza?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Pienza to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.