Pienza holiday rentals

We found 1,671 holiday rentals — enter your dates for availability

Select from 27 houses, 44 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.
  • Peace of mind

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  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

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)
  • Valdorcia Terre Senesi (5.7 mi / 9.2 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)
  • 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)
  • 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 home?
Monticchiello is one of the most popular locations where you can book a Stayz holiday home in Pienza. Take a look at our relaxing stays and then prepare to experience the best of this destination.
What is the most popular type of holiday home accommodation in Pienza?
The most sought-after types of holiday homes in Pienza are villas. Ready for more choices? Stayz offers a variety of options to match the needs of our guests, so you'll see properties in all sizes and shapes. The perfect fit is waiting for you — get yours today.
How much does it cost to rent a holiday home in Pienza?
Different things affect how much you pay for a holiday home in Pienza, including the length of stay, season and type of property. Still, all of our holiday homes have one thing in common — incredible value. Just enter your travel dates to find your home away from home.
How much does it cost to rent a beach house in Pienza?
Prices for beach houses in Pienza can vary depending on the style and size of the property and when you plan to travel. Simply enter your travel dates into Stayz and the number of guests to view holiday home options and prices. From there you can use our filter tool to tailor your search results by ratings, nearby activities and more.
Are there pet-friendly holiday homes in Pienza?
Pack a suitcase for the pup in your life because Pienza has 102 stays that throw open their doors to pets. Let your four-legged pal get in on the family fun at one of our pet-friendly holiday homes on Stayz. Simply enter your destination and dates, then check our "Pets allowed" filter box.
Can I rent a house with a pool in Pienza?
Grab your swimming gear and inflatable lounger, because there are 75 houses with a private pool in Pienza. Unwind at one of these sought-after holiday homes and every day can be a pool day. Simply enter your travel dates into Stayz, then use the "pool" filter to find the perfect place to make a splash!
What are popular home amenities in Pienza?
A sauna, a nearby river and an electric car charging station are the most popular home amenities in Pienza. Whether you're travelling solo, with your significant other or as a family group, Stayz will help you find a holiday home that suits your tastes with all the options you need.
Are there large group holiday homes in Pienza?
Pienza has 42 holiday homes that can host 10 or more people. These properties come with all the space you need to enjoy good times with your nearest and dearest.
Are there holiday homes in Pienza that welcome kids?
Bring the whole family together for fun-filled adventures in Pienza at one of our 101 family-friendly holiday homes. These stays come with amenities that are ideally suited to trips with children, like dining rooms, bunk beds and pools. Simply check the "Properties good for families" filter and select your favourite.
What are the top attractions for families in Pienza?
Keep the kids occupied at these fun family-friendly attractions in Pienza:

  • Piscine Termali Theia
  • Terme di Montepulciano Spa
  • Palazzo Piccolomini

Are there one-bedroom holiday homes in Pienza?
Pienza has 15 one-bedroom homes on offer. Often situated in well-regarded areas due to their compact size, a one-bedroom holiday home is ideal if you're travelling with your partner or a friend. And with comforts such as air conditioning and more privacy than a standard hotel, you'll be able to kick back and relax while sightseeing around this exciting destination.
Can I find two-bedroom holiday homes in Pienza?
Gather your nearest and dearest and enjoy peace, privacy and comfort in one of the 20 two-bedroom holiday homes Pienza has to offer.
Are there holiday homes with WiFi in Pienza?
You can pick from 39 holiday homes with WiFi in Pienza. If you want to disconnect from daily life during your trip, but still need to be connected to the internet, these getaways are for you. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Pienza?
Pienza has 52 holiday homes where you'll be able to relax in air-conditioned comfort. To book a property on Stayz that provides this amenity, enter your desired travel dates and use the handy filters to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Pienza?
The minimum age allowed can differ across properties on Stayz, so look at the rules of the holiday home in Pienza you're interested in. But normally, it's 16, 18 or 21.
How long can I rent a holiday home in Pienza for?
The amount of time you can stay in a Pienza holiday home for is down to each property. Simply enter your dates of travel to find options offering extended stays. They feature all you need to make your extended getaway more enjoyable and convenient, such as laundries and air conditioning. Some holiday homes may also offer weekly or monthly discounted prices, so you can stay longer for less money.