Pienza holiday lettings

We found 1,748 holiday rentals — enter your dates for availability

Select from 29 houses, 48 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:17 Oct - 24 Oct
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Why visit Pienza

  • Stunning architecture: Explore the historic centre of Pienza, a UNESCO World Heritage Site, featuring beautiful Renaissance buildings and the impressive Pienza Cathedral.
  • Charming piazzas: Relax in picturesque squares where you can enjoy local cuisine and soak in the vibrant atmosphere.
  • Scenic landscapes: Wander through the breathtaking Val d'Orcia countryside, perfect for leisurely strolls and photography.
  • Cultural heritage: Immerse yourself in the rich history by visiting peaceful monasteries and churches scattered throughout the town.
  • Variety of accommodations: Choose from luxurious villas to cosy apartments, ensuring a memorable stay in this enchanting destination.

Popular types of accommodation in Pienza

Discover the charm of Pienza with a variety of holiday rentals to suit every need. Whether you're seeking a luxurious villa, a cozy private vacation home, or a stylish apartment, we have the perfect accommodation for your stay in Pienza. Our offerings include stunning suites and family-friendly options, ensuring a memorable getaway in this enchanting Tuscan town. Explore your ideal Pienza villa rental or apartment today!

  • Villas: The top choice for holidaymakers in Pienza, offering spacious and luxurious living with stunning views of the Tuscan countryside.
  • Houses: A popular option for families or groups, providing a home-like atmosphere with all the comforts you need.
  • Apartments: Ideal for couples or solo travellers, these cosy accommodations are conveniently located near local attractions.
  • Cottages: Quaint and charming, perfect for a romantic getaway or a peaceful retreat in a rural setting.
  • Caravan Parks: A budget-friendly option, great for those who enjoy an outdoor lifestyle and community atmosphere.**

Top attractions in and around Pienza

Pienza, nestled in the stunning Val d'Orcia, is perfect for a romantic getaway steeped in culture and outdoor experiences. Key attractions include the historic centre, the Pienza Cathedral, and charming piazzas, alongside peaceful monasteries and churches. Visitors can enjoy leisurely strolls through the picturesque streets, soaking in the rich heritage and breathtaking landscapes that define this UNESCO World Heritage Site.

  • Pienza Cathedral: A stunning example of Renaissance architecture, Pienza Cathedral boasts intricate designs and cultural significance. Its serene atmosphere invites reflection, offering visitors a glimpse into the spiritual life of the town.
  • Historic Centre of Pienza: This UNESCO World Heritage site is a charming village filled with narrow streets, beautiful piazzas, and quaint shops. The rich history and culture create a unique ambience that transports visitors back in time.
  • Dome of Montepulciano: Located 3.1km from Pienza, this impressive church features a magnificent dome and stunning artwork. The serene environment provides a peaceful retreat and an opportunity to appreciate local religious heritage.

Things to do recommended for couples

For a romantic getaway in Pienza, explore the serene Chapel of Our Lady of Vitaleta, indulge in relaxation at Terme di Chianciano spa, and enjoy a delightful wine tasting at Cantina Contucci. Each experience offers a touch of luxury, wellness, and romance perfect for couples.

Things to do recommended for families

Families will have a thrilling time at the Siena Circuit, a karting track located 11.8km from Pienza, where adventure awaits. This exciting experience promises fun and laughter for all ages, making it a perfect outing for the whole family.

Things to do recommended for groups

Explore the Valdichiana Outlet Village for a delightful shopping experience, then visit RI Crea RE for unique local finds. For those who enjoy sports, the Golf Club Valdichiana offers a fantastic outdoor golfing experience, all just 7.5km from Pienza.

Booking with Vrbo is simple

Are you hoping to cut costs on your next getaway? It might be worth being flexible with your travel dates, as prices can vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Where to stay near Pienza

Pienza, nestled in the heart of Tuscany, offers a delightful blend of outdoor adventures and rich cultural experiences. Known for its stunning scenery and romantic atmosphere, this charming city is perfect for those seeking a relaxing getaway. Explore the historical streets, visit beautiful villas, and immerse yourself in the friendly local vibe. Don't miss the chance to discover nearby towns that enhance your Tuscany experience, providing a perfect backdrop for a memorable holiday.

  • Montepulciano: Nestled approximately 3.7km from Pienza, Montepulciano is a charming hilltop town renowned for its rich cultural heritage and stunning vistas. The city's cobbled streets are lined with Renaissance palaces, making it a delightful destination for those seeking a romantic and culturally themed experience. Visitors can indulge in rejuvenating spa treatments while enjoying the local wines, particularly the famed Vino Nobile. Montepulciano's historic landmarks, including the impressive Piazza Grande and ancient churches, are must-sees for history buffs and leisurely strollers alike.
  • Montalcino: Located about 6.2km from Pienza, Montalcino is celebrated for its breathtaking landscapes and vibrant wine culture. This picturesque town invites travellers to explore its romantic charm and numerous outdoor activities. Montalcino is home to the renowned Brunello di Montalcino wine, and visitors can partake in vineyard tours and tastings. The town's historic sites, including the impressive fortress of Fortezza di Montalcino, add to its allure, making it a fantastic spot for those keen on entertainment and history.
  • San Quirico d'Orcia: Just 2.5km from Pienza, San Quirico d'Orcia is a quaint town that offers an enchanting blend of outdoor activities and romantic experiences. Known for its stunning landscapes, visitors can enjoy leisurely walks through the beautiful countryside or relax in the local spas. The town's historic places, such as the charming Collegiata Church and the nearby hot springs, provide a unique glimpse into the region’s past, making it an ideal destination for those seeking both relaxation and exploration.

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

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

Regardless of whether you’re travelling with a group, as a family, with your pets, or seeking longer stays, be sure to apply the appropriate filters that align with your priorities. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Pienza with a group: Think about how many bedrooms you'll require, as well as any amenities you might desire, like a fully equipped kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these features and many more on Vrbo.
  • Traveling to Pienza with young kids: Journeying with young children can present its own set of 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 many, a family holiday isn’t truly finished without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. The majority of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels completely at home.
  • Planning for a long term stay visiting Pienza: If you’re in search of holiday rentals offering discounts for stays of a month or more, you’ve come to the perfect spot. By using the appropriate filter, you can effortlessly discover and save on monthly accommodations. You might also want to consider including amenities such as a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a handy platform for you to plan your next adventures, resume your previous searches, or manage your travel arrangements. You can easily view your saved or booked properties, which are thoughtfully organised under Potential, Upcoming, or Current Trips. To begin exploring 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:

  • Cantina del Redi (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?
Monticchiello is one of the most popular locations where you can book a Vrbo 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 rental accommodation in Pienza?
The most sought-after types of holiday rentals in Pienza are villas. Ready for more choices? Vrbo 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 rental in Pienza?
Different things affect how much you pay for a holiday rental 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 Vrbo and the number of guests to view holiday rental 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 rentals 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 rentals on Vrbo. 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 rentals and every day can be a pool day. Simply enter your travel dates into Vrbo, then use the "pool" filter to find the perfect place to make a splash!
What are popular rental amenities in Pienza?
A sauna, a nearby river and an electric car charging station are the most popular rental amenities in Pienza. Whether you're travelling solo, with your significant other or as a family group, Vrbo will help you find a holiday home that suits your tastes with all the options you need.
Are there large group holiday rentals 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 rentals in Pienza that welcome kids?
Bring the whole family together for fun-filled adventures in Pienza at one of our 101 family-friendly holiday rentals. 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 rentals in Pienza?
Pienza has 15 one-bedroom rentals on offer. Often situated in well-regarded areas due to their compact size, a one-bedroom holiday rental 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 rentals 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 rentals with WiFi in Pienza?
You can pick from 39 holiday rentals 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 Vrbo.
How can I find holiday rentals with air conditioning in Pienza?
Pienza has 52 holiday rentals where you'll be able to relax in air-conditioned comfort. To book a property on Vrbo 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 rental in Pienza?
The minimum age allowed can differ across properties on Vrbo, so look at the rules of the holiday rental in Pienza you're interested in. But normally, it's 16, 18 or 21.
How long can I rent a holiday rental in Pienza for?
The amount of time you can stay in a Pienza holiday rental 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.