Pienza vacation rentals

We found 1,735 vacation rentals — enter your dates for availability

Select from 29 houses, 46 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.

Vacation rentals with weekly discounts - Pienza

Showing deals for:Sep 19 - Sep 26
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Find out more about Pienza

Find out more about Pienza

Why visit Pienza

  1. Stunning landscapes: Pienza is nestled in the picturesque Val d'Orcia, known for its rolling hills and vineyards.
  2. Historic charm: Wander through its quaint streets and explore beautiful churches and historic monasteries.
  3. UNESCO World Heritage site: Experience the cultural significance of Pienza, recognized for its architectural beauty and history.
  4. Outdoor adventures: Enjoy activities like the scenic Pienza to Montepulciano trail and various hiking opportunities.
  5. Diverse accommodations: Choose from luxurious villas to cozy apartments, ensuring a perfect stay tailored to your needs.

Popular types of accommodation in Pienza

Explore the charm of Pienza with a variety of vacation rentals that cater to every traveler's needs. Whether you're seeking a luxurious villa, a cozy apartment, or a private vacation home, Pienza accommodation options abound. Our platform connects you with the best Pienza vacation rentals, ensuring transparency and savings for your perfect getaway. Choose the ideal vacation rental that suits your style and enjoy the beauty of this enchanting destination.

  • Villas: The top choice for travelers seeking luxury and spacious accommodations in Pienza, perfect for families or groups.
  • Apartments: A popular option for those desiring a home-like atmosphere, offering convenience and independence.
  • Houses: Ideal for those who want a unique and personalized stay, suitable for families or couples.
  • Cottages: A delightful option for a cozy and quaint experience, often nestled in picturesque surroundings.
  • Caravan Parks: A budget-friendly choice for adventurous travelers looking to enjoy the outdoors while exploring Pienza.**

Top attractions in and around Pienza

Pienza, Tuscany is the perfect destination for outdoor enthusiasts and culture lovers alike. Explore the charming piazzas, historic monasteries, and beautiful churches while enjoying the romantic atmosphere. Don't miss the scenic Pienza to Montepulciano trail and consider day trips to nearby attractions like Palazzo Piccolomini. Whether you're ticking items off your bucket list or simply soaking in the local culture, Pienza offers an unforgettable experience for every traveler.

  1. Pienza Cathedral: Nestled in the heart of Pienza, this stunning cathedral boasts Renaissance architecture and rich cultural vibes, making it a must-visit for history enthusiasts and architecture lovers alike.
  2. Historic Centre of Pienza: A UNESCO World Heritage site, the historic center offers charming streets, beautiful squares, and a glimpse into the town's rich history and culture, perfect for leisurely exploration.
  3. Piazza Grande: Located 5 miles away, this vibrant square is the social hub of Pienza, featuring lively cafés and shops, where you can soak up the local culture and enjoy the picturesque surroundings.

Things to do recommended for couples

For a romantic getaway in Pienza, visit the serene Chapel of Our Lady of Vitaleta, indulge in wellness at Terme di Chianciano, and savor exquisite wines at Consorzio del Vino Nobile di Montepulciano. Each experience offers unique luxury, relaxation, and romance just a short drive away.

Things to do recommended for families

Families will have a blast at the Siena Circuit, a thrilling karting track located 19 miles from Pienza. With its adventure vibes, it's the perfect place for kids and adults alike to enjoy some friendly competition and create lasting memories together.

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

If you're planning a trip with a group, family, or pets, or if you're interested in extended stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Pienza with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Pienza with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, as well as provide suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Pienza: For many, a family vacation isn't truly fulfilling without their furry companion by their side. If that resonates with you, take a look at Vrbo listings that welcome pets. Many of these pet-friendly properties offer 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 with discounts 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 rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Pienza

Pienza, a charming gem in Tuscany, offers an unforgettable travel experience with its stunning landscapes and rich culture. Explore the picturesque Val d'Orcia, renowned for its rolling hills and vineyards, or wander through the quaint streets of this UNESCO World Heritage site. With a romantic atmosphere, friendly locals, and a blend of luxury and tranquility, Pienza is the perfect base for discovering the beauty of the Tuscany countryside and indulging in an enchanting holiday in Italy.

  • Montepulciano: Located 6 miles from Pienza, Montepulciano is a charming hilltop town renowned for its Renaissance architecture and stunning panoramic views of the surrounding vineyards and valleys. Visitors flock here for a romantic atmosphere complemented by cultural experiences, such as wine tastings and local festivals. Popular attractions include historic sites like the Piazza Grande and the impressive Palazzo Comunale. Don't miss the chance to unwind at one of the local spas, where you can indulge in rejuvenating body treatments after a day of exploring the quaint shopping areas.
  • San Quirico d'Orcia: Just 4 miles from Pienza, San Quirico d'Orcia is a delightful town that offers a perfect blend of outdoor adventures and romantic settings. Known for its picturesque landscapes and vibrant historic center, visitors can explore the charming streets and relax in the local spas. The town is famous for its beautiful gardens and the Hotspring of Bagno Vignoni, providing a unique experience for those seeking relaxation and entertainment. The nearby scenic countryside is perfect for hiking and enjoying the stunning views of the rolling hills.
  • Montalcino: Situated 10 miles from Pienza, Montalcino is famed for its exquisite Brunello wine and captivating medieval architecture. This hilltop city provides an idyllic escape for romance and outdoor fun, with numerous vineyards and olive groves to explore. Visitors can tour historic sites, such as the impressive Fortress of Montalcino, and enjoy the vibrant tourist precinct filled with local artisan shops and restaurants. The region's natural beauty makes it an excellent spot for outdoor activities, ensuring an unforgettable experience in Tuscany.

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 SunnyAverageAverage
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 LowSlightly Low
December42.1°F (5.6°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is a breeze

Planning your next adventure and hoping to save some money? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay to unlock even greater savings. To discover a Vrbo property that aligns with your budget, utilize our filters to narrow down options by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve an eligible Vrbo for your group getaway and earn OneKeyCash™ on your booking. Being the planner definitely has its perks! By enrolling in our travel rewards program, One Key, you can immediately access member discounts and earn as well as redeem OneKeyCash™ on qualifying reservations. Sign up today and start enjoying the savings!

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a dedicated area to plan new trips, pick up where you left off, or easily view and manage your travel plans. You can now find properties you've saved and booked under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/en-ca/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:

  • 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)
  • 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 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)
  • 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)

Frequently asked questions

How much does it cost to rent a vacation rental in Pienza?
A range of factors can determine what you'll pay for a vacation rental in Pienza, including the type of property, season and length of stay. Still, all of our vacation homes have something in common --- exceptional value. Simply enter your travel dates to find your perfect match.
How much does it cost to rent a beach house in Pienza?
The average price for a vacation rental close to the beach in Pienza depends on when you're traveling and the style and size of property you're looking for. You can find prices quickly and easily on Vrbo by entering your preferred travel dates. Then use the handy filter tool to choose the number of bedrooms and amenities important to you, such as WiFi, a pool and air conditioning.
What are the top attractions for families in Pienza?
There are plenty of awesome things to see and do with the family in Pienza, including:
  • Artemisia Gallery
  • Palazzo Comunale
  • Pienza Cathedral

How old do you have to be to rent a vacation rental in Pienza?
We recommend you check with the Pienza vacation home you're considering on Vrbo as the minimum age varies. However, normally it's 16, 18 or 21.
How long can I rent a vacation rental in Pienza for?
The length of time you can rent a vacation rental in Pienza is up to the property. Simply enter your desired dates to look at a list of options offering extended stays. With lots of creature comforts such as kitchens and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to find a perfect place to call your home away from home in Pienza.
Does Vrbo offer discounts for vacation homes in Pienza?
In Pienza, you'll find some fantastic bargains and discounts for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether you're after a short getaway or an extended stay, we've got plenty of options to suit every kind of traveler.

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