Pienza vacation rentals

We found 1,688 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.
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Find out more about Pienza

Find out more about Pienza

Why visit Pienza

  1. Picturesque Piazza: Stroll through the charming main square, surrounded by beautiful architecture and lively cafés.
  2. Rich Cultural Heritage: Discover historical landmarks and serene monasteries that showcase Pienza's artistic legacy.
  3. Soothing Hot Springs: Relax in nearby natural hot springs, perfect for unwinding after a day of exploration.
  4. Scenic Landscapes: Enjoy breathtaking views of the Tuscan countryside, ideal for photography and nature walks.
  5. Diverse Accommodation: Choose from luxurious villas to cozy apartments, ensuring a comfortable stay in this idyllic town.

Popular types of accommodation in Pienza

Discover the charm of Pienza with our diverse selection of vacation rentals. Whether you’re seeking a luxurious villa, a cozy apartment, or a private vacation home, we have options to suit every traveller. Our platform offers transparent information on the best accommodations, including top hotels and picturesque farmhouses in Pienza. Let us help you find the perfect place to relax and enjoy your Italian getaway.

  • Villas: The top choice for vacation rentals in Pienza, offering spacious living and luxurious amenities for an unforgettable stay.
  • Apartments: A popular option for travelers, these provide a home-like atmosphere with convenient access to local attractions.
  • Houses: Ideal for families or groups, these homes offer privacy and comfort during your Tuscan getaway.
  • Cottages: A charming and quaint option, perfect for those seeking a cozy retreat in the heart of the countryside.
  • Caravan Parks: A unique alternative for adventurous spirits, offering a chance to connect with nature while enjoying essential amenities.**

Top attractions in Pienza

Pienza, a charming destination in Tuscany, is perfect for outdoor enthusiasts and culture lovers alike, making it an ideal romantic getaway. Explore highlights such as the picturesque piazza, serene monasteries, and soothing hot springs. Whether you're discovering the quaint streets of Pienza or enjoying the stunning surroundings, there's something for every type of traveller. Make the most of your visit by immersing yourself in the rich culture and beautiful landscapes that this enchanting town has to offer.

  1. Pienza Cathedral: A stunning example of Renaissance architecture, Pienza Cathedral boasts beautiful frescoes and an impressive altar. Its serene atmosphere invites reflection and appreciation of its cultural significance.
  2. Historic Centre of Pienza: A UNESCO World Heritage site, this charming historic village features narrow streets, exquisite buildings, and a rich cultural vibe that reflects the essence of Tuscany's heritage.
  3. Piazza Grande: Located 8.0km from Pienza, this lively square is the heart of local life, surrounded by shops and cafés, offering a perfect spot to enjoy the vibrant city atmosphere.

Things to do recommended for couples

For a romantic getaway in Pienza, visit the luxurious Chapel of Our Lady of Vitaleta, unwind at the serene Terme di Chianciano spa, and indulge in wine tasting at the charming Consorzio del Vino Nobile di Montepulciano. Each offers a unique blend of romance and relaxation.

Things to do recommended for families

Families visiting Pienza can have an exhilarating time at the Siena Circuit, a karting track located 30.6km away. With its adventure vibes, it's perfect for thrilling races and creating unforgettable memories together!

Things to do recommended for groups

Groups visiting Pienza can enjoy a shopping spree at the Valdichiana Outlet Village, just 19.3km away, or explore the local charm at RI Crea RE. For those who love sports, the Golf Club Valdichiana offers a beautiful outdoor setting, also 19.3km from Pienza.

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

If you're travelling with a group, family, pets, or planning an extended stay, be sure to prioritise your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Pienza with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Pienza with young kids: Traveling with young children can present its own set of challenges. It’s important to prioritize their comfort and safety, along with ensuring that there are age-appropriate amenities available, such as a private pool. Additionally, it's wise to think about how close you are to attractions that are suitable for families.
  • Taking your pets with you to Pienza: For many families, a vacation wouldn’t feel complete without their furry companion. If that resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that all members of the family feel comfortable and at home.
  • Planning for a long term stay visiting Pienza: If you're seeking vacation rentals with great deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can easily discover and save on monthly rentals. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search as well.

Where to stay in Pienza

Pienza, a charming city in Tuscany, offers an enchanting blend of outdoor adventures, rich culture, and romantic escapes. As you explore beautiful Pienza, you'll be captivated by its stunning scenery and historical landmarks. Nearby, the serene landscapes and friendly atmosphere invite relaxation and discovery. Don't miss the chance to visit nearby towns that enhance your Tuscan experience, making your vacation truly unforgettable in this idyllic region of Italy.

  • Montepulciano: Nestled approximately 9.7km from Pienza, Montepulciano is a charming hilltop town renowned for its rich culture and stunning landscapes. Visitors are drawn here for a romantic getaway, outdoor adventures, and a taste of local traditions. The town boasts several spas and body treatment centres, perfect for indulging in relaxation. Stroll through its historic streets, where you can admire landmarks like ancient monuments and serene lakes, offering picturesque views ideal for photography enthusiasts. The vibrant shopping area provides a delightful experience for those looking to take home unique souvenirs.
  • San Quirico d'Orcia: Located about 6.4km from Pienza, San Quirico d'Orcia is a quaint town that promises a mix of outdoor activities and romantic encounters. Known for its beautiful countryside, this area is perfect for hiking and exploring nature. Visitors can enjoy luxurious spa services and unwind at country private clubs. The local attractions include historic sites and soothing hotsprings, making it a perfect spot for relaxation and cultural exploration. San Quirico d'Orcia offers a peaceful atmosphere that allows you to appreciate the stunning Tuscan landscape.
  • Montalcino: Situated approximately 16.1km from Pienza, Montalcino is famed for its breathtaking views and rich historical significance. This city is a haven for romance, entertainment, and outdoor activities, making it a popular destination for couples and adventure seekers alike. Visitors can indulge in spa treatments and explore the great outdoors. The area is home to several historic places and sites, including a vibrant tourist precinct where you can sample local wines, particularly the renowned Brunello di Montalcino. Montalcino's enchanting atmosphere is sure to leave a lasting impression.

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 simple

Are you hoping to save on your upcoming adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that aligns with your budget, make use of our filters to sort 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 provides a convenient platform for you to plan new adventures, refine your travel arrangements, or manage your existing bookings. The properties you've saved or reserved are neatly categorized into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please 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:

  • Consorzio del Vino Nobile di Montepulciano (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 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)
  • 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 vacation rental?
Monticchiello is one of the most popular locations where you can book a Vrbo vacation 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 vacation rental accommodation in Pienza?
The most sought-after types of vacation 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 vacation rental in Pienza?
Different things affect how much you pay for a vacation rental in Pienza, including the length of stay, season and type of property. Still, all of our vacation 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 vacation 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 vacation 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 vacation 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 vacation 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 traveling solo, with your significant other or as a family group, Vrbo will help you find a vacation home that suits your tastes with all the options you need.
Are there large group vacation rentals in Pienza?
Pienza has 42 vacation 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 vacation rentals in Pienza that welcome kids?
Bring the whole family together for fun-filled adventures in Pienza at one of our 101 family-friendly vacation 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 favorite.
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 vacation 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 vacation rental is ideal if you’re traveling 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 vacation rentals in Pienza?
Gather your nearest and dearest and enjoy peace, privacy and comfort in one of the 20 two-bedroom vacation homes Pienza has to offer.
Are there vacation rentals with WiFi in Pienza?
You can pick from 39 vacation 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 vacation rentals with air conditioning in Pienza?
Pienza has 52 vacation 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 vacation rental in Pienza?
The minimum age allowed can differ across properties on Vrbo, so look at the rules of the vacation rental in Pienza you’re interested in. But normally, it’s 16, 18 or 21.
How long can I rent a vacation rental in Pienza for?
The amount of time you can stay in a Pienza vacation 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 vacation homes may also offer weekly or monthly discounted prices, so you can stay longer for less money.

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