Discover a selection of 1,500 vacation rentals in Pienza, IT that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $83 per night, and villas and houses are popular options for a stay in Pienza. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Pienza
Destination guide

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, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Things to do

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:

  • Enoteca Di Ghino (0.1 mi / 0.1 km)
  • 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)
Natural features

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:

  • 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)
  • Baths of San Filippo (10.2 mi / 16.5 km)
  • Monte Amiata (13.3 mi / 21.5 km)

What are the top vacation rentals in or near Pienza?

Whether you're seeking a cozy retreat for you and your sweetie or somewhere spacious to fit the family, you'll find some top vacation rentals in and around Pienza. Here are a couple we think you'll like:

  • Make the most of handy amenities like an electric kettle and a hair dryer at "Farmhouse In The Heart Of The Real Chiantishire". Situated around 35 miles from Pienza, this leading option has 2 bedrooms and is a hit with guests.
  • Another enticing choice is "La Casina Toscana - Near Center", which is around 5 miles from Pienza. With 3 bedrooms, nearby museums and books, it has everything you need to keep you comfortable and content.

For even more great options, use the search bar at the top of the page to find the perfect Pienza vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Pienza?

Your Monday to Friday will be much easier to face if you've got something fabulous planned for the weekend. Give yourself something fun to look forward to by locking in one of these top weekend getaways in or near Pienza:

  • Book a stay at "Apartment In The Historic Center Of Pienza", around 1 mile to the northwest of Pienza, and you've got yourself the best kind of weekend break. You'll have nature spots like Piscine Termali Theia and Cascate del Mulino on your doorstep and conveniences like internet services and a kitchen to make the most of.
  • "Holiday Vacation Large Villa Rental Italy" is also perfect for a whirlwind getaway. Located approximately 1 mile to the east of Pienza, this vacation rental offers amenities such as a phone and a washing machine. Riserva Naturale Regionale Valle dell'Inferno e Bandella and La Foce should be on your sightseeing list if you stay here.

Can I find studio apartments for rent in and around Pienza?

Discover the energy and culture of Pienza from the comfort of a studio apartment. Whether you're eager to get away on your own or live it up with a few friends, you'll find the ideal studio apartment for rent in or near Pienza:

  • Make "Apartment In The Historic Center Of Pienza" your home for a few days or more. This top vacation rental comes with amenities including shopping and coffee and tea making facilities.
  • Another tempting choice is "Il Focolare" Superior Apartment In Monticchiello". Take advantage of free WiFi, nearby museums and other handy amenities during your getaway.

With the money you save on your studio apartment, you'll be able to discover more of Pienza. Cultural sights like Museum of Sacred Art in Val d’Arbia and National Museum of Archaeology will help you better understand the personality of this destination.

Can I find short term rentals in or near Pienza?

Just because you only have a few short days off work doesn't mean you have to spend it in a characterless hotel room. Go on vacation but still have the comforts of home at one of these short-term rentals in or around Pienza:

  • Located close to the center of Pienza, "Holiday Vacation Large Villa Rental Italy" is ideal for a quick getaway. While you're around, make sure you get to leading sights like Monte Oliveto Maggiore Abbey and La Porta Gallery.
  • "Lavanda Apartment Overlooking The Val D'orcia" is another appealing option. Don't forget to add Museum of Sacred Art in Val d’Arbia and Museo della Mezzadria to your list when it's time to sightsee.

What are the best romantic weekend getaways in or near Pienza?

Whether spent in a rustic cabin or a luxury condo, a romantic weekend getaway is a wonderful way to add some zing to your relationship. Whisk your sweetheart away for a couple of leisurely days at one of these escapes in or near Pienza:

  • Around 5 miles from Pienza, "La Casina Toscana - Near Center" is the perfect place for lovestruck couples. Beauty services and a fireplace are just some of the amenities here.
  • Alternatively, spend your break enjoying each other's company at "Podere Lamino With Swimming Pool", around 1 mile from Pienza. Winery tours and beauty services will help ramp up the romance.

What are the best large group vacation rentals in or near Pienza?

Big groups mean big fun. They also mean finding a place that'll effortlessly fit your entire crew. Browse our large group vacation rentals in or around Pienza and get everyone together under the same roof:

  • You'll have loads of space to move around at "Luxury Farmhouse In Tuscany, Val D'orcia With Two Large Independent Apartments". Around 2 miles southeast of Pienza, this sizable property has 6 bedrooms accommodating up to 12 guests. Quality amenities include a fireplace and a swimming pool.
  • Nothing is more important than spending time with the people you love, and "Whole Big Tuscan Villa With Pool And Vineyards In The Heart Of Tuscany" is the perfect place to do that. Located around 2 miles to the southeast of Pienza, as many as 20 guests can stay in this vacation rental which has 9 bedrooms. A swimming pool and a fireplace are among the numerous amenities you'll have at hand.

What are the best houses for rent with a pool in or near Pienza?

Of all the amenities a vacation rental can offer, a pool is hands down the most fun. Have a look at these houses for rent with a pool in or near Pienza and spend your time splashing around. Just remember to bring your flamingo floatie:

  • Say hello to "The House In The Village - Angelica Apartment", where your top priority will be relaxing by the pool. Amenities such as a fridge and a kitchen help make this escape a guest favorite.
  • Spend lazy vacation days swimming or catching a few peaceful moments beside the water at "The House Annavittoria / Garden In The Village Of Monticchiello". This vacation rental is another guest favorite and features a barbecue grill, a dishwasher and more.

Don't know how to pack your suitcase for your Pienza break? This leading destination has an oceanic climate. During the summer months, expect average temperatures of between 60 ºF and 85 ºF. Check out our range of Pienza vacation rentals by using the search bar at the top of the page. Simply adjust the filters to get more ideas about where to stay.

What are the best large family vacation rentals in or near Pienza?

A family get-together should be a memorable one. Whether you're planning a fun escape with the kids or a reunion with the extended family, Vrbo's large family vacation rentals in or near Pienza offer a comfy home away from home with enough space for everyone:

  • Get your nearest and dearest together at "Large Villa - Charming Provencal Village", which has 4 bedrooms sleeping up to 8 guests. This getaway is located 1 mile to the southeast of Pienza and features amenities such as free toiletries and a nearby laundromat.
  • "Holiday Vacation Large Villa Rental Italy" is another popular option. It's about 1 mile to the east of Pienza, has 7 bedrooms and can accommodate up to 14 guests. Handy amenities here include a living room and a phone.

If you want to see some family-friendly attractions around the area, you won't have far to go. Palazzo Pubblico, Palazzo Piccolomini and Monteriggioni Castle promise lots of fun for all the gang.

What are the best large houses to rent with indoor pools in or near Pienza?

Add some serious grandeur to your vacation by booking somewhere with an indoor pool. These gorgeous large houses in or near Pienza have a swimming space that's all your own, along with lots of room for whoever is fortunate enough to be coming with you:

  • Book a few nights at "Villa I Cipressini Tuscany Private Luxury Heated Pool Spa Gym Pienza Siena" and while away your days poolside. This popular option has 5 bedrooms that sleep up to 10 guests and a range of other top-notch amenities. A swimming pool and a garden are among them.
  • Alternatively, make a booking at "Private Villa With Sauna, A/c, Wifi", which has 13 bedrooms and caters for up to 26 guests. Along with that fancy pool hidden away inside, a sauna and a swimming pool will help keep everybody happy and comfortable.

If you'd like to see even more options, use the search bar at the top of the page and adjust the filters to find the Pienza vacation rental that's perfect for your needs.

Are there one-bedroom vacation rentals in or near Pienza?

Romantic retreats, business trips or adventures of the solo kind — a one-bedroom vacation property is an ideal solution for a multitude of occasions. One of these options in or near Pienza is sure to impress:

  • Great things come in little packages, and "Apartment In The Historic Center Of Pienza" is a fabulous example of this. This one-bedroom vacation rental is just a short distance from the center and offers amenities like a kitchen and off-street parking options.
  • Also within easy reach of all the excitement of Pienza, "Il Focolare" Superior Apartment In Monticchiello" is another popular one-bedroom option. After a big day of seeing the sights, return and take advantage of a garden and a fireplace.