Photo by Robert Bilos

Holiday Rentals in Pienza

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Our top choices for Pienza holiday rentals

Townhouse in Pienza

TuscanyLettings Studio&Room
10.0 out of 10, Exceptional, (1)
"メイン通りの好立地。 客室は豪華でエレガント。 ウェルカムキットも良く、アメニティも良好。 次回も必ず利用したい。 スタッフの方、いろいろありがとうございました。"
Japan
keita
The price is €93
includes taxes & fees
9 Jan - 10 Jan 2026
TuscanyLettings Studio&Room

Townhouse in Pienza

Affitacamere Maria Gabriella
9.8 out of 10, Exceptional, (51)
"This property has a lovely view, great garden, attentive staff with good breakfast. Stayed in the cottage and the patio was very sunny and relaxing. "
United States
Lenise
Affitacamere Maria Gabriella

Townhouse in Pienza

PienzaLettings Suites
10.0 out of 10, Exceptional, (1)
"Fantastic room in the city center, close to everything in Pienza"
Norway
Tom
The price is €84
includes taxes & fees
6 Jan - 7 Jan 2026
PienzaLettings Suites

Apartment in Pienza

Casa Gioia - Casa Olivieri
The price is €94
includes taxes & fees
6 Jan - 7 Jan 2026
Casa Gioia - Casa Olivieri

Residence in Pienza

Hotel San Gregorio
3.0 star property
9.4 out of 10, Exceptional, (134)
"Such friendly staff, loved Pienza and the property was such a good location! "
United Kingdom
Bethan
The price is €176
includes taxes & fees
4 Jan - 5 Jan 2026
Hotel San Gregorio
The price is €100
includes taxes & fees
28 Jan - 29 Jan 2026
Apartment 'La Dimora Di Pienza in Val D'Orcia' with Wi-Fi
The price is €100
includes taxes & fees
28 Jan - 29 Jan 2026
Finestra Dell'Angelo in Pienza – Elegant Apartment with Stunning Views

Apartment in Pienza

Finestra Dell'Angelo
10.0 out of 10, Exceptional, (1)
"Our family of twelve, aged 8 to 80 years, stayed in three separate apartments. Two were in the same building on separate floors, and the third was a 5 minute walk away. All units were located in beautiful downtown Pienza with many dining, shopping and tourist sites within an easy walk for all members of the family. For a family of Midwest Americans staying in the middle of an old city walkable to nearly everything was w amazing. The separate units worked out fine for us as walking the town was...
United States
James M.
Finestra Dell'Angelo
10.0 out of 10, Exceptional, (3)
"Wonderful views, accommodating hosts"
United States
Pete and Alison C.
The price is €272
includes taxes & fees
4 Jan - 5 Jan 2026
Il Podere di Casa Rossa Pienza
The price is €220
includes taxes & fees
2 Jan - 3 Jan 2026
Studio 'La Casina Mag' with Wi-Fi

Townhouse in San Casciano dei Bagni

FonteLiving
10.0 out of 10, Exceptional, (5)
"Comfortable apartment in quiet block. Nicely furnished excellent housekeeping nice spacious bathrooms great view from the terrace."
United Kingdom
R
The price is €73
includes taxes & fees
11 Jan - 12 Jan 2026
FonteLiving

Townhouse in Chiusi

La Piccola Locanda
8.8 out of 10, Excellent, (8)
"This was a great place to stay for two nights in late October and to take out and back day trips by train to Siena and Florence on back-to-back days. Very close to the train station - very convenient. Breakfast in the restaurant in the morning was small, but good. Highly recommend this location! It's small, but serviced and supported very well by the staff at the restaurant. "
United States
Jeffery
La Piccola Locanda

Townhouse in Cetona

La Locanda Di Cetona
9.2 out of 10, Wonderful, (5)
"A lovely hotel and very welcoming staff. Cetona is a delight. "
Australia
Julian
La Locanda Di Cetona

Residence in Trequanda

Abbadia Sicille Relais
4.0 star property
8.8 out of 10, Excellent, (166)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is €71
includes taxes & fees
19 Jan - 20 Jan 2026
Abbadia Sicille Relais

Residence in Seggiano

La Dimora di Dida
The price is €75
includes taxes & fees
6 Jan - 7 Jan 2026
La Dimora di Dida

Aparthotel in Sovicille

Tuscasì Aparthotel
9.2 out of 10, Wonderful, (25)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is €77
includes taxes & fees
10 Jan - 11 Jan 2026
Tuscasì Aparthotel

Holiday Home in Acquapendente

Agriturismo San Filippo
9.0 out of 10, Wonderful, (13)
"Excellent experience!"
United States
Richard
Agriturismo San Filippo
The price is €6,450
includes taxes & fees
3 Jan - 4 Jan 2026
VILLA BRUNELLO - Luxury Country Retreat 10 minutes to Montalcino
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pienza Hotel Reviews

Find out more about Pienza

Everything you need to know about Pienza holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pienza holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pienza holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Pienza holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pienza. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pienza holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pienza holiday rentals we have selected for you start as low as €71 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pienza rentals

At Expedia, we put the best Pienza holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Pienza rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pienza holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pienza. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Pienza?

Yes, there are holiday rentals in Pienza close to RI Crea RE, or you can select a more secluded option if you're looking for a relaxing stay. Pienza is known for its churches and wineries. Make sure you have time to check out the temples while you're in the area.

How many holiday rentals are there in Pienza?

Expedia has 31 holiday rentals for your stay in Pienza.

What’s there to see and do in Pienza?

Cultural attractions include Palazzo Borgia and Artemisia Gallery, whereas Historic Centre of Pienza and Val di Chiana are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Palazzo Piccolomini and Pienza Cathedral.

What’s a holiday rental in Pienza like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Pienza. Holiday rentals feature amenities such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.