A historic square with a prominent tower and statues.

Pienza Holiday Rentals

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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Pienza holiday rentals

Laptop workspace, iron/ironing board, free WiFi

1. TuscanyLettings Studio&Room

TuscanyLettings Studio&Room
Pienza
10.0 out of 10, Exceptional, (3 reviews)
"Lugar maravilhoso, localização perfeita, super limpo e aconchegante."
Brazil
Lucas
The price is HK$763
HK$875 total
includes taxes & fees
31 Jul - 1 Aug
TuscanyLettings Studio&Room
Terrace/patio

2. PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (5 reviews)
"Fantastic room in the city center, close to everything in Pienza"
Norway
Tom
The price is HK$811
HK$928 total
includes taxes & fees
31 Jul - 1 Aug
PienzaLettings Suites
Food and drink

3. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (152 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is HK$1,767
HK$1,997 total
includes taxes & fees
9 Aug - 10 Aug
Hotel San Gregorio
Exterior

4. Casa Gioia - Casa Olivieri

Casa Gioia - Casa Olivieri
Pienza
10.0 out of 10, Exceptional, (3 reviews)
"Good communication with management through WhatsApp. The taxi dropped us off one minute from the property. Very cozy top floor with only a few steps. The 2 bedroom unit is very comfortable, the kids enjoyed sleeping in the loft. Air conditioning worked very well. We had everything we needed, the location is wonderful. We really enjoyed our stay. Thank you!"
United States
Nancy
The price is HK$920
HK$1,048 total
includes taxes & fees
31 Jul - 1 Aug
Casa Gioia - Casa Olivieri
1 bedroom, iron/ironing board, WiFi

5. Finestra Dell'Angelo in Pienza – Elegant Apartment with Stunning Views

Finestra Dell'Angelo in Pienza – Elegant Apartment with Stunning Views
Pienza
8.0 out of 10, Very good, (1 review)
"Very nice property and easily walkable to all of Pienza. It was also a convenient base to explore the Tuscany region. The property was clean and the bed was comfortable. A lot of restaurants and shopping in less than a 5 minute walk. The photos of the apartment were accurate. I would add to the property description that parking is not at the property but public parking is nearby (for clarity).Overall, I was happy with my stay."
United States
Michael H.
The price is HK$1,053
HK$1,376 total
includes taxes & fees
31 Jul - 1 Aug
Finestra Dell'Angelo in Pienza – Elegant Apartment with Stunning Views
Exterior detail

6. Apartment 'La Dimora Di Pienza in Val D'Orcia' with Wi-Fi

Apartment 'La Dimora Di Pienza in Val D'Orcia' with Wi-Fi
Pienza
The price is HK$1,166
HK$1,382 total
includes taxes & fees
31 Jul - 1 Aug
Apartment 'La Dimora Di Pienza in Val D'Orcia' with Wi-Fi
Outdoor dining

7. Il Podere di Casa Rossa Pienza

Il Podere di Casa Rossa Pienza
Pienza
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful views, accommodating hosts"
United States
Pete and Alison C.
The price is HK$1,911
HK$2,694 total
includes taxes & fees
10 Aug - 11 Aug
Il Podere di Casa Rossa Pienza
Courtyard view

8. L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (25 reviews)
"Absolutely first class and friendly Perfect location "
United States
Jennifer
The price is HK$3,599
HK$3,995 total
includes taxes & fees
3 Aug - 4 Aug
L'Olmo
Couples treatment room(s), sauna, hot tub, steam room, body treatments

9. Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
San Quirico d'Orcia
9.0 out of 10, Wonderful, (49 reviews)
"Our stay was great. "
United States
Elena
The price is HK$773
HK$886 total
includes taxes & fees
2 Aug - 3 Aug
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
Property entrance

10. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (104 reviews)
"Staff was great, and they even scheduled transportation to and from the train station for us. Great location on the main strip of Montepluciano!"
United States
Nicholas
The price is HK$635
HK$734 total
includes taxes & fees
2 Aug - 3 Aug
Residenza Fabroni
1 treatment room, massages

11. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (92 reviews)
"Our stay at Casanova Panoramic Rooms was absolutely wonderful. The room was beautiful, spotless, and the view was simply breathtaking. The entire check-in process was smooth and welcoming, and having convenient parking made everything even easier. We also loved the restaurant—the food was delicious, and breakfast was excellent. Every part of our stay exceeded our expectations. We would definitely stay here again and highly recommend it to anyone visiting the area."
United States
Anonymous traveller
The price is HK$1,480
HK$1,664 total
includes taxes & fees
30 Aug - 31 Aug
Casanova - Panoramic Rooms and Suites
Exterior

12. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (139 reviews)
"Wonderful place - clean, comfortable, quiet with excellent hosts. Perfect location near everything in town including the parking. Can’t wait to return!"
United States
Shelly
The price is HK$1,058
HK$1,200 total
includes taxes & fees
6 Aug - 7 Aug
Bed & Breakfast Vicolo dell'Oste
Terrace/patio

13. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (178 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is HK$1,362
HK$1,525 total
includes taxes & fees
31 Jul - 1 Aug
Abbadia Sicille Relais
Food court

14. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (146 reviews)
"Lucca was the perfect host, very accommodating to any queries we had and was always willing to help during our stay Couldn’t recommend staying here highly enough - we had a great time staying here and would highly recommend if you are in the area definitely book here"
United Kingdom
Jonathan
The price is HK$1,079
HK$1,223 total
includes taxes & fees
6 Aug - 7 Aug
La Locanda di San Francesco
Property grounds

15. Dimora del Poggio - cozy Tuscan apartment

Dimora del Poggio - cozy Tuscan apartment
San Quirico d'Orcia
10.0 out of 10, Exceptional, (5 reviews)
"Our hosts were fantastic, the apartment was clean, roomy, and comfortable, and the location was perfect. Easy walk to enjoy shops and dining."
United States
Joe B.
The price is HK$1,161
HK$1,619 total
includes taxes & fees
13 Aug - 14 Aug
Dimora del Poggio - cozy Tuscan apartment
Interior

16. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (115 reviews)
"It was very well located ."
Canada
Marlenne
The price is HK$1,282
HK$1,446 total
includes taxes & fees
31 Jul - 1 Aug
Meublé Il Riccio
Front of property

17. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (7 reviews)
"Beautiful place, view and city."
United States
Federico
The price is HK$942
HK$1,072 total
includes taxes & fees
5 Aug - 6 Aug
montorio
Terrace/patio

18. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (38 reviews)
"Time transported to the Renaissance at this beautiful, well-kept palazzo… Riccardo’s family did a truly amazing job restoring this place and the facilities are modern & without any discomfort."
American Samoa
Melissa Hyun Joo
The price is HK$1,379
HK$1,553 total
includes taxes & fees
31 Jul - 1 Aug
Delcorto Suites
Exterior detail

19. Vicolo Nobile - Romantic Heart of Montepulciano

Vicolo Nobile - Romantic Heart of Montepulciano
Montepulciano
10.0 out of 10, Exceptional, (3 reviews)
"Our 7 nights at this property was perfect in every way. The host was so helpful with transportation, restaurants, wineries and more. The space itself was clean, well appointed, relaxing and in a perfect location within Montepulciano. I highly recommend this property for an authentic and unforgettable Italian getaway."
United States
Keelin C.
The price is HK$891
HK$1,089 total
includes taxes & fees
3 Aug - 4 Aug
Vicolo Nobile - Romantic Heart of Montepulciano
Front of property

20. Bellarmino Boutique Apartments

Bellarmino Boutique Apartments
Montepulciano
6.0 out of 10, (3 reviews)
"I wish I knew more about the check in process ahead of time of that they contacted me ok WhatsApp. But it was clean, comfortable, as pictured, great location, and a great stay. "
United States
Nicole
The price is HK$678
HK$782 total
includes taxes & fees
24 Aug - 25 Aug
Bellarmino Boutique Apartments
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

Sant'Anna in Camprena Agriturismo

Sant'Anna in Camprena Agriturismo

10/10 Excellent
"It’s amazingly beautiful, pictures don’t do it justice. The views at gorgeous and the property is so serene and lovely"
Hajra 2-night trip
Posted 19 hours ago
Sant'Anna in Camprena Agriturismo

Find out more about Pienza

Search for holiday rentals in Pienza on Expedia! You can easily find your home rentals, villas, holiday apartments in Pienza using one of the methods below:

  • View our selection of featured holiday rentals in Pienza
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  • Enter your travel dates to view the best deals on holiday rentals in Pienza while they last

Look no further and take a look at our great range of rental properties in Pienza!

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.

What are some of the best holiday rentals that Pienza has to offer?

Idyllic guest house in Tuscan country house style with swimming pool: This holiday home rental outside of Pienza is located in a rural location, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a patio and a garden.

How many holiday rentals are there in Pienza?

Expedia has 24 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 Pienza Cathedral and Palazzo Piccolomini.

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.