A historic square with a prominent tower and statues.

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Pienza holiday rentals

Monolocale Exclusive, vista città, secondo piano senza ascensore | 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 ฿3,597
฿4,109 total
includes taxes & fees
18 Aug - 19 Aug
TuscanyLettings Studio&Room
Suite Bernardo, Panoramica al terzo piano senza ascensore | Terrace/patio

2. PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (5 reviews)
"Clean room with friendly and helpful staff. Thank you so much for the wonderful stay"
United States
Pearlyn
The price is ฿3,631
฿4,147 total
includes taxes & fees
25 Aug - 26 Aug
PienzaLettings Suites
Exterior

3. 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 ฿4,293
฿4,875 total
includes taxes & fees
27 Aug - 28 Aug
Casa Gioia - Casa Olivieri
Food and drink

4. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (153 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is ฿7,790
฿8,797 total
includes taxes & fees
25 Aug - 26 Aug
Hotel San Gregorio
Suite, 2 Bedrooms | Courtyard view

5. 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 ฿24,042
฿26,598 total
includes taxes & fees
16 Aug - 17 Aug
L'Olmo
Couples treatment room(s), sauna, hot tub, steam room, body treatments

6. 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 ฿4,868
฿5,508 total
includes taxes & fees
14 Aug - 15 Aug
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
Food court

7. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (147 reviews)
"Incredible views from our room"
United Kingdom
Isabelle
The price is ฿4,510
฿5,114 total
includes taxes & fees
25 Aug - 26 Aug
La Locanda di San Francesco
Exterior

8. 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 ฿4,309
฿4,892 total
includes taxes & fees
14 Aug - 15 Aug
Bed & Breakfast Vicolo dell'Oste
1 treatment room, massages

9. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (93 reviews)
"Very good accommodation in the heart of Val’d’Orcia. Reasonably priced"
Finland
Jarkko
The price is ฿6,106
฿6,869 total
includes taxes & fees
30 Aug - 31 Aug
Casanova - Panoramic Rooms and Suites
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 ฿2,862
฿3,301 total
includes taxes & fees
20 Aug - 21 Aug
Residenza Fabroni
Front of property

11. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (7 reviews)
"Beautiful place, view and city."
United States
Federico
The price is ฿3,841
฿4,377 total
includes taxes & fees
25 Aug - 26 Aug
montorio
Interior

12. 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 ฿5,438
฿6,134 total
includes taxes & fees
14 Aug - 15 Aug
Meublé Il Riccio
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 ฿6,291
฿7,035 total
includes taxes & fees
23 Aug - 24 Aug
Abbadia Sicille Relais
Front of property

14. Bellarmino Boutique Apartments

Bellarmino Boutique Apartments
Montepulciano
5.6 out of 10, (4 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 ฿2,473
฿2,873 total
includes taxes & fees
27 Aug - 28 Aug
Bellarmino Boutique Apartments
Breakfast, lunch and dinner served

15. Palazzo Saloni

Palazzo Saloni
Montalcino
10.0 out of 10, Exceptional, (4 reviews)
"Amazing stay! The staff are exceptional- so helpful and kind with every aspect of the stay. The rooms are beautiful and lovely amenities upon arrival. Would definitely go back again!"
United States
Victoria
The price is ฿10,819
฿12,207 total
includes taxes & fees
14 Aug - 15 Aug
Palazzo Saloni
Suite Aria | Terrace/patio

16. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (40 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 ฿6,463
฿7,262 total
includes taxes & fees
18 Aug - 19 Aug
Delcorto Suites
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

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

8/10 Good
"Precise Tale Poggio Alla Sala is a beautiful, peaceful property in a stunning and remote location near Montepulciano. The rooms and entire establishment were exceptionally clean and well maintained. The staff were friendly and welcoming, and the property is especially family- and kid-friendly, making it a great choice for families looking for a relaxing stay. Breakfast was included and offered eggs, fresh fruit, a variety of breads, and cold cuts. The selection was good, but it was essentially the same every day with little variation. The breakfast staff were pleasant, although the service could have been more attentive. Unfortunately, the service at the pool and restaurant was the biggest weakness of our stay. There is a walk-up snack and drink bar, but empty glasses and plates were rarely collected. There was no real pool service, and water was not consistently refilled. At the restaurant, tables were often left with empty plates for extended periods, and wait staff rarely checked on guests after the food was served. For a property at this price point, we expected a more attentive level of service. The setting, cleanliness, and family-friendly atmosphere are excellent, but the lack of consistent service at the pool and restaurant took away from what could otherwise be an exceptional experience. Overall, this is a gorgeous and very clean property with friendly people, a peaceful atmosphere, and a great environment for families with children. The location and surroundings"
Luis 5-night trip
Posted 9 hours ago
Precise Tale Poggio Alla Sala

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:

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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 29 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.