A historic square with a prominent tower and statues.

Pienza Vacation Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Pienza holiday rentals

Exterior

1. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (65 reviews)
"I had a fantastic experience with this place. Great people!!!"
South Korea
Young Rok
The price is RM456
RM619 total
includes taxes & fees
4 Oct - 5 Oct
Affitacamere Maria Gabriella
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 RM490
RM558 total
includes taxes & fees
18 Sept - 19 Sept
PienzaLettings Suites
Laptop workspace, iron/ironing board, free WiFi

3. 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 RM466
RM531 total
includes taxes & fees
6 Oct - 7 Oct
TuscanyLettings Studio&Room
Food and drink

4. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (155 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is RM805
RM914 total
includes taxes & fees
6 Oct - 7 Oct
Hotel San Gregorio
Exterior

5. 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 RM498
RM567 total
includes taxes & fees
6 Oct - 7 Oct
Casa Gioia - Casa Olivieri
Courtyard view

6. 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 RM2,963
RM3,279 total
includes taxes & fees
14 Sept - 15 Sept
L'Olmo
Couples treatment room(s), sauna, hot tub, steam room, body treatments

7. 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 RM659
RM743 total
includes taxes & fees
9 Sept - 10 Sept
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
1 treatment room, massages

8. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (94 reviews)
"Very good accommodation in the heart of Val’d’Orcia. Reasonably priced"
Finland
Jarkko
The price is RM715
RM805 total
includes taxes & fees
13 Sept - 14 Sept
Casanova - Panoramic Rooms and Suites
Front of property – evening/night

9. 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 RM565
RM635 total
includes taxes & fees
6 Oct - 7 Oct
Abbadia Sicille Relais
Front of property

10. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (8 reviews)
"Beautiful place, view and city."
United States
Federico
The price is RM473
RM540 total
includes taxes & fees
3 Oct - 4 Oct
montorio
Property entrance

11. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (108 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 RM351
RM405 total
includes taxes & fees
13 Sept - 14 Sept
Residenza Fabroni
Interior

12. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (117 reviews)
"It was very well located ."
Canada
Marlenne
The price is RM669
RM755 total
includes taxes & fees
15 Sept - 16 Sept
Meublé Il Riccio
Exterior

13. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (140 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 RM509
RM579 total
includes taxes & fees
9 Sept - 10 Sept
Bed & Breakfast Vicolo dell'Oste
Food court

14. 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 RM962
RM1,077 total
includes taxes & fees
8 Oct - 9 Oct
La Locanda di San Francesco
Interior

15. Podere Tre Berte - The Sleeping Beauty

Podere Tre Berte - The Sleeping Beauty
Toscana
Podere Tre Berte - The Sleeping Beauty
Terrace/patio

16. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (43 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is RM844
RM948 total
includes taxes & fees
9 Sept - 10 Sept
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

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"EVERYTHING WAS AMAZING!! From the check in to the checkout and everything in between! Eleanora and Matteo at the front desk, the bartenders and waiters by the oook and Lorenzo and Alessandro at the restaurant! Our beds were changed everyday along with our towels and anything else we used. Fresh bottles of water everyday (no charge) and turn down every night. We were treated with a hand written note by Flavia, the manager when we arrived with chocolates and candy. She left another handwritten note thanking us for our stay when we left with a bottle of Amaro from a Tuscany. She stopped to talk with us everytime we saw her to see how everything was! If there were 100 stars, that is what I would give this hotel because it is out of this world from the views to the beautiful decor and chandleliers! We enjoyed the pool and they arranged cars, wine tastings and train transportation for us. They went above and beyond and always with a smile. If you are planning a trip to that area and you don’t stay there, you are missing out! We will definitely be back because everyone made us feel as if we were part of the family. And everyone speaks English in Cortona!"
Paola 3-night trip
Posted 5 hours ago
Monastero di Cortona Hotel & Spa

Find out more about Pienza

Search for holiday rentals in Pienza on Expedia.co.uk! 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 Art Studio di Adelina Quadri, 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 32 holiday rentals for your stay in Pienza.

What’s there to see and do in Pienza?

Cultural attractions include Artemisia Gallery and Palazzo Borgia, 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.