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

Terrace/patio

1. 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 HK$729
HK$838 total
includes taxes & fees
2 Aug - 3 Aug
PienzaLettings Suites
Laptop workspace, iron/ironing board, free WiFi

2. TuscanyLettings Studio&Room

TuscanyLettings Studio&Room
Pienza
10.0 out of 10, Exceptional, (3 reviews)
The price is HK$852
HK$973 total
includes taxes & fees
6 Aug - 7 Aug
TuscanyLettings Studio&Room
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 HK$1,017
HK$1,155 total
includes taxes & fees
31 Aug - 1 Sept
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, (152 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is HK$1,808
HK$2,043 total
includes taxes & fees
25 Aug - 26 Aug
Hotel San Gregorio
Exterior detail

5. 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$1,172
HK$1,389 total
includes taxes & fees
2 Aug - 3 Aug
Apartment 'La Dimora Di Pienza in Val D'Orcia' with Wi-Fi
Outdoor dining

6. Suite Gioconda - Podere Casa Rossa in Pienza

Suite Gioconda - Podere Casa Rossa in Pienza
Pienza
10.0 out of 10, Exceptional, (5 reviews)
"Comfortable, clean and the hosts are over the top welcoming! Walking distance to Pienza with gorgeous views. Loved staying here and hope to come back someday! "
United States
Doug H.
The price is HK$1,774
HK$2,289 total
includes taxes & fees
5 Aug - 6 Aug
Suite Gioconda - Podere Casa Rossa in Pienza
Courtyard view

7. 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$3,616
HK$4,014 total
includes taxes & fees
3 Aug - 4 Aug
L'Olmo
1 bedroom, iron/ironing board, WiFi

8. 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$2,343
HK$2,669 total
includes taxes & fees
2 Aug - 3 Aug
Finestra Dell'Angelo in Pienza – Elegant Apartment with Stunning Views
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$783
HK$897 total
includes taxes & fees
4 Aug - 5 Aug
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
Exterior

10. 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$1,004
HK$1,140 total
includes taxes & fees
8 Aug - 9 Aug
Bed & Breakfast Vicolo dell'Oste
Food court

11. 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$1,093
HK$1,239 total
includes taxes & fees
6 Aug - 7 Aug
La Locanda di San Francesco
1 treatment room, massages

12. 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$1,446
HK$1,627 total
includes taxes & fees
31 Aug - 1 Sept
Casanova - Panoramic Rooms and Suites
Property entrance

13. 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$677
HK$780 total
includes taxes & fees
13 Aug - 14 Aug
Residenza Fabroni
Interior

14. 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$1,288
HK$1,453 total
includes taxes & fees
12 Aug - 13 Aug
Meublé Il Riccio
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$1,166
HK$1,627 total
includes taxes & fees
30 Aug - 31 Aug
Dimora del Poggio - cozy Tuscan apartment
Terrace/patio

16. 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$1,339
HK$1,500 total
includes taxes & fees
2 Aug - 3 Aug
Abbadia Sicille Relais
Front of property

17. 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$586
HK$681 total
includes taxes & fees
31 Aug - 1 Sept
Bellarmino Boutique Apartments
Front of property

18. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (7 reviews)
"Beautiful place, view and city."
United States
Federico
The price is HK$954
HK$1,086 total
includes taxes & fees
2 Aug - 3 Aug
montorio
Breakfast, lunch and dinner served

19. 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 HK$2,008
HK$2,282 total
includes taxes & fees
2 Aug - 3 Aug
Palazzo Saloni
Terrace/patio

20. 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$1,378
HK$1,552 total
includes taxes & fees
2 Aug - 3 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

Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

8/10 Good
"La vu exceptionnel le service excelent. Malheureusement une seul piscine et elle est thermal alors que la température extérieur est de 37 c. La piscine est à 40c Pas du tout agréable. Autre chose. Je comprend les prix de cette établissement mais quand même difficile de payer 28€ pour un apéros spritz quand suer les belles terasse des superbe village environnant les vende généralement de 5 à 6€ L’écart est exagérer et enlève totalement de commander un cocktail au abord d’une piscine. 40c ……… Le reste excelent pour nous"
Luc 2-night trip
Posted 4 hours ago
Castello di Velona Resort Thermal SPA & Winery

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
  • Use the map to find apartments and other holiday homes in the Pienza neighbourhood you prefer
  • 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.