A historic square with a prominent tower and statues.

Pienza Vacation Rentals

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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 vacation rentals

Monolocale Exclusive, vista città, secondo piano senza ascensore | Laptop workspace, iron/ironing board, WiFi (free)

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 AED 363
AED 416 total
includes taxes & fees
12 Aug - 13 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 AED 399
AED 456 total
includes taxes & fees
12 Aug - 13 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 AED 473
AED 537 total
includes taxes & fees
31 Aug - 1 Sep
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 AED 809
AED 915 total
includes taxes & fees
13 Aug - 14 Aug
Hotel San Gregorio
Outdoor dining

5. 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 AED 833
AED 1,088 total
includes taxes & fees
12 Aug - 13 Aug
Suite Gioconda - Podere Casa Rossa in Pienza
1 bedroom, iron/ironing board, WiFi

6. 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 AED 660
AED 813 total
includes taxes & fees
18 Aug - 19 Aug
Finestra Dell'Angelo in Pienza – Elegant Apartment with Stunning Views
Suite, 2 Bedrooms | 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 AED 2,675
AED 2,959 total
includes taxes & fees
16 Aug - 17 Aug
L'Olmo
Exterior detail

8. 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 AED 630
AED 732 total
includes taxes & fees
11 Aug - 12 Aug
Apartment 'La Dimora Di Pienza in Val D'Orcia' with Wi-Fi
Couples treatment rooms, 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 AED 419
AED 478 total
includes taxes & fees
11 Aug - 12 Aug
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
Food court

10. 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 AED 495
AED 562 total
includes taxes & fees
27 Aug - 28 Aug
La Locanda di San Francesco
Exterior

11. 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 AED 435
AED 496 total
includes taxes & fees
12 Aug - 13 Aug
Bed & Breakfast Vicolo dell'Oste
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, (93 reviews)
"Very good accommodation in the heart of Val’d’Orcia. Reasonably priced"
Finland
Jarkko
The price is AED 632
AED 713 total
includes taxes & fees
30 Aug - 31 Aug
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 AED 286
AED 332 total
includes taxes & fees
18 Aug - 19 Aug
Residenza Fabroni
Property grounds

14. 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 AED 493
AED 701 total
includes taxes & fees
13 Aug - 14 Aug
Dimora del Poggio - cozy Tuscan apartment
Front of property

15. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (7 reviews)
"Beautiful place, view and city."
United States
Federico
The price is AED 427
AED 487 total
includes taxes & fees
11 Aug - 12 Aug
montorio
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 AED 599
AED 676 total
includes taxes & fees
12 Aug - 13 Aug
Meublé Il Riccio
Terrace/patio

17. 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 AED 749
AED 837 total
includes taxes & fees
24 Aug - 25 Aug
Abbadia Sicille Relais
Front of property

18. 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 AED 275
AED 320 total
includes taxes & fees
26 Aug - 27 Aug
Bellarmino Boutique Apartments
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 AED 1,202
AED 1,356 total
includes taxes & fees
25 Aug - 26 Aug
Palazzo Saloni
Suite Aria | Terrace/patio

20. 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 AED 651
AED 733 total
includes taxes & fees
11 Aug - 12 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

Agriturismo La Sovana

Agriturismo La Sovana

10/10 Excellent
"Beautiful stay here. Restaurant was fantastic and they prepared special dishes to meet our vegetarian needs. Buffet breakfast with fresh cappuccinos was wonderful. Room was impeccably clean with daily cleaning service. This was our second time here and we are hoping to return to this authentic Tuscany resort. You will likely not find a better place to stay at in Tuscany."
Karen 4-night trip
Posted 1 day ago
Agriturismo La Sovana

Frequently asked questions

Can I find a vacation rental in Pienza?

Yes, we give you a choice of vacation rentals in Pienza close to RI Crea RE, or you can go with a secluded option if you want 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 vacation home rentals in Pienza?

House with private pool with beautiful view Val d 'Orcia: Visitors give good reviews to this Pienza vacation home rental, which is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many vacation rentals are there in Pienza?

Expedia has 29 vacation 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 vacation rental in Pienza like?

Vacation rentals are private properties you can book for a long or short time in Pienza. Vacation rentals feature amenities like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for a small group gathering.