A historic square with a prominent tower and statues.

Pienza Vacation Rentals

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Our top choices for Pienza vacation rentals

1. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (171 reviews)
"Great location. Clean and quiet with good breakfast"
United States
Michael
The price is CA $193
CA $221 total
includes taxes & fees
Nov 9 - Nov 10
Hotel San Gregorio

2. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (75 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is CA $145
CA $199 total
includes taxes & fees
Nov 9 - Nov 10
Affitacamere Maria Gabriella

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 CA $119
CA $137 total
includes taxes & fees
Dec 9 - Dec 10
TuscanyLettings Studio&Room

4. PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (7 reviews)
"Clean room with friendly and helpful staff. Thank you so much for the wonderful stay"
United States
Pearlyn
The price is CA $132
CA $151 total
includes taxes & fees
Dec 8 - Dec 9
PienzaLettings Suites

5. L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (28 reviews)
"We were so comfortable and impressed with L'Olmo. Communication prior to our trip was perfect. We got there and the grounds were immaculate, the room was stunning, and the location was extremely convenient. The staff was very helpful. We loved staying here and can recommend it whole heartedly."
United States
Michelle
L'Olmo

6. 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 CA $116
CA $134 total
includes taxes & fees
Dec 8 - Dec 9
Casa Gioia - Casa Olivieri

7. 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 CA $184
CA $230 total
includes taxes & fees
Nov 15 - Nov 16
Apartment 'La Dimora di Pienza in Val d'Orcia' with Wi-Fi

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 CA $227
CA $283 total
includes taxes & fees
Nov 9 - Nov 10
Finestra Dell'Angelo in Pienza – Elegant Apartment with Stunning Views

9. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.0 out of 10, Wonderful, (105 reviews)
"Hotel had beautiful views and amenities like breakfast and spa were amazing."
United States
Oscar
The price is CA $252
CA $283 total
includes taxes & fees
Nov 18 - Nov 19
Casanova - Panoramic Rooms and Suites

10. 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, (50 reviews)
"Our stay was great. "
United States
Elena
The price is CA $144
CA $165 total
includes taxes & fees
Nov 10 - Nov 11
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

11. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (185 reviews)
"Great Historical location."
Canada
Robert
The price is CA $89
CA $102 total
includes taxes & fees
Dec 8 - Dec 9
Abbadia Sicille Relais

12. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (152 reviews)
"This place was great. Amazing view the room. Extremely friendly and helpful staff. This hotel made our trip - highly recommend"
Canada
Colin
The price is CA $209
CA $236 total
includes taxes & fees
Nov 25 - Nov 26
La Locanda di San Francesco

13. Sarna Residence

Sarna Residence
San Quirico d'Orcia
9.4 out of 10, Exceptional, (40 reviews)
"We enjoyed our stay. The room was very clean. The staff was helpful."
United States
Bokang
The price is CA $154
CA $195 total
includes taxes & fees
Nov 9 - Nov 10
Sarna Residence

14. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (121 reviews)
"What a gem! Absolutely loved the hotel and enjoyed our stay. Staff very friendly and helpful, and our room was outstanding. The view from our balcony was breathtaking. Top of our list!"
United States
Christopher
The price is CA $200
CA $226 total
includes taxes & fees
Nov 17 - Nov 18
Meublé Il Riccio

15. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (50 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is CA $240
CA $270 total
includes taxes & fees
Nov 10 - Nov 11
Delcorto Suites

16. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (11 reviews)
"Amazing location, beautiful property"
United States
Joseph
The price is CA $169
CA $192 total
includes taxes & fees
Nov 9 - Nov 10
montorio

17. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (145 reviews)
"We really enjoyed the room. Comfortable bed. Great location."
United States
Melissa
The price is CA $136
CA $156 total
includes taxes & fees
Nov 10 - Nov 11
Bed & Breakfast Vicolo dell'Oste

18. Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (141 reviews)
"Excellent room, service and food. The best."
United States
Valerie
The price is CA $318
CA $356 total
includes taxes & fees
Dec 8 - Dec 9
Il Tosco

19. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (115 reviews)
"Very charming property in a fantastic location. The host was very responsive and we had a marvelous stay. Bear in mind this is a historic property and accordingly has some quirks. Those looking for modernity and perfect fixtures may not appreciate those quirks."
United States
Marc
The price is CA $126
CA $145 total
includes taxes & fees
Nov 9 - Nov 10
Residenza Fabroni

20. Palazzo Saloni

Palazzo Saloni
Montalcino
10.0 out of 10, Exceptional, (14 reviews)
"Excellent location to tour wine country montalcino."
United States
Michael
The price is CA $362
CA $414 total
includes taxes & fees
Dec 8 - Dec 9
Palazzo Saloni
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

Find out more about Pienza

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Pienza. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find a vacation rental in Pienza?

Yes, we give you a choice of vacation rentals in Pienza close to Art Studio di Adelina Quadri, 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: This highly rated vacation home rental in Pienza 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. Another good choice for your trip to Pienza is Villa I Cipressini Tuscany Private luxury pool spa.

How many vacation rentals are there in Pienza?

Expedia has 30 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 Palazzo Piccolomini and Pienza Cathedral.

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.