A historic square with a prominent tower and statues.

Pienza Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Pienza vacation rentals

Suite Bernardo, Panoramica al terzo piano senza ascensore | 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
$91 nightly
The price is $105
Aug 2 - Aug 3
Total with taxes and fees
PienzaLettings Suites
Monolocale Exclusive, vista città, secondo piano senza ascensore | Laptop workspace, iron/ironing board, WiFi (free)

2. 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
$103 nightly
The price is $118
Aug 6 - Aug 7
Total with taxes and fees
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
$123 nightly
The price is $140
Aug 7 - Aug 8
Total with taxes and fees
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
$231 nightly
The price is $261
Aug 25 - Aug 26
Total with taxes and fees
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
$172 nightly
The price is $177
Aug 1 - Aug 2
Total with taxes and fees
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.
$287 nightly
The price is $292
Aug 6 - Aug 7
Total with taxes and fees
Suite Gioconda - Podere Casa Rossa in Pienza
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
$459 nightly
The price is $509
Aug 4 - Aug 5
Total with taxes and fees
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.
$334 nightly
The price is $339
Aug 2 - Aug 3
Total with taxes and fees
Finestra Dell'Angelo in Pienza – Elegant Apartment with Stunning Views
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
$99 nightly
The price is $113
Aug 4 - Aug 5
Total with taxes and fees
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
$108 nightly
The price is $124
Aug 4 - Aug 5
Total with taxes and fees
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
$122 nightly
The price is $139
Aug 6 - Aug 7
Total with taxes and fees
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 traveler
$172 nightly
The price is $194
Aug 31 - Sep 1
Total with taxes and fees
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
$82 nightly
The price is $95
Aug 6 - Aug 7
Total with taxes and fees
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
$159 nightly
The price is $179
Aug 11 - Aug 12
Total with taxes and fees
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.
$203 nightly
The price is $208
Aug 13 - Aug 14
Total with taxes and fees
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
$200 nightly
The price is $223
Aug 1 - Aug 2
Total with taxes and fees
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
$70 nightly
The price is $82
Aug 31 - Sep 1
Total with taxes and fees
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
$122 nightly
The price is $138
Aug 1 - Aug 2
Total with taxes and fees
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
$255 nightly
The price is $290
Aug 9 - Aug 10
Total with taxes and fees
Palazzo Saloni
Suite Aria | 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
$176 nightly
The price is $198
Aug 1 - Aug 2
Total with taxes and fees
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

Sant'Anna in Camprena Agriturismo

Sant'Anna in Camprena Agriturismo

10/10 Excellent
"It’s amazingly beautiful, pictures don’t do it justice. The views at gorgeous and the property is so serene and lovely"
Hajra 2-night trip
Posted 2 days ago
Sant'Anna in Camprena Agriturismo

Find out more about Pienza

Everything you need to know about Pienza vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pienza vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pienza vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pienza vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pienza. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Pienza in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $95 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pienza rentals

At Expedia, we put the best Pienza vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Pienza rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pienza vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pienza. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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 26 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.