Pienza Holiday Rentals from NZ$147: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Pienza has to offer?

House with private pool with beautiful view Val d 'Orcia : This highly rated holiday home rental in Pienza is located on a lake, and has a fireplace, a balcony and a BBQ 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 .

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Pienza holiday rentals

A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

1. Hotel San Gregorio

Pienza

Michael

includes taxes & fees

8 Nov - 9 Nov

A patio area with outdoor seating, potted plants, and a view of the landscape.

2. Affitacamere Maria Gabriella

Pienza

Janine und Thomas

includes taxes & fees

28 Oct - 29 Oct

A bedroom with a brick archway, a bed with white linens, a small table with a magazine, and a painting on the wall.

3. TuscanyLettings Studio&Room

Pienza

Lucas

includes taxes & fees

5 Nov - 6 Nov

A stone building with a wooden door, a staircase, and a small window with a metal grill.

4. Casa Gioia - Casa Olivieri

Pienza

Nancy

includes taxes & fees

23 Oct - 24 Oct

A balcony with a metal railing, a small table with a chair, potted plants, and a view of the sea.

5. PienzaLettings Suites

Pienza

Pearlyn

includes taxes & fees

2 Nov - 3 Nov

A cozy outdoor seating area with stone walls and red foliage, featuring a table and chairs, and a door leading to a covered entrance.

6. L'Olmo

Pienza

Michelle

includes taxes & fees

2 Nov - 3 Nov

A narrow alleyway with stone walls, potted plants, and a wooden door.

7. Apartment 'La Dimora Di Pienza in Val D'Orcia' with Wi-Fi

Pienza

includes taxes & fees

2 Nov - 3 Nov

An outdoor patio with a wooden pergola, a table with chairs, and potted plants.

8. Suite Gioconda - Podere Casa Rossa in Pienza

Pienza

Doug H.

includes taxes & fees

26 Oct - 27 Oct

A bedroom with a large bed, a wooden wardrobe, a mirror, a chandelier, and a wall-mounted light fixture.

9. Finestra Dell'Angelo in Pienza – Elegant Apartment with Stunning Views

Pienza

"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."

Michael H.

includes taxes & fees

20 Oct - 21 Oct

A historic building with a tower, a courtyard, and a well-lit entrance.

10. Abbadia Sicille Relais

Trequanda

Robert

includes taxes & fees

19 Nov - 20 Nov

A poolside area with two glasses of water, candles, and a stone pathway.

11. Casanova - Panoramic Rooms and Suites

San Quirico d'Orcia

DANIELA

includes taxes & fees

20 Oct - 21 Oct

A stone building with a courtyard, outdoor seating, and a warm light setting.

12. Sarna Residence

San Quirico d'Orcia

Bokang

includes taxes & fees

3 Nov - 4 Nov

A stone-walled room with a large bathtub, a fireplace, and a set of stone steps leading to the tub.

13. Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

San Quirico d'Orcia

Elena

includes taxes & fees

19 Nov - 20 Nov

An arched doorway leading to a building with a wooden door and a staircase.

14. Residenza Fabroni

Montepulciano

Nicholas

includes taxes & fees

22 Oct - 23 Oct

A narrow alleyway with buildings on either side, string lights hanging above, and a sign reading "ROOMS".

15. Bed & Breakfast Vicolo dell'Oste

Montepulciano

Shelly

includes taxes & fees

3 Nov - 4 Nov

16. montorio

Montepulciano

Federico

includes taxes & fees

20 Oct - 21 Oct

A crowded restaurant with brick walls and multiple tables and chairs.

17. La Locanda di San Francesco

Montepulciano

Colin

includes taxes & fees

3 Nov - 4 Nov

A terrace with a table set for breakfast, overlooking a scenic landscape.

18. Delcorto Suites

Montepulciano

Denise

includes taxes & fees

20 Oct - 21 Oct

A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

19. Idolina Guest House

Montalcino

Jaiden

includes taxes & fees

29 Oct - 30 Oct

An interior courtyard with stone columns, arches, and a mosaic.

20. Meublé Il Riccio

Montepulciano

Christopher

includes taxes & fees

20 Oct - 21 Oct

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Top Pienza Hotel Reviews

Hotel Certosa Di Maggiano

10/10 Excellent

"By the time you check out. You feel like you are saying goodbye to family. This hotel goes above and beyond for their guests. From Michelle, Lorenzo, Faith, etc. the whole team made out stay 5/5+. We cannot wait to go back!"

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent

"This was an amazing stay recommended by a friend and we really loved this place. The only immediate issues were the A/C broke and the TV was hard to setup, and the toilet seat was cracked and broke when I sat on it. But they fixed all that on day 1 and we had an amazing time - staff was amazing, grounds, parking, quiet, romantic, everything. The restaurant was amazing wine cellar. The food a little exotic so if you want more basic - then head over to Cortona with a car 15 min drive up the hill. Best part of trip was having a car. The people amazing, Daniel, Enrico, and cant remember everyone - everyone was amazing."

Podere Spedalone

8/10 Good

"The shower drain was not adequate and bath room as well as into bedroom pooled with water. Had to use shower with very low flow. No coffee machine in the room, one machine in breakfast room which staff only operated starting at 8;00am. Definitely a minus as wanted coffee earlier, and like to still be in pajamas in room. Pillows were flat and not supportive of neck or head. One mile of very bumpy road leading to property. Lots of flies around due to chickens and sheep on property. Room would be quite warm in summer"

Tenuta Santo Pietro

10/10 Excellent

"Tenuta Santo Pietro is truly a hidden gem, but what makes it so special is Bertina. She is, without a doubt, one of the most wonderful people I have ever encountered in all my years of traveling. Her warmth, kindness, attentiveness, and genuine love for what she does made our entire stay unforgettable. She goes above and beyond in every way and makes you feel so welcomed and cared for. I honestly cannot say enough wonderful things about her! The property is beautiful, the rooms are spacious, and the beds are incredibly comfortable. The restaurant is also absolutely incredible. After 10 days traveling throughout Italy, some of our favorite meals of the entire trip were here. From the exceptional wine to the pasta, desserts, and everything in between, every meal felt special. Tenuta Santo Pietro is a magical place, and Bertina is the heart of it. She made our stay truly unforgettable, and I cannot wait to return. I only hope she will be there to welcome us again. I have stayed in many wonderful places, but it is rare to meet someone who leaves such a lasting impression. Bertina is an absolute gem, and this property is so lucky to have her!"

Find out more about Pienza

Everything you need to know about Pienza holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pienza holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pienza holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pienza holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pienza holiday rentals we have selected for you start as low as NZ$147 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pienza rentals

At Expedia, we put the best Pienza holiday 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 holiday.

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.

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.

What are some of the best holiday rentals that Pienza has to offer?

House with private pool with beautiful view Val d 'Orcia: This highly rated holiday home rental in Pienza is located on a lake, and has a fireplace, a balcony and a BBQ 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 holiday rentals are there in Pienza?

Expedia has 30 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 Palazzo Piccolomini and Pienza Cathedral.

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.

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Check prices for these dates

Our top choices for Pienza holiday rentals

1. Hotel San Gregorio

2. Affitacamere Maria Gabriella

3. TuscanyLettings Studio&Room

4. Casa Gioia - Casa Olivieri

5. PienzaLettings Suites

6. L'Olmo

7. Apartment 'La Dimora Di Pienza in Val D'Orcia' with Wi-Fi

8. Suite Gioconda - Podere Casa Rossa in Pienza

9. Finestra Dell'Angelo in Pienza – Elegant Apartment with Stunning Views

10. Abbadia Sicille Relais

11. Casanova - Panoramic Rooms and Suites

12. Sarna Residence

13. Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

14. Residenza Fabroni

15. Bed & Breakfast Vicolo dell'Oste

16. montorio

17. La Locanda di San Francesco

18. Delcorto Suites

19. Idolina Guest House

20. Meublé Il Riccio

Find holiday rentals that suit your style

Top Pienza Hotel Reviews

Hotel Certosa Di Maggiano

Hotel Villa Ricci

Hotel Corsignano

Villa di Piazzano - Small Luxury Hotel of the World

Castello di Velona Resort Thermal SPA & Winery

Hotel San Gregorio

L'Orto delle Terme

Podere Spedalone

Tenuta Santo Pietro

Find out more about Pienza

Frequently asked questions

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