Pienza Holiday Rentals: Short-Term Accommodations for Rent

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 .

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In two weeks

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Our top choices for Pienza holiday rentals

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

1. Affitacamere Maria Gabriella

Pienza

Christopher

HK$1,197 total

includes taxes & fees

4 Oct - 5 Oct

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

2. Hotel San Gregorio

Pienza

Nancy

HK$1,792 total

includes taxes & fees

10 Oct - 11 Oct

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

3. PienzaLettings Suites

Pienza

Pearlyn

HK$986 total

includes taxes & fees

14 Oct - 15 Oct

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

4. TuscanyLettings Studio&Room

Pienza

Lucas

HK$1,027 total

includes taxes & fees

15 Sept - 16 Sept

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

5. Casa Gioia - Casa Olivieri

Pienza

Nancy

HK$1,050 total

includes taxes & fees

12 Oct - 13 Oct

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

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

Pienza

HK$1,355 total

includes taxes & fees

27 Sept - 28 Sept

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

7. 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.

HK$1,621 total

includes taxes & fees

15 Sept - 16 Sept

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.

HK$2,182 total

includes taxes & fees

21 Sept - 22 Sept

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

9. L'Olmo

Pienza

Jennifer

HK$6,340 total

includes taxes & fees

17 Sept - 18 Sept

10. Podere Manafiore - historical villa with swimming pool

Monticchiello

Caroline R.

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

11. Meublé Il Riccio

Montepulciano

Marlenne

HK$1,462 total

includes taxes & fees

16 Sept - 17 Sept

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

12. La Locanda di San Francesco

Montepulciano

Isabelle

HK$1,974 total

includes taxes & fees

27 Sept - 28 Sept

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

13. Bed & Breakfast Vicolo dell'Oste

Montepulciano

Shelly

HK$1,213 total

includes taxes & fees

22 Sept - 23 Sept

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

14. Casanova - Panoramic Rooms and Suites

San Quirico d'Orcia

Jarkko

HK$1,637 total

includes taxes & fees

16 Sept - 17 Sept

15. montorio

Montepulciano

Federico

HK$1,043 total

includes taxes & fees

3 Oct - 4 Oct

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

16. Abbadia Sicille Relais

Trequanda

Robert

HK$1,228 total

includes taxes & fees

12 Oct - 13 Oct

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

17. Residenza Fabroni

Montepulciano

Nicholas

HK$802 total

includes taxes & fees

22 Sept - 23 Sept

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

18. Delcorto Suites

Montepulciano

Denise

HK$1,655 total

includes taxes & fees

16 Sept - 17 Sept

A rectangular pool with a metal ladder, surrounded by wooden lounge chairs and a stone deck.

19. Corte Francigena - Apartments

Montalcino

Ryan

HK$1,437 total

includes taxes & fees

7 Oct - 8 Oct

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

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

San Quirico d'Orcia

Elena

HK$1,692 total

includes taxes & fees

15 Sept - 16 Sept

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Top Pienza Hotel Reviews

Monastero di Cortona Hotel & Spa

10/10 Excellent

"I never write hotel reviews, but this hotel was so exceptional that I had to share my experience. The room was beautiful, spotless, and incredibly comfortable, with thoughtful turn-down service every evening. The staff were truly the most attentive and welcoming I’ve ever experienced. They helped arrange pickup from the train station, made restaurant reservations, and went above and beyond in so many little ways. Those small details made me feel genuinely cared for. The breakfast was lovely and served in such a beautiful setting — the perfect way to start the day. I absolutely loved my stay here and would come back to Cortona for this hotel alone. A truly special place with exceptional hospitality. Highly recommend!"

Hotel Corsignano

10/10 Excellent

"My husband and I had an absolutely wonderful experience at Hotel Corsignano. From beginning to end, the staff went above and beyond to make us feel welcome and cared for. When we arrived a little later than expected, they were genuinely concerned about us and even made sure to save a parking spot for us. That level of thoughtfulness and hospitality really stood out. The hotel was exceptionally clean and in a fantastic location, just a few steps from the historic center of Pienza. And the breakfast was wonderful, with plenty of delicious options to choose from. We truly felt welcomed and well taken care of throughout our stay. We would happily stay here again and highly recommend Hotel Corsignano!"

Castello di Velona Resort Thermal SPA & Winery

8/10 Good

"Staying here was a wonderful and truly unique experience. The only reason I’m giving it 4 stars instead of 5 was because of the challenges we had with the air conditioning in our room. That said, the staff really did make an effort to find a workaround for us. While it wasn’t a perfect solution, it definitely helped, and we appreciated how responsive and accommodating they were. The hotel itself is an old castle, and that alone makes staying here such a special experience. The property is beautiful, incredibly charming, and very well maintained. You simply can’t replicate the character, history, and ambiance that come with staying in a property like this. The setting and surroundings are beautiful. It was definitely one of those experiences that felt uniquely Italian and added something special to our trip. My only recommendation would be to visit when the temperatures aren’t quite as hot. Given the age and historic nature of the property, I can appreciate that modernizing certain things like the air conditioning may not be as straightforward as it would be in a newer hotel. During cooler weather, I imagine our experience would have been close to perfect. Overall, we really enjoyed our stay and are glad we had the opportunity to experience such a beautiful and unique property. I would absolutely recommend it, just perhaps not during the hottest part of the summer!"

Precise Tale Poggio Alla Sala

10/10 Excellent

"Incredible stay in a beautiful location. The staff were amazing and the hospitality was top tier. We will most definitely be back. The recommendations given were brilliant and the room was stunning along with the rest of the hotel. We didn’t dine in the restaurant but our breakfast each morning was also wonderful."

Find out more about Pienza

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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 33 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.

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Check prices for these dates

Our top choices for Pienza holiday rentals

1. Affitacamere Maria Gabriella

2. Hotel San Gregorio

3. PienzaLettings Suites

4. TuscanyLettings Studio&Room

5. Casa Gioia - Casa Olivieri

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

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

8. Suite Gioconda - Podere Casa Rossa in Pienza

9. L'Olmo

10. Podere Manafiore - historical villa with swimming pool

11. Meublé Il Riccio

12. La Locanda di San Francesco

13. Bed & Breakfast Vicolo dell'Oste

14. Casanova - Panoramic Rooms and Suites

15. montorio

16. Abbadia Sicille Relais

17. Residenza Fabroni

18. Delcorto Suites

19. Corte Francigena - Apartments

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

Find holiday rentals that suit your style

Top Pienza Hotel Reviews

Monastero di Cortona Hotel & Spa

Agriturismo Poggio Tobruk

Castiglion del Bosco, A Rosewood Hotel

Hotel Corsignano

Tenuta Santo Pietro

Nuovo Etruria Resort

Castello di Velona Resort Thermal SPA & Winery

Fonteverde Thermal Spa Resort Tuscany

Precise Tale Poggio Alla Sala

Find out more about Pienza

Frequently asked questions

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