Pienza Vacation Rentals from ￥16,630: Search Short-Term Rentals

Q: 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.

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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

Pienza

Lucas

￥19,595 total

includes taxes & fees

Aug 19 - Aug 20

Suite Bernardo, Panoramica al terzo piano senza ascensore | Terrace/patio

2. PienzaLettings Suites

Pienza

Pearlyn

￥19,917 total

includes taxes & fees

Aug 25 - Aug 26

3. Casa Gioia - Casa Olivieri

Pienza

Nancy

￥23,244 total

includes taxes & fees

Aug 31 - Sep 1

4. Hotel San Gregorio

Pienza

Nancy

￥41,940 total

includes taxes & fees

Aug 25 - Aug 26

5. Suite Gioconda - Podere Casa Rossa in Pienza

Pienza

Doug H.

￥46,889 total

includes taxes & fees

Aug 16 - Aug 17

6. 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.

￥35,220 total

includes taxes & fees

Sep 12 - Sep 13

7. L'Olmo

Pienza

Jennifer

￥128,063 total

includes taxes & fees

Aug 16 - Aug 17

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

Pienza

￥82,130 total

includes taxes & fees

Aug 31 - Sep 1

Couples treatment rooms, sauna, hot tub, steam room, body treatments

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

San Quirico d'Orcia

Elena

￥22,884 total

includes taxes & fees

Aug 16 - Aug 17

10. La Locanda di San Francesco

Montepulciano

Isabelle

￥23,665 total

includes taxes & fees

Aug 25 - Aug 26

11. Bed & Breakfast Vicolo dell'Oste

Montepulciano

Shelly

￥24,030 total

includes taxes & fees

Aug 18 - Aug 19

12. Casanova - Panoramic Rooms and Suites

San Quirico d'Orcia

Jarkko

￥31,175 total

includes taxes & fees

Aug 30 - Aug 31

13. Residenza Fabroni

Montepulciano

Nicholas

￥16,718 total

includes taxes & fees

Aug 21 - Aug 22

14. Dimora del Poggio - cozy Tuscan apartment

San Quirico d'Orcia

Joe B.

￥33,073 total

includes taxes & fees

Aug 23 - Aug 24

15. montorio

Montepulciano

Federico

￥21,074 total

includes taxes & fees

Aug 19 - Aug 20

16. Meublé Il Riccio

Montepulciano

Marlenne

￥28,696 total

includes taxes & fees

Aug 31 - Sep 1

17. Abbadia Sicille Relais

Trequanda

Robert

￥33,789 total

includes taxes & fees

Aug 23 - Aug 24

18. Bellarmino Boutique Apartments

Montepulciano

Nicole

￥13,703 total

includes taxes & fees

Aug 27 - Aug 28

19. Palazzo Saloni

Montalcino

Victoria

￥58,771 total

includes taxes & fees

Aug 15 - Aug 16

20. Delcorto Suites

Montepulciano

Melissa Hyun Joo

￥34,964 total

includes taxes & fees

Aug 18 - Aug 19

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Top Pienza Hotel Reviews

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent

"This property was amazing from the moment we booked. Chiara was extremely helpful with looking into horseback riding and other tours for us. I made a mistake in booking and she caught it and corrected it before we even arrived. She was great. Additionally, the room was beautiful and really clean. The food was delicious and every waitstaff that we encountered was polite and attentive--it could not have been a better experience."

Precise Tale Poggio Alla Sala

8/10 Good

"Precise Tale Poggio Alla Sala is a beautiful, peaceful property in a stunning and remote location near Montepulciano. The rooms and entire establishment were exceptionally clean and well maintained. The staff were friendly and welcoming, and the property is especially family- and kid-friendly, making it a great choice for families looking for a relaxing stay. Breakfast was included and offered eggs, fresh fruit, a variety of breads, and cold cuts. The selection was good, but it was essentially the same every day with little variation. The breakfast staff were pleasant, although the service could have been more attentive. Unfortunately, the service at the pool and restaurant was the biggest weakness of our stay. There is a walk-up snack and drink bar, but empty glasses and plates were rarely collected. There was no real pool service, and water was not consistently refilled. At the restaurant, tables were often left with empty plates for extended periods, and wait staff rarely checked on guests after the food was served. For a property at this price point, we expected a more attentive level of service. The setting, cleanliness, and family-friendly atmosphere are excellent, but the lack of consistent service at the pool and restaurant took away from what could otherwise be an exceptional experience. Overall, this is a gorgeous and very clean property with friendly people, a peaceful atmosphere, and a great environment for families with children. The location and surroundings"

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."

Castello di Leonina Relais

8/10 Good

"The view from the dining area was perfect. The included breakfast was amazing and the complimentary ebike rentals were perfect to get around outside of the hotel to catch more amazing views! The food at dinner was perfect. The only thing that was lacking was the bathroom showers. Ours was leaking. Other than that it was a perfect stay."

Find out more about Pienza

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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 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 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.

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Check prices for these dates

Our top choices for Pienza vacation rentals

1. TuscanyLettings Studio&Room

2. PienzaLettings Suites

3. Casa Gioia - Casa Olivieri

4. Hotel San Gregorio

5. Suite Gioconda - Podere Casa Rossa in Pienza

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

7. L'Olmo

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

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

10. La Locanda di San Francesco

11. Bed & Breakfast Vicolo dell'Oste

12. Casanova - Panoramic Rooms and Suites

13. Residenza Fabroni

14. Dimora del Poggio - cozy Tuscan apartment

15. montorio

16. Meublé Il Riccio

17. Abbadia Sicille Relais

18. Bellarmino Boutique Apartments

19. Palazzo Saloni

20. Delcorto Suites

Find vacation rentals that suit your style

Top Pienza Hotel Reviews

Castello di Velona Resort Thermal SPA & Winery

Precise Tale Poggio Alla Sala

Fonteverde Thermal Spa Resort Tuscany

Agriturismo La Sovana

Mastrojanni Relais - Small Luxury Hotels of the World

Sant'Anna in Camprena Agriturismo

Castiglion del Bosco, A Rosewood Hotel

L'Orto delle Terme

Castello di Leonina Relais

Find out more about Pienza

Frequently asked questions

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