Pienza Short-Term Rentals from S$87: Search Holiday Rentals

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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

13 Dec - 14 Dec

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

2 Dec - 3 Dec

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

includes taxes & fees

10 Dec - 11 Dec

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

includes taxes & fees

15 Dec - 16 Dec

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

5. Casa Gioia - Casa Olivieri

Pienza

Nancy

includes taxes & fees

8 Dec - 9 Dec

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

6. Casanova - Panoramic Rooms and Suites

San Quirico d'Orcia

Oscar

includes taxes & fees

18 Nov - 19 Nov

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

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

San Quirico d'Orcia

Elena

includes taxes & fees

26 Nov - 27 Nov

A covered corridor with brick columns, potted plants, and a view of a lush landscape.

8. Abbadia Sicille Relais

Trequanda

Robert

includes taxes & fees

8 Dec - 9 Dec

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

9. Sarna Residence

San Quirico d'Orcia

Bokang

includes taxes & fees

15 Nov - 16 Nov

A stone building with a tiled roof, surrounded by tall trees and a gravel path.

10. montorio

Montepulciano

Joseph

includes taxes & fees

13 Dec - 14 Dec

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

11. Delcorto Suites

Montepulciano

Denise

includes taxes & fees

16 Nov - 17 Nov

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

12. Meublé Il Riccio

Montepulciano

Slimane

includes taxes & fees

9 Dec - 10 Dec

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

13. La Locanda di San Francesco

Montepulciano

Colin

includes taxes & fees

26 Nov - 27 Nov

A narrow cobblestone street flanked by historic stone buildings with arched doorways and windows.

14. Il Tosco

Montepulciano

Janine

includes taxes & fees

8 Dec - 9 Dec

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

15. Bed & Breakfast Vicolo dell'Oste

Montepulciano

Melissa

includes taxes & fees

15 Nov - 16 Nov

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

16. Residenza Fabroni

Montepulciano

Andrew

includes taxes & fees

16 Nov - 17 Nov

A rustic dining area with a brick fireplace, wooden furniture, and hanging lanterns.

17. Borgo Lucignanello Bandini

Montalcino

Marc

includes taxes & fees

15 Nov - 16 Nov

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

18. Idolina Guest House

Montalcino

Jaiden

includes taxes & fees

26 Nov - 27 Nov

A dining table with a bottle of wine, two wine glasses, a candle, and a vase with flowers.

19. B&B Le Scalette di Piazza

Montalcino

Morris

includes taxes & fees

15 Nov - 16 Nov

A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.

20. Palazzo Saloni

Montalcino

Michael

includes taxes & fees

14 Dec - 15 Dec

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Top Pienza Hotel Reviews

L'Orto delle Terme

10/10 Excellent

"This was a wonderful stay. Bagno Vignoni and the surrounding area are truly magical and i absolutely loved staying at Orto Le Terme - this is one of those instances where the room photos did not do it justice. I loved the room - it felt warm and inviting with supremely tasteful decor and a big comfortable bathroom with separate shower and freestanding bath. The breakfasts were next level. I think one of the best hotel breakfasts i've had. Lots of amazing local Tuscan produce. Cannot recommend enough."

Agriturismo Poggio Tobruk

10/10 Excellent

"Did you ever want to say that you stayed in one of the Pope's guest houses? The Agriturismo Poggio Tobruk may be a place for you, and that is only a starter. The Poggio is a working farm (wheat, clover, olives) and it is managed by Marco, a Sardinaian, and his brother. Marco works the villa as well as running the farm with his brother. One of our group worked a wheat farm in Colorado, so a lot of time was spent looking at equipment and discussing crops. We picniked in the olive grove and basked on the lawn, both with marvelous views of the countryside and Pienza on its own hill just a few kilometers away. We bought products from the farm, and of course the friendly Marco gave us more products to take along. Poggio Tobruk is a great place to visit, and not just because the Pope once hosted guests there!"

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"

Agriturismo Il Macchione

8/10 Good

"We stayed at the olive Farmhouse across the street from the main property. Rooms were cozy and clean with some interesting toiletries to use (made from olive oil). The property also has a range of activities (extra) to choose from. Just a note that eventhough the farmhouse is close to the main property, you have to walk uphill to get to the property for breakfast or the pool. Also it is close to Pienza but on the north side (personally I think the south side is more picturesque). But overall, a good stay and property! Staff was very professional, friendly and always courteous"

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.

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. PienzaLettings Suites

4. TuscanyLettings Studio&Room

5. Casa Gioia - Casa Olivieri

6. Casanova - Panoramic Rooms and Suites

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

8. Abbadia Sicille Relais

9. Sarna Residence

10. montorio

11. Delcorto Suites

12. Meublé Il Riccio

13. La Locanda di San Francesco

14. Il Tosco

15. Bed & Breakfast Vicolo dell'Oste

16. Residenza Fabroni

17. Borgo Lucignanello Bandini

18. Idolina Guest House

19. B&B Le Scalette di Piazza

20. Palazzo Saloni

Find holiday rentals that suit your style

Top Pienza Hotel Reviews

L'Orto delle Terme

Castello di Velona Resort Thermal SPA & Winery

Monastero di Cortona Hotel & Spa

Castiglion del Bosco, A Rosewood Hotel

Agriturismo Poggio Tobruk

Hotel Villa Ricci

Podere Spedalone

Agriturismo Il Macchione

Frequently asked questions

Go further with the Expedia app

Pienza Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Pienza holiday rentals

1. Hotel San Gregorio

2. Affitacamere Maria Gabriella

3. PienzaLettings Suites

4. TuscanyLettings Studio&Room

5. Casa Gioia - Casa Olivieri

6. Casanova - Panoramic Rooms and Suites

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

8. Abbadia Sicille Relais

9. Sarna Residence

10. montorio

11. Delcorto Suites

12. Meublé Il Riccio

13. La Locanda di San Francesco

14. Il Tosco

15. Bed & Breakfast Vicolo dell'Oste

16. Residenza Fabroni

17. Borgo Lucignanello Bandini

18. Idolina Guest House

19. B&B Le Scalette di Piazza

20. Palazzo Saloni

Find holiday rentals that suit your style

Top Pienza Hotel Reviews

L'Orto delle Terme

Frequently asked questions

Go further with the Expedia app