Pienza Vacation Rentals from ￥10,227: 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 : This highly rated vacation home rental in Pienza 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. Another good choice for your trip to Pienza is Villa I Cipressini Tuscany Private luxury pool spa .

A historic town perched on a hillside with a prominent church tower, surrounded by lush greenery and rolling hills in the background.

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Our top choices for Pienza vacation rentals

A swimming pool with a water feature, surrounded by greenery and a table with chairs.

1. Hotel San Gregorio

Pienza

Michael

￥24,763 total

includes taxes & fees

Dec 13 - Dec 14

A garden with two chairs under trees, a table, and a view of the landscape.

2. Affitacamere Maria Gabriella

Pienza

Janine und Thomas

￥22,220 total

includes taxes & fees

Nov 15 - Nov 16

A bedroom with a bed, a nightstand, a painting, and a view of the upper floor.

3. PienzaLettings Suites

Pienza

Pearlyn

￥15,260 total

includes taxes & fees

Dec 10 - Dec 11

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

￥13,785 total

includes taxes & fees

Dec 9 - Dec 10

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

5. Casa Gioia - Casa Olivieri

Pienza

Nancy

￥14,964 total

includes taxes & fees

Dec 8 - Dec 9

A pool area with lounge chairs and umbrellas, surrounded by tall cypress trees and a view of distant hills.

6. Casanova - Panoramic Rooms and Suites

San Quirico d'Orcia

Oscar

￥30,139 total

includes taxes & fees

Dec 10 - Dec 11

A narrow cobblestone street with a rustic building featuring a brick archway and ivy-covered walls. There is a wooden chair and a table with a checkered tablecloth outside.

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

San Quirico d'Orcia

Elena

￥16,645 total

includes taxes & fees

Nov 26 - Nov 27

A row of wooden wine barrels in a dimly lit, arched cellar with stone walls and a concrete floor.

8. Abbadia Sicille Relais

Trequanda

Robert

￥11,778 total

includes taxes & fees

Dec 10 - Dec 11

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

9. Sarna Residence

San Quirico d'Orcia

Bokang

￥21,111 total

includes taxes & fees

Nov 15 - Nov 16

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

10. montorio

Montepulciano

Joseph

￥21,460 total

includes taxes & fees

Nov 15 - Nov 16

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

11. Delcorto Suites

Montepulciano

Denise

￥30,222 total

includes taxes & fees

Nov 15 - Nov 16

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

12. Meublé Il Riccio

Montepulciano

Slimane

￥24,436 total

includes taxes & fees

Nov 15 - Nov 16

An outdoor dining table with a meal consisting of bread, tomatoes, and cured meat, accompanied by a glass of white wine.

13. La Locanda di San Francesco

Montepulciano

Colin

￥25,173 total

includes taxes & fees

Nov 26 - Nov 27

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

14. Il Tosco

Montepulciano

Janine

￥40,631 total

includes taxes & fees

Nov 15 - Nov 16

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

￥17,103 total

includes taxes & fees

Nov 15 - Nov 16

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

16. Residenza Fabroni

Montepulciano

Andrew

￥14,996 total

includes taxes & fees

Nov 16 - Nov 17

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

17. Borgo Lucignanello Bandini

Montalcino

Marc

A bedroom with a wooden wardrobe, a bedside table with a lamp, a radiator, and a chair.

18. Idolina Guest House

Montalcino

Jaiden

￥16,892 total

includes taxes & fees

Nov 26 - Nov 27

A kitchen area with a marble countertop, a refrigerator, and various food items.

19. B&B Le Scalette di Piazza

Montalcino

Morris

￥21,301 total

includes taxes & fees

Nov 15 - Nov 16

A view through a window of a town with traditional architecture, cobblestone streets, and a rural landscape.

20. Palazzo Saloni

Montalcino

Michael

￥46,482 total

includes taxes & fees

Dec 14 - Dec 15

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Find vacation rentals that suit your style

Top Pienza Hotel Reviews

PienzaLettings Suites

Pienza

10/10 Excellent

Shannon

A rustic stone building with a stone wall and a wooden fence.

Vento Dorcia

Pienza

10/10 Excellent

Katie

Terra Antica Resort

Montepulciano

10/10 Excellent

Nikhil

A stone house with a tiled roof, a patio with a lounge chair, and a view of rolling hills in the background.

Relais Val d'Orcia

Pienza

10/10 Excellent

Justine

A large estate with multiple buildings, a well-maintained garden, and a vineyard in the background.

Lupaia

Torrita di Siena

10/10 Excellent

This was the most amazing place to stay! This was our favorite stop on a 30-day trip to Greece, Italy and Switzerland. The surrounding countryside is stunning. Our room had a Turkish Bath - what a fun experience. We were a couple of weeks in to our vacation, and we were ready for some down time. Having a private little garden, overlooking the Tuscan hillside was WONDERFUL. The dinner we had on site was one of the best of our entire trip. Breakfast in the morning was an incredible display...

KC Traveler

A large estate with multiple buildings, a swimming pool, and expansive green fields.

Borgo Sant'Ambrogio Resort

Trequanda

10/10 Excellent

Neha

Palazzo Saloni

Montalcino

10/10 Excellent

My husband and I spent 6 fabulous nights here. From the moment I made the reservation, I felt in good hands with great communication about any question I had. The front desk can assist with wine excursions, spa, cooking class and even are connected with a nice local gym you can attend for a small fee. We rented a car and it is a big bonus that this property has on-site parking included in the rate. The Palazzo is located in a prime location, also easy to get in and out which can be tricky in...

Laura

An outdoor patio with stone walls, a pergola, and a table set for dining.

Dimora delle Muse

Montalcino

10/10 Excellent

Anonymous traveler

A villa with a swimming pool, terraced garden, and a view of distant mountains.

Agriturismo Il Macchione

Pienza

10/10 Excellent

Farasley

A garden pathway leading to a building with a yellow facade and arched windows.

Residenza Dei Ricci Relais

Chiusi

10/10 Excellent

My husband and I spent one night at Residenza dei Ricci last weekend and cannot wait to return. It is ideally situated for exploring Chiusi and the surrounding area. Our short time spent under the care of Donatella and Raffaele was one of the best travel experiences we have ever had. They are talented, congenial and generous hosts. The residenza is beautifully appointed with all the amenities one would expect at a luxury hotel -- combined with all the warmth one feels while staying at the home...

Tim

A person relaxing in a hot tub with a view of a vineyard and mountains in the background.

Villa Le Prata - Residenza del Vescovo

Montalcino

10/10 Excellent

Villa Le Prata is absolutely exceptional. A historic villa with truly personalized service that the discerning traveler always seeks. Here, that aspiration is a reality. Centrally placed near Montalcino, you are able to breathe in the Tuscan countryside outside your window. And considering they are located on their own highly regarded Brunello vineyard, what more could you ask for? A Michelin-rated property, you seriously cannot do better if coming to Tuscany. We WILL be back!!!❤️❤️❤️

Scott

La Locanda di San Francesco

Montepulciano

10/10 Excellent

Roy

A stone building with a courtyard, outdoor seating, and a view of the surrounding landscape.

LOCANDA DELLA PICCA

Citta della Pieve

10/10 Excellent

Charles

A motorcycle parked in front of a brick building with arched doorways and a street lamp.

Torre del Fuggisole

Siena City Centre

10/10 Excellent

Charles

Meublé Il Riccio

Montepulciano

10/10 Excellent

Slimane

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 Art Studio di Adelina Quadri, 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: This highly rated vacation home rental in Pienza 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. Another good choice for your trip to Pienza is Villa I Cipressini Tuscany Private luxury pool spa.

How many vacation rentals are there in Pienza?

Expedia has 30 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.

Pienza Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Pienza vacation 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 vacation rentals that suit your style

Top Pienza Hotel Reviews

PienzaLettings Suites

10/10 Excellent

Find out more about Pienza

Frequently Asked Questions

Can I find a vacation rental in Pienza?

What are some of the best vacation home rentals in Pienza?

How many vacation rentals are there in Pienza?

What’s there to see and do in Pienza?

What’s a vacation rental in Pienza like?