Pienza Vacation Rentals from $76: 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 .

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Our top choices for Pienza vacation rentals

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

1. Hotel San Gregorio

Pienza

Michael

$129 nightly

Nov 8 - Nov 9

Total with taxes and fees

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

2. Affitacamere Maria Gabriella

Pienza

Janine und Thomas

$117 nightly

Oct 19 - Oct 20

Total with taxes and fees

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

$84 nightly

Nov 4 - Nov 5

Total with taxes and fees

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

4. Casa Gioia - Casa Olivieri

Pienza

Nancy

$95 nightly

Nov 5 - Nov 6

Total with taxes and fees

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

$79 nightly

Nov 3 - Nov 4

Total with taxes and fees

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

$447 nightly

Nov 3 - Nov 4

Total with taxes and fees

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

$189 nightly

Oct 18 - Oct 19

Total with taxes and fees

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.

$264 nightly

Oct 22 - Oct 23

Total with taxes and fees

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.

$349 nightly

Oct 20 - Oct 21

Total with taxes and fees

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

10. Abbadia Sicille Relais

Trequanda

Robert

$91 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

11. Casanova - Panoramic Rooms and Suites

San Quirico d'Orcia

DANIELA

$167 nightly

Oct 30 - Oct 31

Total with taxes and fees

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

12. Sarna Residence

San Quirico d'Orcia

Bokang

$110 nightly

Nov 3 - Nov 4

Total with taxes and fees

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

$122 nightly

Nov 1 - Nov 2

Total with taxes and fees

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

14. Residenza Fabroni

Montepulciano

$85 nightly

Oct 21 - Oct 22

Total with taxes and fees

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

$105 nightly

Nov 3 - Nov 4

Total with taxes and fees

16. montorio

Montepulciano

Federico

$112 nightly

Oct 18 - Oct 19

Total with taxes and fees

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

17. La Locanda di San Francesco

Montepulciano

Colin

$170 nightly

Nov 3 - Nov 4

Total with taxes and fees

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

18. Delcorto Suites

Montepulciano

Denise

$185 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

$96 nightly

Nov 14 - Nov 15

Total with taxes and fees

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

20. Meublé Il Riccio

Montepulciano

Christopher

$148 nightly

Oct 25 - Oct 26

Total with taxes and fees

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Top Pienza Hotel Reviews

L'Orto delle Terme

10/10 Excellent

"Clean room and beautiful Suite. Breakfast was excellent!"

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!"

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"

Find out more about Pienza

Everything you need to know about Pienza vacation rentals

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

Pienza vacation 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 low season months. For more hustle and bustle, you may prefer to visit Pienza in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $76 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pienza rentals

At Expedia, we put the best Pienza vacation 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 vacation.

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.

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Things to do in Pienza

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

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Check prices for these dates

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

Top Pienza Hotel Reviews

L'Orto delle Terme

Find out more about Pienza

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Frequently asked questions

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