Pienza Vacation Rentals from $75: 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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In two weeks

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Our top choices for Pienza vacation rentals

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

1. TuscanyLettings Studio&Room

Pienza

Lucas

$77 nightly

Nov 4 - Nov 5

Total with taxes and fees

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

2. Hotel San Gregorio

Pienza

Michael

$137 nightly

Nov 5 - Nov 6

Total with taxes and fees

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

3. Affitacamere Maria Gabriella

Pienza

Janine und Thomas

$118 nightly

Nov 4 - Nov 5

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.

4. PienzaLettings Suites

Pienza

Pearlyn

$80 nightly

Nov 2 - Nov 3

Total with taxes and fees

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

5. Casa Gioia - Casa Olivieri

Pienza

Nancy

$101 nightly

Nov 4 - Nov 5

Total with taxes and fees

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

$245 nightly

Nov 1 - Nov 2

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.

7. L'Olmo

Pienza

Michelle

$446 nightly

Nov 4 - Nov 5

Total with taxes and fees

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

8. 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.

$196 nightly

Nov 5 - Nov 6

Total with taxes and fees

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

9. Abbadia Sicille Relais

Trequanda

Robert

$65 nightly

Nov 26 - Nov 27

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.

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

San Quirico d'Orcia

Elena

$98 nightly

Nov 4 - Nov 5

Total with taxes and fees

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

11. Sarna Residence

San Quirico d'Orcia

Bokang

$110 nightly

Nov 9 - Nov 10

Total with taxes and fees

12. montorio

Montepulciano

Joseph

$120 nightly

Nov 5 - Nov 6

Total with taxes and fees

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

13. Casanova - Panoramic Rooms and Suites

San Quirico d'Orcia

DANIELA

$170 nightly

Nov 29 - Nov 30

Total with taxes and fees

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

14. La Locanda di San Francesco

Montepulciano

Colin

$153 nightly

Nov 25 - Nov 26

Total with taxes and fees

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

15. Idolina Guest House

Montalcino

Jaiden

$82 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

16. Bed & Breakfast Vicolo dell'Oste

Montepulciano

Shelly

$102 nightly

Dec 1 - Dec 2

Total with taxes and fees

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

17. Residenza Fabroni

Montepulciano

Marc

$95 nightly

Nov 5 - Nov 6

Total with taxes and fees

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

18. Meublé Il Riccio

Montepulciano

Christopher

$137 nightly

Nov 8 - Nov 9

Total with taxes and fees

A stone archway leading to a building entrance with a wooden door.

19. Bellarmino Boutique Apartments

Montepulciano

Abel

$52 nightly

Nov 5 - Nov 6

Total with taxes and fees

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

20. B&B Le Scalette di Piazza

Montalcino

Morris

$119 nightly

Nov 2 - Nov 3

Total with taxes and fees

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Top Pienza Hotel Reviews

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent

"Unique property well maintained and quite Serene , great staff"

Fonteverde Thermal Spa Resort Tuscany

10/10 Excellent

"We travel a lot and this was our favorite hotel ever!! Natural hot springs designed into a luxurious set of pools with jets, waterfalls, and even poolside bistrot! The breakfast was the best European hot breakfast we’ve ever had as well. The rooms were beautiful too."

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!"

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent

"Stayed at the hotel for our honeymoon and it was an incredible experience. The view is simply breathtaking and the castle is extremely charming. Food (breakfast and diner) and wine at the restaurants are high quality, inspired and locally sourced, though expensive. Their Brunello is VERY good. The thermal spa experience is unique in the region and is awsome, especially during the fall season when it is cooler outside. The room was super clean and the staff was very helpful throughout the entire week, and we felt welcomed at any time of day. 15 min by car from Montalcino, strongly recommend to rent a car since it is slightly remote. Overall 9.5/10, strongly recommend for a special occasion."

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"

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 $75 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. TuscanyLettings Studio&Room

2. Hotel San Gregorio

3. Affitacamere Maria Gabriella

4. PienzaLettings Suites

5. Casa Gioia - Casa Olivieri

6. Apartment 'La Dimora di Pienza in Val d'Orcia' with Wi-Fi

7. L'Olmo

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

9. Abbadia Sicille Relais

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

11. Sarna Residence

12. montorio

13. Casanova - Panoramic Rooms and Suites

14. La Locanda di San Francesco

15. Idolina Guest House

16. Bed & Breakfast Vicolo dell'Oste

17. Residenza Fabroni

18. Meublé Il Riccio

19. Bellarmino Boutique Apartments

20. B&B Le Scalette di Piazza

Find vacation rentals that suit your style

Top Pienza Hotel Reviews

Castiglion del Bosco, A Rosewood Hotel

Find out more about Pienza

Explore a world of travel with Expedia

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