Pienza Vacation Rentals from AED 253: 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 swimming pool with a water feature, surrounded by greenery and a table with chairs.

1. Hotel San Gregorio

Pienza

Michael

AED 580 total

includes taxes & fees

16 Nov - 17 Nov

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

2. Affitacamere Maria Gabriella

Pienza

Janine und Thomas

AED 497 total

includes taxes & fees

11 Dec - 12 Dec

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

AED 330 total

includes taxes & fees

9 Dec - 10 Dec

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

AED 357 total

includes taxes & fees

10 Dec - 11 Dec

A cozy outdoor seating area with stone walls and red foliage, featuring a table and chairs, and a door leading to a covered entrance.

5. L'Olmo

Pienza

Michelle

A traditional stone building with multiple windows and doors, a courtyard with a table and chairs, and a clear blue sky with clouds.

6. Casa Gioia - Casa Olivieri

Pienza

Nancy

AED 304 total

includes taxes & fees

11 Dec - 12 Dec

A window with a view of a cityscape, a bottle of wine, and various fruits and cheeses on a table.

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

Pienza

AED 1,356 total

includes taxes & fees

11 Dec - 12 Dec

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.

AED 631 total

includes taxes & fees

12 Nov - 13 Nov

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

9. Casanova - Panoramic Rooms and Suites

San Quirico d'Orcia

Oscar

AED 701 total

includes taxes & fees

10 Dec - 11 Dec

A stone-walled room with a fireplace, a hot tub, candles, and a tray with snacks.

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

San Quirico d'Orcia

Elena

AED 458 total

includes taxes & fees

23 Nov - 24 Nov

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

11. Abbadia Sicille Relais

Trequanda

Robert

AED 276 total

includes taxes & fees

26 Nov - 27 Nov

A hotel room with a bed, a chair, a lamp, and a view of the outdoors.

12. La Locanda di San Francesco

Montepulciano

Colin

AED 627 total

includes taxes & fees

26 Nov - 27 Nov

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

13. Sarna Residence

San Quirico d'Orcia

Bokang

AED 491 total

includes taxes & fees

15 Nov - 16 Nov

A balcony with a view of a historic town, featuring terracotta-roofed buildings and a prominent church tower.

14. Meublé Il Riccio

Montepulciano

Slimane

AED 579 total

includes taxes & fees

23 Nov - 24 Nov

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

15. Delcorto Suites

Montepulciano

Denise

AED 708 total

includes taxes & fees

11 Nov - 12 Nov

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

16. montorio

Montepulciano

Joseph

AED 502 total

includes taxes & fees

11 Nov - 12 Nov

A bedroom with a wooden ceiling, a bed with white bedding, a bedside table with a lamp, and a window with sheer curtains.

17. Bed & Breakfast Vicolo dell'Oste

Montepulciano

Melissa

AED 400 total

includes taxes & fees

11 Nov - 12 Nov

A window with a view of a green landscape and hills.

18. Il Tosco

Montepulciano

Valerie

AED 945 total

includes taxes & fees

9 Dec - 10 Dec

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

19. Residenza Fabroni

Montepulciano

Marc

AED 336 total

includes taxes & fees

12 Nov - 13 Nov

A courtyard with outdoor seating, a building with multiple windows, and a stone wall.

20. Palazzo Saloni

Montalcino

Michael

AED 1,067 total

includes taxes & fees

11 Dec - 12 Dec

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Top Pienza Hotel Reviews

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent

"Extremely attentive and polite staff made us feel special. The location, thermal pools and bike rental made our stay incredible and unforgettable. Can’t wait to stay again!"

L'Orto delle Terme

10/10 Excellent

"Bed and breakfast is very convenient. alternative to the main hotel. Rooms are very good and have access to the main hotel restaurant for breakfast. If you want to use their spa facilities and stay in the bed and breakfast, you need to pay them separately though. It’s a great property in a beautiful Location."

Tenuta Santo Pietro

10/10 Excellent

"This place was a Gem. The property and amenities were awesome and very homey. Very lovely and well seasoned staffed that know how to cater to their guests. I would recommend this spot to anyone who wants to be taken care of in a very special and specific manner. We had Dinner there both nights we stayed there and not only was it convenient but it was delicious. Traditional meals served simply, yet beautifully."

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"

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.

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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. PienzaLettings Suites

5. L'Olmo

6. Casa Gioia - Casa Olivieri

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

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

9. Casanova - Panoramic Rooms and Suites

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

11. Abbadia Sicille Relais

12. La Locanda di San Francesco

13. Sarna Residence

14. Meublé Il Riccio

15. Delcorto Suites

16. montorio

17. Bed & Breakfast Vicolo dell'Oste

18. Il Tosco

19. Residenza Fabroni

20. Palazzo Saloni

Find vacation rentals that suit your style

Top Pienza Hotel Reviews

Castello di Velona Resort Thermal SPA & Winery

L'Orto delle Terme

Hotel San Gregorio

Monastero di Cortona Hotel & Spa

Tenuta Santo Pietro

Castiglion del Bosco, A Rosewood Hotel

Agriturismo Poggio Tobruk

Hotel Villa Ricci

Podere Spedalone

Frequently asked questions

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