A historic square with a prominent tower and statues.

Pienza Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Pienza vacation rentals

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

1. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (67 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is ￥16,502
￥22,614 total
includes taxes & fees
Oct 8 - Oct 9
Affitacamere Maria Gabriella
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

2. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (157 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is ￥22,803
￥26,159 total
includes taxes & fees
Oct 28 - Oct 29
Hotel San Gregorio
A balcony with a metal railing, a small table with a chair, potted plants, and a view of the sea.

3. PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (5 reviews)
"Clean room with friendly and helpful staff. Thank you so much for the wonderful stay"
United States
Pearlyn
The price is ￥16,155
￥18,487 total
includes taxes & fees
Oct 25 - Oct 26
PienzaLettings Suites
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

TuscanyLettings Studio&Room
Pienza
10.0 out of 10, Exceptional, (3 reviews)
"Lugar maravilhoso, localização perfeita, super limpo e aconchegante."
Brazil
Lucas
The price is ￥16,346
￥18,698 total
includes taxes & fees
Sep 30 - Oct 1
TuscanyLettings Studio&Room
A stone building with a wooden door, a staircase, and a small window with a metal grill.

5. Casa Gioia - Casa Olivieri

Casa Gioia - Casa Olivieri
Pienza
10.0 out of 10, Exceptional, (3 reviews)
"Good communication with management through WhatsApp. The taxi dropped us off one minute from the property. Very cozy top floor with only a few steps. The 2 bedroom unit is very comfortable, the kids enjoyed sleeping in the loft. Air conditioning worked very well. We had everything we needed, the location is wonderful. We really enjoyed our stay. Thank you!"
United States
Nancy
The price is ￥16,689
￥19,075 total
includes taxes & fees
Oct 18 - Oct 19
Casa Gioia - Casa Olivieri
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

Apartment 'La Dimora Di Pienza in Val D'Orcia' with Wi-Fi
Pienza
The price is ￥22,574
￥27,770 total
includes taxes & fees
Oct 5 - Oct 6
Apartment 'La Dimora Di Pienza in Val D'Orcia' with Wi-Fi
An outdoor patio with a wooden pergola, a table with chairs, and potted plants.

7. Suite Gioconda - Podere Casa Rossa in Pienza

Suite Gioconda - Podere Casa Rossa in Pienza
Pienza
10.0 out of 10, Exceptional, (5 reviews)
"Comfortable, clean and the hosts are over the top welcoming! Walking distance to Pienza with gorgeous views. Loved staying here and hope to come back someday! "
United States
Doug H.
The price is ￥32,409
￥40,830 total
includes taxes & fees
Oct 5 - Oct 6
Suite Gioconda - Podere Casa Rossa in Pienza
A cozy outdoor seating area with stone walls and red foliage, featuring a table and chairs, and a door leading to a covered entrance.

8. L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (25 reviews)
"Absolutely first class and friendly Perfect location "
United States
Jennifer
The price is ￥112,868
￥124,872 total
includes taxes & fees
Oct 18 - Oct 19
L'Olmo
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

Finestra Dell'Angelo in Pienza – Elegant Apartment with Stunning Views
Pienza
8.0 out of 10, Very good, (1 review)
"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."
United States
Michael H.
Finestra Dell'Angelo in Pienza – Elegant Apartment with Stunning Views

10. Podere Manafiore - historical villa with swimming pool

Podere Manafiore - historical villa with swimming pool
Monticchiello
10.0 out of 10, Exceptional, (1 review)
"the villa was all we hoped for. Directions finding the villa was not clear, it took us for ever to locate the villa. The road to the villa was hardly drivable. It was wonderfully furnished. "
United States
Caroline R.
Podere Manafiore - historical villa with swimming pool
A stone-walled room with a large bathtub, a fireplace, and a set of stone steps leading to the tub.

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

Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
San Quirico d'Orcia
9.0 out of 10, Wonderful, (49 reviews)
"Our stay was great. "
United States
Elena
The price is ￥23,544
￥26,616 total
includes taxes & fees
Oct 1 - Oct 2
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
A poolside area with two glasses of water, candles, and a stone pathway.

12. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (97 reviews)
"The room snd entire property were spotless clean. Staff wete helpful and friendly. Our room and patio overlooked the d'Orcia valley, gorgeous any time, especially in the morning. The entire grounds, pool, loungers, plants were well maintained. This was our third time at Cassanova and we would come again. A short walk into San Quirico d'Orcia with several good restaurants and a COOP store for drinks and groceries."
Canada
Zoltan
The price is ￥27,232
￥30,672 total
includes taxes & fees
Oct 4 - Oct 5
Casanova - Panoramic Rooms and Suites
A historic building with a tower, a courtyard, and a well-lit entrance.

13. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (182 reviews)
"Great Historical location."
Canada
Robert
The price is ￥17,935
￥20,266 total
includes taxes & fees
Oct 28 - Oct 29
Abbadia Sicille Relais
An arched doorway leading to a building with a wooden door and a staircase.

14. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (110 reviews)
"Staff was great, and they even scheduled transportation to and from the train station for us. Great location on the main strip of Montepluciano!"
United States
Nicholas
The price is ￥12,583
￥14,558 total
includes taxes & fees
Oct 19 - Oct 20
Residenza Fabroni
An interior courtyard with stone columns, arches, and a mosaic.

15. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (118 reviews)
"What a gem! Absolutely loved the hotel and enjoyed our stay. Staff very friendly and helpful, and our room was outstanding. The view from our balcony was breathtaking. Top of our list!"
United States
Christopher
The price is ￥25,274
￥28,518 total
includes taxes & fees
Oct 1 - Oct 2
Meublé Il Riccio
A narrow alleyway with buildings on either side, string lights hanging above, and a sign reading "ROOMS".

16. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (141 reviews)
"Wonderful place - clean, comfortable, quiet with excellent hosts. Perfect location near everything in town including the parking. Can’t wait to return!"
United States
Shelly
The price is ￥19,386
￥22,041 total
includes taxes & fees
Oct 14 - Oct 15
Bed & Breakfast Vicolo dell'Oste

17. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (8 reviews)
"Beautiful place, view and city."
United States
Federico
The price is ￥18,030
￥20,549 total
includes taxes & fees
Oct 5 - Oct 6
montorio
A terrace with a table set for breakfast, overlooking a scenic landscape.

18. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (44 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is ￥30,040
￥33,761 total
includes taxes & fees
Oct 29 - Oct 30
Delcorto Suites
A narrow stone-paved street flanked by stone walls and buildings with multiple windows.

19. Dimora del Poggio - cozy Tuscan apartment

Dimora del Poggio - cozy Tuscan apartment
San Quirico d'Orcia
10.0 out of 10, Exceptional, (5 reviews)
"Our hosts were fantastic, the apartment was clean, roomy, and comfortable, and the location was perfect. Easy walk to enjoy shops and dining."
United States
Joe B.
The price is ￥24,903
￥33,324 total
includes taxes & fees
Oct 11 - Oct 12
Dimora del Poggio - cozy Tuscan apartment
A crowded restaurant with brick walls and multiple tables and chairs.

20. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (148 reviews)
"This place was great. Amazing view the room. Extremely friendly and helpful staff. This hotel made our trip - highly recommend"
Canada
Colin
The price is ￥33,224
￥37,263 total
includes taxes & fees
Oct 12 - Oct 13
La Locanda di San Francesco
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pienza Hotel Reviews

La Bandita Townhouse

La Bandita Townhouse

10/10 Excellent
"Great 12 room boutique hotel in the heart of Pienza."
Robert 1-night trip
Posted 1 hour ago
La Bandita Townhouse

Find out more about Pienza

Search for holiday rentals in Pienza on Expedia! You can easily find your home rentals, villas, holiday apartments in Pienza using one of the methods below:

  • View our selection of featured holiday rentals in Pienza
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  • Enter your travel dates to view the best deals on holiday rentals in Pienza while they last

Look no further and take a look at our great range of rental properties 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 31 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.