Pienza Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (171 reviews)
"Great location. Clean and quiet with good breakfast"
United States
Michael
The price is P8,601
P9,883 total
includes taxes & fees
Nov 16 - Nov 17
Hotel San Gregorio
A patio area with outdoor seating, potted plants, and a view of the landscape.

2. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (75 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is P6,812
P9,242 total
includes taxes & fees
Nov 10 - Nov 11
Affitacamere Maria Gabriella
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

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 P5,518
P6,351 total
includes taxes & fees
Dec 9 - Dec 10
TuscanyLettings Studio&Room
A balcony with a metal railing, a small table with a chair, potted plants, and a view of the sea.

4. PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (7 reviews)
"Clean room with friendly and helpful staff. Thank you so much for the wonderful stay"
United States
Pearlyn
The price is P5,334
P6,149 total
includes taxes & fees
Dec 10 - Dec 11
PienzaLettings Suites
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

L'Olmo
Pienza
10.0 out of 10, Exceptional, (28 reviews)
"We were so comfortable and impressed with L'Olmo. Communication prior to our trip was perfect. We got there and the grounds were immaculate, the room was stunning, and the location was extremely convenient. The staff was very helpful. We loved staying here and can recommend it whole heartedly."
United States
Michelle
L'Olmo
A stone building with a wooden door, a staircase, and a small window with a metal grill.

6. 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 P5,174
P5,972 total
includes taxes & fees
Dec 8 - Dec 9
Casa Gioia - Casa Olivieri
A poolside area with two glasses of water, candles, and a stone pathway.

7. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.0 out of 10, Wonderful, (105 reviews)
"Hotel had beautiful views and amenities like breakfast and spa were amazing."
United States
Oscar
The price is P10,679
P12,028 total
includes taxes & fees
Nov 18 - Nov 19
Casanova - Panoramic Rooms and Suites
A stone-walled room with a large bathtub, a fireplace, and a set of stone steps leading to the tub.

8. 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, (50 reviews)
"Our stay was great. "
United States
Elena
The price is P6,438
P7,363 total
includes taxes & fees
Nov 10 - Nov 11
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
A covered corridor with brick columns, potted plants, and a view of a lush landscape.

9. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (185 reviews)
"Great Historical location."
Canada
Robert
The price is P4,081
P4,700 total
includes taxes & fees
Nov 26 - Nov 27
Abbadia Sicille Relais
A crowded restaurant with brick walls and multiple tables and chairs.

10. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (152 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 P9,580
P10,819 total
includes taxes & fees
Nov 26 - Nov 27
La Locanda di San Francesco
A stone building with a courtyard, outdoor seating, and a warm light setting.

11. Sarna Residence

Sarna Residence
San Quirico d'Orcia
9.4 out of 10, Exceptional, (40 reviews)
"We enjoyed our stay. The room was very clean. The staff was helpful."
United States
Bokang
The price is P6,962
P8,782 total
includes taxes & fees
Nov 16 - Nov 17
Sarna Residence
An interior courtyard with stone columns, arches, and a mosaic.

12. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (122 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 P10,012
P11,294 total
includes taxes & fees
Nov 10 - Nov 11
Meublé Il Riccio
A terrace with a table set for breakfast, overlooking a scenic landscape.

13. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (50 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is P10,769
P12,127 total
includes taxes & fees
Nov 10 - Nov 11
Delcorto Suites
A stone building with a tiled roof, surrounded by tall trees and a gravel path.

14. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (11 reviews)
"Amazing location, beautiful property"
United States
Joseph
The price is P7,530
P8,564 total
includes taxes & fees
Nov 10 - Nov 11
montorio
A narrow alleyway with buildings on either side, string lights hanging above, and a sign reading "ROOMS".

15. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (145 reviews)
"We really enjoyed the room. Comfortable bed. Great location."
United States
Melissa
The price is P6,081
P6,971 total
includes taxes & fees
Nov 10 - Nov 11
Bed & Breakfast Vicolo dell'Oste
A narrow cobblestone street flanked by historic stone buildings with arched doorways and windows.

16. Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (141 reviews)
"Excellent room, service and food. The best."
United States
Valerie
The price is P14,486
P16,215 total
includes taxes & fees
Nov 10 - Nov 11
Il Tosco
An arched doorway leading to a building with a wooden door and a staircase.

17. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (116 reviews)
"Very charming property in a fantastic location. The host was very responsive and we had a marvelous stay. Bear in mind this is a historic property and accordingly has some quirks. Those looking for modernity and perfect fixtures may not appreciate those quirks."
United States
Marc
The price is P5,633
P6,478 total
includes taxes & fees
Nov 11 - Nov 12
Residenza Fabroni
A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.

18. Palazzo Saloni

Palazzo Saloni
Montalcino
10.0 out of 10, Exceptional, (14 reviews)
"Excellent location to tour wine country montalcino."
United States
Michael
The price is P16,167
P18,486 total
includes taxes & fees
Dec 9 - Dec 10
Palazzo Saloni
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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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.

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.