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 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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, (157 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is P12,309
P13,968 total
includes taxes & fees
Oct 4 - Oct 5
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, (67 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is P6,913
P9,380 total
includes taxes & fees
Oct 7 - Oct 8
Affitacamere Maria Gabriella
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 P6,429
P7,357 total
includes taxes & fees
Oct 18 - Oct 19
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 P7,056
P8,047 total
includes taxes & fees
Oct 15 - Oct 16
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 P7,219
P8,226 total
includes taxes & fees
Oct 12 - Oct 13
Casa Gioia - Casa Olivieri
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

L'Olmo
Pienza
10.0 out of 10, Exceptional, (25 reviews)
"Absolutely first class and friendly Perfect location "
United States
Jennifer
The price is P44,920
P49,697 total
includes taxes & fees
Oct 18 - Oct 19
L'Olmo
An interior courtyard with stone columns, arches, and a mosaic.

7. 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 P10,160
P11,462 total
includes taxes & fees
Sep 27 - Sep 28
Meublé Il Riccio
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, (49 reviews)
"Our stay was great. "
United States
Elena
The price is P10,890
P12,264 total
includes taxes & fees
Sep 25 - Sep 26
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
A narrow alleyway with buildings on either side, string lights hanging above, and a sign reading "ROOMS".

9. 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 P7,715
P8,772 total
includes taxes & fees
Oct 14 - Oct 15
Bed & Breakfast Vicolo dell'Oste
A poolside area with two glasses of water, candles, and a stone pathway.

10. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (96 reviews)
"Very good accommodation in the heart of Val’d’Orcia. Reasonably priced"
Finland
Jarkko
The price is P10,838
P12,207 total
includes taxes & fees
Oct 4 - Oct 5
Casanova - Panoramic Rooms and Suites
An arched doorway leading to a building with a wooden door and a staircase.

11. 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 P6,300
P7,216 total
includes taxes & fees
Oct 13 - Oct 14
Residenza Fabroni
A historic building with a tower, a courtyard, and a well-lit entrance.

12. 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 P7,759
P8,749 total
includes taxes & fees
Oct 25 - Oct 26
Abbadia Sicille Relais
A crowded restaurant with brick walls and multiple tables and chairs.

13. 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 P13,353
P14,973 total
includes taxes & fees
Sep 27 - Sep 28
La Locanda di San Francesco

14. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (8 reviews)
"Beautiful place, view and city."
United States
Federico
The price is P7,176
P8,178 total
includes taxes & fees
Oct 7 - Oct 8
montorio
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

Hotel Corsignano

Hotel Corsignano

10/10 Excellent
"Everything was perfect the staff the hotel."
steve 1-night trip
Posted 4 hours ago
Hotel Corsignano

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:

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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 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.