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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Pienza holiday rentals

Food and drink

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (141 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is ฿7,918
฿8,938 total
includes taxes & fees
24 May - 25 May
Hotel San Gregorio
Suite, 2 Bedrooms | Courtyard view

L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (24 reviews)
"Absolutely first class and friendly Perfect location "
United States
Jennifer
L'Olmo
Exterior detail

Il Rifugio del Borgo

Il Rifugio del Borgo
Città della Pieve
The price is ฿4,203
฿4,700 total
includes taxes & fees
7 May - 8 May
Il Rifugio del Borgo
Exterior

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (130 reviews)
"Loved this place ! Clean, modern, large rooms, perfect location and the owner kind and beyond attentive."
United States
Melissa
The price is ฿4,472
฿5,071 total
includes taxes & fees
18 May - 19 May
Bed & Breakfast Vicolo dell'Oste
Exterior

Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16 reviews)
"Great host, lovely place near Siena"
United Kingdom
Prem
The price is ฿3,461
฿3,960 total
includes taxes & fees
25 May - 26 May
Il Pozzo di Sant'Andrea
Exterior

B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (92 reviews)
"Great location, nice room, and great host!"
United States
Chris
The price is ฿4,635
฿5,251 total
includes taxes & fees
12 May - 13 May
B&B Le Scalette di Piazza
Property grounds

Agriturismo San Filippo

Agriturismo San Filippo
Acquapendente
8.6 out of 10, Excellent, (14 reviews)
"Excellent experience!"
United States
Richard
The price is ฿2,956
฿3,251 total
includes taxes & fees
10 May - 11 May
Agriturismo San Filippo
Classic Apartment, 2 Bedrooms | Terrace/patio

FonteLiving

FonteLiving
San Casciano dei Bagni
9.8 out of 10, Exceptional, (10 reviews)
"Excellent experience, location, and environment."
Taiwan
Chia-Hung
The price is ฿2,458
฿2,780 total
includes taxes & fees
12 May - 13 May
FonteLiving
Couples treatment room(s), sauna, hot tub, steam room, body treatments

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, (47 reviews)
"Our stay was great. "
United States
Elena
The price is ฿4,433
฿5,029 total
includes taxes & fees
7 May - 8 May
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
Interior

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (94 reviews)
"Nothing negative could be said about this absolutely fabulous property. Great staff, great location, best room of our 22 day, 11 stop trip. Easy luggage so off, great everything. We will be back and will definitely stay here again. "
United States
Michael
The price is ฿5,419
฿6,113 total
includes taxes & fees
23 May - 24 May
Meublé Il Riccio
Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | Private spa tub

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (28 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is ฿3,119
฿3,583 total
includes taxes & fees
25 May - 26 May
DormiVeglia B&B
Front of property

Residence al Lago

Residence al Lago
Contrada Fontivegge
8.6 out of 10, Excellent, (38 reviews)
"We stayed for one night, but the rooms are only good for night, it was very expensive for the room and location "
United States
Hananeh
The price is ฿3,636
฿4,153 total
includes taxes & fees
20 May - 21 May
Residence al Lago
Terrace/patio

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (173 reviews)
"The room was really clean and as described. Unfortunately, the hotel restaurant was closed and that was not mentioned on the site. I learned about it the day before my arrival. Fortunately, the host had good restaurant suggestions. The hotel advertise a pool and a jacuzzi, they have both but the pool was VERY cold (normal in April) and the jacuzzi was not inviting (bee nest, Luke warm, in the shade...). Concerning the breakfast, note that it is not a buffet, a box get delivered to your room. You...
Canada
Chantal
The price is ฿6,346
฿7,095 total
includes taxes & fees
3 Jun - 4 Jun
Abbadia Sicille Relais
BBQ/picnic Area

Residenza d'epoca Ca' de Principi

Residenza d'epoca Ca' de Principi
Piegaro
9.8 out of 10, Exceptional, (13 reviews)
"The hotel was charming, and the staff really nice. Breakfast had lots of options. The room was large and beautiful view of the hills. The bed was comfortable."
United States
Robyn
The price is ฿4,494
฿4,943 total
includes taxes & fees
20 May - 21 May
Residenza d'epoca Ca' de Principi
Exterior

Idolina Guest House

Idolina Guest House
Montalcino
9.4 out of 10, Exceptional, (107 reviews)
"Excellent service, ideal location"
United Kingdom
Nigel
The price is ฿3,422
฿4,069 total
includes taxes & fees
13 May - 14 May
Idolina Guest House
Bar (on property)

La Piccola Locanda

La Piccola Locanda
Chiusi
7.8 out of 10, Good, (11 reviews)
"This was a great place to stay for two nights in late October and to take out and back day trips by train to Siena and Florence on back-to-back days. Very close to the train station - very convenient. Breakfast in the restaurant in the morning was small, but good. Highly recommend this location! It's small, but serviced and supported very well by the staff at the restaurant. "
United States
Jeffery
The price is ฿4,039
฿4,519 total
includes taxes & fees
14 May - 15 May
La Piccola Locanda
Lobby

B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.6 out of 10, Exceptional, (21 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is ฿4,369
฿4,958 total
includes taxes & fees
18 May - 19 May
B&B Piccolo Hotel
Interior detail

La Coroncina Lodging

La Coroncina Lodging
Siena
10.0 out of 10, Exceptional, (43 reviews)
"Fantastic place, and I highly recommend it."
United States
Hassan
The price is ฿4,950
฿5,597 total
includes taxes & fees
29 May - 30 May
La Coroncina Lodging
Food court

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (137 reviews)
"Beautiful quaint place to stay in Montepulciano. Stairs are doable to carry up luggage and the views of the valley are spectacular. Great location, can’t wait to stay again!"
Canada
Melissa
The price is ฿7,481
฿8,382 total
includes taxes & fees
10 May - 11 May
La Locanda di San Francesco
Aerial view

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (65 reviews)
"Pros: 1. Beautiful property with an amazing view. 2. Spacious family suite 3. Comfortable bed 4. Quiet, waking up to birds singing in the morning. Cons: 1. Stink bugs in the suite; once we understood they are common this time of year and easy to capture and release outside, it was ok. 2. Showers are very small. 3. A/C not turned on this time of year; was not offered fans until the last day. 4. Minimal amenities. 5. Few outlets The villa is beautiful, just be prepared for a “rustic”...
United States
Niyo
The price is ฿5,833
฿6,721 total
includes taxes & fees
15 May - 16 May
Villa Curina Resort
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
"Beautiful hotel. Excellent location and friendly staff. Breakfast was wonderful. Especially appreciated the large bath tub."
Leah 2-night trip
Posted 20 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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Look no further and take a look at our great range of rental properties in Pienza!

Frequently asked questions

Can I find a holiday rental in Pienza?

Yes, there are holiday rentals in Pienza close to RI Crea RE, or you can select a more secluded option if you're looking for 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 holiday rentals are there in Pienza?

Expedia has 28 holiday 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 holiday rental in Pienza like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Pienza. Holiday rentals feature amenities such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.