Pienza Vacation Rentals

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Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for Pienza vacation rentals

Free daily buffet breakfast

Relais La Saracina

Relais La Saracina
Pienza
Relais La Saracina
Panoramic Cottage, 1 Bedroom | Exterior

Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (51 reviews)
"This property has a lovely view, great garden, attentive staff with good breakfast. Stayed in the cottage and the patio was very sunny and relaxing. "
United States
Lenise
Affitacamere Maria Gabriella
Exterior

Casa Gioia - Casa Olivieri

Casa Gioia - Casa Olivieri
Pienza
The price is ￥14,326
￥16,496 total
includes taxes & fees
Mar 29 - Mar 30
Casa Gioia - Casa Olivieri
Monolocale Exclusive, vista città, secondo piano senza ascensore | Laptop workspace, iron/ironing board, free WiFi

TuscanyLettings Studio&Room

TuscanyLettings Studio&Room
Pienza
10.0 out of 10, Exceptional, (1 review)
"メイン通りの好立地。 客室は豪華でエレガント。 ウェルカムキットも良く、アメニティも良好。 次回も必ず利用したい。 スタッフの方、いろいろありがとうございました。"
Japan
keita
The price is ￥13,572
￥15,667 total
includes taxes & fees
Mar 27 - Mar 28
TuscanyLettings Studio&Room
Property grounds

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 ￥13,934
￥19,647 total
includes taxes & fees
Mar 29 - Mar 30
Apartment 'La Dimora Di Pienza in Val D'Orcia' with Wi-Fi
Suite, 2 Bedrooms | Courtyard view

L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (22 reviews)
"Absolutely first class and friendly Perfect location "
United States
Jennifer
The price is ￥73,724
￥81,833 total
includes taxes & fees
Apr 12 - Apr 13
L'Olmo
Fridge, microwave, stovetop, dishwasher

"Il Focolare" Superior Apartment in Monticchiello

"Il Focolare" Superior Apartment in Monticchiello
Monticchiello
10.0 out of 10, Exceptional, (8 reviews)
"An wonderfully presented apartment in a beautiful town away from the tourist areas but close enough with a short drive. It’s a beautiful town and the apartment is a welcome retreat when you have enjoyed enough of the Tuscan sun. It’s clear the owner has attention to detail and that made our stay even better! "
Australia
Dan
The price is ￥18,431
￥22,486 total
includes taxes & fees
Apr 2 - Apr 3
"Il Focolare" Superior Apartment in Monticchiello
2 bedrooms, desk, iron/ironing board, travel crib

The house in the village - Angelica apartment - Vald'Orcia

The house in the village - Angelica apartment - Vald'Orcia
Monticchiello
10.0 out of 10, Exceptional, (11 reviews)
"Marco was great to work with, was easily available for any of our questions and the stay was wonderful. The apartment is in a great location and had all we needed for our stay."
United States
Melissa B.
The price is ￥17,417
￥21,104 total
includes taxes & fees
Mar 26 - Mar 27
The house in the village - Angelica apartment - Vald'Orcia
Food and drink

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (139 reviews)
"This hotel was the highlight of our Tuscany trip. It is very well decorated, stunning italian furniture and arts on the wall. There is a restaurant for dining. About 2 minutes walking from Pienza old town entrance. Staff was super nice, even their mascot, an yellow cat, came to greet us. It is a must come back for us."
United States
Edison
The price is ￥28,588
￥32,553 total
includes taxes & fees
Apr 9 - Apr 10
Hotel San Gregorio
Suite Bernardo, Panoramica al terzo piano senza ascensore | Terrace/patio

PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (2 reviews)
"Fantastic room in the city center, close to everything in Pienza"
Norway
Tom
The price is ￥15,744
￥18,055 total
includes taxes & fees
Mar 26 - Mar 27
PienzaLettings Suites
Outdoor dining

Il Podere di Casa Rossa Pienza

Il Podere di Casa Rossa Pienza
Pienza
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful views, accommodating hosts"
United States
Pete and Alison C.
The price is ￥33,176
￥47,552 total
includes taxes & fees
Mar 29 - Mar 30
Il Podere di Casa Rossa Pienza
Exterior detail

Cozy 2-bedroom apartment in the historic center, located in a quiet area.

Cozy 2-bedroom apartment in the historic center, located in a quiet area.
Pienza
8.0 out of 10, Very Good, (1 review)
"Very central convenient location.Perhaps there should have been a mention of the 30 steps between street level and the apartment ."
United Kingdom
Wendy L.
The price is ￥18,578
￥27,609 total
includes taxes & fees
Apr 7 - Apr 8
Cozy 2-bedroom apartment in the historic center, located in a quiet area.
Outdoor dining

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

Finestra Dell'Angelo in Pienza – Elegant Apartment with Stunning Views
Pienza
The price is ￥21,564
￥27,277 total
includes taxes & fees
Mar 27 - Mar 28
Finestra Dell'Angelo in Pienza – Elegant Apartment with Stunning Views
Bar (on property)

La Piccola Locanda

La Piccola Locanda
Chiusi
8.6 out of 10, Excellent, (9 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
La Piccola Locanda
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
Il Pozzo di Sant'Andrea
Exterior

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (129 reviews)
"Loved this place ! Clean, modern, large rooms, perfect location and the owner kind and beyond attentive."
United States
Melissa
Bed & Breakfast Vicolo dell'Oste
Exterior

Luxury resort in the Tuscan countryside

Luxury resort in the Tuscan countryside
Trequanda
Luxury resort in the Tuscan countryside
View from property

Agriturismo Casale Le Crete

Agriturismo Casale Le Crete
Acquapendente
10.0 out of 10, Exceptional, (2 reviews)
"Buongiorno, abbiamo soggiornato al Casale Le Crete per due notti e ci siamo trovati molto bene. Eline è stata molto accogliente e disponibile e ci ha messo subito a nostro agio e ci siamo sentiti subito a nostro agio! torneremo sicuramente"
Italy
Francesca
Agriturismo Casale Le Crete
1 bedroom, free WiFi, bed sheets

Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti

Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
Monteaperti
10.0 out of 10, Exceptional, (2 reviews)
"We loved this place. Modern cabin set in a rustic Tuscan setting. Beautiful property, very comfortable stay, and very attentive staff. Family owned and operated. Amazing restaurant just steps away. A perfect place for respite"
United States
Ian F.
The price is ￥26,540
￥31,332 total
includes taxes & fees
Mar 26 - Mar 27
Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
Studio | Terrace/patio

La Dimora di Dida

La Dimora di Dida
Seggiano
The price is ￥12,065
￥13,271 total
includes taxes & fees
Mar 26 - Mar 27
La Dimora di Dida
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 San Gregorio

Hotel San Gregorio

10/10 Excellent
"A wonderful hotel - great location, friendly staff, comfortable rooms. "
beverly 1-night trip
Posted 8 hours ago
Hotel San Gregorio

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 vacation rental in Pienza?

Yes, we give you a choice of vacation rentals in Pienza close to RI Crea RE, 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?

The House of Alice, charm and relaxation: This vacation home rental near Pienza is located in a rural location and has a fireplace, a terrace, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a coffee maker. Kick off your shoes and enjoy yourself with a garden and a selection of books.

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 Piazza Pio II.

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.