Pienza Vacation Rentals

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Check prices for these dates

Tonight
Dec 25 - Dec 26
Tomorrow
Dec 26 - Dec 27
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Pienza vacation rentals

Breakfast, lunch, dinner served; local cuisine
Hotel San Gregorio

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (134)
"Such friendly staff, loved Pienza and the property was such a good location! "
United Kingdom
Bethan
The price is ￥30,518
￥34,675 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Hotel San Gregorio
Suite Bernardo, Panoramica al terzo piano senza ascensore | 1 bedroom, desk, laptop workspace, iron/ironing board
PienzaLettings Suites

PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (1)
"Fantastic room in the city center, close to everything in Pienza"
Norway
Tom
The price is ￥13,363
￥15,435 total
includes taxes & fees
Jan 15 - Jan 16, 2026
PienzaLettings Suites
Deluxe Double Room | View from room
Affitacamere Maria Gabriella

Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (51)
"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
Camera Superior, vista città, primo piano senza ascensore | Laptop workspace, iron/ironing board, free WiFi
TuscanyLettings Studio&Room

TuscanyLettings Studio&Room

TuscanyLettings Studio&Room
Pienza
10.0 out of 10, Exceptional, (1)
"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 ￥14,255
￥16,415 total
includes taxes & fees
Jan 25 - Jan 26, 2026
TuscanyLettings Studio&Room
Casa Gioia, vista città, 2 piano senza ascensore | Private kitchen | Fridge, microwave, stovetop, electric kettle
Casa Gioia - Casa Olivieri

Casa Gioia - Casa Olivieri

Casa Gioia - Casa Olivieri
Pienza
The price is ￥13,525
￥15,613 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Casa Gioia - Casa Olivieri
Exterior
The house in the village - Angelica apartment - Vald'Orcia

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)
"Nice and comfortable house in a beautiful tiny village "
United States
Lana A.
The price is ￥17,357
￥21,030 total
includes taxes & fees
Jan 6 - Jan 7, 2026
The house in the village - Angelica apartment - Vald'Orcia
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

Apartment 'La Dimora Di Pienza in Val D'Orcia' with Wi-Fi
Pienza
The price is ￥17,680
￥18,417 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Apartment 'La Dimora Di Pienza in Val D'Orcia' with Wi-Fi
Outdoor dining
Il Podere di Casa Rossa Pienza

Il Podere di Casa Rossa Pienza

Il Podere di Casa Rossa Pienza
Pienza
10.0 out of 10, Exceptional, (3)
"Wonderful views, accommodating hosts"
United States
Pete and Alison C.
The price is ￥33,061
￥48,674 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Il Podere di Casa Rossa Pienza
Fridge, microwave, stovetop, coffee/tea maker
Finestra Dell'Angelo in Pienza – Elegant Apartment with Stunning Views

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

Finestra Dell'Angelo in Pienza – Elegant Apartment with Stunning Views
Pienza
The price is ￥39,674
￥40,409 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Finestra Dell'Angelo in Pienza – Elegant Apartment with Stunning Views
Exterior
Studio 'La Casina Mag' with Wi-Fi

Studio 'La Casina Mag' with Wi-Fi

Studio 'La Casina Mag' with Wi-Fi
Pienza
The price is ￥28,012
￥36,116 total
includes taxes & fees
Dec 27 - Dec 28
Studio 'La Casina Mag' with Wi-Fi
Interior
"Il Focolare" Superior Apartment in Monticchiello

"Il Focolare" Superior Apartment in Monticchiello

"Il Focolare" Superior Apartment in Monticchiello
Monticchiello
10.0 out of 10, Exceptional, (8)
"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 ￥18,367
￥22,408 total
includes taxes & fees
Jan 5 - Jan 6, 2026
"Il Focolare" Superior Apartment in Monticchiello
Exterior
Meublé Il Riccio

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (86)
"Staff is great and many good restaurants in short walking distance."
United States
Mark
Meublé Il Riccio
Premium bedding, down comforters, minibar, in-room safe
La Locanda di San Francesco

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (131)
"Great room-great staff-great location"
United States
Richard
The price is ￥27,252
￥30,713 total
includes taxes & fees
Jan 18 - Jan 19, 2026
La Locanda di San Francesco
Seasonal outdoor pool, an infinity pool, pool umbrellas, sun loungers
FonteLiving

FonteLiving

FonteLiving
San Casciano dei Bagni
10.0 out of 10, Exceptional, (5)
"Comfortable apartment in quiet block. Nicely furnished excellent housekeeping nice spacious bathrooms great view from the terrace."
United Kingdom
R
The price is ￥11,754
￥13,297 total
includes taxes & fees
Jan 8 - Jan 9, 2026
FonteLiving
View from room
Abbadia Sicille Relais

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (166)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is ￥10,078
￥11,639 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Abbadia Sicille Relais
Exterior
Agriturismo San Filippo

Agriturismo San Filippo

Agriturismo San Filippo
Acquapendente
9.0 out of 10, Wonderful, (13)
"Excellent experience!"
United States
Richard
Agriturismo San Filippo
Lobby
Residenza Fabroni

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (94)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is ￥13,703
￥15,809 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Residenza Fabroni
Pillowtop beds, minibar, in-room safe, individually decorated
La Locanda Di Cetona

La Locanda Di Cetona

La Locanda Di Cetona
Cetona
9.2 out of 10, Wonderful, (5)
"A lovely hotel and very welcoming staff. Cetona is a delight. "
Australia
Julian
La Locanda Di Cetona
Front of property - evening/night
Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.0 out of 10, Wonderful, (78)
"Fantastic place"
United States
Clifford
Casanova - Panoramic Rooms and Suites
Bar (on property)
La Piccola Locanda

La Piccola Locanda

La Piccola Locanda
Chiusi
8.8 out of 10, Excellent, (8)
"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
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

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Everything was perfect! Would like to give this Property a 6 Star rating. The staff made you feel like royalty!!"
Sabrina 4-night trip
Posted 7 days ago
Monastero di Cortona Hotel & Spa

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 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 kitchenware. 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 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.