Search Holiday Rentals in Pienza

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Pienza holiday rentals

Food and drink
Hotel San Gregorio

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (134 reviews)
"Such friendly staff, loved Pienza and the property was such a good location! "
United Kingdom
Bethan
Hotel San Gregorio
Suite Bernardo, Panoramica al terzo piano senza ascensore | Terrace/patio
PienzaLettings Suites

PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (1 review)
"Fantastic room in the city center, close to everything in Pienza"
Norway
Tom
The price is 2.048.125 ₫
2.375.204 ₫ total
includes taxes & fees
14 Jan - 15 Jan
PienzaLettings Suites
Monolocale Exclusive, vista città, secondo 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 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 2.470.955 ₫
2.840.317 ₫ total
includes taxes & fees
14 Jan - 15 Jan
TuscanyLettings Studio&Room
Panoramic Cottage, 1 Bedroom | Exterior
Affitacamere Maria Gabriella

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

Casa Gioia - Casa Olivieri
Pienza
The price is 2.500.915 ₫
2.873.274 ₫ total
includes taxes & fees
14 Jan - 15 Jan
Casa Gioia - Casa Olivieri
Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | Private spa tub
DormiVeglia B&B

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (27 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
DormiVeglia B&B
Interior
Meublé Il Riccio

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (86 reviews)
"Staff is great and many good restaurants in short walking distance."
United States
Mark
Meublé Il Riccio
Exterior
La Locanda Di Cetona

La Locanda Di Cetona

La Locanda Di Cetona
Cetona
9.2 out of 10, Wonderful, (5 reviews)
"A lovely hotel and very welcoming staff. Cetona is a delight. "
Australia
Julian
La Locanda Di Cetona
Property grounds
Agriturismo San Filippo

Agriturismo San Filippo

Agriturismo San Filippo
Acquapendente
8.6 out of 10, Excellent, (14 reviews)
"The property is not as advertised. It is not an individual stand alone home where you have an entire house to yourself. They have a confusing description. It is either an apartment or an entire home. It can’t be both They need to get their description corrected. It is also not a classic apartment. It is an old horse stable covered into multiple apartments. The apartment in the picture was not the apartment offered. On the listing it only lists one place available, but upon arrival we were not...
United States
Jeremy
Agriturismo San Filippo
Bar (on property)
La Piccola Locanda

La Piccola Locanda

La Piccola Locanda
Chiusi
8.8 out of 10, Excellent, (8 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
Classic Apartment, 2 Bedrooms | Terrace/patio
FonteLiving

FonteLiving

FonteLiving
San Casciano dei Bagni
10.0 out of 10, Exceptional, (6 reviews)
"Excellent experience, location, and environment."
Taiwan
Chia-Hung
The price is 1.850.677 ₫
2.096.878 ₫ total
includes taxes & fees
14 Jan - 15 Jan
FonteLiving
Food court
La Locanda di San Francesco

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (131 reviews)
"Great room-great staff-great location"
United States
Richard
The price is 4.223.712 ₫
4.768.350 ₫ total
includes taxes & fees
19 Jan - 20 Jan
La Locanda di San Francesco
Exterior
Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (128 reviews)
"Great hosts, central location "
United States
Alexander
Bed & Breakfast Vicolo dell'Oste
Exterior
Idolina Guest House

Idolina Guest House

Idolina Guest House
Montalcino
9.4 out of 10, Exceptional, (105 reviews)
"The building is lovely - traditional Italian construction with big Chestnut beams in the ceiling. The owner/manager is very pleasant and helpful. Overall, a very nice place to stay. "
Canada
Carl
Idolina Guest House
Premium bedding, down duvets, pillow-top beds, minibar
Tuscasì Aparthotel

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.0 out of 10, Wonderful, (26 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is 1.807.960 ₫
2.386.123 ₫ total
includes taxes & fees
16 Jan - 17 Jan
Tuscasì Aparthotel
Interior detail
La Coroncina Lodging

La Coroncina Lodging

La Coroncina Lodging
Siena
10.0 out of 10, Exceptional, (42 reviews)
"Fantastic place, and I highly recommend it."
United States
Hassan
The price is 2.551.183 ₫
2.928.569 ₫ total
includes taxes & fees
14 Jan - 15 Jan
La Coroncina Lodging
Interior entrance
Poggio del Sole

Poggio del Sole

Poggio del Sole
Castiglione del Lago
8.0 out of 10, Very good, (4 reviews)
"El hotel no alcanzó el agua caliente y no se pudo bañar parte de la familia no contaba con suficientes amenidades "
Mexico
RAUL
Poggio del Sole
Exterior
Artisti del Cavallo Tourism

Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (24 reviews)
"Good house for one night. "
Germany
Heiner
The price is 2.217.478 ₫
2.500.359 ₫ total
includes taxes & fees
15 Jan - 16 Jan
Artisti del Cavallo Tourism
Front of property
Podere La Chiusella

Podere La Chiusella

Podere La Chiusella
Rapolano Terme
9.4 out of 10, Exceptional, (30 reviews)
"Et sjarmerende lite B&B. Har nok vært utrolig vakkert i sine glansdager, men områdene rundt bærer preg av lite vedlikehold. Leiligheten var helt grei for en overnatting. Gulvet på badet var ikke rent. Når vi tørket opp etter oss ble håndkleet møkkete. Men overnattingen var helt grei alt i alt. Når vi skulle sjekke ut var det ikke et menneske å se, resepsjonen var stengt. Endte med å sette nøklene i døra og dra da alt var betalt ved bestilling."
Norway
Elisabeth
Podere La Chiusella
Terrace/patio
Abbadia Sicille Relais

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (166 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is 1.755.335 ₫
2.022.814 ₫ total
includes taxes & fees
14 Jan - 15 Jan
Abbadia Sicille Relais
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pienza Hotel Reviews

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Everything was great! Lovely hotel "
Laura 2-night trip
Posted 9 days ago
Monastero di Cortona Hotel & Spa

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 30 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 Piazza Pio II.

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.