Book Holiday Homes in Pienza

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Pienza

Welcome to Sarteano Look forward to a holiday in Italy.

Welcome to Sarteano Look forward to a holiday in Italy.

Sarteano
With a stay at this vacation home in Sarteano, you'll be on a lake, just steps from Val di Chiana and a 4-minute drive from Archaeological Museum of ...
Welcome to Sarteano Look forward to a holiday in Italy.
House / Villa - Monte San Savino

House / Villa - Monte San Savino

Monte San Savino
Located in Monte San Savino, this vacation home is on a lake, within a 10-minute drive of Val di Chiana and Comune di Monte San Savino.
House / Villa - Monte San Savino
A cozy nest for a pair

A cozy nest for a pair

Civitella Paganico
Located in Civitella Paganico, this vacation home is on a river, within a 10-minute drive of Terme Petriolo and Basso Merse Nature Reserve.
A cozy nest for a pair
Save an average of 15% on thousands of hotels when you're signed in
The House of Alice, charm and relaxation

The House of Alice, charm and relaxation

Montalcino (SI)
The price is AU$292 per night from 26 Nov to 27 Nov
AU$292
includes taxes & fees
26 Nov - 27 Nov
Located in Montalcino, this vacation home is by the sea, a 4-minute drive from Abbazia di Sant'Antimo and 9 minutes from Museum of Brunello.
The House of Alice, charm and relaxation
Podere Casorbica with free parking, large garden, swimming pool.

Podere Casorbica with free parking, large garden, swimming pool.

cortona
Located in Cortona, this vacation home is in a rural location, a 4-minute drive from Santa Maria delle Grazie and 5 minutes from Cortona Cathedral.
Podere Casorbica with free parking, large garden, swimming pool.
Townhouse in ancient tower in medieval Cetona

Townhouse in ancient tower in medieval Cetona

Cetona
A stay at this vacation home places you in the heart of Cetona, a 1-minute drive from Val di Chiana and 8 minutes from Archaeological Museum of Sarteano.
Townhouse in ancient tower in medieval Cetona
Villa I Cipressini Tuscany Private luxury pool spa

Villa I Cipressini Tuscany Private luxury pool spa

Pienza
With a stay at this vacation home in Pienza, you'll be within a 5-minute drive of Enoteca Di Ghino and Artemisia Gallery.
Villa I Cipressini Tuscany Private luxury pool spa
La Dolce Collina

La Dolce Collina

VOC. CANTAGALLINA, 6, Castiglione del Lago, PG
Located in Castiglione del Lago, La Dolce Collina is in a rural location, within a 10-minute drive of Torre Beccati Quest'Altro and Chiusi Lake.
La Dolce Collina
Casa delle Rose: charming house with stunning balcony in the heart of Cortona

Casa delle Rose: charming house with stunning balcony in the heart of Cortona

Cortona
With a stay at this vacation home in Cortona (Cortona Old Town), you'll be within a 15-minute drive of Lake Trasimeno and Cortona Cathedral.
Casa delle Rose: charming house with stunning balcony in the heart of Cortona
Don't see what you're looking for?
See all available properties in Pienza
View all properties
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.

Pienza Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Pienza vacation homes are the perfect way for you to wing it.

Holiday houses in Pienza let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Pienza in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Pienza adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Pienza with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Pienza vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Pienza Holiday Homes essential information

Accommodation
1019 Holiday Homes
Lowest Price
AU$182
Highest Price
AU$292
Popular accommodation
Welcome to Sarteano Look forward to a holiday in Italy., House / Villa - Monte San Savino, A cozy nest for a pair, The House of Alice, charm and relaxation, Podere Casorbica with free parking, large garden, swimming pool., Townhouse in ancient tower in medieval Cetona, Villa I Cipressini Tuscany Private luxury pool spa, La Dolce Collina, Casa delle Rose: charming house with stunning balcony in the heart of Cortona

Top trending hotels in Pienza

Hotel Relais II Chiostro di Pienza

Hotel Relais II Chiostro di Pienza

4 out of 5
Corso Rossellino 26, Pienza, SI
When you a stay at Hotel Relais II Chiostro di Pienza in Pienza, you'll be in the historical district, just steps from Palazzo Piccolomini and Historic Centre ...
Hotel Relais II Chiostro di Pienza
Hotel Corsignano

Hotel Corsignano

4 out of 5
Via Della Madonnina 11, Pienza, SI
The price is AU$182 per night from 6 Dec to 7 Dec
AU$182
includes taxes & fees
6 Dec - 7 Dec
Located in Pienza, Hotel Corsignano is in a regional park, a 4-minute walk from Pienza Cathedral and 6 minutes by foot from Piazza Pio II.
Hotel Corsignano
Hotel San Gregorio

Hotel San Gregorio

3 out of 5
Via Della Madonnina 4, Pienza, Siena
Fully refundableReserve now, pay when you stay
The price is AU$246 per night from 28 Nov to 29 Nov
AU$246
includes taxes & fees
28 Nov - 29 Nov
When you stay at Hotel San Gregorio in Pienza, you'll be in the historical district and 16.5 mi (26.5 km) from Monte Oliveto Maggiore Abbey.
Hotel San Gregorio
Save an average of 15% on thousands of hotels when you're signed in
Podere Spedalone

Podere Spedalone

1 out of 5
Strada per Cosona SP71, Pienza, SI
The price is AU$263 per night from 26 Nov to 27 Nov
AU$263
includes taxes & fees
26 Nov - 27 Nov
Located in Pienza, Podere Spedalone is in the mountains, within a 15-minute drive of Monastery of Sant'Anna in Camprena and Palazzo Piccolomini.
Podere Spedalone
Don't see what you're looking for?
See all available properties in Pienza
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.