A historic square with a prominent tower and statues.

Pienza Vacation Rentals

  • 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
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Pienza vacation homes

Coffee/tea maker, fridge, microwave, stovetop

1. "Il Focolare" Superior Apartment in Monticchiello

"Il Focolare" Superior Apartment in Monticchiello
Monticchiello
10.0 out of 10, Exceptional, (11 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 CA $161
CA $196 total
includes taxes & fees
Sep 28 - Sep 29
"Il Focolare" Superior Apartment in Monticchiello
Outdoor dining

2. Suite Gioconda - Podere Casa Rossa in Pienza

Suite Gioconda - Podere Casa Rossa in Pienza
Pienza
10.0 out of 10, Exceptional, (5 reviews)
"Comfortable, clean and the hosts are over the top welcoming! Walking distance to Pienza with gorgeous views. Loved staying here and hope to come back someday! "
United States
Doug H.
The price is CA $290
CA $385 total
includes taxes & fees
Sep 21 - Sep 22
Suite Gioconda - Podere Casa Rossa in Pienza
Front of property

3. Zampugna

Zampugna
Trequanda
9.2 out of 10, Wonderful, (5 reviews)
"Beautiful and host is great!"
United States
August
Zampugna
Pool

4. Agritourism in val d'orcia

Agritourism in val d'orcia
montalcino
The price is CA $241
CA $544 total
includes taxes & fees
Sep 23 - Sep 24
Agritourism in val d'orcia
1 bedroom, iron/ironing board, WiFi, bed sheets

5. Double room with private bathroom in the countryside 5 minutes from Montepulciano

Double room with private bathroom in the countryside 5 minutes from Montepulciano
Toscana
The price is CA $173
CA $258 total
includes taxes & fees
Oct 1 - Oct 2
Double room with private bathroom in the countryside 5 minutes from Montepulciano
Property grounds

6. Romantic farm in the Sienese hills

Romantic farm in the Sienese hills
Trequanda, Siena
7.0 out of 10, Good, (2 reviews)
"Zum positiven: Kommunikation mit dem Gastgeber war sehr gut und informativ. Check in war gut, Antonio der die Übergabe der Schlüssel und die Erläuterung zum Appartement machte sprach leider nur italienisch, aber er war sehr freundlich und mit Händen und Füßen funktionierte es gut. Das Apartment war wirklich sehr schön und mit Liebe zum Detail eingerichtet. Die Location war wirklich sehr schön.Nun zum negativen: An allen Fenstern der Unterkunft waren keine Fliegengitter angebracht was es...
United States
Harald B.
The price is CA $173
CA $328 total
includes taxes & fees
Sep 19 - Sep 20
Romantic farm in the Sienese hills
Exterior

7. Oasi del Borgo Montefollonico

Oasi del Borgo Montefollonico
Montefollonico
The price is CA $390
CA $453 total
includes taxes & fees
Sep 21 - Sep 22
Oasi del Borgo Montefollonico
Property grounds

8. The Gelda house, relax with a view

The Gelda house, relax with a view
Castelnuovo dell'Abate
9.6 out of 10, Exceptional, (14 reviews)
"Loved our stay...lovely and quiet..great location "
Australia
Lisa K.
The price is CA $161
CA $214 total
includes taxes & fees
Oct 2 - Oct 3
The Gelda house, relax with a view
Property grounds

9. A typical Tuscan country house

A typical Tuscan country house
Montalcino
The price is CA $115
CA $183 total
includes taxes & fees
Sep 20 - Sep 21
A typical Tuscan country house
Exterior

10. Secluded Villa Banditello with Panoramic Valley Views near Montepulciano

Secluded Villa Banditello with Panoramic Valley Views near Montepulciano
Torrita di Siena
The price is CA $812
CA $819 total
includes taxes & fees
Sep 22 - Sep 23
Secluded Villa Banditello with Panoramic Valley Views near Montepulciano
Exterior

11. Eagle House

Eagle House
CHIANCIANO
10.0 out of 10, Exceptional, (3 reviews)
"Paolo and Monica were such gracious and enthusiastic hosts. The property is beautiful, and the hospitality was great. Paolo and Monica helped plan our itinerary each day which made for a stress-free week. The highlight was the interaction with owls, eagles, and other animals, as well as the wine cave and the history behind it. Thanks again, Paolo and Monica! "
United States
Rob C.
The price is CA $320
CA $458 total
includes taxes & fees
Oct 13 - Oct 14
Eagle House
Pool

12. Apartment with A/C, WIFI, pool, TV, terrace, pets allowed, panoramic view, close to Montepulciano

Apartment with A/C, WIFI, pool, TV, terrace, pets allowed, panoramic view, close to Montepulciano
Torrita Di Siena
The price is CA $391
CA $395 total
includes taxes & fees
Oct 6 - Oct 7
Apartment with A/C, WIFI, pool, TV, terrace, pets allowed, panoramic view, close to Montepulciano
Outdoor dining

13. Il Borghetto - The House of Elba, rooftop panoramic terrace

Il Borghetto - The House of Elba, rooftop panoramic terrace
Castelnuovo dell'Abate
The price is CA $193
CA $262 total
includes taxes & fees
Oct 6 - Oct 7
Il Borghetto - The House of Elba, rooftop panoramic terrace
Terrace/patio

14. Charming Siena Countryside Stay

Charming Siena Countryside Stay
Monterongriffoli
The price is CA $434
CA $549 total
includes taxes & fees
Oct 2 - Oct 3
Charming Siena Countryside Stay
Exterior

15. Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning

Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning
Buonconvento
The price is CA $188
CA $192 total
includes taxes & fees
Sep 24 - Sep 25
Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning
2 bedrooms, iron/ironing board, WiFi (free), bed sheets

16. Terme house

Terme house
Bagni San Filippo
The price is CA $152
CA $219 total
includes taxes & fees
Sep 29 - Sep 30
Terme house
Outdoor dining

17. Podere Belsogno-camera Lavanda

Podere Belsogno-camera Lavanda
Montalcino
10.0 out of 10, Exceptional, (5 reviews)
"The stay was very pleasant, the room was very tidy and cosy. The view when waking up is breathtaking, as well as the whole place. Exactly as stated in the pictures. We were very welcomed by the host and you get a good breakfast. Would definitely come back again if I‘m in the area! Thank you very much for the stay!"
Austria
Johannes S.
The price is CA $192
CA $225 total
includes taxes & fees
Sep 29 - Sep 30
Podere Belsogno-camera Lavanda
Property grounds

18. La Casa del Viandante – Holiday Apartment in Radicofani, Val d’Orcia

La Casa del Viandante – Holiday Apartment in Radicofani, Val d’Orcia
Radicofani
The price is CA $159
CA $194 total
includes taxes & fees
Sep 21 - Sep 22
La Casa del Viandante – Holiday Apartment in Radicofani, Val d’Orcia
Outdoor dining

19. Villa Mulinello, secluded in greenery with panoramic views over the Montepulciano Valley

Villa Mulinello, secluded in greenery with panoramic views over the Montepulciano Valley
Torrita di Siena
The price is CA $1,093
CA $1,099 total
includes taxes & fees
Sep 21 - Sep 22
Villa Mulinello, secluded in greenery with panoramic views over the Montepulciano Valley
Outdoor dining

20. Holiday Home in Villa Pandolfina near Montepulciano

Holiday Home in Villa Pandolfina near Montepulciano
Acquaviva
10.0 out of 10, Exceptional, (1 review)
"Pros: L'appartamento è molto spazioso e comodo con una vista panoramica sulla campagna di Montepulciano Cons: Nulla da rilevare"
Italy
Anonymous traveller
The price is CA $471
CA $558 total
includes taxes & fees
Sep 21 - Sep 22
Holiday Home in Villa Pandolfina near Montepulciano
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

Corte Francigena - Apartments

Corte Francigena - Apartments

10/10 Excellent
"We absolutely loved staying here - the location was very central in Tuscany, it was a beautiful property with a lovely view and a very nice pool area. The staff was amazing and the value was incredible. We would definitely stay here again."
Davide 3-night trip
Posted 10 hours ago
Corte Francigena - Apartments

Find out more about Pienza

Pienza Vacation Homes information

Number of reviews
46
Accommodation
1161 Vacation Homes
Lowest Price
CA $183
Highest Price
CA $1,099