A historic square with a prominent tower and statues.

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Check prices for these dates

In two weeks
18 Sep - 20 Sep
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

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 AED 426
AED 519 total
includes taxes & fees
3 Sep - 4 Sep
"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 AED 855
AED 1,115 total
includes taxes & fees
15 Sep - 16 Sep
Suite Gioconda - Podere Casa Rossa in Pienza
Pool

3. Agritourism in val d'orcia

Agritourism in val d'orcia
montalcino
The price is AED 640
AED 1,463 total
includes taxes & fees
2 Sep - 3 Sep
Agritourism in val d'orcia
Front of property

4. Zampugna

Zampugna
Trequanda
9.2 out of 10, Wonderful, (5 reviews)
"Beautiful and host is great!"
United States
August
The price is AED 1,796
AED 1,988 total
includes taxes & fees
4 Sep - 5 Sep
Zampugna
Exterior

5. Oasi del Borgo Montefollonico

Oasi del Borgo Montefollonico
Montefollonico
The price is AED 1,056
AED 1,222 total
includes taxes & fees
5 Sep - 6 Sep
Oasi del Borgo Montefollonico
1 bedroom, iron/ironing board, WiFi, bed sheets

6. 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 AED 461
AED 687 total
includes taxes & fees
2 Sep - 3 Sep
Double room with private bathroom in the countryside 5 minutes from Montepulciano
Property grounds

7. 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 AED 427
AED 606 total
includes taxes & fees
2 Oct - 3 Oct
The Gelda house, relax with a view
Property grounds

8. A typical Tuscan country house

A typical Tuscan country house
Montalcino
The price is AED 307
AED 529 total
includes taxes & fees
3 Sep - 4 Sep
A typical Tuscan country house
Property grounds

9. 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 AED 461
AED 875 total
includes taxes & fees
2 Sep - 3 Sep
Romantic farm in the Sienese hills
Exterior

10. 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 AED 845
AED 1,207 total
includes taxes & fees
2 Sep - 3 Sep
Eagle House
Exterior

11. Secluded Villa Banditello with Panoramic Valley Views near Montepulciano

Secluded Villa Banditello with Panoramic Valley Views near Montepulciano
Torrita di Siena
The price is AED 2,258
AED 2,275 total
includes taxes & fees
7 Sep - 8 Sep
Secluded Villa Banditello with Panoramic Valley Views near Montepulciano
Pool

12. Cosy apartment with pool, WIFI, A/C, TV, patio, pets allowed, panoramic view, close to Montepulciano

Cosy apartment with pool, WIFI, A/C, TV, patio, pets allowed, panoramic view, close to Montepulciano
Torrita Di Siena
The price is AED 1,038
AED 1,050 total
includes taxes & fees
20 Sep - 21 Sep
Cosy apartment with pool, WIFI, A/C, TV, patio, pets allowed, panoramic view, close to Montepulciano
Living area

13. Villino Basilico - Cignella Resort Toscana

Villino Basilico - Cignella Resort Toscana
Toscana
The price is AED 1,066
AED 1,216 total
includes taxes & fees
22 Sep - 23 Sep
Villino Basilico - Cignella Resort Toscana
Terrace/patio

14. Charming Siena Countryside Stay

Charming Siena Countryside Stay
Monterongriffoli
The price is AED 1,280
AED 1,698 total
includes taxes & fees
2 Oct - 3 Oct
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 AED 554
AED 566 total
includes taxes & fees
23 Sep - 24 Sep
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 AED 421
AED 600 total
includes taxes & fees
2 Sep - 3 Sep
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 AED 512
AED 597 total
includes taxes & fees
2 Sep - 3 Sep
Podere Belsogno-camera Lavanda
Outdoor pool

18. Villa Pesca - Cignella Resort Val D'orcia Toscana

Villa Pesca - Cignella Resort Val D'orcia Toscana
Toscana
The price is AED 21,330
AED 23,868 total
includes taxes & fees
2 Sep - 3 Sep
Villa Pesca - Cignella Resort Val D'orcia Toscana
Property grounds

19. Holiday Home 'Colline' with Balcony and Wi-Fi

Holiday Home 'Colline' with Balcony and Wi-Fi
Radicofani
8.0 out of 10, Very Good, (1 review)
The price is AED 747
AED 849 total
includes taxes & fees
1 Oct - 2 Oct
Holiday Home 'Colline' with Balcony and Wi-Fi
Property grounds

20. 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 AED 422
AED 516 total
includes taxes & fees
3 Sep - 4 Sep
La Casa del Viandante – Holiday Apartment in Radicofani, Val d’Orcia
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

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent
"It was a spectacular stay and so peaceful! All the staff were super helpful and the quality of service, amenities, and food really shined. Before we actually arrived, the staff would check in with us leading up to make sure we were all set up and all our requests answered. They also helped us prepare a wonderful birthday surprise for someone in our party."
Zifan 2-night trip
Posted 5 hours ago
Villa di Piazzano - Small Luxury Hotel of the World

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