A historic square with a prominent tower and statues.

Pienza Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Pienza vacation homes

A kitchen with a granite countertop, a hanging pendant light, and a brick archway.

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 14 - Sep 15
"Il Focolare" Superior Apartment in Monticchiello
An outdoor patio with a wooden pergola, a table with chairs, and potted plants.

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 $323
CA $421 total
includes taxes & fees
Oct 5 - Oct 6
Suite Gioconda - Podere Casa Rossa in Pienza
A stone building with a tiled roof, surrounded by dry grass and trees, set in a hilly landscape.

3. Zampugna

Zampugna
Trequanda
9.2 out of 10, Wonderful, (5 reviews)
"Beautiful and host is great!"
United States
August
The price is CA $420
CA $467 total
includes taxes & fees
Sep 13 - Sep 14
Zampugna
A swimming pool with a wooden deck and lounge chairs, surrounded by a scenic landscape with hills and a clear sky.

4. Agritourism in val d'orcia

Agritourism in val d'orcia
montalcino
The price is CA $241
CA $551 total
includes taxes & fees
Sep 13 - Sep 14
Agritourism in val d'orcia
A stone building with a sign reading "Borgo di Mezzo".

5. 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 $228 total
includes taxes & fees
Oct 2 - Oct 3
The Gelda house, relax with a view
A neatly made bed with a dark patterned bedspread, two bedside tables with lamps, and two framed pictures on the wall.

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 CA $173
CA $259 total
includes taxes & fees
Sep 23 - Sep 24
Double room with private bathroom in the countryside 5 minutes from Montepulciano
A narrow street lined with stone buildings, some with wooden shutters, and potted plants.

7. Oasi del Borgo Montefollonico

Oasi del Borgo Montefollonico
Montefollonico
The price is CA $390
CA $453 total
includes taxes & fees
Sep 29 - Sep 30
Oasi del Borgo Montefollonico
A pathway leading to a building with stone walls and a tree.

8. A typical Tuscan country house

A typical Tuscan country house
Montalcino
The price is CA $116
CA $199 total
includes taxes & fees
Sep 15 - Sep 16
A typical Tuscan country house
A narrow stone pathway leading through an old stone building with arched doorways and potted plants.

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 CA $173
CA $331 total
includes taxes & fees
Sep 14 - Sep 15
Romantic farm in the Sienese hills
A stone building with a dirt path leading to it, surrounded by greenery and trees.

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 $850
CA $857 total
includes taxes & fees
Sep 15 - Sep 16
Secluded Villa Banditello with Panoramic Valley Views near Montepulciano
An aerial view of a rural property with vineyards, olive groves, and a red-roofed building with a swimming pool.

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 $337
CA $477 total
includes taxes & fees
Oct 6 - Oct 7
Eagle House
A terrace with a table set for breakfast, overlooking a mountainous landscape.

12. 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
A rectangular swimming pool with stone steps leading into it, surrounded by a grassy area with trees and umbrellas.

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

Apartment with WIFI, A/C, pool, TV, patio, pets allowed, panoramic view, close to Montepulciano
Torrita Di Siena
The price is CA $391
CA $396 total
includes taxes & fees
Sep 20 - Sep 21
Apartment with WIFI, A/C, pool, TV, patio, pets allowed, panoramic view, close to Montepulciano
A patio area with a gravel floor, potted plants, and a white umbrella.

14. Charming Siena Countryside Stay

Charming Siena Countryside Stay
Monterongriffoli
The price is CA $483
CA $642 total
includes taxes & fees
Oct 7 - Oct 8
Charming Siena Countryside Stay
A modern bedroom with a wooden headboard, a large bed with a textured blanket, bedside tables with lamps, and a mirror.

15. Terme house

Terme house
Bagni San Filippo
The price is CA $159
CA $227 total
includes taxes & fees
Sep 14 - Sep 15
Terme house
A neatly made bed with white linens and two pillows, a dark headboard, and two wall-mounted lamps on either side.

16. House Sant Angelo

House Sant Angelo
Acquapendente
The price is CA $152
CA $181 total
includes taxes & fees
Sep 13 - Sep 14
House Sant Angelo
A street with outdoor seating, a building with a shop entrance, and a sign with a prohibition symbol.

17. 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 $208
CA $213 total
includes taxes & fees
Sep 23 - Sep 24
Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning
An outdoor patio with tables and chairs, surrounded by greenery and a view of distant hills.

18. 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 $193
CA $225 total
includes taxes & fees
Sep 17 - Sep 18
Podere Belsogno-camera Lavanda
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
"Excelent"
Roberto 5-night trip
Posted 1 day ago
Monastero di Cortona Hotel & Spa

Find out more about Pienza

Pienza Vacation Homes information

Number of reviews
45
Accommodation
1161 Vacation Homes
Lowest Price
CA $181
Highest Price
CA $857