A historic square with a prominent tower and statues.

Pienza Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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, (12 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 $157
CA $191 total
includes taxes & fees
Oct 29 - Oct 30
"Il Focolare" Superior Apartment in Monticchiello
A swimming pool with a wooden deck and lounge chairs, surrounded by a scenic landscape with hills and a clear sky.

2. Agritourism in Val d'Orcia

Agritourism in Val d'Orcia
montalcino
The price is CA $235
CA $538 total
includes taxes & fees
Oct 27 - Oct 28
Agritourism in Val d'Orcia
A neatly made bed with a dark patterned bedspread, two bedside tables with lamps, and two framed pictures on the wall.

3. 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 $169
CA $251 total
includes taxes & fees
Oct 27 - Oct 28
Double room with private bathroom in the countryside, 5 minutes from Montepulciano
A stone building with a sign reading "Borgo di Mezzo".

4. The Gelda house, relax with a view

The Gelda house, relax with a view
Castelnuovo dell'Abate
9.6 out of 10, Exceptional, (15 reviews)
"Loved our stay...lovely and quiet..great location "
Australia
Lisa K.
The price is CA $157
CA $223 total
includes taxes & fees
Oct 27 - Oct 28
The Gelda house, relax with a view
A stone patio with a round table and chairs, surrounded by lush greenery and potted plants.

5. 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 $169
CA $323 total
includes taxes & fees
Oct 27 - Oct 28
Romantic farm in the Sienese hills
A rustic room with a stone wall, a fireplace, a white sofa, and a wooden bench.

6. The House of Alice, charm and relaxation

The House of Alice, charm and relaxation
Montalcino (SI)
9.8 out of 10, Exceptional, (78 reviews)
"Stunning location in a beautiful part of the country."
United States
Robert S.
The price is CA $235
CA $318 total
includes taxes & fees
Nov 1 - Nov 2
The House of Alice, charm and relaxation
A pathway leading to a building with stone walls and a tree.

7. A typical Tuscan country house

A typical Tuscan country house
Montalcino
The price is CA $151
CA $233 total
includes taxes & fees
Nov 23 - Nov 24
A typical Tuscan country house
An outdoor patio with tables and chairs, surrounded by greenery and a view of distant hills.

8. 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 $188
CA $220 total
includes taxes & fees
Nov 1 - Nov 2
Podere Belsogno-camera Lavanda
A bedroom with a bed, a bedside table, a lamp, a mirror, a chair, a dresser, and a door leading to another room.

9. Il Borghetto - The House on Elba, Rooftop Terrace with Panoramic Views

Il Borghetto - The House on Elba, Rooftop Terrace with Panoramic Views
Castelnuovo dell'Abate
10.0 out of 10, Exceptional, (1 review)
"Il Borghetto is a renovated house in the little village of Castelnuovo dell'Abate, one of the medieval hilltop villages in the UNESCO world heritage-listed Val D'Orcia. It is charming and the beds are very comfortable, but be prepared to take luggage up a steep street to the front door and then steep stairs to both bedrooms. Each bedroom is on a different floor so there is considerable privacy. The piece de la resistance is the rooftop terrace, with 180 degree panoramic views over the valley and...
Australia
Judith F.
The price is CA $188
CA $256 total
includes taxes & fees
Oct 27 - Oct 28
Il Borghetto - The House on Elba, Rooftop Terrace with Panoramic Views
A swimming pool with lounge chairs, a stone building, and a garden with various plants and a large terracotta pot.

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 CA $296
CA $428 total
includes taxes & fees
Oct 27 - Oct 28
Eagle House
A stone building with a wooden door and two windows with shutters.

11. The Casetta di Brunello, quiet and breathtaking views

The Casetta di Brunello, quiet and breathtaking views
Montalcino
9.6 out of 10, Exceptional, (23 reviews)
"We loved our stay, the beautiful views and quiet neighborhood were just amazing."
United States
MICHAEL H.
The price is CA $235
CA $320 total
includes taxes & fees
Nov 3 - Nov 4
The Casetta di Brunello, quiet and breathtaking views
A patio area with a gravel floor, potted plants, and a white umbrella.

12. Charming Siena Countryside Stay

Charming Siena Countryside Stay
Monterongriffoli
The price is CA $424
CA $573 total
includes taxes & fees
Oct 29 - Oct 30
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.

13. Terme bagni san filippo La Balena Bianca a due passi: Casa Nuova con Terrazza

Terme bagni san filippo La Balena Bianca a due passi: Casa Nuova con Terrazza
Bagni San Filippo
10.0 out of 10, Exceptional, (1 review)
"Terme House is just as described. It had all of the amenities mentioned and was clean. We wanted a place just off ss2 - perfect location and quiet town. 5 stars!!!"
United States
Lori
The price is CA $155
CA $221 total
includes taxes & fees
Oct 29 - Oct 30
Terme bagni san filippo La Balena Bianca a due passi: Casa Nuova con Terrazza
A rectangular swimming pool with stone steps leading into it, surrounded by a grassy area with trees and umbrellas.

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

Apartment with WIFI, pool, A/C, TV, terrace, pets allowed, panoramic view, close to Montepulciano
Torrita Di Siena
The price is CA $382
CA $386 total
includes taxes & fees
Nov 2 - Nov 3
Apartment with WIFI, pool, A/C, TV, terrace, pets allowed, panoramic view, close to Montepulciano
A stone building with a dirt path leading to it, surrounded by greenery and trees.

15. 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 $1,474
CA $1,480 total
includes taxes & fees
Nov 2 - Nov 3
Secluded Villa Banditello with Panoramic Valley Views near Montepulciano
A covered patio with a brick wall, a round table with chairs, and a view of greenery.

16. 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 $205
CA $289 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Home in Villa Pandolfina near Montepulciano
A stone building with a stone wall and a small bridge, surrounded by trees and grass.

17. 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 CA $247
CA $300 total
includes taxes & fees
Oct 27 - Oct 28
Holiday Home 'Colline' with Balcony and Wi-Fi
A rustic brick building with a mural, a clock, and various potted plants.

18. Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

Casa di Cristina - Tra Montepulciano e il Lago Trasimeno
Casamaggiore
10.0 out of 10, Exceptional, (1 review)
"Stayed 2 nights in June 2026. Beautiful place with garden and private parking and outdoor terrace - all you can need in quite spacious studio condo. Comfy big bed, aircon and a ceiling fan, dining table with 4 chairs and a kitchenette if you want to cook your own dinners (full with cutlery and crockery, fridge and coffee machine). Clean private bathroom with shower, toilet and bidet. Host was very lovely too, we need an iron and we could borrow it with no fuss alongside ironing board. Very...
United Kingdom
Anna
The price is CA $110
CA $144 total
includes taxes & fees
Oct 27 - Oct 28
Casa di Cristina - Tra Montepulciano e il Lago Trasimeno
A brick building with a large sliding glass door, a brown door, and a small potted plant.

19. Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning

Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
Foiano della Chiana
The price is CA $121
CA $127 total
includes taxes & fees
Oct 27 - Oct 28
Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
A stone building with a wooden door and shutters, a small outdoor seating area with a table and chairs, and potted plants.

20. Federico's Cantuccio, a cozy apartment in the heart of Radicofani

Federico's Cantuccio, a cozy apartment in the heart of Radicofani
Radicofani
The price is CA $113
CA $147 total
includes taxes & fees
Oct 29 - Oct 30
Federico's Cantuccio, a cozy apartment in the heart of Radicofani
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
"Beautiful historic property well located with just enough to do. Very relaxing ."
Peter 4-night trip
Posted 6 hours ago
Monastero di Cortona Hotel & Spa

Find out more about Pienza

Pienza Vacation Homes information

Number of reviews
49
Accommodation
950 Vacation Homes
Lowest Price
CA $127
Highest Price
CA $1,480