A historic square with a prominent tower and statues.

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Our top choices for Pienza vacation homes

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 AED 410
AED 471 total
includes taxes & fees
5 Nov - 6 Nov
"Il Focolare" Superior Apartment in Monticchiello

2. 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 443
AED 631 total
includes taxes & fees
4 Nov - 5 Nov
Double room with private bathroom in the countryside, 5 minutes from Montepulciano

3. 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 AED 410
AED 553 total
includes taxes & fees
4 Nov - 5 Nov
The Gelda house, relax with a view

4. 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 443
AED 803 total
includes taxes & fees
4 Nov - 5 Nov
Romantic farm in the Sienese hills

5. 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 492
AED 545 total
includes taxes & fees
4 Nov - 5 Nov
Podere Belsogno-camera Lavanda

6. The House of Alice, charm and relaxation

The House of Alice, charm and relaxation
Montalcino (SI)
9.8 out of 10, Exceptional, (79 reviews)
"Stunning location in a beautiful part of the country."
United States
Robert S.
The price is AED 615
AED 795 total
includes taxes & fees
4 Nov - 5 Nov
The House of Alice, charm and relaxation

7. 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 AED 615
AED 795 total
includes taxes & fees
4 Nov - 5 Nov
The Casetta di Brunello, quiet and breathtaking views

8. A typical Tuscan country house

A typical Tuscan country house
Montalcino
The price is AED 439
AED 628 total
includes taxes & fees
4 Nov - 5 Nov
A typical Tuscan country house

9. 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 861
AED 1,148 total
includes taxes & fees
30 Nov - 1 Dec
Eagle House

10. Charming Siena Countryside Stay

Charming Siena Countryside Stay
Monterongriffoli
The price is AED 1,107
AED 1,410 total
includes taxes & fees
4 Nov - 5 Nov
Charming Siena Countryside Stay

11. 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 AED 492
AED 639 total
includes taxes & fees
4 Nov - 5 Nov
Il Borghetto - The House on Elba, Rooftop Terrace with Panoramic Views

12. 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 AED 2,601
AED 2,617 total
includes taxes & fees
4 Nov - 5 Nov
Villa Mulinello, secluded in greenery with panoramic views over the Montepulciano Valley

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 AED 406
AED 549 total
includes taxes & fees
6 Nov - 7 Nov
Terme bagni san filippo La Balena Bianca a due passi: Casa Nuova con Terrazza

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

Apartment with WIFI, A/C, pool, TV, terrace, pets allowed, panoramic view, close to Montepulciano
Torrita Di Siena
The price is AED 997
AED 1,009 total
includes taxes & fees
4 Nov - 5 Nov
Apartment with WIFI, A/C, pool, TV, terrace, pets allowed, panoramic view, close to Montepulciano

15. 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 AED 309
AED 401 total
includes taxes & fees
25 Nov - 26 Nov
Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

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 traveler
The price is AED 952
AED 1,173 total
includes taxes & fees
4 Nov - 5 Nov
Holiday Home in Villa Pandolfina near Montepulciano

17. Chalet "Azzurro" with Mountain View, Shared Pool & Wi-Fi

Chalet "Azzurro" with Mountain View, Shared Pool & Wi-Fi
Trequanda
The price is AED 1,918
AED 1,931 total
includes taxes & fees
4 Nov - 5 Nov
Chalet "Azzurro" with Mountain View, Shared Pool & Wi-Fi

18. 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 664
AED 803 total
includes taxes & fees
4 Nov - 5 Nov
Holiday Home 'Colline' with Balcony and Wi-Fi

19. Double bedroom with private bathroom, private access, garden and swimming pool

Double bedroom with private bathroom, private access, garden and swimming pool
Radicofani
The price is AED 328
AED 344 total
includes taxes & fees
4 Nov - 5 Nov
Double bedroom with private bathroom, private access, garden and swimming pool

20. Secluded Villa Banditello with Panoramic Valley Views near Montepulciano

Secluded Villa Banditello with Panoramic Valley Views near Montepulciano
Torrita di Siena
Secluded Villa Banditello with Panoramic Valley Views 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.
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