Pienza Vacation Home Rentals from CA $181: Search Top Private Vacation Homes for Rent

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Pienza vacation homes

Coffee/tea maker, fridge, microwave, stovetop

1. "Il Focolare" Superior Apartment in Monticchiello

Monticchiello

Dan

CA $196 total

includes taxes & fees

Sep 14 - Sep 15

2. Suite Gioconda - Podere Casa Rossa in Pienza

Pienza

Doug H.

CA $422 total

includes taxes & fees

Oct 5 - Oct 6

3. Zampugna

Trequanda

August

CA $506 total

includes taxes & fees

Oct 13 - Oct 14

4. Agritourism in val d'orcia

montalcino

CA $552 total

includes taxes & fees

Sep 14 - Sep 15

5. The Gelda house, relax with a view

Castelnuovo dell'Abate

Lisa K.

CA $228 total

includes taxes & fees

Oct 2 - Oct 3

1 bedroom, iron/ironing board, WiFi, bed sheets

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

Toscana

CA $259 total

includes taxes & fees

Sep 14 - Sep 15

7. Oasi del Borgo Montefollonico

Montefollonico

CA $497 total

includes taxes & fees

Sep 21 - Sep 22

8. A typical Tuscan country house

Montalcino

CA $200 total

includes taxes & fees

Sep 15 - Sep 16

9. Romantic farm in the Sienese hills

Trequanda, Siena

"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...

Harald B.

CA $331 total

includes taxes & fees

Sep 14 - Sep 15

10. Secluded Villa Banditello with Panoramic Valley Views near Montepulciano

Torrita di Siena

CA $820 total

includes taxes & fees

Sep 21 - Sep 22

11. Eagle House

CHIANCIANO

Rob C.

CA $478 total

includes taxes & fees

Oct 6 - Oct 7

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

Castelnuovo dell'Abate

CA $262 total

includes taxes & fees

Oct 6 - Oct 7

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

Torrita Di Siena

CA $396 total

includes taxes & fees

Sep 20 - Sep 21

14. Charming Siena Countryside Stay

Monterongriffoli

CA $642 total

includes taxes & fees

Oct 6 - Oct 7

2 bedrooms, iron/ironing board, WiFi (free), bed sheets

15. Terme house

Bagni San Filippo

CA $227 total

includes taxes & fees

Sep 14 - Sep 15

16. House Sant Angelo

Acquapendente

CA $181 total

includes taxes & fees

Sep 14 - Sep 15

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

Buonconvento

CA $214 total

includes taxes & fees

Sep 23 - Sep 24

18. Podere Belsogno-camera Lavanda

Montalcino

Johannes S.

CA $225 total

includes taxes & fees

Sep 17 - Sep 18

View all properties

Find vacation rentals that suit your style

Aparthotels

Apartments

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

Monastero di Cortona Hotel & Spa

10/10 Excellent

"I never write hotel reviews, but this hotel was so exceptional that I had to share my experience. The room was beautiful, spotless, and incredibly comfortable, with thoughtful turn-down service every evening. The staff were truly the most attentive and welcoming I’ve ever experienced. They helped arrange pickup from the train station, made restaurant reservations, and went above and beyond in so many little ways. Those small details made me feel genuinely cared for. The breakfast was lovely and served in such a beautiful setting — the perfect way to start the day. I absolutely loved my stay here and would come back to Cortona for this hotel alone. A truly special place with exceptional hospitality. Highly recommend!"

Hotel Corsignano

10/10 Excellent

"My husband and I had an absolutely wonderful experience at Hotel Corsignano. From beginning to end, the staff went above and beyond to make us feel welcome and cared for. When we arrived a little later than expected, they were genuinely concerned about us and even made sure to save a parking spot for us. That level of thoughtfulness and hospitality really stood out. The hotel was exceptionally clean and in a fantastic location, just a few steps from the historic center of Pienza. And the breakfast was wonderful, with plenty of delicious options to choose from. We truly felt welcomed and well taken care of throughout our stay. We would happily stay here again and highly recommend Hotel Corsignano!"

Castello di Velona Resort Thermal SPA & Winery

8/10 Good

"Staying here was a wonderful and truly unique experience. The only reason I’m giving it 4 stars instead of 5 was because of the challenges we had with the air conditioning in our room. That said, the staff really did make an effort to find a workaround for us. While it wasn’t a perfect solution, it definitely helped, and we appreciated how responsive and accommodating they were. The hotel itself is an old castle, and that alone makes staying here such a special experience. The property is beautiful, incredibly charming, and very well maintained. You simply can’t replicate the character, history, and ambiance that come with staying in a property like this. The setting and surroundings are beautiful. It was definitely one of those experiences that felt uniquely Italian and added something special to our trip. My only recommendation would be to visit when the temperatures aren’t quite as hot. Given the age and historic nature of the property, I can appreciate that modernizing certain things like the air conditioning may not be as straightforward as it would be in a newer hotel. During cooler weather, I imagine our experience would have been close to perfect. Overall, we really enjoyed our stay and are glad we had the opportunity to experience such a beautiful and unique property. I would absolutely recommend it, just perhaps not during the hottest part of the summer!"

Precise Tale Poggio Alla Sala

10/10 Excellent

"Incredible stay in a beautiful location. The staff were amazing and the hospitality was top tier. We will most definitely be back. The recommendations given were brilliant and the room was stunning along with the rest of the hotel. We didn’t dine in the restaurant but our breakfast each morning was also wonderful."

Find out more about Pienza

Pienza Vacation Homes information

Number of reviews	45
Accommodation	1161 Vacation Homes
Lowest Price	CA $181
Highest Price	CA $820

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Pienza vacation homes

1. "Il Focolare" Superior Apartment in Monticchiello