Pienza Vacation Home Rentals from CA $189: Search Top Private Vacation Homes for Rent

A historic square with a prominent tower and statues.

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Our top choices for Pienza vacation homes

An outdoor patio with a wooden pergola, a table with chairs, and potted plants.

1. Suite Gioconda - Podere Casa Rossa in Pienza

Pienza

Doug H.

CA $385 total

includes taxes & fees

Oct 12 - Oct 13

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

2. "Il Focolare" Superior Apartment in Monticchiello

Monticchiello

Dan

CA $196 total

includes taxes & fees

Oct 19 - Oct 20

A swimming pool with a wooden deck and lounge chairs, surrounded by a scenic landscape with hills and a clear sky.

3. Agritourism in val d'orcia

montalcino

CA $550 total

includes taxes & fees

Oct 6 - Oct 7

A neatly made bed with a dark patterned bedspread, two bedside tables with lamps, and two framed pictures on the wall.

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

Toscana

CA $258 total

includes taxes & fees

Oct 6 - Oct 7

A stone building with a sign reading "Borgo di Mezzo".

5. The Gelda house, relax with a view

Castelnuovo dell'Abate

Lisa K.

CA $228 total

includes taxes & fees

Oct 18 - Oct 19

A narrow street lined with stone buildings, some with wooden shutters, and potted plants.

6. Oasi del Borgo Montefollonico

Montefollonico

CA $452 total

includes taxes & fees

Oct 7 - Oct 8

A narrow stone alley with potted plants and benches.

7. The House of Alice, charm and relaxation

Montalcino (SI)

Robert S.

CA $322 total

includes taxes & fees

Nov 1 - Nov 2

A narrow stone pathway leading through an old stone building with arched doorways and potted plants.

8. 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 $330 total

includes taxes & fees

Oct 6 - Oct 7

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Top Pienza Hotel Reviews

Monastero di Cortona Hotel & Spa

10/10 Excellent

"From the moment we arrived at Monastero di Cortona, everything was wonderful. We were welcomed with a cold, delicious drink and invited to sit and relax while the staff took care of everything else for us. Anna then gave us a lovely tour of the hotel, which was such a nice way to begin our stay. When we walked into our room, there was a beautiful welcome table waiting for us with waters, chocolates, and even a lovely necklace charm, which was such a thoughtful touch. The room smelled absolutely amazing, and the view was stunning. Even the shower felt like a spa experience, with chromotherapy lighting and water that left our skin feeling incredibly soft. The complimentary breakfast was amazing, beautifully presented, and the staff was so attentive and made sure we had everything we needed. We also spent time at the spa and absolutely loved it. The Turkish bath, sauna, and massaging pool were all incredibly relaxing, and we also had massages that were absolutely amazing. Even as we were leaving, the thoughtfulness continued—the housekeeping staff left us a departing gift, which was such a sweet and unexpected touch and made us feel special right up until the end. From the beautiful surroundings to all the thoughtful little details and wonderful service, our stay felt luxurious, peaceful, and very special. We truly felt taken care of from the moment we arrived until the moment we left."

Precise Tale Poggio Alla Sala

10/10 Excellent

"A beautiful, luxury estate in the countryside. While we traveled as a couple, it seemed a popular destination for families with children. The restaurant on site was excellent and the rooms were well appointed and comfortable. We stayed in a junior suite which had stairs from the living room/bathroom up to the bedroom loft. *something to be aware of when booking"

Castiglion del Bosco, A Rosewood Hotel

8/10 Good

"Although the property and the staff were great, our room was a bit of a disappointment. Junior Sweet was just a giant room with furniture that was uncomfortable to use. In general the room needs an update. Not exactly what we expected. We unfortunately had a neighbor who opened up the gate outside in between our terrace which should have never happen if it had been locked. He did that because he said my husbands iPad was too loud when in fact, his was too loud and my husband who had headphones on could not hear his show so took them off so he could hear it. Needless to say we avoided our terrace after that. Shout out to Chiara and Samantha who took a desert request seriously and made two of my evenings! Michael and David’s were also wonderful!"

Hotel Certosa Di Maggiano

10/10 Excellent

"Our stay for our honeymoon was amazing. We loved our room and we were upgraded to a suite because they had it available. All the staff were kind and helpful. They carried our luggage up two flights of stairs to our room, helped make reservations, called taxis for us, etc. The property was beautiful, maintained nicely, and was very quiet. Really have no complaints. To note it is outside of city Centre of Siena so you will need taxis back and forth to the city for meals etc. which can get quite pricey so just plan ahead. Our room could’ve been cleaned a little better in between each day but overall it was still very clean. We would definitely stay there again!!"

Find out more about Pienza

Pienza Vacation Homes information

Number of reviews	127
Accommodation	1161 Vacation Homes
Lowest Price	CA $189
Highest Price	CA $1,080

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Our top choices for Pienza vacation homes

1. Suite Gioconda - Podere Casa Rossa in Pienza