Search Vacation Homes in Pienza

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
28 Rab. I - 30 Rab. I
In two weeks
4 Rab. II - 6 Rab. II
In one month
18 Rab. II - 20 Rab. II
In two months
16 Jum. I - 18 Jum. I

Compare 1130 Vacation Homes in Pienza with updated reviews, rates, and availability.

Casa delle Rose: charming house with stunning balcony in the heart of Cortona
Outdoor dining

Casa delle Rose: charming house with stunning balcony in the heart of Cortona

9.8 out of 10, Exceptional, (8)
"Casa Delle Rosa had everything we needed and was very well equipped but the view… amazing. We were able to walk everywhere in Cortona and hope to return during warmer weather. Thank you Isabella and the team at Together in Tuscany for making it a seamlessly easy stay"
Casa delle Rose: charming house with stunning balcony in the heart of Cortona
Beautiful home in Sarteano with WiFi
Pool

Beautiful home in Sarteano with WiFi

10.0 out of 10, Exceptional, (1)
"So schön, dass wir nächstes Jahr wiederkommen. Haben direkt wieder gebucht. Tolle herzliche Gastgeber und eine wunderschöne Umgeht"
Beautiful home in Sarteano with WiFi
INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING
Interior

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

9.8 out of 10, Exceptional, (66)
"The views from this house are fantastic! And the location is perfect - steps from the old town of Montepulciano. Communication with Erika, the host was great. She prepared us with lots of details and recommendations for things to do nearby. We had some questions during our stay and Erika was very responsive. There is so much to do in the area - I almost wished we had more time to hang out on the beautiful terraces!"
INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING
House / Villa - Cetona
Pool

House / Villa - Cetona

9.6 out of 10, Exceptional, (39)
"This is our second stay at the house and our third visit to Pallazone. We love the area which is very peaceful and beautiful. Serenella, who looks after the hoyse, is wonderful."
House / Villa - Cetona
Farmhouse in the greenery of the Tuscany countryside with private pool and view
Outdoor pool

Farmhouse in the greenery of the Tuscany countryside with private pool and view

9.6 out of 10, Exceptional, (45)
"This property is several kilometers up a gravel road from Murlo, Italy. The road is okay but we got a little concerned after it had been raining for a while. The property is remote and near several hiking paths. It is great for people who want to get out and hike around the hills of Italy. The gardens are really nice. We would have spent more time outside if the weather had cooperated more. We went in the fall so it was getting a little cooler up in the hills. There was a nice fireplace that...
Farmhouse in the greenery of the Tuscany countryside with private pool and view
Casa Bacco - private house with a remarkable garden in the centre of Cortona
Outdoor dining

Casa Bacco - private house with a remarkable garden in the centre of Cortona

10.0 out of 10, Exceptional, (4)
"Our two adult children who were studying abroad met us here with our younger two children. We had two nights in a 12 day stay in Italy. Of all our stops, this was by far our favorite. The house was like a story book. The garden was so lovely, we spent an afternoon eating and sharing a bottle of wine. We were here in November and the weather was very mild compared to Chicago winters. Most of the stores and restaurants were open with far less people. We weren’t really here to see anything, we were...
Casa Bacco - private house with a remarkable garden in the centre of Cortona
The House of Alice, charm and relaxation
Point of interest

The House of Alice, charm and relaxation

9.6 out of 10, Exceptional, (55)
"Quaint apartment, with enough amenities for a great six day stay! The parking is a little tough, but the location and views are fabulous. The pellet stove needs to have directions for the renter when it is cooler weather. I would definitely say again. Francesco was great and helped me with a lot of questions!:)"
The price is SAR 529
SAR 733 total
includes taxes & fees
24 Mar - 25 Mar
The House of Alice, charm and relaxation
Podere Casorbica with free parking, large garden, private pool.
Exterior

Podere Casorbica with free parking, large garden, private pool.

9.4 out of 10, Exceptional, (13)
"The property was lovely. Wifi was intermittently availble throughout our stay."
Podere Casorbica with free parking, large garden, private pool.
Beautiful Residence in the Old Town
Dining

Beautiful Residence in the Old Town

10.0 out of 10, Exceptional, (44)
"Perfect location to explore the surrounding area and the town—close to shopping and restaurants. Royce was a very helpful and gracious host. One alert: the apt rooms are on separate levels so be prepared for a few to several stairs between levels."
Beautiful Residence in the Old Town
Tuscan village in SIena. farmhouse surrounded by garden,pool and panoramic view
Pool

Tuscan village in SIena. farmhouse surrounded by garden,pool and panoramic view

10.0 out of 10, Exceptional, (41)
"Our family of 5 adults truly loved our stay here with the beauty of Tuscany around us. Our trip started in Rome which we loved - but so glad the last part of our trip was in this relaxing home and area. We stepped in and instantly felt relaxed and at home. Beautiful home and gardens. Towns we visited while there were Chianti (loved Poggio Amorelli winery!), Siena, Florence and Montepulciano. Nicoletta was very prompt in communication and very sweet. Highly recommend this booking!"
Tuscan village in SIena. farmhouse surrounded by garden,pool and panoramic view
Beautiful house on garden with shared pool just a few minutes Siena Tuscany
Exterior

Beautiful house on garden with shared pool just a few minutes Siena Tuscany

10.0 out of 10, Exceptional, (32)
"This is a fantastic place, with lots of space, a wonderful kitchen and amazing views. Wine tasting with Lorenzo was great and the wines are top notch. "
Beautiful house on garden with shared pool just a few minutes Siena Tuscany
Farmhouse, private garden and fenced swimming pool on Tuscany-Umbria border
Exterior

Farmhouse, private garden and fenced swimming pool on Tuscany-Umbria border

10.0 out of 10, Exceptional, (47)
"This was a week long birthday party. Friends and family came together from Europe and the USA. I could not have chosen a better place. The farmhouse is just perfect. The setting is superb. The hosts are charming, kind and unbelievably helpful. We had a superb time and want to thank Maria and her husband for their care and kindness. The town, Citta della Pieve - just up the hill, is enchanting. We hiked, we dined, we wine tasted, we explored hilltop towns. We had a phenomenal time. A fairy tale...
Farmhouse, private garden and fenced swimming pool on Tuscany-Umbria border
House in Val d'Orcia excellent families CIN IT052024C2APXZK7PD
Exterior

House in Val d'Orcia excellent families CIN IT052024C2APXZK7PD

9.6 out of 10, Exceptional, (43)
"Beautiful home and location. Silvano is excellent host."
House in Val d'Orcia excellent families CIN IT052024C2APXZK7PD
A MAGICAL HOLIDAY IN TUSCANY
4 bedrooms, desk, iron/ironing board, travel crib

A MAGICAL HOLIDAY IN TUSCANY

10.0 out of 10, Exceptional, (4)
"We had a fantastic stay for 2 nights. Perfectly located in the heart of the town. Comfortable rooms of lots of space. "
A MAGICAL HOLIDAY IN TUSCANY
Stunning Town House Cortona, Tuscany. Private Courtyard & Rooftop Terrace
Outdoor dining

Stunning Town House Cortona, Tuscany. Private Courtyard & Rooftop Terrace

Stunning Town House Cortona, Tuscany. Private Courtyard & Rooftop Terrace
Belvilla by OYO Rapiti da Valentino
House | View from property

Belvilla by OYO Rapiti da Valentino

Belvilla by OYO Rapiti da Valentino
"Il gelsomino del Perugino" home with garden, a stone's throw from the center.
Outdoor dining

"Il gelsomino del Perugino" home with garden, a stone's throw from the center.

10.0 out of 10, Exceptional, (2)
"Wir (3 Erwachsene) haben 2 sehr angenehme Wochen in Stefanias Haus verbracht. Liebevoll eingerichtet und sauber gehalten fühlten wir uns sehr wohl dort. Stefania ist eine sehr herzliche Gastgeberin, die uns mit allem, was ein italienisches Frühstück erfordert ausgestattet und uns zum Abschied sogar noch mit ein leckeren Kuchen verwöhnt hat. Bei Problemen war sie in kürzester Zeit für uns da. Wir können diese Unterkunft für einen Aufenthalt in dem wunderschönen Ort Città della Pieve im herrlichen...
"Il gelsomino del Perugino" home with garden, a stone's throw from the center.
La Dolce Collina
Aerial view

La Dolce Collina

La Dolce Collina
Belvilla by OYO Elegant Flat in Historic Villa
House | Pool | Outdoor pool

Belvilla by OYO Elegant Flat in Historic Villa

Belvilla by OYO Elegant Flat in Historic Villa
Charming house in historical Chianti Estate
Terrace/patio

Charming house in historical Chianti Estate

Charming house in historical Chianti Estate
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.
Don't see what you're looking for?
See all available properties in Pienza
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Pienza

Hotel San Gregorio
Seasonal outdoor pool, sun loungers

Hotel San Gregorio

3.0 star property
9.2 out of 10, Wonderful, (111)
"Very nice staff, great service, super clean. Will stay again."
The price is SAR 437
SAR 505 total
includes taxes & fees
23 Mar - 24 Mar
Hotel San Gregorio
Casanova - Panoramic Rooms and Suites
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

Casanova - Panoramic Rooms and Suites

3.0 star property
9.2 out of 10, Wonderful, (43)
"It was a nice property- unfortunate what they charge to just swim"
The price is SAR 662
SAR 749 total
includes taxes & fees
27 Mar - 28 Mar
Casanova - Panoramic Rooms and Suites
Bosco della Spina
Exterior

Bosco della Spina

9.4 out of 10, Exceptional, (143)
"We were met by the property owner who was pleasant and informative. The room was exactly as depicted in the photos and property was in excellent condition. We would recommend to anyone staying the area at any time of year/ "
The price is SAR 279
SAR 323 total
includes taxes & fees
26 Mar - 27 Mar
Bosco della Spina
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.