Title: Pienza Vacation Rentals from CA $90: Short-Term Rentals for 2026 | Expedia.ca

[Pienza Travel Guide](https://expedia.ca/Pienza.dx6023645)[Hotels in Pienza](https://expedia.ca/Pienza-Hotels.d6023645.Travel-Guide-Hotels)[Flights to Pienza](https://expedia.ca/Cheap-Flights-To-Pienza.d6023645.Travel-Guide-Flights)[Things to do in Pienza](https://expedia.ca/Things-To-Do-In-Pienza.d6023645.Travel-Guide-Activities)[Pienza Car Rentals](https://expedia.ca/Car-Rentals-In-Pienza.d6023645.Car-Rental-Guide)[Pienza Vacation Packages](https://expedia.ca/Pienza.d6023645.Destination-Travel-Guides)

![Pienza showing a monument, a square or plaza and heritage architecture](https://images.trvl-media.com/place/6023645/9d678ea5-9752-4000-8f7c-af307fb65e61.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6023645/9d678ea5-9752-4000-8f7c-af307fb65e61.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Pienza vacation rentals

![Panoramic Cottage, 1 Bedroom | Exterior](https://images.trvl-media.com/lodging/23000000/22940000/22938800/22938763/020483c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Panoramic Cottage, 1 Bedroom](https://images.trvl-media.com/lodging/23000000/22940000/22938800/22938763/83ad69a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/23000000/22940000/22938800/22938763/e878f092.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/23000000/22940000/22938800/22938763/a39f2057.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Pienza

[](https://www.expedia.ca/Pienza-Hotels-Affitacamere-Maria-Gabriella.h22938763.Hotel-Information)

9.8/10

Exceptional

(51 reviews)

"This property has a lovely view, great garden, attentive staff with good breakfast. Stayed in the cottage and the patio was very sunny and relaxing. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lenise

CA $152

CA $208 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Pienza-Hotels-Affitacamere-Maria-Gabriella.h22938763.Hotel-Information)

![Monolocale Exclusive, vista città, secondo piano senza ascensore](https://images.trvl-media.com/lodging/115000000/114870000/114863300/114863278/f7106947.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Monolocale Exclusive, vista città, secondo piano senza ascensore | Private kitchen](https://images.trvl-media.com/lodging/115000000/114870000/114863300/114863278/4381c139.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Camera Superior, vista città, primo piano senza ascensore](https://images.trvl-media.com/lodging/115000000/114870000/114863300/114863278/e4f61737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Monolocale Exclusive, vista città, secondo piano senza ascensore | Living area](https://images.trvl-media.com/lodging/115000000/114870000/114863300/114863278/6be6d8fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Pienza

[](https://www.expedia.ca/Pienza-Hotels-TuscanyLettings-StudioRoom.h114863278.Hotel-Information)

10/10

Exceptional

(1 review)

"メイン通りの好立地。 客室は豪華でエレガント。 ウェルカムキットも良く、アメニティも良好。 次回も必ず利用したい。 スタッフの方、いろいろありがとうございました。"

![Japan](https://a.travel-assets.com/egds/marks/flags/jp.svg)

keita

CA $130

CA $150 total

includes taxes & fees

Mar 4 - Mar 5

[](https://www.expedia.ca/Pienza-Hotels-TuscanyLettings-StudioRoom.h114863278.Hotel-Information)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124120000/124117300/124117240/0c33efbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124120000/124117300/124117240/6349a215.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124120000/124117300/124117240/f0b51bf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/125000000/124120000/124117300/124117240/d13d4ce2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Pienza

[](https://www.expedia.ca/Pienza-Hotels-Apartment-La-Dimora-Di-Pienza-In-Val-DOrcia-With-Wi-Fi.h124117240.Hotel-Information)

CA $109

CA $148 total

includes taxes & fees

Feb 26 - Feb 27

[](https://www.expedia.ca/Pienza-Hotels-Apartment-La-Dimora-Di-Pienza-In-Val-DOrcia-With-Wi-Fi.h124117240.Hotel-Information)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/37000000/36370000/36364900/36364803/6e91d9be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/37000000/36370000/36364900/36364803/49bf4281.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/37000000/36370000/36364900/36364803/5d93306f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/37000000/36370000/36364900/36364803/824ca8c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Monticchiello

[](https://www.expedia.ca/Pienza-Hotels-Il-Focolare-Superior-Apartment-In-Monticchiello.h36364803.Hotel-Information)

10/10

Exceptional

(8 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](https://a.travel-assets.com/egds/marks/flags/au.svg)

Dan

CA $161

CA $197 total

includes taxes & fees

Mar 4 - Mar 5

[](https://www.expedia.ca/Pienza-Hotels-Il-Focolare-Superior-Apartment-In-Monticchiello.h36364803.Hotel-Information)

![Food and drink](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/0e5f89fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast buffet](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/cd7670ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/4a89a1fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/882d4e56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Residence in Pienza

[](https://www.expedia.ca/Pienza-Hotels-Hotel-San-Gregorio.h2692135.Hotel-Information)

9.4/10

Exceptional

(134 reviews)

"Super convenient location steps to the historic center. Possibly the only hotel with its own dedicated secure / covered parking. Well decorated and breakfast was great!"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Mark

CA $204

CA $234 total

includes taxes & fees

Mar 21 - Mar 22

[](https://www.expedia.ca/Pienza-Hotels-Hotel-San-Gregorio.h2692135.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/116000000/115080000/115077100/115077012/w1068h1589x0y0-ab9335e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Casa Olivieri, vista città, 1 piano senza ascensore | Private kitchen](https://images.trvl-media.com/lodging/116000000/115080000/115077100/115077012/f32e69c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Casa Olivieri, vista città, 1 piano senza ascensore](https://images.trvl-media.com/lodging/116000000/115080000/115077100/115077012/61781dd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/116000000/115080000/115077100/115077012/5ded1ab2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Pienza

[](https://www.expedia.ca/Pienza-Hotels-Casa-Gioia-Casa-Olivieri.h115077012.Hotel-Information)

CA $131

CA $151 total

includes taxes & fees

Mar 2 - Mar 3

[](https://www.expedia.ca/Pienza-Hotels-Casa-Gioia-Casa-Olivieri.h115077012.Hotel-Information)

![Suite Bernardo, Panoramica al terzo piano senza ascensore | Terrace/patio](https://images.trvl-media.com/lodging/113000000/112330000/112327700/112327681/4f1f04f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/113000000/112330000/112327700/112327681/0f43b292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite Silvio al secondo piano senza ascensore](https://images.trvl-media.com/lodging/113000000/112330000/112327700/112327681/884c0781.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite Bernardo, Panoramica al terzo piano senza ascensore](https://images.trvl-media.com/lodging/113000000/112330000/112327700/112327681/8ce91a76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Pienza

[](https://www.expedia.ca/Pienza-Hotels-PienzaLettings-Suites.h112327681.Hotel-Information)

10/10

Exceptional

(2 reviews)

"Fantastic room in the city center, close to everything in Pienza"

![Norway](https://a.travel-assets.com/egds/marks/flags/no.svg)

Tom

CA $134

CA $154 total

includes taxes & fees

Mar 8 - Mar 9

[](https://www.expedia.ca/Pienza-Hotels-PienzaLettings-Suites.h112327681.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/104000000/103830000/103821200/103821142/23bc7f03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103830000/103821200/103821142/aba65f5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103830000/103821200/103821142/56d165e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/104000000/103830000/103821200/103821142/81a6e134.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Pienza

[](https://www.expedia.ca/Pienza-Hotels-Il-Podere-Di-Casa-Rossa-Pienza.h103821142.Hotel-Information)

10/10

Exceptional

(3 reviews)

"Wonderful views, accommodating hosts"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Pete and Alison C.

CA $291

CA $430 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Pienza-Hotels-Il-Podere-Di-Casa-Rossa-Pienza.h103821142.Hotel-Information)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/49000000/48840000/48837200/48837118/e139d884.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/49000000/48840000/48837200/48837118/aaa84aae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/49000000/48840000/48837200/48837118/9a24ba4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/49000000/48840000/48837200/48837118/68f580ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Monticchiello

[](https://www.expedia.ca/Pienza-Hotels-The-House-In-The-Village-Angelica-Apartment-ValdOrcia.h48837118.Hotel-Information)

10/10

Exceptional

(11 reviews)

"Marco was great to work with, was easily available for any of our questions and the stay was wonderful. The apartment is in a great location and had all we needed for our stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Melissa B.

CA $144

CA $176 total

includes taxes & fees

Mar 8 - Mar 9

[](https://www.expedia.ca/Pienza-Hotels-The-House-In-The-Village-Angelica-Apartment-ValdOrcia.h48837118.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/125000000/124120000/124117300/124117285/w2400h1799x0y0-de5fdc44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/125000000/124120000/124117300/124117285/w2400h1799x0y0-1b5eec48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124120000/124117300/124117285/fccd5ea1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/125000000/124120000/124117300/124117285/9bef289d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Pienza

[](https://www.expedia.ca/Pienza-Hotels-Finestra-DellAngelo-In-Pienza-Elegant-Apartment-With-Stunning-Views.h124117285.Hotel-Information)

CA $129

CA $176 total

includes taxes & fees

Feb 27 - Feb 28

[](https://www.expedia.ca/Pienza-Hotels-Finestra-DellAngelo-In-Pienza-Elegant-Apartment-With-Stunning-Views.h124117285.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/25000000/24950000/24941200/24941118/190e02d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/25000000/24950000/24941200/24941118/a47cb16a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/25000000/24950000/24941200/24941118/64c8d4c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Single Room](https://images.trvl-media.com/lodging/25000000/24950000/24941200/24941118/914c3e6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Siena

[](https://www.expedia.ca/Siena-Hotels-Il-Pozzo-Di-SantAndrea.h24941118.Hotel-Information)

9.8/10

Exceptional

(16 reviews)

"Great host, lovely place near Siena"

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

Prem

[](https://www.expedia.ca/Siena-Hotels-Il-Pozzo-Di-SantAndrea.h24941118.Hotel-Information)

![Bar (on property)](https://images.trvl-media.com/lodging/43000000/42010000/42001200/42001140/d732a716.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Porch](https://images.trvl-media.com/lodging/43000000/42010000/42001200/42001140/a8e96dc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, Terrace](https://images.trvl-media.com/lodging/43000000/42010000/42001200/42001140/93858826.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room | Bathroom](https://images.trvl-media.com/lodging/43000000/42010000/42001200/42001140/8842009b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Chiusi

[](https://www.expedia.ca/Chiusi-Hotels-La-Piccola-Locanda.h42001140.Hotel-Information)

8.6/10

Excellent

(9 reviews)

"This was a great place to stay for two nights in late October and to take out and back day trips by train to Siena and Florence on back-to-back days. Very close to the train station - very convenient. Breakfast in the restaurant in the morning was small, but good. Highly recommend this location! It's small, but serviced and supported very well by the staff at the restaurant. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jeffery

[](https://www.expedia.ca/Chiusi-Hotels-La-Piccola-Locanda.h42001140.Hotel-Information)

![Courtyard](https://images.trvl-media.com/lodging/1000000/580000/573300/573299/45afcf8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/580000/573300/573299/f10ff9a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV](https://images.trvl-media.com/lodging/1000000/580000/573300/573299/9445d3b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden views ](https://images.trvl-media.com/lodging/1000000/580000/573300/573299/49f6e464.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Foiano della Chiana

[](https://www.expedia.ca/Arezzo-Hotels-Fontelunga-Hotel-Villas.h573299.Hotel-Information)

10/10

Exceptional

(5 reviews)

"Amazing stay at this hotel I would recommend it. Great hospitality, clean and picture postcard views. "

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

Liam

[](https://www.expedia.ca/Arezzo-Hotels-Fontelunga-Hotel-Villas.h573299.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/101000000/100900000/100896100/100896059/f0bca152.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100900000/100896100/100896059/5c9c109c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/101000000/100900000/100896100/100896059/65f08668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Villa | Living area](https://images.trvl-media.com/lodging/101000000/100900000/100896100/100896059/58622732.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo resort in Trequanda

[](https://www.expedia.ca/Trequanda-Hotels-Luxury-Resort-In-The-Tuscan-Countryside.h100896059.Hotel-Information)

[](https://www.expedia.ca/Trequanda-Hotels-Luxury-Resort-In-The-Tuscan-Countryside.h100896059.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/39e29e99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Royal Suite, Hot Tub (SPA) | Private spa tub](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/8f72c3f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/38f51959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Suite, 1 Double Bed | Living room](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/274ea02b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Residence in Trequanda

[](https://www.expedia.ca/Trequanda-Hotels-Abbadia-Sicille.h10652908.Hotel-Information)

8.8/10

Excellent

(168 reviews)

"Room was beyond expectations. Helpful staff and overall great experience. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Robert

CA $119

CA $136 total

includes taxes & fees

Mar 2 - Mar 3

[](https://www.expedia.ca/Trequanda-Hotels-Abbadia-Sicille.h10652908.Hotel-Information)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116960000/116957400/116957378/7e336ded.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, bidet, towels](https://images.trvl-media.com/lodging/117000000/116960000/116957400/116957378/3c123570.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/117000000/116960000/116957400/116957378/86cd748c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116960000/116957400/116957378/a00997c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Monteaperti

[](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Cosy-Double-Room-In-Pretty-Cottage-With-WiFi-And-AC-In-Enchanting-Monteaperti.h116957378.Hotel-Information)

10/10

Exceptional

(2 reviews)

"We loved this place. Modern cabin set in a rustic Tuscan setting. Beautiful property, very comfortable stay, and very attentive staff. Family owned and operated. Amazing restaurant just steps away. A perfect place for respite"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ian F.

CA $232

CA $271 total

includes taxes & fees

Feb 27 - Feb 28

[](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Cosy-Double-Room-In-Pretty-Cottage-With-WiFi-And-AC-In-Enchanting-Monteaperti.h116957378.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/19000000/18980000/18976500/18976420/a4b435e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/19000000/18980000/18976500/18976420/90089355.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/19000000/18980000/18976500/18976420/f4b5c97e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, books](https://images.trvl-media.com/lodging/19000000/18980000/18976500/18976420/65605df2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Montalcino (SI)

[](https://www.expedia.ca/Montalcino-Hotels-The-House-Of-Alice.h18976420.Hotel-Information)

9.8/10

Exceptional

(69 reviews)

"Really enjoyed our stay. Loved the town and the accommodation was superb. "

![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg)

Michelle C.

CA $242

CA $326 total

includes taxes & fees

Feb 27 - Feb 28

[](https://www.expedia.ca/Montalcino-Hotels-The-House-Of-Alice.h18976420.Hotel-Information)

![1 treatment room, massages](https://images.trvl-media.com/lodging/52000000/51830000/51829000/51828901/9867dcf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/52000000/51830000/51829000/51828901/7dd03bcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/52000000/51830000/51829000/51828901/ce312570.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Room, Terrace, Valley View](https://images.trvl-media.com/lodging/52000000/51830000/51829000/51828901/2f810565.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Residence in San Quirico d'Orcia

[](https://www.expedia.ca/San-Quirico-DOrcia-Hotels-Resort-Casanova-Panoramic-Rooms-And-Suites.h51828901.Hotel-Information)

9.2/10

Wonderful

(79 reviews)

"Fantastic place"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Clifford

CA $267

CA $300 total

includes taxes & fees

Mar 6 - Mar 7

[](https://www.expedia.ca/San-Quirico-DOrcia-Hotels-Resort-Casanova-Panoramic-Rooms-And-Suites.h51828901.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/37000000/36080000/36077800/36077744/d9c4aea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/37000000/36080000/36077800/36077744/1f2f52d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/37000000/36080000/36077800/36077744/3b9ae1e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/37000000/36080000/36077800/36077744/13261dd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Montalcino

[](https://www.expedia.ca/Montalcino-Hotels-La-Casetta-Di-Brunello.h36077744.Hotel-Information)

9.6/10

Exceptional

(17 reviews)

"Love this apartment and the quiet little town. Great place to spend a week. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Stan F.

CA $242

CA $326 total

includes taxes & fees

Feb 26 - Feb 27

[](https://www.expedia.ca/Montalcino-Hotels-La-Casetta-Di-Brunello.h36077744.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/32000000/31530000/31527300/31527256/7be16d35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/32000000/31530000/31527300/31527256/1f1554d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/32000000/31530000/31527300/31527256/7838807c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/32000000/31530000/31527300/31527256/6cc52516.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Acquapendente

[](https://www.expedia.ca/Acquapendente-Hotels-Agriturismo-San-Filippo.h31527256.Hotel-Information)

8.6/10

Excellent

(14 reviews)

"Excellent experience!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Richard

[](https://www.expedia.ca/Acquapendente-Hotels-Agriturismo-San-Filippo.h31527256.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-03-11&endDate=2026-03-12&regionId=6023645&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Find vacation rentals that suit your style

Villas

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Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Pienza%2C+Tuscany%2C+Italy&regionId=6023645&latLong=43.076766%2C11.678764&adults=2&startDate=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=VACATION_HOME)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Pienza%2C+Tuscany%2C+Italy&regionId=6023645&latLong=43.076766%2C11.678764&adults=2&startDate=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=APARTMENT)

Residences

[](https://www.expedia.ca/Hotel-Search?destination=Pienza%2C+Tuscany%2C+Italy&regionId=6023645&latLong=43.076766%2C11.678764&adults=2&startDate=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=RESIDENCE)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Pienza%2C+Tuscany%2C+Italy&regionId=6023645&latLong=43.076766%2C11.678764&adults=2&startDate=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=COTTAGE)

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Pienza%2C+Tuscany%2C+Italy&regionId=6023645&latLong=43.076766%2C11.678764&adults=2&startDate=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=APART_HOTEL)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Pienza%2C+Tuscany%2C+Italy&regionId=6023645&latLong=43.076766%2C11.678764&adults=2&startDate=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=CHALET)

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## Top Pienza Hotel Reviews

![Fonteverde Lifestyle & Thermal Retreat](https://images.trvl-media.com/lodging/1000000/910000/909000/908918/f6fb188e_y.jpg)

### Fonteverde Lifestyle & Thermal Retreat

10/10 Excellent

"Great place! Excellent service by everyone we encountered. "

[](https://expedia.ca/San-Casciano-Dei-Bagni-Hotels-Fonteverde.h908918.Hotel-Information)

![Albergo San Biagio](https://images.trvl-media.com/lodging/4000000/3230000/3224200/3224141/c85acee6_y.jpg)

### Albergo San Biagio

10/10 Excellent

"Muy amable "

[](https://expedia.ca/Montepulciano-Hotels-Albergo-San-Biagio.h3224141.Hotel-Information)

![Monastero di Cortona Hotel & Spa](https://images.trvl-media.com/lodging/24000000/23270000/23264500/23264410/cea3a0e9_y.jpg)

### Monastero di Cortona Hotel & Spa

10/10 Excellent

"Everything was great! Lovely hotel "

[](https://expedia.ca/Cortona-Hotels-Monastero-Di-Cortona-Hotel-Spa.h23264410.Hotel-Information)

![Hotel Relais II Chiostro di Pienza](https://images.trvl-media.com/lodging/1000000/900000/893100/893017/ef61d192_y.jpg)

### Hotel Relais II Chiostro di Pienza

10/10 Excellent

"A little tired, extremely clean, with an amazing staff"

[](https://expedia.ca/Pienza-Hotels-Hotel-Relais-II-Chiostro-Di-Pienza.h893017.Hotel-Information)

![Hotel Certosa Di Maggiano](https://images.trvl-media.com/lodging/1000000/530000/528500/528470/edea64a5_y.jpg)

### Hotel Certosa Di Maggiano

10/10 Excellent

"The best in Siena."

[](https://expedia.ca/Siena-Hotels-Hotel-Certosa-Di-Maggiano.h528470.Hotel-Information)

![Relais Villa Grazianella - UNA Esperienze](https://images.trvl-media.com/lodging/5000000/4320000/4310500/4310479/8b3fbbcc_y.jpg)

### Relais Villa Grazianella - UNA Esperienze

10/10 Excellent

"Everything was perfect. Warm welcome, comfortable and spacious rooms, great breakfast. The staff was very kind and friendly. I also recommend the wine tasting experience. Highly recommended!"

[](https://expedia.ca/Montepulciano-Hotels-Relais-Villa-Grazianella-UNA-Esperienze.h4310479.Hotel-Information)

![Hotel Corsignano](https://images.trvl-media.com/lodging/3000000/2530000/2525700/2525690/e0c5b2be_y.jpg)

### Hotel Corsignano

10/10 Excellent

"Wonderful stay. Very welcoming staff and check in was quick and simple. Very convenient as parking provided. Room was spacious especially bathroom with great bathtub Breakfast was perfect"

[](https://expedia.ca/Pienza-Hotels-Hotel-Corsignano.h2525690.Hotel-Information)

![Hotel Santa Caterina](https://images.trvl-media.com/lodging/3000000/2550000/2540800/2540753/3b315dde_y.jpg)

### Hotel Santa Caterina

10/10 Excellent

"Amazing staff, great food and an even better view from the garden. "

[](https://expedia.ca/Siena-Hotels-Hotel-Santa-Caterina.h2540753.Hotel-Information)

![Castello di Velona Resort Thermal SPA & Winery](https://images.trvl-media.com/lodging/2000000/1040000/1037900/1037832/87359911_y.jpg)

### Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent

"The property was exquisite. The view spectacular and the staff top notch. The indoor and outdoor thermal pools and sauna made our stay very relaxing. The buffet breakfast was amazing."

[](https://expedia.ca/Montalcino-Hotels-Castello-Di-Velona-Resort-The-Leading-Hotels-Of-The-World.h1037832.Hotel-Information)

## Find out more about Pienza

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Pienza. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Prince Edward Island Vacation Rentals ](https://www.expedia.ca/Destinations-In-Prince-Edward-Island.d6058122.Vacation-Rental-Destinations)
- [Québec Vacation Rentals ](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

## Frequently asked questions

### Can I find a vacation rental in Pienza?

### What are some of the best vacation home rentals in Pienza?

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### What’s there to see and do in Pienza?

### What’s a vacation rental in Pienza like?

### Expedia's Latest Trends

Hotels

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Flights

- [Flights to Florence](https://expedia.ca/Cheap-Flights-To-Florence.d1222.Travel-Guide-Flights)
- [Flights to Pisa](https://expedia.ca/Cheap-Flights-To-Pisa.d2877.Travel-Guide-Flights)

Cars

- [Car rentals in Siena](https://expedia.ca/Car-Rentals-In-Siena.d9821.Car-Rental-Guide)
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Activities

- [Things to do in Pisa](https://expedia.ca/Things-To-Do-In-Pisa.d2877.Travel-Guide-Activities)
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Packages

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General

- [Visit Florence](https://expedia.ca/Florence.dx1222)
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