Title: Pienza Vacation Rentals from CA $111: 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 Tuscany

#Golden](https://images.trvl-media.com/place/6023645/e640ba3e-762e-48a2-a091-83506ea0e2e9.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Robert Bilos

# Pienza Vacation Rentals

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## Check prices for these dates

In two weeks

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2026-04-17&endDate=2026-04-19&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

![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)

![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)

![Breakfast buffet](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/cd7670ac.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)

"Such friendly staff, loved Pienza and the property was such a good location! "

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

Bethan

CA $270

CA $307 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Pienza-Hotels-Hotel-San-Gregorio.h2692135.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 Enea al primo piano senza ascensore | Living area](https://images.trvl-media.com/lodging/113000000/112330000/112327700/112327681/04ed7e2f.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

(1)

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

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

Tom

CA $117

CA $136 total

includes taxes & fees

Jan 8 - Jan 9, 2026

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

![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)

![Interior](https://images.trvl-media.com/lodging/23000000/22940000/22938800/22938763/a39f2057.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)

### Townhouse in Pienza

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

9.8/10

Exceptional

(51)

"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

[](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 | Living area](https://images.trvl-media.com/lodging/115000000/114870000/114863300/114863278/6be6d8fd.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)

### Townhouse in Pienza

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

10/10

Exceptional

(1)

"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 $125

CA $145 total

includes taxes & fees

Jan 9 - Jan 10, 2026

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

![Exterior](https://images.trvl-media.com/lodging/116000000/115080000/115077100/115077012/d953c731.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 $119

CA $137 total

includes taxes & fees

Jan 21 - Jan 22, 2026

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

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/49000000/48840000/48837200/48837118/da956da6.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)

### Apartment in Monticchiello

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

10/10

Exceptional

(11)

"Nice and comfortable house in a beautiful tiny village "

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

Lana A.

CA $153

CA $185 total

includes taxes & fees

Jan 6 - Jan 7, 2026

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

![Exterior detail](https://images.trvl-media.com/lodging/125000000/124120000/124117300/124117240/4deddac1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124120000/124117300/124117240/008e8f03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/125000000/124120000/124117300/124117240/a61b3db1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124120000/124117300/124117240/f62fd5f8.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 $155

CA $161 total

includes taxes & fees

Jan 11 - Jan 12, 2026

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

![Property grounds](https://images.trvl-media.com/lodging/104000000/103830000/103821200/103821142/2035a69b.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)

"Wonderful views, accommodating hosts"

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

Pete and Alison C.

CA $291

CA $428 total

includes taxes & fees

Dec 28 - Dec 29

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

![Interior](https://images.trvl-media.com/lodging/125000000/124120000/124117300/124117285/w2400h1799x0y0-43294846.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)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124120000/124117300/124117285/w2400h1799x0y0-0a78ed7a.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 $310

CA $316 total

includes taxes & fees

Jan 23 - Jan 24, 2026

[](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/113000000/112280000/112279700/112279685/4793cff9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/113000000/112280000/112279700/112279685/0ccb55cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112280000/112279700/112279685/d1d93860.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/113000000/112280000/112279700/112279685/efa4325b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Pienza

[](https://www.expedia.ca/Pienza-Hotels-Studio-La-Casina-Mag-With-Wi-Fi.h112279685.Hotel-Information)

CA $246

CA $317 total

includes taxes & fees

Dec 26 - Dec 27

[](https://www.expedia.ca/Pienza-Hotels-Studio-La-Casina-Mag-With-Wi-Fi.h112279685.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)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/37000000/36370000/36364900/36364803/64e505a2.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)

![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)

### Vacation Home in Monticchiello

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

10/10

Exceptional

(8)

"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 $153

CA $189 total

includes taxes & fees

Dec 25 - Dec 26

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

![Interior](https://images.trvl-media.com/lodging/47000000/46280000/46279800/46279780/0aaa13a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/47000000/46280000/46279800/46279780/cabc4072.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Balcony](https://images.trvl-media.com/lodging/47000000/46280000/46279800/46279780/45d9565e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Daily buffet breakfast (EUR 10 per person)](https://images.trvl-media.com/lodging/47000000/46280000/46279800/46279780/8011dd87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Montepulciano

[](https://www.expedia.ca/Montepulciano-Hotels-Meuble-Il-Riccio.h46279780.Hotel-Information)

9.8/10

Exceptional

(86)

"Staff is great and many good restaurants in short walking distance."

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

Mark

[](https://www.expedia.ca/Montepulciano-Hotels-Meuble-Il-Riccio.h46279780.Hotel-Information)

![Food court](https://images.trvl-media.com/lodging/8000000/7280000/7272500/7272465/0263d307.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, down comforters, minibar, in-room safe](https://images.trvl-media.com/lodging/8000000/7280000/7272500/7272465/f4cb97cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/8000000/7280000/7272500/7272465/bfee31ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Food and drink](https://images.trvl-media.com/lodging/8000000/7280000/7272500/7272465/26e5f82d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Montepulciano

[](https://www.expedia.ca/Montepulciano-Hotels-La-Locanda-Di-San-Francesco.h7272465.Hotel-Information)

9.8/10

Exceptional

(131)

"Great room-great staff-great location"

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

Richard

CA $243

CA $274 total

includes taxes & fees

Jan 18 - Jan 19, 2026

[](https://www.expedia.ca/Montepulciano-Hotels-La-Locanda-Di-San-Francesco.h7272465.Hotel-Information)

![Seasonal outdoor pool, an infinity pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/16000000/15920000/15919700/15919621/2c20c3fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Apartment, 2 Bedrooms | Living area](https://images.trvl-media.com/lodging/16000000/15920000/15919700/15919621/92b34c63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Royal Apartment, 2 Bedrooms | Living area](https://images.trvl-media.com/lodging/16000000/15920000/15919700/15919621/d924506c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Executive Apartment, 2 Bedrooms | Living area](https://images.trvl-media.com/lodging/16000000/15920000/15919700/15919621/002ed7eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in San Casciano dei Bagni

[](https://www.expedia.ca/San-Casciano-Dei-Bagni-Hotels-FonteLiving.h15919621.Hotel-Information)

10/10

Exceptional

(5)

"Comfortable apartment in quiet block. Nicely furnished excellent housekeeping nice spacious bathrooms great view from the terrace."

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

R

CA $102

CA $116 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/San-Casciano-Dei-Bagni-Hotels-FonteLiving.h15919621.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)

![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)

![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)

![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

(166)

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

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

Robert

CA $96

CA $111 total

includes taxes & fees

Jan 7 - Jan 8, 2026

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

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

![Property grounds](https://images.trvl-media.com/lodging/32000000/31530000/31527300/31527256/59a284ad.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)

### Vacation Home in Acquapendente

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

9.0/10

Wonderful

(13)

"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)

![Property entrance](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/124b8b86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/12afb28e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/a1afa9f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/1def40b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Residence in Montepulciano

[](https://www.expedia.ca/Montepulciano-Hotels-Residenza-Fabroni.h8204306.Hotel-Information)

8.8/10

Excellent

(94)

"gorgeous historical property, very attentive host, great location"

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

Sarah

CA $121

CA $139 total

includes taxes & fees

Jan 13 - Jan 14, 2026

[](https://www.expedia.ca/Montepulciano-Hotels-Residenza-Fabroni.h8204306.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/43000000/42240000/42239300/42239240/ebbc46be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/43000000/42240000/42239300/42239240/f199e1c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pillowtop beds, minibar, in-room safe, individually decorated](https://images.trvl-media.com/lodging/43000000/42240000/42239300/42239240/9b46c6f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite | Living area](https://images.trvl-media.com/lodging/43000000/42240000/42239300/42239240/35d091bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Townhouse in Cetona

[](https://www.expedia.ca/Cetona-Hotels-La-Locanda-Di-Cetona.h42239240.Hotel-Information)

9.2/10

Wonderful

(5)

"A lovely hotel and very welcoming staff. Cetona is a delight. "

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

Julian

[](https://www.expedia.ca/Cetona-Hotels-La-Locanda-Di-Cetona.h42239240.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)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/52000000/51830000/51829000/51828901/ba51ed0b.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)

![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)

9.0/10

Wonderful

(78)

"Fantastic place"

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

Clifford

CA $317

CA $355 total

includes taxes & fees

Dec 28 - Dec 29

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

![Exterior](https://images.trvl-media.com/lodging/43000000/42010000/42001200/42001140/9d10099d.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)

![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)

### Townhouse in Chiusi

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

8.8/10

Excellent

(8)

"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)

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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## Find vacation rentals that suit your style

Villas

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Apartments

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Private vacation homes

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Residences

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Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Pienza%2C+Tuscany%2C+Italy&regionId=6023645&latLong=43.076766%2C11.678764&adults=2&startDate=2026-03-24&d1=2026-03-24&endDate=2026-03-27&d2=2026-03-27&lodging=COTTAGE)

Aparthotels

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Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Pienza%2C+Tuscany%2C+Italy&regionId=6023645&latLong=43.076766%2C11.678764&adults=2&startDate=2026-03-24&d1=2026-03-24&endDate=2026-03-27&d2=2026-03-27&lodging=CHALET)

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## Top Pienza Hotel Reviews

![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 perfect! Would like to give this Property a 6 Star rating. The staff made you feel like royalty!!"

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

![Abbadia Sicille Relais](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/80de574a_y.jpg)

### Abbadia Sicille Relais

10/10 Excellent

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

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

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

### Albergo San Biagio

10/10 Excellent

"gorgeous spot below the town, what an incredible view from the balcony "

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

![Rosewood Castiglion del Bosco](https://images.trvl-media.com/lodging/3000000/2180000/2173600/2173539/9ace3d4a_y.jpg)

### Rosewood Castiglion del Bosco

10/10 Excellent

"Wonderful stay "

[](https://expedia.ca/Montalcino-Hotels-Rosewood-Castiglion-Del-Bosco.h2173539.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

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