Title: Pienza Vacation Rentals from CA $103: 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 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2026-05-01&endDate=2026-05-03&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)

![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)

![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)

![Superior Double or Twin Room, 1 Bedroom](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/47a2d1db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel San Gregorio

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

Pienza

9.4/10

Exceptional

(134 reviews)

"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 $203

CA $233 total

includes taxes & fees

Jan 13 - Jan 14

[](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)

![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)

![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)

### PienzaLettings Suites

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

Pienza

10/10

Exceptional

(1 review)

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

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

Tom

CA $105

CA $123 total

includes taxes & fees

Jan 13 - Jan 14

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

![Exterior](https://images.trvl-media.com/lodging/115000000/114870000/114863300/114863278/cc713796.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)

![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)

### TuscanyLettings Studio&Room

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

Pienza

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 $131

CA $150 total

includes taxes & fees

Jan 12 - Jan 13

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

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

### Affitacamere Maria Gabriella

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

Pienza

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 $151

CA $207 total

includes taxes & fees

Jan 16 - Jan 17

[](https://www.expedia.ca/Pienza-Hotels-Affitacamere-Maria-Gabriella.h22938763.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/d953c731.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 Gioia - Casa Olivieri 

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

Pienza

CA $119

CA $138 total

includes taxes & fees

Jan 12 - Jan 13

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

![Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | Private spa tub](https://images.trvl-media.com/lodging/25000000/24990000/24986600/24986573/w5467h3644x6y6-bfae763b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Daily buffet breakfast (EUR 10 per person)](https://images.trvl-media.com/lodging/25000000/24990000/24986600/24986573/w5470h3644x0y0-9c1f6ad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/25000000/24990000/24986600/24986573/543e1f7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/25000000/24990000/24986600/24986573/81c3f8ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### DormiVeglia B&B

[](https://www.expedia.ca/Monte-San-Savino-Hotels-DormiVeglia-BB.h24986573.Hotel-Information)

Monte San Savino

10/10

Exceptional

(27 reviews)

"Amazing, warm, sweet, lovely, such a gem of a place!"

![American Samoa](https://a.travel-assets.com/egds/marks/flags/as.svg)

Melissa Hyun Joo

[](https://www.expedia.ca/Monte-San-Savino-Hotels-DormiVeglia-BB.h24986573.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)

![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)

![Junior Suite, Balcony](https://images.trvl-media.com/lodging/47000000/46280000/46279800/46279780/2ef8f95c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Meublé Il Riccio

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

Montepulciano

9.8/10

Exceptional

(86 reviews)

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

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

Mark

CA $210

CA $237 total

includes taxes & fees

Jan 12 - Jan 13

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

![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)

![Restaurant](https://images.trvl-media.com/lodging/43000000/42240000/42239300/42239240/bcab148b.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)

### La Locanda Di Cetona

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

Cetona

9.2/10

Wonderful

(5 reviews)

"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)

![Property grounds](https://images.trvl-media.com/lodging/32000000/31530000/31527300/31527256/7be16d35.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/32000000/31530000/31527300/31527256/59a284ad.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)

### Agriturismo San Filippo

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

Acquapendente

8.6/10

Excellent

(14 reviews)

"The property is not as advertised. It is not an individual stand alone home where you have an entire house to yourself. They have a confusing description. It is either an apartment or an entire home. It can’t be both They need to get their description corrected. It is also not a classic apartment. It is an old horse stable covered into multiple apartments. The apartment in the picture was not the apartment offered. On the listing it only lists one place available, but upon arrival we were not...

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

Jeremy

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

![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)

![Exterior](https://images.trvl-media.com/lodging/43000000/42010000/42001200/42001140/9d10099d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### La Piccola Locanda

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

Chiusi

8.8/10

Excellent

(8 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)

![Classic Apartment, 2 Bedrooms | Terrace/patio](https://images.trvl-media.com/lodging/16000000/15920000/15919700/15919621/9142c384.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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/16000000/15920000/15919700/15919621/93516f21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/16000000/15920000/15919700/15919621/565416e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### FonteLiving

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

San Casciano dei Bagni

10/10

Exceptional

(6 reviews)

"Excellent experience, location, and environment."

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

Chia-Hung

CA $98

CA $111 total

includes taxes & fees

Jan 15 - Jan 16

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

![Lunch, dinner served; local cuisine, alfresco dining ](https://images.trvl-media.com/lodging/8000000/7280000/7272500/7272465/0ce3602b.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)

### La Locanda di San Francesco

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

Montepulciano

9.8/10

Exceptional

(131 reviews)

"Great room-great staff-great location"

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

Richard

CA $211

CA $239 total

includes taxes & fees

Jan 18 - Jan 19

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

![Exterior](https://images.trvl-media.com/lodging/5000000/4840000/4837100/4837070/0d27663a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hallway](https://images.trvl-media.com/lodging/5000000/4840000/4837100/4837070/da2f0709.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Room, Jetted Tub | Deep soaking bathtub](https://images.trvl-media.com/lodging/5000000/4840000/4837100/4837070/188597d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Room](https://images.trvl-media.com/lodging/5000000/4840000/4837100/4837070/d191efd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bed & Breakfast Vicolo dell'Oste

[](https://www.expedia.ca/Montepulciano-Hotels-Bed-Breakfast-Vicolo-DellOste.h4837070.Hotel-Information)

Montepulciano

9.6/10

Exceptional

(128 reviews)

"Great hosts, central location "

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

Alexander

[](https://www.expedia.ca/Montepulciano-Hotels-Bed-Breakfast-Vicolo-DellOste.h4837070.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/10000000/9760000/9754500/9754480/001e488b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Apartment | Living area](https://images.trvl-media.com/lodging/10000000/9760000/9754500/9754480/824e4462.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Economy Double Room, 1 Double Bed, Private Bathroom](https://images.trvl-media.com/lodging/10000000/9760000/9754500/9754480/ba266d45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Apartment | Private kitchen](https://images.trvl-media.com/lodging/10000000/9760000/9754500/9754480/8c83167a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Idolina Guest House

[](https://www.expedia.ca/Montalcino-Hotels-Idolina-Guest-House.h9754480.Hotel-Information)

Montalcino

9.4/10

Exceptional

(105 reviews)

"The building is lovely - traditional Italian construction with big Chestnut beams in the ceiling. The owner/manager is very pleasant and helpful. Overall, a very nice place to stay. "

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

Carl

[](https://www.expedia.ca/Montalcino-Hotels-Idolina-Guest-House.h9754480.Hotel-Information)

![Premium bedding, down comforters, pillowtop beds, minibar](https://images.trvl-media.com/lodging/106000000/105580000/105570300/105570206/7fe98579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/106000000/105580000/105570300/105570206/971773cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Royal Apartment | Private kitchen](https://images.trvl-media.com/lodging/106000000/105580000/105570300/105570206/53d9424a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/106000000/105580000/105570300/105570206/a763977c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tuscasì Aparthotel

[](https://www.expedia.ca/Sovicille-Hotels-Tuscasi-Aparthotel.h105570206.Hotel-Information)

Sovicille

9.0/10

Wonderful

(26 reviews)

"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "

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

Sergey

CA $88

CA $118 total

includes taxes & fees

Feb 5 - Feb 6

[](https://www.expedia.ca/Sovicille-Hotels-Tuscasi-Aparthotel.h105570206.Hotel-Information)

![Interior detail](https://images.trvl-media.com/lodging/16000000/15910000/15907000/15906915/cdb3c15d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family dining](https://images.trvl-media.com/lodging/16000000/15910000/15907000/15906915/56594a0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, Garden View](https://images.trvl-media.com/lodging/16000000/15910000/15907000/15906915/3a6f7416.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free self parking](https://images.trvl-media.com/lodging/16000000/15910000/15907000/15906915/396ff949.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### La Coroncina Lodging

[](https://www.expedia.ca/Siena-Hotels-La-Coroncina-Lodging.h15906915.Hotel-Information)

Siena

10/10

Exceptional

(42 reviews)

"Fantastic place, and I highly recommend it."

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

Hassan

CA $135

CA $156 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Siena-Hotels-La-Coroncina-Lodging.h15906915.Hotel-Information)

![Interior entrance](https://images.trvl-media.com/lodging/20000000/19990000/19986400/19986371/6beb29de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/20000000/19990000/19986400/19986371/6fa594b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/20000000/19990000/19986400/19986371/50df5603.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/20000000/19990000/19986400/19986371/73fff45b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Poggio del Sole

[](https://www.expedia.ca/Castiglione-Del-Lago-Hotels-Poggio-Del-Sole.h19986371.Hotel-Information)

Castiglione del Lago

8.0/10

Very good

(4 reviews)

"El hotel no alcanzó el agua caliente y no se pudo bañar parte de la familia no contaba con suficientes amenidades "

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

RAUL

[](https://www.expedia.ca/Castiglione-Del-Lago-Hotels-Poggio-Del-Sole.h19986371.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/e04fd69c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/100f6cff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Gazebo](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/c1f8c360.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Triple Room | Bathroom](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/c721d6f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Artisti del Cavallo Tourism

[](https://www.expedia.ca/Foiano-Della-Chiana-Hotels-Agriturismo-Artisti-Del-Cavallo.h26499959.Hotel-Information)

Foiano della Chiana

8.4/10

Very good

(24 reviews)

"Good house for one night. "

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

Heiner

CA $113

CA $128 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Foiano-Della-Chiana-Hotels-Agriturismo-Artisti-Del-Cavallo.h26499959.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/10000000/9590000/9581000/9580990/1944c386.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/10000000/9590000/9581000/9580990/e63cb2b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Traditional Studio (Il Capanno)](https://images.trvl-media.com/lodging/10000000/9590000/9581000/9580990/0c2f0b6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/10000000/9590000/9581000/9580990/cbd34f5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Podere La Chiusella

[](https://www.expedia.ca/Rapolano-Terme-Hotels-Podere-La-Chiusella.h9580990.Hotel-Information)

Rapolano Terme

9.4/10

Exceptional

(30 reviews)

"Et sjarmerende lite B&B. Har nok vært utrolig vakkert i sine glansdager, men områdene rundt bærer preg av lite vedlikehold. Leiligheten var helt grei for en overnatting. Gulvet på badet var ikke rent. Når vi tørket opp etter oss ble håndkleet møkkete. Men overnattingen var helt grei alt i alt. Når vi skulle sjekke ut var det ikke et menneske å se, resepsjonen var stengt. Endte med å sette nøklene i døra og dra da alt var betalt ved bestilling."

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

Elisabeth

[](https://www.expedia.ca/Rapolano-Terme-Hotels-Podere-La-Chiusella.h9580990.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)

![Meeting facility](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/9c2d8838.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)

### Abbadia Sicille Relais

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

Trequanda

8.8/10

Excellent

(166 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 $89

CA $103 total

includes taxes & fees

Jan 18 - Jan 19

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

Private vacation homes

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Aparthotels

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Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Pienza%2C+Tuscany%2C+Italy&regionId=6023645&latLong=43.076766%2C11.678764&adults=2&startDate=2026-04-10&d1=2026-04-10&endDate=2026-04-13&d2=2026-04-13&lodging=APARTMENT)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Pienza%2C+Tuscany%2C+Italy&regionId=6023645&latLong=43.076766%2C11.678764&adults=2&startDate=2026-04-10&d1=2026-04-10&endDate=2026-04-13&d2=2026-04-13&lodging=VILLA)

Residences

[](https://www.expedia.ca/Hotel-Search?destination=Pienza%2C+Tuscany%2C+Italy&regionId=6023645&latLong=43.076766%2C11.678764&adults=2&startDate=2026-04-10&d1=2026-04-10&endDate=2026-04-13&d2=2026-04-13&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=2026-04-10&d1=2026-04-10&endDate=2026-04-13&d2=2026-04-13&lodging=COTTAGE)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Pienza%2C+Tuscany%2C+Italy&regionId=6023645&latLong=43.076766%2C11.678764&adults=2&startDate=2026-04-10&d1=2026-04-10&endDate=2026-04-13&d2=2026-04-13&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 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)

![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)

![Villa di Piazzano - Small Luxury Hotel of the World](https://images.trvl-media.com/lodging/1000000/980000/972000/971985/473f66a9_y.jpg)

### Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent

"Room was wonderful, bathroom spacious and well appointed. Staff amazing and so friendly "

[](https://expedia.ca/Cortona-Hotels-Villa-Di-Piazzano-Small-Luxury-Hotel-Of-The-World.h971985.Hotel-Information)

![Precise Tale Poggio Alla Sala](https://images.trvl-media.com/lodging/91000000/90890000/90888700/90888666/8fbdd5cc_y.jpg)

### Precise Tale Poggio Alla Sala

10/10 Excellent

"Fantastic hotel in an incredible setting. Staff were extremely helpful, attentive and understanding. The perfect location for a relaxing break and a centre for exploring Tuscany"

[](https://expedia.ca/Montepulciano-Hotels-Precise-Tale-Poggio-Alla-Sala.h90888666.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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- [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 a vacation rental in Pienza like?

### Expedia's Latest Trends

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Flights

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Cars

- [Car rentals in Cortona](https://expedia.ca/Car-Rentals-In-Cortona.d601360.Car-Rental-Guide)

Activities

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