Title: Pienza Vacation Rentals from CA $108: Short-Term Rentals for 2025 | 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://a.travel-assets.com/findyours-php/viewfinder/images/res70/157000/157955-Pienza.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Pienza Vacation Rentals ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Vacation Rentals in Pienza ![Breakfast, lunch, dinner served; local cuisine ](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/9fda43a3.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) ### Hotel San Gregorio Pienza 9.4/10 Exceptional (130) "Such friendly staff, loved Pienza and the property was such a good location! " CA $166 CA $192 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Pienza-Hotels-Hotel-San-Gregorio.h2692135.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/34000000/33740000/33736700/33736684/7a01fd7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player](https://images.trvl-media.com/lodging/34000000/33740000/33736700/33736684/d549fb7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33740000/33736700/33736684/16ad62df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![9 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33740000/33736700/33736684/2c20aa4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Whole big Tuscan Villa with Pool & Vineyards in the Heart of Tuscany Pienza 9.6/10 Exceptional (17) "The view from the house is spectacular! What a great spot for a group of friends or a large family. Close to vineyards and shopping. We love sitting on the back patio having dinner. The dog and cats were an extra. Lily and her husband were very helpful and we really enjoyed having the meals cooked by the chef while we were there. The last night with the fish was the best!" [](https://www.expedia.ca/Pienza-Hotels-Whole-Big-Tuscan-Villa-With-Pool-Vineyards-In-The-Heart-Of-Tuscany.h33736684.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/37000000/36380000/36378600/36378551/3dd7b50b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/37000000/36380000/36378600/36378551/4c3b30ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/37000000/36380000/36378600/36378551/fa516210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/37000000/36380000/36378600/36378551/c886b883.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool Pienza 10/10 Exceptional (3) "Beautiful historic villa. Loved the vibe. Would definitely stay here again! " [](https://www.expedia.ca/Pienza-Hotels-Beautiful-Tuscan-Farmhouse-In-A-Great-Location-Near-Val-DOrcia-Private-Pool.h36378551.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/45000000/44550000/44541000/44540981/b8f22b72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa, Multiple Bedrooms, Private Pool, Mountain View | Private kitchen](https://images.trvl-media.com/lodging/45000000/44550000/44541000/44540981/308ddd8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/45000000/44550000/44541000/44540981/7ab081de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, individually furnished, cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/45000000/44550000/44541000/44540981/5785f8d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Privacy in the Heart of Tuscany Pienza [](https://www.expedia.ca/Pienza-Hotels-Luxury-Privacy-In-The-Heart-Of-Tuscany.h44540981.Hotel-Information) ![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) ![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) ![Aerial view](https://images.trvl-media.com/lodging/52000000/51830000/51829000/51828901/b1604ed6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casanova - Panoramic Rooms and Suites San Quirico d'Orcia 9.0/10 Wonderful (70) "Delightful stay. The room was lovely, and the view from our private terrace was wonderful. Dinner was first rate. Easily walkable into San Quirico, short drive to Montalcino, Pienza, and Montalcino. Nice massage and spa. A very good value." CA $256 CA $288 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/San-Quirico-DOrcia-Hotels-Resort-Casanova-Panoramic-Rooms-And-Suites.h51828901.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/80de574a.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) ![Billiards](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/a6535507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Billiards](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/cd3bbebf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Abbadia Sicille Relais Trequanda 8.8/10 Excellent (159) "Great Historical location." CA $93 CA $108 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Trequanda-Hotels-Abbadia-Sicille.h10652908.Hotel-Information) ![Royal Apartment | View from room](https://images.trvl-media.com/lodging/106000000/105580000/105570300/105570206/8b57b476.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Elite Apartment | Terrace/patio](https://images.trvl-media.com/lodging/106000000/105580000/105570300/105570206/c89c2c15.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) ![Royal Apartment | Private kitchen](https://images.trvl-media.com/lodging/106000000/105580000/105570300/105570206/1808f82b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tuscasì Aparthotel Sovicille 9.2/10 Wonderful (22) "Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. " CA $93 CA $108 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Sovicille-Hotels-Tuscasi-Aparthotel.h105570206.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/36000000/35330000/35330000/35329902/822e6f62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/36000000/35330000/35330000/35329902/0dd7cc53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/36000000/35330000/35330000/35329902/3fbaa990.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/36000000/35330000/35330000/35329902/2f21d9f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private and cozy retreat in Montalcino with private pool surrounded by vineyards Siena 9.4/10 Exceptional (66) "What a lovely place, I will recommend this fabulous home to friends and family and will be returning sometime soon." [](https://www.expedia.ca/Montalcino-Hotels-Private-And-Cozy-Retreat-In-Montalcino-With-Private-Pool-Surrounded-By-Vineyards.h35329902.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/2000000/1210000/1206200/1206161/46c3ab32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Room](https://images.trvl-media.com/lodging/2000000/1210000/1206200/1206161/007eaefe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1210000/1206200/1206161/f58a3308.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![43-inch TV with satellite channels](https://images.trvl-media.com/lodging/2000000/1210000/1206200/1206161/6795409f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bosco della Spina Murlo 9.6/10 Exceptional (164) "We enjoyed the scenery and service! Clean and comfortable. " [](https://www.expedia.ca/Murlo-Hotels-Bosco-Della-Spina.h1206161.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/91000000/90310000/90300100/90300061/b96fbe26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, in-room safe, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/91000000/90310000/90300100/90300061/ea7982e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/91000000/90310000/90300100/90300061/691c226c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90310000/90300100/90300061/9980acef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Montalcino, exclusive for you, stunning view!!! Montalcino 10/10 Exceptional (84) "Lovely villa in a beautiful location. " [](https://www.expedia.ca/Montalcino-Hotels-Villa-In-Montalcino.h90300061.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/19000000/18770000/18767800/18767781/2ae00c85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18770000/18767800/18767781/4d576b3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18770000/18767800/18767781/36a0aef3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18770000/18767800/18767781/4c2a1ae4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sun-Soaked Private View Terrace in the Historical Centre of Cortona. Cortona Old Town 9.6/10 Exceptional (71) "My husband and I loved our stay here! It was so close to town and the terrace was absolutely stunning. Would definitely stay here again! " [](https://www.expedia.ca/Cortona-Hotels-Sun-Soaked-Private-View-Terrace-In-The-Historical-Centre-Of-Cortona.h18767781.Hotel-Information) ![Deluxe Apartment, 2 Bedrooms, Balcony](https://images.trvl-media.com/lodging/120000000/119060000/119052900/119052871/18007833.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/120000000/119060000/119052900/119052871/85f0e899.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Apartment, 2 Bedrooms, Balcony](https://images.trvl-media.com/lodging/120000000/119060000/119052900/119052871/302bfcfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119060000/119052900/119052871/60c79c9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bellarmino Boutique Apartments Montepulciano CA $143 CA $164 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Montepulciano-Hotels-Bellarmino-Boutique-Apartments.h119052871.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/19000000/18770000/18764200/18764107/7dffae86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18770000/18764200/18764107/660dd65a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor banquet area](https://images.trvl-media.com/lodging/19000000/18770000/18764200/18764107/ce0b1bfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/19000000/18770000/18764200/18764107/8205fa6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS chiusi 10/10 Exceptional (53) "We had a very nice stay and a well organized pizza night in the villa. Glad to come again:) " [](https://www.expedia.ca/Chiusi-Hotels-PRIVATE-TUSCAN-VILLA-WITH-HEATED-SWIMMING-POOL-JACUZZI-SPA-SAUNA-EVENTS.h18764107.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34030000/34024200/34024116/e5c35199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34030000/34024200/34024116/c341d493.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/35000000/34030000/34024200/34024116/4108e65d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34030000/34024200/34024116/b43cefc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilltop house in the heart of Tuscany with private pool Montisi 9.8/10 Exceptional (93) "Wonderful, quiet, beautiful. Everything you could want in country stay near a small village." [](https://www.expedia.ca/Montalcino-Hotels-Hilltop-House-In-The-Heart-Of-Tuscany-With-Private-Pool.h34024116.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/093ed3b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/124b8b86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/17ae36fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Suite, 2 Bedrooms](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/c477a48b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residenza Fabroni Montepulciano 8.8/10 Excellent (90) "We had a wonderful stay, the staff was extremely friendly and helpful. Restaurants and shops were right at our doorstep." CA $123 CA $142 total includes taxes & fees Oct 24 - Oct 25 [](https://www.expedia.ca/Montepulciano-Hotels-Residenza-Fabroni.h8204306.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/19000000/18980000/18976500/18976420/8def11f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18980000/18976500/18976420/8e2d77d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18980000/18976500/18976420/5d163297.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18980000/18976500/18976420/26d5f3cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The House of Alice, charm and relaxation Montalcino (SI) 9.8/10 Exceptional (66) "Unbelievable ambience and beauty of the region and the house. Francesco was super helpful. " CA $260 CA $351 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Montalcino-Hotels-The-House-Of-Alice.h18976420.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/39000000/38390000/38385000/38384931/463354ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Studio](https://images.trvl-media.com/lodging/39000000/38390000/38385000/38384931/5a69584c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Studio | Balcony view](https://images.trvl-media.com/lodging/39000000/38390000/38385000/38384931/663ab820.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/39000000/38390000/38385000/38384931/a3ffbf1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Porta Pispini Residence Siena Historical Center 9.6/10 Exceptional (18) "That’s not a hotel room, that’s small apartment with guest room and kitchen with washer and dishwasher Amazing window view Free parking Very clean 3 minutes walk from the city wall More than reasonable price " [](https://www.expedia.ca/Siena-Hotels-Porta-Pispini-Residence.h38384931.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/19000000/18770000/18768900/18768895/06ac7272.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/19000000/18770000/18768900/18768895/68022c7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18770000/18768900/18768895/632252a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/19000000/18770000/18768900/18768895/15e9955b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gite Montemirello, with garden and swimming pool Casciano di Murlo - Siena 9.8/10 Exceptional (59) "Very nice stay and very nuce Host :)" [](https://www.expedia.ca/Murlo-Hotels-Gite-Montemirello.h18768895.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/6a82a5cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/8099b959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/f6eed317.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/ff9693c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Il Poggio dell'Eremita Sinalunga 10/10 Exceptional (56) "Located in a peaceful location, the house is charming and homey. The hosts are very kind and accommodating, and we had a wonderful stay. The view from the bedroom balcony is spectacular." CA $192 CA $224 total includes taxes & fees Oct 11 - Oct 12 [](https://www.expedia.ca/Sinalunga-Hotels-Il-Poggio-Delleremita.h27448054.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/7000000/6310000/6309600/6309554/3e489ee1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite, 2 Queen Beds, City View](https://images.trvl-media.com/lodging/7000000/6310000/6309600/6309554/fe06c21c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/7000000/6310000/6309600/6309554/e6496db8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, memory foam beds, free minibar items](https://images.trvl-media.com/lodging/7000000/6310000/6309600/6309554/397666d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Il Tosco Montepulciano 10/10 Exceptional (112) "The people here are authentic and welcoming! The building, rooms and facilities are gorgeous! One of our most beautiful stays in our many trips to Italy " CA $392 CA $438 total includes taxes & fees Nov 8 - Nov 9 [](https://www.expedia.ca/Montepulciano-Hotels-Il-Tosco.h6309554.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=2025-10-22&endDate=2025-10-23®ionId=6023645&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FPienza-Vacation-Rentals.d6023645.Travel-Guide-VacationRentals)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPienza-Vacation-Rentals.d6023645.Travel-Guide-VacationRentals) ## Top Pienza Hotel Reviews ![Tenuta Santo Pietro](//images.trvl-media.com/lodging/3000000/2760000/2750300/2750235/4fa44438_y.jpg) ### Tenuta Santo Pietro 10/10 Excellent "Great countryside stay" [](https://expedia.ca/Pienza-Hotels-Tenuta-Santo-Pietro.h2750235.Hotel-Information) ![Hotel Relais II Chiostro di Pienza](//images.trvl-media.com/lodging/1000000/900000/893100/893017/ef61d192_y.jpg) ### Hotel Relais II Chiostro di Pienza 10/10 Excellent "The perfect location. Gorgeous property. Excellent breakfast. " [](https://expedia.ca/Pienza-Hotels-Hotel-Relais-II-Chiostro-Di-Pienza.h893017.Hotel-Information) ![Hotel Certosa Di Maggiano](//images.trvl-media.com/lodging/1000000/530000/528500/528470/4c3dd1ab_y.jpg) ### Hotel Certosa Di Maggiano 10/10 Excellent "A wonderfully peaceful hotel in the middle of Tuscany. Amazing views. Great staff - friendly, professional and very helpful & accommodating. " [](https://expedia.ca/Siena-Hotels-Hotel-Certosa-Di-Maggiano.h528470.Hotel-Information) ![Fonteverde Lifestyle & Thermal Retreat](//images.trvl-media.com/lodging/1000000/910000/909000/908918/f6fb188e_y.jpg) ### Fonteverde Lifestyle & Thermal Retreat 10/10 Excellent "Fine" [](https://expedia.ca/San-Casciano-Dei-Bagni-Hotels-Fonteverde.h908918.Hotel-Information) ![Nuovo Etruria Resort](//images.trvl-media.com/lodging/114000000/113750000/113748300/113748275/5960f205_y.jpg) ### Nuovo Etruria Resort 10/10 Excellent "Such an oasis of calm and relaxation. The room was large and cool with a very comfortable bed. The pool was beautiful and very refreshing. The staff were very friendly and helpful. A wonderful setting and just a short walk from the beautiful town and many fantastic restaurants. Would definitely recommend this hotel to others visiting Montepulciano." [](https://expedia.ca/Montepulciano-Hotels-Nuovo-Etrurua-Resort.h113748275.Hotel-Information) ![Precise Tale Poggio Alla Sala](//images.trvl-media.com/lodging/91000000/90890000/90888700/90888666/8fbdd5cc_y.jpg) ### Precise Tale Poggio Alla Sala 10/10 Excellent "Property is very well maintained with amazing views. The main building is gorgeous with a beautiful dining area. Overall an amazing experience and one i really want to repeat" [](https://expedia.ca/Montepulciano-Hotels-Precise-Tale-Poggio-Alla-Sala.h90888666.Hotel-Information) ![Monastero di Cortona Hotel & Spa](//images.trvl-media.com/lodging/24000000/23270000/23264500/23264410/cea3a0e9_y.jpg) ### Monastero di Cortona Hotel & Spa 10/10 Excellent "Beautiful, unique property! Stunning views of the countryside. The staff were all very helpful and friendly. We will definitely recommend!" [](https://expedia.ca/Cortona-Hotels-Monastero-Di-Cortona-Hotel-Spa.h23264410.Hotel-Information) ![Hotel Corsignano](//images.trvl-media.com/lodging/3000000/2530000/2525700/2525690/e0c5b2be_y.jpg) ### Hotel Corsignano 10/10 Excellent "Wonderful hotel! Beautiful, very clean, staff was great, friendly and helpful. Perfect location for seeing the town and hiking to amazing views. Loved it!" [](https://expedia.ca/Pienza-Hotels-Hotel-Corsignano.h2525690.Hotel-Information) ![Precise House Montaperti Siena](//images.trvl-media.com/lodging/2000000/1120000/1110900/1110834/2f957dff_y.jpg) ### Precise House Montaperti Siena 8/10 Good "Lovely staff. Misleading advertisement regarding queen bed and single bed in the apartment. There are 2 single beds and a pull out couch." [](https://expedia.ca/Asciano-Hotels-Precise-House-Montaperti-Siena.h1110834.Hotel-Information) ## Find out more about Pienza **Everything you need to know about** **Pienza** **vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pienza vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on! There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pienza vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.  **Pienza vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Pienza. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in .  Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pienza vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pienza vacation rentals we have selected for you start as low as CA $108 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Pienza rentals** At Expedia, we put the best Pienza vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.  To find some top Pienza rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pienza vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pienza. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.  ## Explore a world of travel with Expedia - Trending destinations on Expedia.ca ### Trending destinations on Expedia.ca - [Canmore Vacation Rentals](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals) - [Maui Vacation Rentals](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Kelowna Vacation Rentals](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals) - [Whistler Vacation Rentals](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals) - [Florida Vacation Rentals](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Victoria Vacation Rentals](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals) - [Vancouver Vacation Rentals](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals) - [Palm Springs Vacation Rentals](https://www.expedia.ca/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals) - [Tofino Vacation Rentals](https://www.expedia.ca/Tofino-Vacation-Rentals.d6094955.Travel-Guide-VacationRentals) - [Calgary Vacation Rentals](https://www.expedia.ca/Calgary-Vacation-Rentals.d178245.Travel-Guide-VacationRentals) - [Costa Rica Vacation Rentals](https://www.expedia.ca/Destinations-In-Costa-Rica.d42.Vacation-Rental-Destinations) - [Vancouver Island Vacation Rentals](https://www.expedia.ca/Vancouver-Island-Vacation-Rentals.d6058387.Travel-Guide-VacationRentals) - [Puerto Vallarta Vacation Rentals](https://www.expedia.ca/Puerto-Vallarta-Vacation-Rentals.d180016.Travel-Guide-VacationRentals) - [Hawaii Vacation Rentals](https://www.expedia.ca/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations) - [Toronto Vacation Rentals](https://www.expedia.ca/Toronto-Vacation-Rentals.d178314.Travel-Guide-VacationRentals) - [Banff Vacation Rentals](https://www.expedia.ca/Banff-Vacation-Rentals.d10550.Travel-Guide-VacationRentals) - [Penticton Vacation Rentals](https://www.expedia.ca/Penticton-Vacation-Rentals.d4135.Travel-Guide-VacationRentals) - [Osoyoos Vacation Rentals](https://www.expedia.ca/Osoyoos-Vacation-Rentals.d181782.Travel-Guide-VacationRentals) - [Mont Tremblant Vacation Rentals](https://www.expedia.ca/Mont-Tremblant-Vacation-Rentals.d55374.Travel-Guide-VacationRentals) - [Big White Ski Resort Vacation Rentals](https://www.expedia.ca/Big-White-Ski-Resort-Vacation-Rentals.d6058319.Travel-Guide-VacationRentals) - [Ontario Vacation Rentals](https://www.expedia.ca/Destinations-In-Ontario.d11178.Vacation-Rental-Destinations) - [British Columbia Vacation Rentals](https://www.expedia.ca/Destinations-In-British-Columbia.d11117.Vacation-Rental-Destinations) - [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? > Yes, we give you a choice of vacation rentals in Pienza close to RI Crea RE, or you can go with a secluded option if you want a relaxing stay. Pienza is known for its churches and wineries. Make sure you have time to check out the temples while you're in the area. ### What are some of the best vacation home rentals in Pienza? > [The House of Alice, charm and relaxation](https://www.expedia.ca/Montalcino-Hotels-The-House-Of-Alice.h18976420.Hotel-Information): This vacation home rental near Pienza is located in a rural location and has a fireplace, a terrace, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a coffee maker. Kick off your shoes and enjoy yourself with a garden and a selection of books. ### How many vacation rentals are there in Pienza? > Expedia has 32 vacation rentals for your stay in Pienza. ### What’s there to see and do in Pienza? > Cultural attractions include Palazzo Borgia and Artemisia Gallery, whereas Historic Centre of Pienza and Val di Chiana are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Palazzo Piccolomini and Pienza Cathedral. ### What’s a vacation rental in Pienza like? > Vacation rentals are private properties you can book for a long or short time in Pienza. Vacation rentals feature amenities like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for a small group gathering. ### Expedia's Latest Trends Hotels - [Montepulciano Winery Hotels](https://expedia.ca/Montepulciano-Hotels-Winery-Hotel.0-0-d601351-tWineryHotel.Travel-Guide-Filter-Hotels) - [Florence Hotels with Free Breakfast](https://expedia.ca/Florence-Hotels-Hotels-With-Free-Breakfast.0-0-d1222-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - [Best Hotels in Sorrento](https://expedia.ca/Sorrento-Hotels.d9716.Travel-Guide-Hotels) - [Best Hotels in Taormina](https://expedia.ca/Taormina-Hotels.d4915.Travel-Guide-Hotels) - [Best Hotels in Siena](https://expedia.ca/Siena-Hotels.d9821.Travel-Guide-Hotels) - [Best Hotels in Lucca](https://expedia.ca/Lucca-Hotels.d8481.Travel-Guide-Hotels) - [Florence All Inclusive Resorts and Hotels](https://expedia.ca/Florence-Hotels-All-Inclusive-Hotel.0-0-d1222-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Best Hotels in Florence](https://expedia.ca/Florence-Hotels.d1222.Travel-Guide-Hotels) - [Best Hotels in Positano](https://expedia.ca/Positano-Hotels.d4330.Travel-Guide-Hotels) - [Best Hotels in San Gimignano](https://expedia.ca/San-Gimignano-Hotels.d11091.Travel-Guide-Hotels) - [Siena Winery Hotels](https://expedia.ca/Siena-Hotels-Winery-Hotel.0-0-d9821-tWineryHotel.Travel-Guide-Filter-Hotels) - [Florence Hotels with Free Airport Shuttle](https://expedia.ca/Florence-Hotels-Hotels-With-Free-Airport-Shuttle.0-0-d1222-tHotelswithFreeAirportShuttle.Travel-Guide-Filter-Hotels) - [Best Hotels in Portofino](https://expedia.ca/Portofino-Hotels.d4324.Travel-Guide-Hotels) - [Best Hotels in Pisa](https://expedia.ca/Pisa-Hotels.d2877.Travel-Guide-Hotels) 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 Cortona](https://expedia.ca/Car-Rentals-In-Cortona.d601360.Car-Rental-Guide) Activities - [Things to do in Pisa](https://expedia.ca/Things-To-Do-In-Pisa.d2877.Travel-Guide-Activities) - [Things to do in Viareggio](https://expedia.ca/Things-To-Do-In-Viareggio.d4894.Travel-Guide-Activities) - [Things to do in San Gimignano](https://expedia.ca/Things-To-Do-In-San-Gimignano.d11091.Travel-Guide-Activities) - [Things to do in Florence](https://expedia.ca/Things-To-Do-In-Florence.d1222.Travel-Guide-Activities) - [Things to do in Forte dei Marmi](https://expedia.ca/Things-To-Do-In-Forte-Dei-Marmi.d4943.Travel-Guide-Activities) Packages - [Florence Holidays](https://expedia.ca/Florence.d1222.Destination-Travel-Guides) General - [Visit Florence](https://expedia.ca/Florence.dx1222) - [Visit Temu](https://expedia.ca/Temu.dx6168461) - [Visit Forte dei Marmi](https://expedia.ca/Forte-Dei-Marmi.dx4943) - [Visit San Gimignano](https://expedia.ca/San-Gimignano.dx11091) - [Visit Barga](https://expedia.ca/Barga.dx6123404) - [Visit Montecatini Terme](https://expedia.ca/Montecatini-Terme.dx4956) - [Visit Follonica](https://expedia.ca/Follonica.dx6123914) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)