Title: The Best Pienza Hotels with Pools from $129 - Hotels with indoor pools in Pienza | Expedia.com [Pienza Travel Guide](https://expedia.com/Pienza.dx6023645)[Hotels in Pienza](https://expedia.com/Pienza-Hotels.d6023645.Travel-Guide-Hotels)[Vacation Rentals in Pienza](https://expedia.com/Pienza-Vacation-Rentals.d6023645.Travel-Guide-VacationRentals)[Flights to Pienza](https://expedia.com/Cheap-Flights-To-Pienza.d6023645.Travel-Guide-Flights)[Things to do in Pienza](https://expedia.com/Things-To-Do-In-Pienza.d6023645.Travel-Guide-Activities)[Car Rentals in Pienza](https://expedia.com/Car-Rentals-In-Pienza.d6023645.Car-Rental-Guide)[Pienza Vacation Packages](https://expedia.com/Pienza.d6023645.Destination-Travel-Guides) ![Pienza showing a small town or village, a monument and heritage architecture](https://images.trvl-media.com/place/6023645/9d678ea5-9752-4000-8f7c-af307fb65e61.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6023645/9d678ea5-9752-4000-8f7c-af307fb65e61.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Upfront pricing Our total price for your stay includes taxes and fees - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save 10% or more on over 100,000 hotels worldwide with Member Prices [Learn about One Key](https://www.expedia.com/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Pienza Hotels with a Pool Tonight [Mar 21 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=6023645&startDate=2026-03-21&endDate=2026-03-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 22 - Mar 23](https://www.expedia.com/Hotel-Search?regionId=6023645&startDate=2026-03-22&endDate=2026-03-23&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=6023645&startDate=2026-03-27&endDate=2026-03-29&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=6023645&startDate=2026-04-03&endDate=2026-04-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Pienza hotels with a pool ![Hiking](https://images.trvl-media.com/lodging/25000000/24050000/24047000/24046952/ec2d862b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/25000000/24050000/24047000/24046952/81ab4662.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Double or Twin Room (Maurino 2) | View from room](https://images.trvl-media.com/lodging/25000000/24050000/24047000/24046952/61c318dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Italian cuisine](https://images.trvl-media.com/lodging/25000000/24050000/24047000/24046952/29bd720d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borgo Sant'Ambrogio Resort [](https://www.expedia.com/Trequanda-Hotels-Borgo-SantAmbrogio-Resort.h24046952.Hotel-Information) Trequanda 9.8/10 Exceptional (100 reviews) - Splashy seasonal pool moments at this lakeside farm stay with Italian restaurant and garden oasis. $114 nightly $129 total Mar 23 - Mar 24 Total with taxes and fees [](https://www.expedia.com/Trequanda-Hotels-Borgo-SantAmbrogio-Resort.h24046952.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/14000000/13170000/13162600/13162502/59916895.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, minibar, in-room safe, desk](https://images.trvl-media.com/lodging/14000000/13170000/13162600/13162502/d091f287.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/14000000/13170000/13162600/13162502/d02ec159.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/14000000/13170000/13162600/13162502/84db21e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Podere Brizio [](https://www.expedia.com/Montalcino-Hotels-Podere-Brizio.h13162502.Hotel-Information) Montalcino 9.8/10 Exceptional (153 reviews) - Vineyard paradise offers blissful pool lounging amidst Tuscan farm stay serenity. $222 nightly $253 total Apr 8 - Apr 9 Total with taxes and fees [](https://www.expedia.com/Montalcino-Hotels-Podere-Brizio.h13162502.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/3000000/2760000/2750300/2750235/2f01bea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/3000000/2760000/2750300/2750235/1f4e227d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2760000/2750300/2750235/77df39f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/3000000/2760000/2750300/2750235/505c05f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tenuta Santo Pietro [](https://www.expedia.com/Pienza-Hotels-Tenuta-Santo-Pietro.h2750235.Hotel-Information) Pienza 9.6/10 Exceptional (119 reviews) - Seasonal outdoor pool nestled among the vineyards welcomes summer travelers with loungers, umbrellas, and poolside drinks service. $224 nightly $252 total Apr 2 - Apr 3 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-Tenuta-Santo-Pietro.h2750235.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/101000000/100990000/100989800/100989748/013f5dbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/101000000/100990000/100989800/100989748/576cc1e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/101000000/100990000/100989800/100989748/7b8c82c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Room | Premium bedding, down comforters, pillowtop beds, minibar](https://images.trvl-media.com/lodging/101000000/100990000/100989800/100989748/9ed992b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Svetoni Wine Resort [](https://www.expedia.com/Montepulciano-Hotels-Villa-Svetoni-Wine-Resort.h100989748.Hotel-Information) Montepulciano 9.6/10 Exceptional (73 reviews) - Poolside relaxation awaits with a seasonal outdoor oasis and dedicated children's pool. [](https://www.expedia.com/Montepulciano-Hotels-Villa-Svetoni-Wine-Resort.h100989748.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/35000000/34840000/34836300/34836233/99dc616f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/35000000/34840000/34836300/34836233/eb22fca2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34840000/34836300/34836233/3907ca23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34840000/34836300/34836233/3ffbc3d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Podere Spedalone [](https://www.expedia.com/Pienza-Hotels-Podere-Spedalone.h34836233.Hotel-Information) Pienza 9.4/10 Exceptional (43 reviews) - Relax in the Tuscan countryside at this farm stay with a seasonal outdoor pool. $193 nightly $217 total Apr 8 - Apr 9 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-Podere-Spedalone.h34836233.Hotel-Information) ![Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/13000000/12570000/12569200/12569107/972c2d9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom | Living area | Flat-screen TV](https://images.trvl-media.com/lodging/13000000/12570000/12569200/12569107/36131190.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms | Courtyard view](https://images.trvl-media.com/lodging/13000000/12570000/12569200/12569107/b9cf6769.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/13000000/12570000/12569200/12569107/17f0963e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### L'Olmo [](https://www.expedia.com/Pienza-Hotels-LOlmo.h12569107.Hotel-Information) Pienza 10/10 Exceptional (22 reviews) - Scenic Tuscan countryside poolside retreat offers loungers, umbrellas, and mountain biking access. $463 nightly $514 total Apr 9 - Apr 10 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-LOlmo.h12569107.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/9000000/8200000/8195100/8195080/093f1a7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/9000000/8200000/8195100/8195080/29e7195d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/9000000/8200000/8195100/8195080/2f7e4438.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/9000000/8200000/8195100/8195080/58ae2bce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relais La Saracina [](https://www.expedia.com/Pienza-Hotels-Relais-La-Saracina.h8195080.Hotel-Information) Pienza $336 nightly $375 total Mar 28 - Mar 29 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-Relais-La-Saracina.h8195080.Hotel-Information) ![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 | Premium bedding, minibar, in-room safe, desk](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/47a2d1db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Hotel San Gregorio [](https://www.expedia.com/Pienza-Hotels-Hotel-San-Gregorio.h2692135.Hotel-Information) Pienza 9.4/10 Exceptional (138 reviews) - Serene Tuscan retreat boasts a seasonal outdoor pool surrounded by lush gardens, with lounge areas for soaking up the Italian sun. $334 nightly $374 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-Hotel-San-Gregorio.h2692135.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/23000000/22950000/22946200/22946136/a05f18a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business center](https://images.trvl-media.com/lodging/23000000/22950000/22946200/22946136/2b73bf10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Tasting room](https://images.trvl-media.com/lodging/23000000/22950000/22946200/22946136/45f0e60b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/23000000/22950000/22946200/22946136/7d84ee76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Agriturismo Il Macchione [](https://www.expedia.com/Pienza-Hotels-Agriturismo-Il-Macchione.h22946136.Hotel-Information) Pienza 9.6/10 Exceptional (60 reviews) - Luxurious Tuscan retreat with outdoor pool, onsite winery, and cycling adventures amid rolling hills near Pienza Cathedral. $150 nightly $170 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-Agriturismo-Il-Macchione.h22946136.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/24000000/23550000/23541400/23541302/700440eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Turkish bath, body treatments, aromatherapy, body wraps, body scrubs](https://images.trvl-media.com/lodging/24000000/23550000/23541400/23541302/be9fe06e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/24000000/23550000/23541400/23541302/f69d0e12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/24000000/23550000/23541400/23541302/f1566451.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Rutiliano Centro Benessere [](https://www.expedia.com/Pienza-Hotels-Hotel-Rutiliano-Centro-Benessere.h23541302.Hotel-Information) Pienza 8.6/10 Excellent (7 reviews) - Seasonal mountain poolside paradise awaits at Hotel Rutiliano's relaxation sanctuary. [](https://www.expedia.com/Pienza-Hotels-Hotel-Rutiliano-Centro-Benessere.h23541302.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.com/Hotel-Search?startDate=2026-04-04&endDate=2026-04-05®ionId=6023645&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Pienza Breakfast included 4 stars 5 stars Spa Hot tub ## Hotels with pools and free breakfast in Pienza ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2760000/2750300/2750235/77df39f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Billiards](https://images.trvl-media.com/lodging/3000000/2760000/2750300/2750235/9500aee5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/3000000/2760000/2750300/2750235/1f4e227d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/3000000/2760000/2750300/2750235/505c05f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tenuta Santo Pietro [](https://www.expedia.com/Pienza-Hotels-Tenuta-Santo-Pietro.h2750235.Hotel-Information) Pienza 9.6/10 Exceptional (119) $224 nightly $252 total Apr 2 - Apr 3 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-Tenuta-Santo-Pietro.h2750235.Hotel-Information) ![Building design](https://images.trvl-media.com/lodging/19000000/18660000/18654200/18654189/94bff947.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, minibar](https://images.trvl-media.com/lodging/19000000/18660000/18654200/18654189/99165480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18660000/18654200/18654189/4205bc76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18660000/18654200/18654189/0d103255.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A440 in Tuscany [](https://www.expedia.com/Pienza-Hotels-A440-In-Tuscany.h18654189.Hotel-Information) Pienza 9.6/10 Exceptional (51) $217 nightly $244 total Apr 7 - Apr 8 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-A440-In-Tuscany.h18654189.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34840000/34836300/34836233/3ffbc3d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/35000000/34840000/34836300/34836233/eb22fca2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34840000/34836300/34836233/3907ca23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/35000000/34840000/34836300/34836233/5a470699.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Podere Spedalone [](https://www.expedia.com/Pienza-Hotels-Podere-Spedalone.h34836233.Hotel-Information) Pienza 9.4/10 Exceptional (43) $193 nightly $217 total Apr 8 - Apr 9 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-Podere-Spedalone.h34836233.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/23000000/22950000/22946200/22946136/a05f18a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business center](https://images.trvl-media.com/lodging/23000000/22950000/22946200/22946136/2b73bf10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Tasting room](https://images.trvl-media.com/lodging/23000000/22950000/22946200/22946136/45f0e60b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/23000000/22950000/22946200/22946136/7d84ee76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Agriturismo Il Macchione [](https://www.expedia.com/Pienza-Hotels-Agriturismo-Il-Macchione.h22946136.Hotel-Information) Pienza 9.6/10 Exceptional (60) $150 nightly $170 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-Agriturismo-Il-Macchione.h22946136.Hotel-Information) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/9000000/8200000/8195100/8195080/2f7e4438.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/9000000/8200000/8195100/8195080/29e7195d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/9000000/8200000/8195100/8195080/58ae2bce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/9000000/8200000/8195100/8195080/94cc9724.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relais La Saracina [](https://www.expedia.com/Pienza-Hotels-Relais-La-Saracina.h8195080.Hotel-Information) Pienza $336 nightly $375 total Mar 28 - Mar 29 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-Relais-La-Saracina.h8195080.Hotel-Information) ![Turkish bath, body treatments, aromatherapy, body wraps, body scrubs](https://images.trvl-media.com/lodging/24000000/23550000/23541400/23541302/f1d9e007.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/24000000/23550000/23541400/23541302/700440eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Turkish bath, body treatments, aromatherapy, body wraps, body scrubs](https://images.trvl-media.com/lodging/24000000/23550000/23541400/23541302/be9fe06e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/24000000/23550000/23541400/23541302/fc49cce8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Rutiliano Centro Benessere [](https://www.expedia.com/Pienza-Hotels-Hotel-Rutiliano-Centro-Benessere.h23541302.Hotel-Information) Pienza 8.6/10 Excellent (7) [](https://www.expedia.com/Pienza-Hotels-Hotel-Rutiliano-Centro-Benessere.h23541302.Hotel-Information) ![Suite, 2 Bedrooms | Courtyard view](https://images.trvl-media.com/lodging/13000000/12570000/12569200/12569107/b9cf6769.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom | Living area | Flat-screen TV](https://images.trvl-media.com/lodging/13000000/12570000/12569200/12569107/36131190.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/13000000/12570000/12569200/12569107/972c2d9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/13000000/12570000/12569200/12569107/17f0963e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### L'Olmo [](https://www.expedia.com/Pienza-Hotels-LOlmo.h12569107.Hotel-Information) Pienza 10/10 Exceptional (22) $463 nightly $514 total Apr 9 - Apr 10 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-LOlmo.h12569107.Hotel-Information) ![Food and drink](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/0e5f89fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double or Twin Room, 1 Bedroom | Premium bedding, minibar, in-room safe, desk](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/47a2d1db.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) ![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 [](https://www.expedia.com/Pienza-Hotels-Hotel-San-Gregorio.h2692135.Hotel-Information) Pienza 9.4/10 Exceptional (138) $334 nightly $374 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-Hotel-San-Gregorio.h2692135.Hotel-Information) ![Seasonal outdoor pool, open 9:00 AM to 7:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/900000/893100/893017/45dfbbfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/1000000/900000/893100/893017/e5a8fbb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/900000/893100/893017/6ed54e03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/900000/893100/893017/ef61d192.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Relais II Chiostro di Pienza [](https://www.expedia.com/Pienza-Hotels-Hotel-Relais-II-Chiostro-Di-Pienza.h893017.Hotel-Information) Pienza 8.8/10 Excellent (635) $77 nightly $91 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-Hotel-Relais-II-Chiostro-Di-Pienza.h893017.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.com/Hotel-Search?startDate=2026-04-04&endDate=2026-04-05®ionId=6023645&adults=2&amenities=POOL&sort=RECOMMENDED&mealPlan=FREE_BREAKFAST&openPlayBack=true) ## Top Pienza Hotel Reviews ![Hotel Corsignano](https://images.trvl-media.com/lodging/3000000/2530000/2525700/2525690/ba2de8ee_y.jpg) ### Hotel Corsignano 10/10 Excellent "La pulizia della camera, così come la gentilezza e la professionalità del personale, sono senza dubbio le migliori tra tutte le strutture in cui ho soggiornato durante il mio viaggio. " [](https://expedia.com/Pienza-Hotels-Hotel-Corsignano.h2525690.Hotel-Information) ![Hotel San Gregorio](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/0e5f89fd_y.jpg) ### Hotel San Gregorio 10/10 Excellent "This hotel was the highlight of our Tuscany trip. It is very well decorated, stunning italian furniture and arts on the wall. There is a restaurant for dining. About 2 minutes walking from Pienza old town entrance. Staff was super nice, even their mascot, an yellow cat, came to greet us. It is a must come back for us." [](https://expedia.com/Pienza-Hotels-Hotel-San-Gregorio.h2692135.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 "Absolutely fantastic stay. Photos don’t do it justice. Amazing food, and had a very fun time at the cocktail bar with Ricardo!" [](https://expedia.com/Siena-Hotels-Hotel-Certosa-Di-Maggiano.h528470.Hotel-Information) ![Fonteverde Lifestyle & Thermal Retreat](https://images.trvl-media.com/lodging/1000000/910000/909000/908918/11ad8811_y.jpg) ### Fonteverde Lifestyle & Thermal Retreat 10/10 Excellent "Great place! Excellent service by everyone we encountered. " [](https://expedia.com/San-Casciano-Dei-Bagni-Hotels-Fonteverde.h908918.Hotel-Information) ![Hotel Relais II Chiostro di Pienza](https://images.trvl-media.com/lodging/1000000/900000/893100/893017/45dfbbfc_y.jpg) ### Hotel Relais II Chiostro di Pienza 10/10 Excellent "A little tired, extremely clean, with an amazing staff" [](https://expedia.com/Pienza-Hotels-Hotel-Relais-II-Chiostro-Di-Pienza.h893017.Hotel-Information) ![Villa di Piazzano - Small Luxury Hotel of the World](https://images.trvl-media.com/lodging/1000000/980000/972000/971985/c358cc6c_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.com/Cortona-Hotels-Villa-Di-Piazzano-Small-Luxury-Hotel-Of-The-World.h971985.Hotel-Information) ![Tenuta Santo Pietro](https://images.trvl-media.com/lodging/3000000/2760000/2750300/2750235/77df39f9_y.jpg) ### Tenuta Santo Pietro 6/10 Okay "We had to buy a bottle of wine before they would give us 2 wine glasses so we could sit outside to enjoy the view! Expecting a little more for the rate. " [](https://expedia.com/Pienza-Hotels-Tenuta-Santo-Pietro.h2750235.Hotel-Information) ## Frequently asked questions ### How much does a hotel with outdoor pool in Pienza cost? ### Are there hotels in Pienza that have private outdoor pools? > Beyond the pool, this charming accommodation features a well-equipped kitchen, making it convenient for families to prepare meals together. Outdoor enthusiasts will appreciate nearby mountain biking opportunities and the secure yard, great for children to play in. The deck and patio areas provide ample space for relaxation, ensuring that your stay is both comfortable and enjoyable. ### What are some of the best Pienza hotels with outdoor pools and scenic views? > Imagine lounging by the pool while soaking in the scenic beauty that surrounds you, or perhaps enjoying a meal on the deck or patio, where the views are as delightful as the food. The house features a fully equipped kitchen, great for families who appreciate the convenience of preparing their meals. Additionally, for those who love adventure, nearby mountain biking trails offer an exciting way to explore the area's natural beauty. ### Is it cheaper to book flights and a Pienza hotel with a pool as a package? ### How can I save on a Pienza hotel with a pool with Expedia? ### Can I cancel my hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - More ways to book - [Hotels near Piazza Pio II ](https://www.expedia.com/Piazza-Pio-II-Hotels.0-l553248621533000907-0.Travel-Guide-Filter-Hotels) - [Hotels near Pienza Cathedral ](https://www.expedia.com/Pienza-Cathedral-Hotels.0-l6105122-0.Travel-Guide-Filter-Hotels) - [Hotels near Palazzo Vescovile ](https://www.expedia.com/Palazzo-Vescovile-Hotels.0-l553248621533000905-0.Travel-Guide-Filter-Hotels) - [Hotels near RI Crea RE ](https://www.expedia.com/RI-Crea-RE-Hotels.0-l553248621562145314-0.Travel-Guide-Filter-Hotels) - [Winery Hotels in Monticchiello ](https://www.expedia.com/Monticchiello-Hotels-Winery-Hotel.0-0-d6285816-tWineryHotel.Travel-Guide-Filter-Hotels) - 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