Title: The Best Pienza Hotels with Pools from $113 - 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) ![](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 [Apr 6 - Apr 7](https://www.expedia.com/Hotel-Search?regionId=6023645&startDate=2026-04-06&endDate=2026-04-07&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Apr 7 - Apr 8](https://www.expedia.com/Hotel-Search?regionId=6023645&startDate=2026-04-07&endDate=2026-04-08&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=6023645&startDate=2026-04-10&endDate=2026-04-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=6023645&startDate=2026-04-17&endDate=2026-04-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Pienza hotels with a pool ![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) ![Property grounds](https://images.trvl-media.com/lodging/3000000/2760000/2750300/2750235/505c05f5.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) ### 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. $247 nightly $276 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-Tenuta-Santo-Pietro.h2750235.Hotel-Information) ![BBQ/picnic area](https://images.trvl-media.com/lodging/24000000/23030000/23028100/23028080/174ef37c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/24000000/23030000/23028100/23028080/421a86ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom | 1 bedroom, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/24000000/23030000/23028100/23028080/8d561de4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast (EUR 10 per person)](https://images.trvl-media.com/lodging/24000000/23030000/23028100/23028080/b524f031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Agriturismo Poggio Tobruk [](https://www.expedia.com/Pienza-Hotels-Agriturismo-Poggio-Tobruk.h23028080.Hotel-Information) Pienza 9.8/10 Exceptional (28 reviews) - Soak in natural hot springs at a charming farm stay with indoor pool access and poolside bliss. $163 nightly $184 total Apr 29 - Apr 30 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-Agriturismo-Poggio-Tobruk.h23028080.Hotel-Information) ![Outdoor pool, open 8:00 AM to 7:30 PM, sun loungers](https://images.trvl-media.com/lodging/10000000/9440000/9434400/9434339/528d18e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite | Bathroom | Shower, hair dryer, bidet, towels](https://images.trvl-media.com/lodging/10000000/9440000/9434400/9434339/21aaead4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite | Premium bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/10000000/9440000/9434400/9434339/6b8f868e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite | Premium bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/10000000/9440000/9434400/9434339/991fb6d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Agriturismo Bonello [](https://www.expedia.com/Pienza-Hotels-Agriturismo-Bonello.h9434339.Hotel-Information) Pienza 9.4/10 Exceptional (25 reviews) - Rural pool sanctuary invites travelers to soak up sunshine and unwind after hiking adventures. [](https://www.expedia.com/Pienza-Hotels-Agriturismo-Bonello.h9434339.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) ![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34840000/34836300/34836233/3ffbc3d6.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) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/35000000/34840000/34836300/34836233/c8bf5c62.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. $190 nightly $213 total Apr 17 - Apr 18 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) ![Tasting room](https://images.trvl-media.com/lodging/23000000/22950000/22946200/22946136/45f0e60b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor banquet area](https://images.trvl-media.com/lodging/23000000/22950000/22946200/22946136/be94ce8c.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) ### Agriturismo Il Macchione [](https://www.expedia.com/Pienza-Hotels-Agriturismo-Il-Macchione.h22946136.Hotel-Information) Pienza 9.6/10 Exceptional (61 reviews) - Luxurious Tuscan retreat with outdoor pool, onsite winery, and cycling adventures amid rolling hills near Pienza Cathedral. $155 nightly $175 total Apr 15 - Apr 16 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-Agriturismo-Il-Macchione.h22946136.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) ![Lobby sitting area](https://images.trvl-media.com/lodging/13000000/12570000/12569200/12569107/w988h640x75y0-aad06d6e.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) ![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. $461 nightly $511 total Apr 15 - Apr 16 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/19000000/18660000/18654200/18654189/a681a42b.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/19000000/18660000/18654200/18654189/0d103255.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) ### A440 in Tuscany [](https://www.expedia.com/Pienza-Hotels-A440-In-Tuscany.h18654189.Hotel-Information) Pienza 9.6/10 Exceptional (51 reviews) - Poolside bliss meets Tuscan charm at this rural farmstay with a 24-hour outdoor pool. $216 nightly $243 total Apr 20 - Apr 21 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-A440-In-Tuscany.h18654189.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) ![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/fc49cce8.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. $203 nightly $228 total May 7 - May 8 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-Hotel-Rutiliano-Centro-Benessere.h23541302.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/893100/893017/2cdcc0a2.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) ### 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 (637 reviews) - Tuscan poolside retreat at Hotel Relais II Chiostro di Pienza offers a refreshing escape in a historic setting. $76 nightly $91 total Apr 9 - Apr 10 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-Hotel-Relais-II-Chiostro-Di-Pienza.h893017.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) ![Breakfast buffet](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/cd7670ac.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 (140 reviews) - Serene Tuscan retreat boasts a seasonal outdoor pool surrounded by lush gardens, with lounge areas for soaking up the Italian sun. $170 nightly $194 total Apr 7 - Apr 8 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-Hotel-San-Gregorio.h2692135.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=2026-04-20&endDate=2026-04-21®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) ![Property grounds](https://images.trvl-media.com/lodging/3000000/2760000/2750300/2750235/505c05f5.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) ### Tenuta Santo Pietro [](https://www.expedia.com/Pienza-Hotels-Tenuta-Santo-Pietro.h2750235.Hotel-Information) Pienza 9.6/10 Exceptional (119) $247 nightly $276 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-Tenuta-Santo-Pietro.h2750235.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/35000000/34840000/34836300/34836233/5a470699.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) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/35000000/34840000/34836300/34836233/c8bf5c62.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) $190 nightly $213 total Apr 17 - Apr 18 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-Podere-Spedalone.h34836233.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) ![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/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) $203 nightly $228 total May 7 - May 8 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-Hotel-Rutiliano-Centro-Benessere.h23541302.Hotel-Information) ![Deluxe Suite | Premium bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/10000000/9440000/9434400/9434339/991fb6d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 8:00 AM to 7:30 PM, sun loungers](https://images.trvl-media.com/lodging/10000000/9440000/9434400/9434339/528d18e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite | Premium bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/10000000/9440000/9434400/9434339/6b8f868e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite | Bathroom | Shower, hair dryer, bidet, towels](https://images.trvl-media.com/lodging/10000000/9440000/9434400/9434339/21aaead4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Agriturismo Bonello [](https://www.expedia.com/Pienza-Hotels-Agriturismo-Bonello.h9434339.Hotel-Information) Pienza 9.4/10 Exceptional (25) [](https://www.expedia.com/Pienza-Hotels-Agriturismo-Bonello.h9434339.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/19000000/18660000/18654200/18654189/0d103255.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) ### A440 in Tuscany [](https://www.expedia.com/Pienza-Hotels-A440-In-Tuscany.h18654189.Hotel-Information) Pienza 9.6/10 Exceptional (51) $216 nightly $243 total Apr 20 - Apr 21 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-A440-In-Tuscany.h18654189.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) ![Tasting room](https://images.trvl-media.com/lodging/23000000/22950000/22946200/22946136/45f0e60b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor banquet area](https://images.trvl-media.com/lodging/23000000/22950000/22946200/22946136/be94ce8c.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) ### Agriturismo Il Macchione [](https://www.expedia.com/Pienza-Hotels-Agriturismo-Il-Macchione.h22946136.Hotel-Information) Pienza 9.6/10 Exceptional (61) $155 nightly $175 total Apr 15 - Apr 16 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-Agriturismo-Il-Macchione.h22946136.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) ![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) ![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 (140) $170 nightly $194 total Apr 7 - Apr 8 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-Hotel-San-Gregorio.h2692135.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) ![Lobby sitting area](https://images.trvl-media.com/lodging/13000000/12570000/12569200/12569107/w988h640x75y0-aad06d6e.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) ![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) $461 nightly $511 total Apr 15 - Apr 16 Total with taxes and fees [](https://www.expedia.com/Pienza-Hotels-LOlmo.h12569107.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/893100/893017/2cdcc0a2.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) ### 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 (637) $76 nightly $91 total Apr 9 - Apr 10 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=2026-04-20&endDate=2026-04-21®ionId=6023645&adults=2&amenities=POOL&sort=RECOMMENDED&mealPlan=FREE_BREAKFAST&openPlayBack=true) ## Top Pienza Hotel Reviews ![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 6/10 Okay "The room was full of ants and other small insects. I was staying in the middle of Tuscany wine country, I would expect my room to have a corkscrew and at least glass glasses. The room only had flimsy plastic cups. " [](https://expedia.com/Pienza-Hotels-Hotel-Relais-II-Chiostro-Di-Pienza.h893017.Hotel-Information) ![Hotel San Gregorio](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/0e5f89fd_y.jpg) ### Hotel San Gregorio 10/10 Excellent "Room was large and very clean. Bed was king sized and comfortable. Check-in was easy with underground parking for a nominal fee. Hotel is right outside downtown area, making it super walkable. Breakfast was great with many options. " [](https://expedia.com/Pienza-Hotels-Hotel-San-Gregorio.h2692135.Hotel-Information) ![Hotel Corsignano](https://images.trvl-media.com/lodging/3000000/2530000/2525700/2525690/ba2de8ee_y.jpg) ### Hotel Corsignano 10/10 Excellent "The heat in the room and bath were not working. Fortunately there were extra blankets ! " [](https://expedia.com/Pienza-Hotels-Hotel-Corsignano.h2525690.Hotel-Information) ![Relais Villa Grazianella - UNA Esperienze](https://images.trvl-media.com/lodging/5000000/4320000/4310500/4310479/cd1e0f87_y.jpg) ### Relais Villa Grazianella - UNA Esperienze 10/10 Excellent "Absolutely breathtaking property. The staff was extremely welcoming and helpful. Truly such a beautiful experience. Highly recommend to anyone " [](https://expedia.com/Montepulciano-Hotels-Relais-Villa-Grazianella-UNA-Esperienze.h4310479.Hotel-Information) ![Fonteverde Lifestyle & Thermal Retreat](https://images.trvl-media.com/lodging/1000000/910000/909000/908918/f6fb188e_y.jpg) ### Fonteverde Lifestyle & Thermal Retreat 10/10 Excellent "Great place! Excellent service by everyone we encountered. " [](https://expedia.com/San-Casciano-Dei-Bagni-Hotels-Fonteverde.h908918.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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