Title: Book the Best Hotels with POOL in Siena in 2026 | Expedia.ca [Siena Travel Guide](https://expedia.ca/Siena.dx9821)[Hotels in Siena](https://expedia.ca/Siena-Hotels.d9821.Travel-Guide-Hotels)[Vacation Rentals in Siena](https://expedia.ca/Siena-Vacation-Rentals.d9821.Travel-Guide-VacationRentals)[Flights to Siena](https://expedia.ca/Cheap-Flights-To-Siena.d9821.Travel-Guide-Flights)[Things to do in Siena](https://expedia.ca/Things-To-Do-In-Siena.d9821.Travel-Guide-Activities)[Siena Car Rentals](https://expedia.ca/Car-Rentals-In-Siena.d9821.Car-Rental-Guide)[Siena Vacation Packages](https://expedia.ca/Siena.d9821.Destination-Travel-Guides) ![](https://images.trvl-media.com/place/9821/7379d030-252a-4e26-a469-e10785470ebc.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Siena from CA $135 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](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) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Siena Hotels with a Pool Tonight [Dec 11 - Dec 12](https://www.expedia.ca/Hotel-Search?regionId=9821&startDate=2025-12-11&endDate=2025-12-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=9821&startDate=2025-12-12&endDate=2025-12-13&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=9821&startDate=2025-12-12&endDate=2025-12-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=9821&startDate=2025-12-19&endDate=2025-12-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Siena hotels with a pool ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/860000/852400/852305/5025427f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 Queen Bed](https://images.trvl-media.com/lodging/1000000/860000/852400/852305/ae8b2f88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/860000/852400/852305/d9e7f9b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/1000000/860000/852400/852305/e65a78e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Points by Sheraton Siena [](https://www.expedia.ca/Siena-Hotels-Four-Points-By-Sheraton-Siena.h852305.Hotel-Information) Scacciapensieri 8.8/10 Excellent (577) "Comfortable rooms, excellent breakfast, lovely pool, and service!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $170 CA $192 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Siena-Hotels-Four-Points-By-Sheraton-Siena.h852305.Hotel-Information) ![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/910000/905800/905710/58e23d32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/910000/905800/905710/5245d9c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/910000/905800/905710/76bac1ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room | Living area](https://images.trvl-media.com/lodging/1000000/910000/905800/905710/a3b179d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borgo Grondaie [](https://www.expedia.ca/Siena-Hotels-Borgo-Grondaie.h905710.Hotel-Information) Siena 9.6/10 Exceptional (440) "A hidden gem overlooking the city set in stunning grounds" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Philip [](https://www.expedia.ca/Siena-Hotels-Borgo-Grondaie.h905710.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/80000/73300/73208/b5937afa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/80000/73300/73208/f690476a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/80000/73300/73208/7664d144.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden views ](https://images.trvl-media.com/lodging/1000000/80000/73300/73208/ba54065b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Ermellina Siena, a Tribute Portfolio Hotel [](https://www.expedia.ca/Siena-Hotels-Hotel-Garden.h73208.Hotel-Information) Camollia 8.4/10 Very good (5) "Unique and cozy prot" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristine CA $189 CA $213 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Siena-Hotels-Hotel-Garden.h73208.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/590000/581400/581362/29635c92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free toiletries, hair dryer, bidet, towels](https://images.trvl-media.com/lodging/1000000/590000/581400/581362/c141139a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Minibar, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/590000/581400/581362/4046f639.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/590000/581400/581362/72604773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sangallo Park Hotel [](https://www.expedia.ca/Siena-Hotels-Sangallo-Park-Hotel.h581362.Hotel-Information) Vico Alto 9.0/10 Wonderful (594) "Spacious accommodation and everything works! Great parking, pool and gardens with views across the valley to nearby Siena. Very nice breakfast and lovely staff. Excellent value too!" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) David CA $119 CA $135 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Siena-Hotels-Sangallo-Park-Hotel.h581362.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/20000000/19940000/19936000/19935909/938c34ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 2 Bedrooms, 2 Bathrooms, Pool View | Living area](https://images.trvl-media.com/lodging/20000000/19940000/19936000/19935909/1bef22aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room dining](https://images.trvl-media.com/lodging/20000000/19940000/19936000/19935909/65140a43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/20000000/19940000/19936000/19935909/93154eb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fattoria Lornano Winery [](https://www.expedia.ca/Monteriggioni-Hotels-Fattoria-Lornano-Agriturismo.h19935909.Hotel-Information) Monteriggioni 8.0/10 Very good (5) "The staff were so friendly and polite to us during our stay. Such a gem of a place to stay and we are very happy we chose to stay there " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Tamara [](https://www.expedia.ca/Monteriggioni-Hotels-Fattoria-Lornano-Agriturismo.h19935909.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/15000000/14620000/14615700/14615633/6656c194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/15000000/14620000/14615700/14615633/32dac20a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom, Ground Floor (Il Campo) | Private kitchen](https://images.trvl-media.com/lodging/15000000/14620000/14615700/14615633/aabc52d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/15000000/14620000/14615700/14615633/82b36c69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Agriturismo Novelleto [](https://www.expedia.ca/Monteriggioni-Hotels-Agriturismo-Novelleto.h14615633.Hotel-Information) Monteriggioni 9.8/10 Exceptional (7) "Beautiful place to stay, and the hosts are very friendly and welcoming. We hope to stay again sometime. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Don [](https://www.expedia.ca/Monteriggioni-Hotels-Agriturismo-Novelleto.h14615633.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/25000000/24950000/24941200/24941118/a47cb16a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/25000000/24950000/24941200/24941118/1889e107.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/25000000/24950000/24941200/24941118/9f25366e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/25000000/24950000/24941200/24941118/64c8d4c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Il Pozzo di Sant'Andrea [](https://www.expedia.ca/Siena-Hotels-Il-Pozzo-Di-SantAndrea.h24941118.Hotel-Information) Siena 9.8/10 Exceptional (16) "Great host, lovely place near Siena" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Prem [](https://www.expedia.ca/Siena-Hotels-Il-Pozzo-Di-SantAndrea.h24941118.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/25000000/24310000/24302900/24302869/df636684.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/25000000/24310000/24302900/24302869/dbadb8e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, cribs/infant beds](https://images.trvl-media.com/lodging/25000000/24310000/24302900/24302869/7a9a9317.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/25000000/24310000/24302900/24302869/a5613856.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Rocca della Magione [](https://www.expedia.ca/Monteriggioni-Hotels-La-Rocca-Della-Magione.h24302869.Hotel-Information) Monteriggioni 9.4/10 Exceptional (6) "Lovely property in a 13th century convent. Situated on a hill overlooking a valley. Family owned, very sweet staff. Visitors (esp Americans) should know the owners speak little to no English, so come with your google translate or try and learn a little Italian prior. One major thing I learned in Italy is the importance of communicating your arrival plan with your host prior to arrival as many establishments are family owned and operated. Owner was very accommodating even though we were... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer [](https://www.expedia.ca/Monteriggioni-Hotels-La-Rocca-Della-Magione.h24302869.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/97000000/96440000/96435700/96435674/b352d4ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Penthouse | Living area](https://images.trvl-media.com/lodging/97000000/96440000/96435700/96435674/2d038652.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast (EUR 15 per person)](https://images.trvl-media.com/lodging/97000000/96440000/96435700/96435674/a43c1792.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Condo | Living area](https://images.trvl-media.com/lodging/97000000/96440000/96435700/96435674/198c4631.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Siena Hills Apartments [](https://www.expedia.ca/Siena-Hotels-Siena-Hills-Apartments.h96435674.Hotel-Information) Scacciapensieri 8.6/10 Excellent (44) "Amazing stay, very nice place with a great pool " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Anthony [](https://www.expedia.ca/Siena-Hotels-Siena-Hills-Apartments.h96435674.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/900000/892600/892517/6c9c19d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Triple Room, 1 Bedroom, Accessible](https://images.trvl-media.com/lodging/1000000/900000/892600/892517/fa624351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner served; Italian cuisine, pool views ](https://images.trvl-media.com/lodging/1000000/900000/892600/892517/87471dd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/1000000/900000/892600/892517/ac60812d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Il Piccolo Castello [](https://www.expedia.ca/Monteriggioni-Hotels-Hotel-Il-Piccolo-Castello.h892517.Hotel-Information) Monteriggioni 8.6/10 Excellent (337) "We enjoyed our stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joshua [](https://www.expedia.ca/Monteriggioni-Hotels-Hotel-Il-Piccolo-Castello.h892517.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=2025-12-25&endDate=2025-12-26®ionId=9821&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Siena Hotel Reviews ![Hotel Athena](https://images.trvl-media.com/lodging/1000000/870000/866600/866580/ab5ee3fb_y.jpg) ### Hotel Athena 10/10 Excellent "Excellent hotel, very helpful staff, highly recommended " [](https://expedia.ca/Siena-Hotels-Hotel-Athena.h866580.Hotel-Information) ![Hotel Italia](https://images.trvl-media.com/lodging/1000000/1000000/997000/996973/7edddb53_y.jpg) ### Hotel Italia 10/10 Excellent "This was a short stay for us in Siena. A great hotel. Friendly staff and the best bargain best breakfast we have had in Italy. Highly recommended" [](https://expedia.ca/Siena-Hotels-Hotel-Italia.h996973.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 "La habitación muy amplia, teníamos armario vestidor, sala, habitación amplia y un gran baño. Excelente la atención del personal. El lugar mágico maravilloso de epoca" [](https://expedia.ca/Siena-Hotels-Hotel-Certosa-Di-Maggiano.h528470.Hotel-Information) ![Villa Scacciapensieri Boutique Hotel](https://images.trvl-media.com/lodging/3000000/2700000/2693500/2693499/b46a6593_y.jpg) ### Villa Scacciapensieri Boutique Hotel 10/10 Excellent "The villa was wonderful and absolutely beautiful. My friends and I absolutely loved our stay here. " [](https://expedia.ca/Siena-Hotels-Villa-Scacciapensieri-Boutique-Hotel.h2693499.Hotel-Information) ![Borgo Grondaie](https://images.trvl-media.com/lodging/1000000/910000/905800/905710/58e23d32_y.jpg) ### Borgo Grondaie 10/10 Excellent "The sta" [](https://expedia.ca/Siena-Hotels-Borgo-Grondaie.h905710.Hotel-Information) ![Villa Ermellina Siena, a Tribute Portfolio Hotel](https://images.trvl-media.com/lodging/1000000/80000/73300/73208/b5937afa_y.jpg) ### Villa Ermellina Siena, a Tribute Portfolio Hotel 10/10 Excellent "Very nice hotel and beautiful hotel. My only complaint is that the king bed I stayed in was very lumpy - I do mean very.. otherwise great place. Good size gym. Clean. Very friendly service." [](https://expedia.ca/Siena-Hotels-Hotel-Garden.h73208.Hotel-Information) ## Frequently asked questions ### What's it like visiting Siena? ### What are some accommodations with pools in Siena? ### How many pool hotels are there in Siena? ### What is there to see and do in Siena? ### When is the best time to book a hotel with a pool in Siena? ### What's the best way to travel around Siena? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [4 Star Hotels in San Rocco a Pilli ](https://www.expedia.ca/4Star-San-Rocco-A-Pilli-Hotels.s40-0-d6285685.Travel-Guide-Filter-Hotels) - [Agostoli Hotels ](https://www.expedia.ca/Agostoli-Hotels.d553248635975863234.Travel-Guide-Hotels) - [Lgbt Friendly Hotels in Bagnaia ](https://www.expedia.ca/Bagnaia-Hotels-LGBT-Friendly-Hotel.0-0-d6046167-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Bossi Hotels ](https://www.expedia.ca/Bossi-Hotels.d553248622858799636.Travel-Guide-Hotels) - 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[Things to do in Quercegrossa ](https://www.expedia.ca/Things-To-Do-In-Quercegrossa.d6047905.Travel-Guide-Activities) - [Things to do in Sovicille ](https://www.expedia.ca/Things-To-Do-In-Sovicille.d602594.Travel-Guide-Activities) - [Book Hotels with a Pool in Siena on Expedia.it ](https://www.expedia.it/Siena-Hotel-Hotel-Con-Piscina.0-0-d9821-tHotelconpiscina.Guida-Viaggi-Filtro-Hotel)