Title: Book the Best Hotels with POOL in São Jorge Island in 2026 | Expedia.ca [São Jorge Island Travel Guide](https://expedia.ca/Sao-Jorge-Island.dx3182)[Hotels in São Jorge Island](https://expedia.ca/Sao-Jorge-Island-Hotels.d3182.Travel-Guide-Hotels)[Vacation Rentals in São Jorge Island](https://expedia.ca/Sao-Jorge-Island-Vacation-Rentals.d3182.Travel-Guide-VacationRentals)[Flights to São Jorge Island](https://expedia.ca/Cheap-Flights-To-Sao-Jorge-Island.d3182.Travel-Guide-Flights)[Things to do in São Jorge Island](https://expedia.ca/Things-To-Do-In-Sao-Jorge-Island.d3182.Travel-Guide-Activities)[São Jorge Island Car Rentals](https://expedia.ca/Car-Rentals-In-Sao-Jorge-Island.d3182.Car-Rental-Guide)[São Jorge Island Vacation Packages](https://expedia.ca/Sao-Jorge-Island.d3182.Destination-Travel-Guides) ![Caught this when everybody was still asleep.](https://images.trvl-media.com/place/182256/87298e7a-54f0-4273-a571-a4c890052590.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Olli Peauty ![](https://images.trvl-media.com/place/182256/87298e7a-54f0-4273-a571-a4c890052590.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 São Jorge Island Hotels with a Pool Tonight [Mar 23 - Mar 24](https://www.expedia.ca/Hotel-Search?regionId=3182&startDate=2026-03-23&endDate=2026-03-24&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 24 - Mar 25](https://www.expedia.ca/Hotel-Search?regionId=3182&startDate=2026-03-24&endDate=2026-03-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=3182&startDate=2026-03-27&endDate=2026-03-29&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=3182&startDate=2026-04-03&endDate=2026-04-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for São Jorge Island hotels with a pool ![2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/89000000/88450000/88444000/88443976/99a62983.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/89000000/88450000/88444000/88443976/f8d9e980.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Steam room ](https://images.trvl-media.com/lodging/89000000/88450000/88444000/88443976/40e06414.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/89000000/88450000/88444000/88443976/9c111add.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kuanza Nature Experience [](https://www.expedia.ca/Calheta-Hotels-Kuanza-Nature-Experience.h88443976.Hotel-Information) Calheta 10/10 Exceptional (8 reviews) "Quite secluded yet very safe. Overall an authentic experience. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Nicolas CA $137 CA $149 total includes taxes & fees Mar 24 - Mar 25 [](https://www.expedia.ca/Calheta-Hotels-Kuanza-Nature-Experience.h88443976.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/3000000/2700000/2691900/2691841/e60c235e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Single Room](https://images.trvl-media.com/lodging/3000000/2700000/2691900/2691841/6ca98512.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/3000000/2700000/2691900/2691841/b206ff61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/3000000/2700000/2691900/2691841/aeff8c80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### São Jorge Garden [](https://www.expedia.ca/Velas-Hotels-Sao-Jorge-Garden.h2691841.Hotel-Information) Velas 9.0/10 Wonderful (102 reviews) "Great location in Velas, beautiful property with pool, sitting deck with ocean view, sunsets and Morro Grande view and hiking within 10 minutes walk. Close to supermarket and restaurants, ideal location in Velas. Good buffet breakfast. Beds were a little too firm for me but great for my partner...highly recommended for location, cleanliness and great staff! " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Jane CA $137 CA $143 total includes taxes & fees Mar 24 - Mar 25 [](https://www.expedia.ca/Velas-Hotels-Sao-Jorge-Garden.h2691841.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/33000000/32730000/32722200/32722172/086535c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/33000000/32730000/32722200/32722172/9b3148d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/33000000/32730000/32722200/32722172/7c80fc68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room (7) | View from room](https://images.trvl-media.com/lodging/33000000/32730000/32722200/32722172/c942b4de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quinta da Magnólia [](https://www.expedia.ca/Velas-Hotels-Quinta-Da-Magnolia.h32722172.Hotel-Information) Velas 9.8/10 Exceptional (30 reviews) "The rooms and property are really lovely and quiet and the staff was very generous and wanted to make our stay special. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deirdre [](https://www.expedia.ca/Velas-Hotels-Quinta-Da-Magnolia.h32722172.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/91000000/90590000/90584000/90583992/5b0f5cdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90590000/90584000/90583992/ef85d514.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90590000/90584000/90583992/cffb0cdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90590000/90584000/90583992/b71d0976.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stylish 2 Bedroom Stone House On Ocean Front In São Jorge, Azores (Belo Surf) [](https://www.expedia.ca/Calheta-Hotels-Stylish-2-Bedroom-Stone-House-On-Ocean-Front-In-Sao-Jorge.h90583992.Hotel-Information) São Jorge 10/10 Exceptional (4 reviews) "location, location, location plus the thoughtful design, adaptive reuse of structures, and the evident and abundant care of ownership and staff all added up to bliss for our group perhaps not for everyone, but the adventure of getting there and provisioning one’s stay can make for an even more satisfying stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David B. CA $330 CA $388 total includes taxes & fees Mar 24 - Mar 25 [](https://www.expedia.ca/Calheta-Hotels-Stylish-2-Bedroom-Stone-House-On-Ocean-Front-In-Sao-Jorge.h90583992.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/91000000/90600000/90598400/90598322/84a679a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90600000/90598400/90598322/07e55406.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90600000/90598400/90598322/ccf7f450.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/91000000/90600000/90598400/90598322/84dd039e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stylish 1 Bedroom Stone House With Sea View In São Jorge, Azores (Belo Malandro) [](https://www.expedia.ca/Calheta-Hotels-Stylish-1-Bedroom-Stone-House-With-Sea-View-In-Sao-Jorge.h90598322.Hotel-Information) São Jorge CA $203 CA $232 total includes taxes & fees Mar 25 - Mar 26 [](https://www.expedia.ca/Calheta-Hotels-Stylish-1-Bedroom-Stone-House-With-Sea-View-In-Sao-Jorge.h90598322.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/90000000/89480000/89474700/89474673/2aec020f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89480000/89474700/89474673/06191928.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/90000000/89480000/89474700/89474673/b41eceda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89480000/89474700/89474673/29f435ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stylish 1 Bedroom Stone House On Ocean Front - São Jorge, Azores (Bela Lua) [](https://www.expedia.ca/Calheta-Hotels-Ocean-Front-House-Surrounded-By-Pure-Nature-Bela-Lua.h89474673.Hotel-Information) Calheta CA $225 CA $265 total includes taxes & fees Mar 24 - Mar 25 [](https://www.expedia.ca/Calheta-Hotels-Ocean-Front-House-Surrounded-By-Pure-Nature-Bela-Lua.h89474673.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/92000000/91270000/91260600/91260534/83afbe1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/92000000/91270000/91260600/91260534/b81a98df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/92000000/91270000/91260600/91260534/0c8d55cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/92000000/91270000/91260600/91260534/2e8d5bf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful 2 Bedroom Ocean Front House In São Jorge, Azores - Mamba [](https://www.expedia.ca/Calheta-Hotels-Beautiful-2-Bedroom-Ocean-Front-House-In-Sao-Jorge.h91260534.Hotel-Information) São Jorge CA $294 CA $333 total includes taxes & fees Mar 24 - Mar 25 [](https://www.expedia.ca/Calheta-Hotels-Beautiful-2-Bedroom-Ocean-Front-House-In-Sao-Jorge.h91260534.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/91000000/90600000/90592900/90592830/d166b737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/91000000/90600000/90592900/90592830/4890e023.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90600000/90592900/90592830/93efe3e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90600000/90592900/90592830/eec60f05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stylish 2 Bedroom Stone House With Stunning Views, São Jorge, Azores (Vista) [](https://www.expedia.ca/Calheta-Hotels-Cosy-2-Bedroom-House-With-Stunning-Views-In-Sao-Jorge.h90592830.Hotel-Information) São Jorge 10/10 Exceptional (1 review) "serviço competente e atencioso, arquitectura enquadrada no contexto, local ideal para passeios e descanso." ![Portugal](https://a.travel-assets.com/egds/marks/flags/pt.svg) Pedro E. CA $310 CA $351 total includes taxes & fees Mar 26 - Mar 27 [](https://www.expedia.ca/Calheta-Hotels-Cosy-2-Bedroom-House-With-Stunning-Views-In-Sao-Jorge.h90592830.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/91000000/90750000/90740100/90740088/64b64159.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90750000/90740100/90740088/62f81f56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/91000000/90750000/90740100/90740088/c48ac4fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90750000/90740100/90740088/38bf9a17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful 2 Bedroom Ocean Front Stone House In São Jorge, Azores (Belo Canto) [](https://www.expedia.ca/Calheta-Hotels-Beautiful-2-Bedroom-Ocean-Front-Stone-House-In-Sao-Jorge.h90740088.Hotel-Information) São Jorge CA $310 CA $351 total includes taxes & fees Mar 24 - Mar 25 [](https://www.expedia.ca/Calheta-Hotels-Beautiful-2-Bedroom-Ocean-Front-Stone-House-In-Sao-Jorge.h90740088.Hotel-Information) ![Deluxe Suite, Private Pool, Mountain View](https://images.trvl-media.com/lodging/116000000/115460000/115456600/115456571/7e1b831f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/116000000/115460000/115456600/115456571/f28d9787.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, Private Pool, Mountain View | Living area](https://images.trvl-media.com/lodging/116000000/115460000/115456600/115456571/3fb3459a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115460000/115456600/115456571/4fbae47e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pico Vineyards [](https://www.expedia.ca/Madalena-Hotels-Pico-Vineyards.h115456571.Hotel-Information) Madalena 9.8/10 Exceptional (6 reviews) "The pool is amazing! and brand new property!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle CA $201 CA $210 total includes taxes & fees Mar 31 - Apr 1 [](https://www.expedia.ca/Madalena-Hotels-Pico-Vineyards.h115456571.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=2026-04-06&endDate=2026-04-07®ionId=3182&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in São Jorge Island Breakfast included 4 stars 5 stars Hot tub Spa ## Top São Jorge Island Hotel Reviews ![Pico Dreams - Sportfish](https://images.trvl-media.com/lodging/8000000/7760000/7759200/7759184/a083f6bd_y.jpg) ### Pico Dreams - Sportfish 10/10 Excellent "This was a no-frills, simple hotel. It was a great value, and was clean, quiet, and relaxing. The staff were so kind, and laid back. The view from the patio in our room was lovely. The shared kitchen area was a nice place to cook a meal, and there were three adorable cats around the property who we loved petting. The location was great for exploring various parts of Pico. " [](https://expedia.ca/Sao-Roque-Do-Pico-Hotels-Pico-Dreams-Sportfish.h7759184.Hotel-Information) ![São Jorge Garden](https://images.trvl-media.com/lodging/3000000/2700000/2691900/2691841/e60c235e_y.jpg) ### São Jorge Garden 8/10 Good "The building is quite aged and need of a refresh. 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