Title: Book the Best Hotels with POOL in Beachside in 2025 | Expedia.ca [Beachside Travel Guide](https://expedia.ca/Key-West-Beachside.dx864982244484468736)[Flights to Key West](https://expedia.ca/Cheap-Flights-To-Key-West.d1187.Travel-Guide-Flights)[Things to do in Key West](https://expedia.ca/Things-To-Do-In-Key-West.d1187.Travel-Guide-Activities)[Beachside Car Rentals](https://expedia.ca/Car-Rentals-In-Beachside.d864982244484468736.Car-Rental-Guide)[Beachside Vacations](https://expedia.ca/Beachside.d864982244484468736.Destination-Travel-Guides) ![Smathers Beach which includes windsurfing, a beach and tropical scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63797-Florida-Keys.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Beachside, FL from CA $155 ![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 availability on Beachside Hotels with a Pool Tonight [Oct 8 - Oct 9](https://www.expedia.ca/Hotel-Search?regionId=864982244484468736&startDate=2025-10-08&endDate=2025-10-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 9 - Oct 10](https://www.expedia.ca/Hotel-Search?regionId=864982244484468736&startDate=2025-10-09&endDate=2025-10-10&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=864982244484468736&startDate=2025-10-10&endDate=2025-10-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=864982244484468736&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Beachside Hotels with a Pool ![Pool](https://images.trvl-media.com/lodging/22000000/21710000/21704700/21704660/7e0aa71f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/22000000/21710000/21704700/21704660/bfe4ee47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/22000000/21710000/21704700/21704660/eb36205f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/22000000/21710000/21704700/21704660/3791b9d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfortable Condo with Pool, Private Balcony, & Beach Access Beachside 8.6/10 Excellent (135) "Nice area, location, and wonderful apartment!" CA $223 CA $802 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Key-West-Hotels-Comfortable-Condo-With-Pool.h21704660.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/37000000/36370000/36361200/36361179/eaeba9f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/37000000/36370000/36361200/36361179/9d3c4038.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/37000000/36370000/36361200/36361179/89903844.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/37000000/36370000/36361200/36361179/1a4cbe04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Colorful beachfront condo w/ ocean view balcony & shared hot tub/pool/tennis Beachside 9.0/10 Wonderful (102) "Very clean and beds are so comfortable. " CA $319 CA $938 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Key-West-Hotels-Colorful-Beachfront-Condo-W-Ocean-View-Balcony-Shared-Hot-Tubpooltennis.h36361179.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/83592c1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/a0504154.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/a36bdda4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/95d2903e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sugar Loaf Lodge Summerland Key 8.2/10 Very good (1001) "Nice family owned spot. " CA $138 CA $155 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/77f11bb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Quadruple Room](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/070a211a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![NYAH Private Balcony Room 6 Single Beds | Balcony view](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/a350e3cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/2f1f2895.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NYAH Key West - Adults Only Key West Historic District 7.8/10 Good (1002) "Staff was excellent! " [](https://www.expedia.ca/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/900000/894100/894030/dc763054.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/900000/894100/894030/f9b09089.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/900000/894100/894030/76b4e71a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/900000/894100/894030/eb0b0d9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Silver Palms Inn Old Town Key West 9.4/10 Exceptional (1008) "Boutique hotel with pool and free parking. " CA $124 CA $234 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Key-West-Hotels-Silver-Palms-Inn.h894030.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/6e8a6b91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/10da66f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/8879ca02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/ec0614f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage with Pool and Dockage, just minutes to Key West Cudjoe Key 9.2/10 Wonderful (154) "Good Fishing, Good local eateries. " CA $209 CA $441 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Summerland-Key-Hotels-Cottage-With-Pool-And-Dockage.h33389096.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/74000000/73240000/73238600/73238505/925121e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73240000/73238600/73238505/4d3ccae9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/74000000/73240000/73238600/73238505/8649ed7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/74000000/73240000/73238600/73238505/25ce0afb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West Cudjoe Key 9.0/10 Wonderful (51) "We enjoyed our stay. Place is exactly as described. We really enjoyed the lanai. Wanted somewhere close to Key West and this turned out perfect. Would definitely stay here again. Thanks!" CA $223 CA $487 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Summerland-Key-Hotels-Old-Florida-Style.h73238505.Hotel-Information) ![Room, Non Smoking, Private Bathroom](https://images.trvl-media.com/lodging/1000000/530000/529300/529277/657b5047.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Non Smoking, Private Bathroom | Bathroom](https://images.trvl-media.com/lodging/1000000/530000/529300/529277/8dc2c8b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/530000/529300/529277/1e7ddd15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/530000/529300/529277/66df4261.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Authors of Key West Guest House Old Town Key West 9.0/10 Wonderful (1001) "Very nice stay with easy street parking and a nice breakfast. " [](https://www.expedia.ca/Key-West-Hotels-Authors-Of-Key-West-Guest-House.h529277.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/58000000/57740000/57737200/57737120/3dd4da20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/58000000/57740000/57737200/57737120/ee42130f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/58000000/57740000/57737200/57737120/977c008c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, coffee/tea maker](https://images.trvl-media.com/lodging/58000000/57740000/57737200/57737120/6a346e42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### CORONA ~ Adults Only, King Room with Community Pool at Azul Mansion! Old Town Key West 9.8/10 Exceptional (159) "Place was clean and had everything we needed to explore key west" CA $127 CA $330 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Key-West-Hotels-CORONA-Adults-Only.h57737120.Hotel-Information) ![2 outdoor pools, open 8:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/e4eb7fd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/54c5f4f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; seafood](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/89147e75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/d6618f5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Perry Hotel & Marina Key West Stock Island 9.4/10 Exceptional (1110) "Beautiful place!" CA $231 CA $341 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.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=864982244484468736&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Beachside Hotel Reviews ![Hyatt Vacation Club at Windward Pointe, Key West](//images.trvl-media.com/lodging/1000000/870000/868700/868697/481a771e_y.jpg) ### Hyatt Vacation Club at Windward Pointe, Key West 10/10 Excellent "Great views from our room excellent staff service. Would definitely stay again" [](https://expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Windward-Pointe.h868697.Hotel-Information) ![Parrot Key Hotel & Villas](//images.trvl-media.com/lodging/1000000/30000/24700/24615/b83a5985_y.jpg) ### Parrot Key Hotel & Villas 10/10 Excellent "Impeccable service" [](https://expedia.ca/Key-West-Hotels-Parrot-Key-Hotel-Villas.h24615.Hotel-Information) ![Pier House Resort & Spa](//images.trvl-media.com/lodging/1000000/20000/19400/19307/ed076ab9_y.jpg) ### Pier House Resort & Spa 10/10 Excellent "Nice rooms" [](https://expedia.ca/Key-West-Hotels-Pier-House-Resort-Spa.h19307.Hotel-Information) ![Hilton Garden Inn Key West / The Keys Collection](//images.trvl-media.com/lodging/1000000/10000/1400/1376/5c83029c_y.jpg) ### Hilton Garden Inn Key West / The Keys Collection 10/10 Excellent "Clean grounds, clean room, loved the shuttle service to town and back to hotel, access to all 3 properties and pools which were wonderful and staff professional and courteous." [](https://expedia.ca/Key-West-Hotels-Hilton-Garden-Inn-Key-West.h1376.Hotel-Information) ![The Perry Hotel & Marina Key West](//images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/e4eb7fd5_y.jpg) ### The Perry Hotel & Marina Key West 10/10 Excellent "Very beautiful, clean, pet friendly resort definitely going back as soon as possible " [](https://expedia.ca/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.Hotel-Information) ![La Concha Key West, Autograph Collection](//images.trvl-media.com/lodging/1000000/10000/3900/3853/a3b28d11_y.jpg) ### La Concha Key West, Autograph Collection 10/10 Excellent "Perfect place to stay in key west " [](https://expedia.ca/Key-West-Hotels-Crowne-Plaza-Key-West-La-Concha.h3853.Hotel-Information) ![Casa Marina Key West, Curio Collection by Hilton](//images.trvl-media.com/lodging/1000000/20000/12400/12346/be8c9450_y.jpg) ### Casa Marina Key West, Curio Collection by Hilton 10/10 Excellent "The property was very pretty. Loved that it is on the beach. There was an elevator that was down so we had to use another one that I think was the staff elevator. It wouldn’t open the one time we used it for several minutes. The inside was very hot as it was not air conditioned. It was kind of scary, thankfully it opened after several minutes. " [](https://expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.Hotel-Information) ![Hyatt Centric Key West Resort and Spa](//images.trvl-media.com/lodging/1000000/10000/1000/901/0b72a249_y.jpg) ### Hyatt Centric Key West Resort and Spa 10/10 Excellent "Beautiful hotel rooms are awesome " [](https://expedia.ca/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.Hotel-Information) ![Oceans Edge Key West Resort, Hotel & Marina](//images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/3a4457a0_y.jpg) ### Oceans Edge Key West Resort, Hotel & Marina 10/10 Excellent "Overall just a good placecto saty whike yiur there" [](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Beachside? > [Margaritaville Beach House Key West](https://www.expedia.ca/Key-West-Hotels-Margaritaville-Beach-House-Key-West.h48713884.Hotel-Information): Hotel located near Duval Street. Features a 24-hour fitness center, an outdoor pool, and televisions. [Oceans Edge Key West Resort, Hotel & Marina](https://www.expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information): Hotel located near Smathers Beach. Offers a snack bar/deli, 6 outdoor pools, and complimentary bicycles. [Southernmost Beach Resort and Guesthouses](https://www.expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information): Hotel steps from South Beach. Provides 2 pool bars, 3 outdoor pools, and a full-service spa. [Parrot Key Hotel & Villas](https://www.expedia.ca/Key-West-Hotels-Parrot-Key-Hotel-Villas.h24615.Hotel-Information): Hotel located near Duval Street. Features a beach shuttle, 4 outdoor pools, and complimentary wireless internet access. [Hyatt Centric Key West Resort and Spa](https://www.expedia.ca/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.Hotel-Information): Resort, 3-minute walk from Duval Street. Offers a full-service spa, a pool, and a snack bar/deli. ### What is there to see and do in Beachside? > Explore places like Duval Street while you're in the area. 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