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 $186 ![](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 Beachside Hotels with a Pool Tonight [Oct 22 - Oct 23](https://www.expedia.ca/Hotel-Search?regionId=864982244484468736&startDate=2025-10-22&endDate=2025-10-23&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 23 - Oct 24](https://www.expedia.ca/Hotel-Search?regionId=864982244484468736&startDate=2025-10-23&endDate=2025-10-24&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=864982244484468736&startDate=2025-10-24&endDate=2025-10-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=864982244484468736&startDate=2025-10-31&endDate=2025-11-02&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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/22000000/21710000/21704700/21704660/61ceb6fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/22000000/21710000/21704700/21704660/7af7f23c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/22000000/21710000/21704700/21704660/2988b7c2.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!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Harald P. CA $206 CA $801 total includes taxes & fees Oct 26 - Oct 27 [](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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/37000000/36370000/36361200/36361179/9d3c4038.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 (103) "Very clean and beds are so comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donny G. CA $280 CA $907 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Key-West-Hotels-Colorful-Beachfront-Condo-W-Ocean-View-Balcony-Shared-Hot-Tubpooltennis.h36361179.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) ![Aerial view](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/d6618f5e.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) ![View from property](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/8475e5b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Perry Hotel & Marina Key West Stock Island 9.4/10 Exceptional (1125) "Nice stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) SHAMBRE CA $156 CA $254 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/9013d891.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (Adults Only) | Private kitchen](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/4c7ce9b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/d8ea2dc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/d8706fe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Duval House Old Town Key West 9.4/10 Exceptional (1027) "Very friendly, good breakfasts, clean rooms " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sandor CA $139 CA $186 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Key-West-Hotels-Duval-House.h900423.Hotel-Information) ![2 outdoor pools, open 7:00 AM to 11:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/cb0a4c1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Poolside bar](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/5792173a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bicycling](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/4a54e511.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/44728c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blue Flamingo Resort Key West New Town 8.0/10 Very good (1624) "Amazing resort with lovely amenities:)" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wakglene CA $125 CA $219 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.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) ![Beach nearby](https://images.trvl-media.com/lodging/74000000/73240000/73238600/73238505/8649ed7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/74000000/73240000/73238600/73238505/db40386c.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!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michele S. CA $224 CA $489 total includes taxes & fees Oct 24 - Oct 25 [](https://www.expedia.ca/Summerland-Key-Hotels-Old-Florida-Style.h73238505.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) ![Balcony](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/a36bdda4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/125c52d9.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) ### Sugar Loaf Lodge Summerland Key 8.2/10 Very good (1000) "Nice family owned spot. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Terry CA $166 CA $187 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/4000000/3930000/3924900/3924835/872463e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite](https://images.trvl-media.com/lodging/4000000/3930000/3924900/3924835/7c366980.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mini Suite, 1 King Bed, Accessible](https://images.trvl-media.com/lodging/4000000/3930000/3924900/3924835/70d203b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3930000/3924900/3924835/894f1440.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Paradise Inn Key West - Adults Only Old Town Key West 9.2/10 Wonderful (1000) "Great place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Noel CA $126 CA $205 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Key-West-Hotels-Paradise-Inn-Key-West-Adults-Only.h3924835.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/4233d834.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/2ac07b2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/62b1909b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/5710a846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Margaritaville Beach House Key West Key West 8.8/10 Excellent (1789) "Wonderful place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kesha CA $250 CA $370 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Key-West-Hotels-Margaritaville-Beach-House-Key-West.h48713884.Hotel-Information) ![Outdoor pool, open 6:00 AM to 10:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/5c83029c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/470ffe1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/d5aad7de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily continental breakfast (USD 18 per person)](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/3484f3ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Key West / The Keys Collection New Town 7.8/10 Good (1100) "Very nice hotel." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew CA $142 CA $199 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Key-West-Hotels-Hilton-Garden-Inn-Key-West.h1376.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=2025-11-06&endDate=2025-11-07®ionId=864982244484468736&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Beachside Hotel Reviews ![Hampton Inn Key West FL](//images.trvl-media.com/lodging/1000000/20000/15800/15720/4075e8ff_y.jpg) ### Hampton Inn Key West FL 10/10 Excellent "Very friendly staff. Loved the shuttle to downtown Key West. Awesome place to stay!" [](https://expedia.ca/Key-West-Hotels-Hampton-Inn-Key-West-FL.h15720.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 "The hotel was very clean, nice staff, the room was beautiful and comfortable " [](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.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 "This hotel is beautiful. Great view from the room. Staff is amazing " [](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 "👍" [](https://expedia.ca/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.Hotel-Information) ![Southernmost Beach Resort and Guesthouses](//images.trvl-media.com/lodging/1000000/870000/863400/863329/026f10af_y.jpg) ### Southernmost Beach Resort and Guesthouses 10/10 Excellent "A great place to stay!" [](https://expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ![DoubleTree Resort by Hilton Grand Key - Key West](//images.trvl-media.com/lodging/1000000/480000/470900/470834/be4147fb_y.jpg) ### DoubleTree Resort by Hilton Grand Key - Key West 10/10 Excellent "Shuttle was great and the staff was great" [](https://expedia.ca/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.Hotel-Information) ![Blue Flamingo Resort Key West](//images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/cb0a4c1e_y.jpg) ### Blue Flamingo Resort Key West 10/10 Excellent "The hotel is amazing. Rooms are super clean. Staff is rude which is sad since the hotel is really nice. " [](https://expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.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 "We loved this hotel! For Key West the price was great, which is the main reason we chose this hotel. And then we were pleasantly surprised. The room itself was beautiful! Very spacious w/ beautiful tile on the floor & shower. The lobby was beautiful, & we loved the pool area, which is right on the beautiful marina! Definitely would stay here again if ever in Key West!" [](https://expedia.ca/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.Hotel-Information) ![Beachside Resort & Residences](//images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a_y.jpg) ### Beachside Resort & Residences 10/10 Excellent "Great!!! As advertised " [](https://expedia.ca/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Beachside? > [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. Features complimentary bicycles, 6 outdoor pools, and complimentary wireless internet access. [Southernmost Beach Resort and Guesthouses](https://www.expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information): Hotel steps from South Beach. Offers 2 pool bars, 3 outdoor pools, and a full-service spa. [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. Provides a 24-hour fitness center, an outdoor pool, and televisions. [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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