Title: Book the Best Hotels with POOL in Diamond Isle in 2026 | Expedia.ca [Diamond Isle Travel Guide](https://expedia.ca/St-Petersburg-Clearwater-Diamond-Isle.dx553248635976469351)[Vacation Rentals in St. Petersburg - Clearwater](https://expedia.ca/St-Petersburg-Clearwater-Vacation-Rentals.d178310.Travel-Guide-VacationRentals)[Flights to St. Petersburg - Clearwater](https://expedia.ca/Cheap-Flights-To-St-Petersburg-Clearwater.d178310.Travel-Guide-Flights)[Things to do in St. Petersburg - Clearwater](https://expedia.ca/Things-To-Do-In-St-Petersburg-Clearwater.d178310.Travel-Guide-Activities)[Diamond Isle Car Rentals](https://expedia.ca/Car-Rentals-In-Diamond-Isle.d553248635976469351.Car-Rental-Guide)[Diamond Isle Vacations](https://expedia.ca/Diamond-Isle.d553248635976469351.Destination-Travel-Guides) ![Sunset at Clearwater beach with Pier 60 fishing pier, white sand beach dramatic colorful sky](https://images.trvl-media.com/place/553248635976469351/4a55f94d-b018-4d6c-b15f-dd26cf6c74bc.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Diamond Isle, FL from CA $139 - ![](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 Diamond Isle Hotels with a Pool Tonight [Dec 2 - Dec 3](https://www.expedia.ca/Hotel-Search?regionId=553248635976469351&startDate=2025-12-02&endDate=2025-12-03&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 3 - Dec 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976469351&startDate=2025-12-03&endDate=2025-12-04&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976469351&startDate=2025-12-05&endDate=2025-12-07&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976469351&startDate=2025-12-12&endDate=2025-12-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Diamond Isle Hotels with a Pool ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914352/3e998290.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Room, 1 King Bed (Gulf Front)](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914352/262b9b5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914352/13b2550b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite, Multiple Beds, Non Smoking | Living area](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914352/9094284d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wyndham Grand Clearwater Beach Clearwater Beach 9.4/10 Exceptional (2846) "Nice resort, clean, friendly staff and plenty of things to eat! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Danielle CA $239 CA $326 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Wyndham-Grand-Clearwater-Beach.h15914352.Hotel-Information) ![Outdoor pool, open 8:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1880000/1871300/1871216/1ed9777c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1880000/1871300/1871216/564ff8dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 8:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1880000/1871300/1871216/2be1291c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1880000/1871300/1871216/6e222c7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Northeast - Gateway St. Petersburg 9.0/10 Wonderful (1001) "Great staff and nice rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Todd CA $123 CA $139 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Comfort-Inn-Suites-Northeast-Gateway.h1871216.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/17000000/16540000/16535900/16535849/fa74a1b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/17000000/16540000/16535900/16535849/4cb7a5f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/17000000/16540000/16535900/16535849/bf850152.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/17000000/16540000/16535900/16535849/4b9d4a92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Avalon Hotel Downtown St. Petersburg Downtown St. Petersburg 9.2/10 Wonderful (1341) "Cozy, clean, friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Agustin Jr [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Avalon-Hotel-Downtown-St-Petersburg.h16535849.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/1000000/20000/16000/15938/4f161320.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach bar](https://images.trvl-media.com/lodging/1000000/20000/16000/15938/ab8b33d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/16000/15938/d117a0d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pillowtop beds, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/20000/16000/15938/1cad0a24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Beachcomber St. Pete Beach 8.0/10 Very good (1004) "Nice place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) brian CA $130 CA $207 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Beachcomber-Beach-Resort.h15938.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/6000000/5650000/5648600/5648579/8956b33d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5650000/5648600/5648579/db1c7762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/6000000/5650000/5648600/5648579/2004de52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/6000000/5650000/5648600/5648579/7fcaa6a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hollander Boutique Hotel Downtown St. Petersburg 9.4/10 Exceptional (2182) "The hotel and rooms are very nice. We will stay there again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JD [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Hollander-Boutique-Hotel.h5648579.Hotel-Information) ![Outdoor pool, open 9:00 AM to 10:00 PM, free cabanas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/13800/13705/2714044c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/13800/13705/abdd10d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast served](https://images.trvl-media.com/lodging/1000000/20000/13800/13705/78697dd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/13800/13705/7128f3ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Alba, Tapestry Collection by Hilton Westshore 8.8/10 Excellent (2407) "Great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maurice CA $162 CA $184 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Tampa-Hotels-Hotel-Alba.h13705.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/30000/25500/25423/72599012.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/30000/25500/25423/cc79499d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/25500/25423/85ff7441.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/25500/25423/ec3240c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Yacht Harbor Inn Downtown Dunedin 8.6/10 Excellent (1021) "Great location and staff with comfortable beds" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matt CA $139 CA $158 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Best-Western-Plus-Yacht-Harbor-Inn.h25423.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/8600/8544/37eb40ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/1000000/10000/8600/8544/805149bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/10000/8600/8544/e8f80777.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/10000/8600/8544/84f52a3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### RumFish Beach at TradeWinds St. Pete Beach 8.2/10 Very good (1535) "Wonderful stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) HOLLY CA $146 CA $252 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-RumFish-Beach-Resort-By-TradeWinds.h8544.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/36000000/35260000/35260000/35259931/17c69051.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/36000000/35260000/35260000/35259931/52106692.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/36000000/35260000/35260000/35259931/2f6a5fd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/36000000/35260000/35260000/35259931/3b4b7f1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Dunedin Dunedin 9.4/10 Exceptional (726) "Mike and female coworker were awesome. Provided great service." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer CA $156 CA $176 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Hampton-Inn-Dunedin.h35259931.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/130000/120400/120312/18c92a79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/130000/120400/120312/ad0dbe1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/130000/120400/120312/66230099.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/130000/120400/120312/e9d3d2df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Tampa/Rocky Point-Airport Rocky Point 8.8/10 Excellent (1001) "Staff was very impressive " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wendy CA $139 CA $158 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Tampa-Hotels-Hampton-Inn-Tampa-Rocky-Point.h120312.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=2025-12-16&endDate=2025-12-17®ionId=553248635976469351&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Diamond Isle Hotel Reviews ![RumFish Beach at TradeWinds](https://images.trvl-media.com/lodging/1000000/10000/8600/8544/37eb40ec_y.jpg) ### RumFish Beach at TradeWinds 10/10 Excellent "Room was spotless very well equipped. Staff or super friendly great places to stay." [](https://expedia.ca/St-Petersburg-Clearwater-Hotels-RumFish-Beach-Resort-By-TradeWinds.h8544.Hotel-Information) ![Hilton Clearwater Beach Resort & Spa](https://images.trvl-media.com/lodging/1000000/30000/28100/28023/da46d3f6_y.jpg) ### Hilton Clearwater Beach Resort & Spa 10/10 Excellent "Exactly " [](https://expedia.ca/St-Petersburg-Clearwater-Hotels-Hilton-Clearwater-Beach-Resort-Spa.h28023.Hotel-Information) ![Hotel Alba, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/1000000/20000/13800/13705/2714044c_y.jpg) ### Hotel Alba, Tapestry Collection by Hilton 10/10 Excellent "I had a great view and the room was very clean. The staff at the front desk was courteous and efficient." [](https://expedia.ca/Tampa-Hotels-Hotel-Alba.h13705.Hotel-Information) ![The Westshore Grand, A Tribute Portfolio Hotel, Tampa](https://images.trvl-media.com/lodging/1000000/10000/5800/5781/bb4afd26_y.jpg) ### The Westshore Grand, A Tribute Portfolio Hotel, Tampa 10/10 Excellent "All was overall great " [](https://expedia.ca/Tampa-Hotels-The-Westshore-Grand.h5781.Hotel-Information) ![DoubleTree by Hilton Tampa Rocky Point Waterfront](https://images.trvl-media.com/lodging/1000000/10000/1400/1366/4c0da1ef_y.jpg) ### DoubleTree by Hilton Tampa Rocky Point Waterfront 10/10 Excellent "Great place, amazing property, beautiful views to the water. Comfortable room and well kept" [](https://expedia.ca/Tampa-Hotels-DoubleTree-By-Hilton-Tampa-Rocky-Point-Waterfront.h1366.Hotel-Information) ![Wyndham Grand Clearwater Beach](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914352/3e998290_y.jpg) ### Wyndham Grand Clearwater Beach 10/10 Excellent "Great customer service and awesome location. Audria at the front desk was awesome and very pleasant. She deserves promotion. Valet staff was extremely professional and considerate. Bar staff was excellent too. I needed some change and it was provided immediately. Keep up the great work. I would definitely recommend and come back to stay. " [](https://expedia.ca/St-Petersburg-Clearwater-Hotels-Wyndham-Grand-Clearwater-Beach.h15914352.Hotel-Information) ![Hyatt Regency Clearwater Beach Resort & Spa](https://images.trvl-media.com/lodging/3000000/2710000/2703500/2703419/c3ff81f1_y.jpg) ### Hyatt Regency Clearwater Beach Resort & Spa 10/10 Excellent "The view 👌" [](https://expedia.ca/St-Petersburg-Clearwater-Hotels-Hyatt-Regency-Clearwater-Beach-Resort-Spa.h2703419.Hotel-Information) ![Ramada by Wyndham Tampa Westshore Airport South](https://images.trvl-media.com/lodging/1000000/30000/27400/27302/cfa6c456_y.jpg) ### Ramada by Wyndham Tampa Westshore Airport South 10/10 Excellent "The place needed some updating, but the service was great. Breakfast was OK Continental." [](https://expedia.ca/Tampa-Hotels-Ramada-By-Wyndham-Tampa-Airport-Westshore.h27302.Hotel-Information) ![Island Grand at TradeWinds](https://images.trvl-media.com/lodging/1000000/10000/2000/1914/6ca26be4_y.jpg) ### Island Grand at TradeWinds 10/10 Excellent "The room was very nice & clean. Only issue was when sitting on balcony, relaxing, enjoying the ocean. There was 5 lady’s next door smoking all night on balcony. They were very loud laughing and having fun at 11:30. I had to go down to the front desk to let them know what was going on. They ask if they wanted to move, yes they upgraded me to a suite which was very nice. The staff was excellent, the restaurants had excellent food, they had a shuttle to their other property, which was very convenient. I would stay there again highly recommend excellent service. " [](https://expedia.ca/St-Petersburg-Clearwater-Hotels-TradeWinds-Island-Grand.h1914.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Diamond Isle? > [DoubleTree by Hilton Tampa Rocky Point Waterfront](https://www.expedia.ca/Tampa-Hotels-DoubleTree-By-Hilton-Tampa-Rocky-Point-Waterfront.h1366.Hotel-Information): Hotel, 9-minute walk from Tampa Bay. Features a snack bar/deli, an outdoor pool, and complimentary wired internet access. [Wyndham Grand Clearwater Beach](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Wyndham-Grand-Clearwater-Beach.h15914352.Hotel-Information): Hotel, 3-minute walk from St. Petersburg - Clearwater Beaches. Offers 3 restaurants, an outdoor pool, and a full-service spa. [RumFish Beach at TradeWinds](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-RumFish-Beach-Resort-By-TradeWinds.h8544.Hotel-Information): Resort, 5-minute walk from St. Petersburg - Clearwater Beaches. Provides 2 restaurants, 4 outdoor pools, and 2 bars. [Grand Hyatt Tampa Bay](https://www.expedia.ca/Tampa-Hotels-Grand-Hyatt-Tampa-Bay.h7558.Hotel-Information): Hotel located near Tampa Bay. Features 2 restaurants, 2 outdoor pools, and complimentary wireless internet access. [Hilton Clearwater Beach Resort & Spa](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Hilton-Clearwater-Beach-Resort-Spa.h28023.Hotel-Information): Resort, 2-minute walk from St. Petersburg - Clearwater Beaches. Offers a private beach, 2 outdoor pools, and 3 restaurants. ### What is there to see and do in Diamond Isle? > Explore places like John's Pass Village & Boardwalk while you're in the area. Make a point to visit attractions like Celebration Station and Florida Botanical Gardens. ## Explore a world of travel with Expedia - Lodging - More ways to book - [Adults Only Resorts & in Clearwater Beach](https://www.expedia.ca/Clearwater-Beach-Hotels-Adults-Only-Resorts.0-0-d10759-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in Clearwater Beach](https://www.expedia.ca/Clearwater-Beach-Hotels-All-Inclusive-Hotel.0-0-d10759-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Clearwater Beach](https://www.expedia.ca/Clearwater-Beach-Hotels-Beach-Hotel.0-0-d10759-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Clearwater Beach](https://www.expedia.ca/Clearwater-Beach-Hotels-Boutique-Hotel.0-0-d10759-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Business Hotels in Clearwater Beach](https://www.expedia.ca/Clearwater-Beach-Hotels-Business-Hotel.0-0-d10759-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Clearwater Beach](https://www.expedia.ca/Clearwater-Beach-Hotels-Cheap-Hotels.0-0-d10759-tCheapHotels.Travel-Guide-Filter-Hotels) - 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