Title: Book the Best Hotels with POOL in Anna Maria in 2025 | Expedia.ca [Hotels in Anna Maria](https://expedia.ca/Anna-Maria-Hotels.d74028.Travel-Guide-Hotels)[Vacation Rentals in Anna Maria](https://expedia.ca/Anna-Maria-Vacation-Rentals.d74028.Travel-Guide-VacationRentals)[Flights to Anna Maria](https://expedia.ca/Cheap-Flights-To-Anna-Maria.d74028.Travel-Guide-Flights)[Anna Maria Car Rentals](https://expedia.ca/Car-Rentals-In-Anna-Maria.d74028.Car-Rental-Guide)[Anna Maria Vacation Packages](https://expedia.ca/Anna-Maria.d74028.Destination-Travel-Guides) ![The day comes to a close over the Gulf of Mexico. Bean Point Beach is at the Northwest end of Anna Maria Island. A nice wide beach with fine white sand. A little more secluded than some of the other beaches nearby.](https://images.trvl-media.com/place/74028/8bf298b4-fe4b-49ec-a6ce-565760a5baca.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by throwingsofas # Find Hotels with a Pool in Anna Maria, FL from CA $402 - ![](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 Anna Maria Hotels with a Pool Tonight [Nov 20 - Nov 21](https://www.expedia.ca/Hotel-Search?regionId=74028&startDate=2025-11-20&endDate=2025-11-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 21 - Nov 22](https://www.expedia.ca/Hotel-Search?regionId=74028&startDate=2025-11-21&endDate=2025-11-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=74028&startDate=2025-11-21&endDate=2025-11-23&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=74028&startDate=2025-11-28&endDate=2025-11-30&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Anna Maria Hotels with a Pool ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579361/933a3ccd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579361/b018f64f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579361/6db8dfc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579361/19ccb378.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand! Anna Maria 9.8/10 Exceptional (36) "Location was perfect" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael S. CA $277 CA $719 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Anna-Maria-Hotels-Anna-Maria-Beach-Cottage-110b-Updated-Studio-Beach-Cottage.h70579361.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/33000000/32740000/32736100/32736045/fd760a5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/33000000/32740000/32736100/32736045/23712015.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32740000/32736100/32736045/3b6455bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/33000000/32740000/32736100/32736045/3dfc9b65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Updated bayside condo with heated pool - across the street from the beach Anna Maria 9.2/10 Wonderful (98) "Very comfortable and modern, great location across the street from bay side beach, a block to restaurant/coffee/ice cream" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey B. CA $104 CA $402 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Anna-Maria-Hotels-Updated-Bayside-Condo-With-Heated-Pool-Across-The-Street-From-The-Beach.h32736045.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/63000000/62990000/62981100/62981008/f623a221.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/63000000/62990000/62981100/62981008/4b767cb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/63000000/62990000/62981100/62981008/a4085363.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/63000000/62990000/62981100/62981008/10e1edaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Freshly Remodeled Island Suite w/ Pool & Pet Friendly Anna Maria 8.6/10 Excellent (38) "Very close to the beach and restaurants!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Danay G. CA $140 CA $472 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Sarasota-Hotels-Incredible-Beach-Condo-Wfree-Wifi.h62981008.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/41000000/40290000/40281600/40281514/ed3fe6a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/41000000/40290000/40281600/40281514/78cb82e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/41000000/40290000/40281600/40281514/716bb273.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/41000000/40290000/40281600/40281514/57ca76e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Bungalow with Pool and Bay Views! Anna Maria 9.8/10 Exceptional (37) "Great location,great property,spacious,clean everything brand new in the property,beach across the street,my family love it!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michel CA $242 CA $548 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Anna-Maria-Hotels-Beautiful-Bungalow-With-Pool-And-Bay-Views-Barefoot-By-The-Bay-At-Bayside-Bun.h40281514.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/63000000/62990000/62982000/62981960/627f1c1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/63000000/62990000/62982000/62981960/5c2376ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/63000000/62990000/62982000/62981960/a0744740.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/63000000/62990000/62982000/62981960/740dc148.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Freshly Remodeled Island Suite w/ Pool & Pet Friendly Anna Maria 9.2/10 Wonderful (56) "We absolutely enjoyed staying here and will be back. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Allie S. CA $191 CA $572 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Anna-Maria-Hotels-Convenient-Condo-Near-The-Beach-WShared-Pool.h62981960.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/33000000/32740000/32735500/32735487/3affb12c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/33000000/32740000/32735500/32735487/936c386a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/33000000/32740000/32735500/32735487/1cd09640.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/33000000/32740000/32735500/32735487/f2e05610.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stylish bayside condo with WiFi & pool - close to the beach & restaurants Anna Maria 9.6/10 Exceptional (102) "Perfect place to stay, loved it, walking distance to everything you need beach right across the street. Loved it." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jason l. CA $131 CA $439 total includes taxes & fees Nov 22 - Nov 23 [](https://www.expedia.ca/Sarasota-Hotels-Bayside-Condo-W-A-Shared-Heated-Pool-Close-To-The-Beach-Restaurants.h32735487.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579352/fa5106d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, offices](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579352/e210d958.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579352/6e21bf07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579352/a1280f33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Anna Maria Beach Cottage 109A -Old-Florida beach cottage, steps to the beach! Anna Maria 9.6/10 Exceptional (21) "Mom and I just stayed for one night and had a lovely trip. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brittany B. CA $291 CA $774 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Anna-Maria-Hotels-Anna-Maria-Beach-Cottage-109a-Old-Florida-Beach-Cottage.h70579352.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/63000000/63000000/62999900/62999855/c29830e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/63000000/63000000/62999900/62999855/5dcb6f39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/63000000/63000000/62999900/62999855/b30e1a81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/63000000/63000000/62999900/62999855/736d7dc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Freshly Remodeled Island Suite w/ Pool & Pet Friendly Anna Maria 8.4/10 Very good (33) "Loved access to the beaches and restaurants." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kenneth C. CA $143 CA $475 total includes taxes & fees Nov 22 - Nov 23 [](https://www.expedia.ca/Anna-Maria-Hotels-Convenient-Well-Equipped-Condo-WShared-Pool.h62999855.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/63000000/62990000/62980600/62980554/2f8dc934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/63000000/62990000/62980600/62980554/b431caa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/63000000/62990000/62980600/62980554/8c637972.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/63000000/62990000/62980600/62980554/b45ac8bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Freshly Remodeled Island Suite w/ Pool & Pet Friendly Anna Maria 8.8/10 Excellent (41) "This was a quiet corner of town and the property was beautiful as well as the pool area. I would stay here again 💯 %" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susie Goodwin S. CA $143 CA $437 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Anna-Maria-Hotels-Friendly-Condo-W-Shared-Pool-In-Great-Location-W-WasherDryer.h62980554.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579349/35eb4794.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579349/2fefe87e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579349/40de95d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579349/eb486336.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes Anna Maria 9.8/10 Exceptional (30) "Enjoyed the property, pool, the closeness to the beach" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susane D. CA $278 CA $738 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Anna-Maria-Hotels-Anna-Maria-Updated-Studio-Moments-From-The-Sand-W-Pool.h70579349.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=2025-12-04&endDate=2025-12-05®ionId=74028&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Anna Maria Hotel Reviews ## Frequently asked questions ### What are some accommodations with pools in Anna Maria? > [Resort-Style Ground Floor Suite Heated Pool/Spa 🐢](https://www.expedia.ca/Sarasota-Hotels-New-Resort-Style-Ground-Floor-Lakefront-Unit-On-North-Shore-Of-Anna-Maria-Island.h65994030.Hotel-Information): Resort, 6-minute walk from Bean Point Beach. Features a water park, a communal pool, and complimentary wireless internet access. [Ground Floor Lakefront Resort, Private Dock, Heated Pool & Spa 🏖️🏖️🏖️🏖️🏖️](https://www.expedia.ca/Sarasota-Hotels-Luxurious-Ground-Level-Lakefront-Resort-With-Private-Dock-And-Heated-Pool-Spa.h65994036.Hotel-Information): Resort, 6-minute walk from Bean Point Beach. Offers a water park, a pool, and complimentary wireless internet access. [Resort-Style Ground Floor 1-Bdr. Suite On Vista Lake, Heated Pool & Spa 🦭](https://www.expedia.ca/Anna-Maria-Hotels-Resort-Style-Ground-Floor-1-Bdr-Suite-On-Vista-Lake.h122332123.Hotel-Information): Resort, 6-minute walk from Bean Point Beach. Features a water park, a communal pool, and complimentary wireless internet access. ### What is there to see and do in Anna Maria? > Explore places like Lido Beach and Tampa Bay while you're in the area. Enjoy a stroll along the shore at Anna Maria Beach and Bean Point Beach. Take in the natural beauty of the island views, beaches, and sunrises in Anna Maria. ### When is the best time to book a hotel with a pool in Anna Maria? > You may want to consider a place to stay that offers an outdoor swimming pool if you plan to visit Anna Maria in the driest months of February, March, or November when the average rainfall is 2 inches. 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