Title: Book the Best HISTORIC Hotels in Anna Maria Island in 2025 | Expedia.ca [Anna Maria Island Travel Guide](https://expedia.ca/Anna-Maria-Island.dx553248622847118534)[Hotels in Anna Maria Island](https://expedia.ca/Anna-Maria-Island-Hotels.d553248622847118534.Travel-Guide-Hotels)[Vacation Rentals in Anna Maria Island](https://expedia.ca/Anna-Maria-Island-Vacation-Rentals.d553248622847118534.Travel-Guide-VacationRentals)[Flights to Anna Maria Island](https://expedia.ca/Cheap-Flights-To-Anna-Maria-Island.d553248622847118534.Travel-Guide-Flights)[Things to do in Anna Maria Island](https://expedia.ca/Things-To-Do-In-Anna-Maria-Island.d553248622847118534.Travel-Guide-Activities)[Anna Maria Island Car Rentals](https://expedia.ca/Car-Rentals-In-Anna-Maria-Island.d553248622847118534.Car-Rental-Guide)[Anna Maria Island Vacation Packages](https://expedia.ca/Anna-Maria-Island.d553248622847118534.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/6e0a40c600747ff11aa2868df9ff0b93.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Anna Maria Island, FL ![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 Anna Maria Island Historic Hotels Tonight [Oct 2 - Oct 3](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-10-02&endDate=2025-10-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 3 - Oct 4](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-10-03&endDate=2025-10-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Anna Maria Island Historic Hotels ![Outdoor pool](https://images.trvl-media.com/lodging/13000000/12940000/12933300/12933229/b5ac7f20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/13000000/12940000/12933300/12933229/d4c55211.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/13000000/12940000/12933300/12933229/2d85b599.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/13000000/12940000/12933300/12933229/04103da4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Crystal Bay Historic Hotel La Vista 9.6/10 Exceptional (1390) "Classic "old Florida" hotel. Full breakfast every morning, exceptional staff, short drive to the beach " CA $168 CA $190 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Crystal-Bay-Hotel.h12933229.Hotel-Information) ![Apartment, 1 Bedroom (Corraline) | Living area](https://images.trvl-media.com/lodging/9000000/8330000/8329900/8329813/4a7e46da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, 1 King Bed, Beach View (Magnolia) | Private kitchen](https://images.trvl-media.com/lodging/9000000/8330000/8329900/8329813/ee97174c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/9000000/8330000/8329900/8329813/0d57e5fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, 1 King Bed, Beach View (Magnolia) | Terrace/patio](https://images.trvl-media.com/lodging/9000000/8330000/8329900/8329813/ff5146c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn on the Beach Pass-a-Grille 9.8/10 Exceptional (353) "Love the location, " CA $262 CA $297 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Inn-On-The-Beach.h8329813.Hotel-Information) ![2 outdoor pools, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/16700/16658/1586307d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges, poolside bar](https://images.trvl-media.com/lodging/1000000/20000/16700/16658/fb17d60b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/16700/16658/bb45bcfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/16700/16658/08b2c739.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Don CeSar St. Pete Beach 9.0/10 Wonderful (1006) "Fantastic hotel" CA $413 CA $529 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-The-Don-CeSar.h16658.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/63000000/62990000/62980600/62980565/a95e1b75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/63000000/62990000/62980600/62980565/4ef31794.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/63000000/62990000/62980600/62980565/10e7f583.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/63000000/62990000/62980600/62980565/9945c7d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Freshly Remodeled Island Suite w/ Pool & Pet Friendly Anna Maria 8.0/10 Very good (29) "It was a great location, and beautiful house." CA $162 CA $494 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Anna-Maria-Hotels-Convenient-Well-Located-Condo-WShared-WasherDryer.h62980565.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/108000000/107310000/107304600/107304567/a69ab543.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107310000/107304600/107304567/719f766e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107310000/107304600/107304567/08b5f4cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/108000000/107310000/107304600/107304567/bfd9f428.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beachside Duplex w/ Pool & Private Suite Anna Maria 8.0/10 Very good (1) "We have stayed here over the years and have enjoyed the perfect location to the beach. The house is a bit dated and needs a few upgrades but overall the house was very clean and comfortable. Please note there were no beach umbrellas supplied but did have plenty of beach chairs. You may want to plan on alternate shade options once there as the sun is intense and can be challenging. We would stay there again as the price was very affordable. " CA $263 CA $631 total includes taxes & fees Oct 4 - Oct 5 [](https://www.expedia.ca/Anna-Maria-Hotels-Beachside-Duplex-W-Pool-Private-Suite.h107304567.Hotel-Information) ![Beach nearby, sun loungers](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579351/339be2ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579351/4fb13f46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579351/c5d2dbca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579351/3adf92de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Adorable Cottage moments to beach w/ pool, beach gear, bikes Anna Maria 9.8/10 Exceptional (11) "Loved how the cottage is wqlking distance to the beach and also restaurants." CA $335 CA $877 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Anna-Maria-Hotels-Adorable-Cottage-Moments-To-Beach-W-Pool.h70579351.Hotel-Information) ![Beach nearby, sun loungers](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579348/16021fd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579348/380d9ac4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579348/e2144f3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579348/4b9de084.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand! Anna Maria 9.6/10 Exceptional (19) "Convenient to the beach, nicely furnished inside." CA $283 CA $743 total includes taxes & fees Oct 3 - Oct 4 [](https://www.expedia.ca/Anna-Maria-Hotels-Anna-Maria-Beach-Cottage-107a-Old-Florida-Beach-Cottage.h70579348.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/94000000/93350000/93343100/93343057/201e4d71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/94000000/93350000/93343100/93343057/4422a8b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/94000000/93350000/93343100/93343057/00f7ec5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/94000000/93350000/93343100/93343057/481c4915.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Hideaway! Beach Block, Near Pine Avenue! Anna Maria 9.4/10 Exceptional (11) "Awesome little house right by the beach, central to EVERYTHING!" CA $203 CA $534 total includes taxes & fees Oct 3 - Oct 4 [](https://www.expedia.ca/Anna-Maria-Hotels-Dog-Friendly-And-Located-In-The-Heart-Of-Anna-Maria-Near-The-Beach.h93343057.Hotel-Information) ![Beach nearby, sun loungers](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579352/d13cc66c.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) ![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) ![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) "The cottage was comfy and as described " CA $290 CA $753 total includes taxes & fees Oct 3 - Oct 4 [](https://www.expedia.ca/Anna-Maria-Hotels-Anna-Maria-Beach-Cottage-109a-Old-Florida-Beach-Cottage.h70579352.Hotel-Information) ![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 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) ![Interior](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579349/a7597990.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 10/10 Exceptional (27) "Had all the essentials. Loved the location." CA $277 CA $717 total includes taxes & fees Oct 3 - Oct 4 [](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=2025-10-16&endDate=2025-10-17®ionId=553248622847118534&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Anna Maria Island Hotel Reviews ![Bridgewalk Resort](//images.trvl-media.com/lodging/2000000/1050000/1045900/1045894/7186dbd7_y.jpg) ### Bridgewalk Resort 10/10 Excellent "As soon as we walked in we wanted to come back" [](https://expedia.ca/Sarasota-Hotels-Bridgewalk-A-Landmark-Resort.h1045894.Hotel-Information) ![Tradewinds Beach Resort](//images.trvl-media.com/lodging/2000000/1150000/1146400/1146353/6dd9a7bc_y.jpg) ### Tradewinds Beach Resort 10/10 Excellent "Very cute place and easy to walk to beach " [](https://expedia.ca/Sarasota-Hotels-Tradewinds-Beach-Resort.h1146353.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - More ways to book - [Adults Only Resorts & in Anna Maria](https://www.expedia.ca/Anna-Maria-Hotels-Adults-Only-Resorts.0-0-d74028-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - 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