Title: Book the Best HISTORIC Hotels in Anna Maria Island in 2026 | 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) ![Anna Maria Island, FL Pier ](https://images.trvl-media.com/place/553248622847118534/f6726703-de53-4942-875e-504e17e1a1f7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/553248622847118534/f6726703-de53-4942-875e-504e17e1a1f7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Island Historic Hotels Tonight [Jan 23 - Jan 24](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2026-01-23&endDate=2026-01-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 24 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2026-01-24&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2026-01-23&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Anna Maria Island historic hotels ![Property grounds](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579361/cc175788.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579361/04e8465a.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) ![Outdoor dining](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579361/49159291.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand! [](https://www.expedia.ca/Anna-Maria-Hotels-Anna-Maria-Beach-Cottage-110b-Updated-Studio-Beach-Cottage.h70579361.Hotel-Information) Anna Maria 9.8/10 Exceptional (37 reviews) "Location was perfect" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael S. CA $219 CA $631 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Anna-Maria-Hotels-Anna-Maria-Beach-Cottage-110b-Updated-Studio-Beach-Cottage.h70579361.Hotel-Information) ![Beach nearby, sun loungers](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579354/f4e43d59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579354/0c26865c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579354/b1d8a0ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579354/7b6ada29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand! [](https://www.expedia.ca/Anna-Maria-Hotels-Anna-Maria-Beach-Cottage-109G-Old-Florida-Beach-Cottage.h70579354.Hotel-Information) Anna Maria 9.6/10 Exceptional (35 reviews) "Great place for a beach stay on Anna Maria!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John F. CA $225 CA $659 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Anna-Maria-Hotels-Anna-Maria-Beach-Cottage-109G-Old-Florida-Beach-Cottage.h70579354.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/74000000/73780000/73773600/73773534/57afa2e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/74000000/73780000/73773600/73773534/6a0ef616.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/74000000/73780000/73773600/73773534/41a5cb58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73780000/73773600/73773534/27653641.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dog friendly cottage - One block to the Bay! [](https://www.expedia.ca/Anna-Maria-Hotels-Dog-Friendly-Cottage-One-Block-To-The-Bay.h73773534.Hotel-Information) Anna Maria 9.4/10 Exceptional (10 reviews) "Great stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mandy R. CA $187 CA $758 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Anna-Maria-Hotels-Dog-Friendly-Cottage-One-Block-To-The-Bay.h73773534.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) ![TV, DVD player, offices](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579348/fb5507ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579348/3443d572.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand! [](https://www.expedia.ca/Anna-Maria-Hotels-Anna-Maria-Beach-Cottage-107a-Old-Florida-Beach-Cottage.h70579348.Hotel-Information) Anna Maria 9.8/10 Exceptional (21 reviews) "My fiancé and I stayed at the cottages this past weekend and it was one of most relaxing weekend. Everyone there was so nice and helpful. We can’t wait to book another trip soon!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew S. CA $248 CA $699 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Anna-Maria-Hotels-Anna-Maria-Beach-Cottage-107a-Old-Florida-Beach-Cottage.h70579348.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/ef694e8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, offices](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579352/87fef08c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579352/6ba32c6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming beach cottage close to the beach with Pool, Bikes, Beach gear and Grill [](https://www.expedia.ca/Anna-Maria-Hotels-Anna-Maria-Beach-Cottage-109a-Old-Florida-Beach-Cottage.h70579352.Hotel-Information) Anna Maria 9.6/10 Exceptional (21 reviews) "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 $243 CA $698 total includes taxes & fees Jan 27 - Jan 28 [](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/71000000/70580000/70579400/70579363/85dc8704.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579363/7ecf21b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, offices](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579363/w2995h1993x3y0-46d287a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579363/6a1e2aa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear! [](https://www.expedia.ca/Anna-Maria-Hotels-Anna-Maria-Beach-Cottage-110G-Updated-Beach-Cottage.h70579363.Hotel-Information) Anna Maria 9.4/10 Exceptional (24 reviews) "Easy walk to the beach and restaurants. Allowed us to check in early since the place was available. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy E. CA $252 CA $712 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Anna-Maria-Hotels-Anna-Maria-Beach-Cottage-110G-Updated-Beach-Cottage.h70579363.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) ![Exterior](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579349/040d7994.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579349/7602fd23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579349/aa613016.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes [](https://www.expedia.ca/Anna-Maria-Hotels-Anna-Maria-Updated-Studio-Moments-From-The-Sand-W-Pool.h70579349.Hotel-Information) Anna Maria 9.8/10 Exceptional (30 reviews) "Enjoyed the property, pool, the closeness to the beach" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susane D. CA $265 CA $713 total includes taxes & fees Jan 31 - Feb 1 [](https://www.expedia.ca/Anna-Maria-Hotels-Anna-Maria-Updated-Studio-Moments-From-The-Sand-W-Pool.h70579349.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) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579351/fb5aa1f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579351/4fb13f46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579351/e17e2719.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill [](https://www.expedia.ca/Anna-Maria-Hotels-Adorable-Cottage-Moments-To-Beach-W-Pool.h70579351.Hotel-Information) Anna Maria 9.8/10 Exceptional (14 reviews) "Loved how the cottage is wqlking distance to the beach and also restaurants." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pamela CA $343 CA $895 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Anna-Maria-Hotels-Adorable-Cottage-Moments-To-Beach-W-Pool.h70579351.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579359/f703cc42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579359/w2048h1533x0y1-32e93535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579359/dae2cab5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579359/f9b02997.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Cottage with modern amenities close to beach w/ pool, beach gear, bikes [](https://www.expedia.ca/Anna-Maria-Hotels-Anna-Maria-Beach-Cottage-110a-Old-Florida-Beach-Cottage-With-Modern-Amenities.h70579359.Hotel-Information) Anna Maria 8.8/10 Excellent (8 reviews) " The place was great, and the location to the beach was wonderful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Norman N. CA $305 CA $837 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Anna-Maria-Hotels-Anna-Maria-Beach-Cottage-110a-Old-Florida-Beach-Cottage-With-Modern-Amenities.h70579359.Hotel-Information) ![Beach nearby, sun loungers](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579356/4cdda96b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579356/01966e82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579356/52202a1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, offices](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579356/b709ba6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Anna Maria Beach Cottage 110 Traditional beach cottage, moments from the sand! [](https://www.expedia.ca/Anna-Maria-Hotels-Anna-Maria-Beach-Cottage-110-Traditional-Beach-Cottage.h70579356.Hotel-Information) Anna Maria 9.6/10 Exceptional (35 reviews) "The cottage was cute and rooms/bathrooms were clean. It's on a nice quiet side street with a very short walk to the beach. Would definitely stay here again and would recommend to others." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) sherri g. CA $303 CA $917 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Anna-Maria-Hotels-Anna-Maria-Beach-Cottage-110-Traditional-Beach-Cottage.h70579356.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=2026-02-06&endDate=2026-02-07®ionId=553248622847118534&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Anna Maria Island Hotel Reviews ![Bridgewalk Resort](https://images.trvl-media.com/lodging/2000000/1050000/1045900/1045894/7186dbd7_y.jpg) ### Bridgewalk Resort 10/10 Excellent "Staff was very courteous .... the room was fantastic and the location was perfect! Looking at booking here again next year." 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