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) # Find Historic Hotels in Anna Maria Island, FL from CA $633 - ![](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 [Dec 21 - Dec 22](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-12-21&endDate=2025-12-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 22 - Dec 23](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-12-22&endDate=2025-12-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2026-01-02&endDate=2026-01-04&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) ![Exterior](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579361/50f9a3da.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 (36) "Location was perfect" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael S. CA $219 CA $633 total includes taxes & fees Jan 12 - Jan 13, 2026 [](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/b88de622.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) ### 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 (34) "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 $657 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Anna-Maria-Hotels-Anna-Maria-Beach-Cottage-109G-Old-Florida-Beach-Cottage.h70579354.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) ### Anna Maria Beach Cottage 109A -Charming beach cottage, pool, steps to the beach! [](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) "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 $237 CA $694 total includes taxes & fees Jan 13 - Jan 14, 2026 [](https://www.expedia.ca/Anna-Maria-Hotels-Anna-Maria-Beach-Cottage-109a-Old-Florida-Beach-Cottage.h70579352.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/102000000/101090000/101082500/101082466/0ffd1156.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/102000000/101090000/101082500/101082466/6c0970f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/102000000/101090000/101082500/101082466/e00a1d77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101090000/101082500/101082466/205d071f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cute Cottage Near Beach and Shops [](https://www.expedia.ca/Anna-Maria-Hotels-Welcome-To-Bikini-So-Tiny.h101082466.Hotel-Information) Anna Maria 10/10 Exceptional (4) "The place was great and as presented on the app. Having a designated parking space was very helpful. Close to many great restaurants, shops, the beach, etc. The north shore cafe and waterfront restaurant were both very good and very close in walking distance " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Justin B. CA $246 CA $796 total includes taxes & fees Jan 13 - Jan 14, 2026 [](https://www.expedia.ca/Anna-Maria-Hotels-Welcome-To-Bikini-So-Tiny.h101082466.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) ![Exterior](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579348/3443d572.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579348/e5ba197f.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 9.6/10 Exceptional (20) "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 $230 CA $676 total includes taxes & fees Jan 13 - Jan 14, 2026 [](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/71000000/70580000/70579400/70579349/40de95d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579349/aa613016.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) ![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) ### 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) "Enjoyed the property, pool, the closeness to the beach" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susane D. CA $228 CA $662 total includes taxes & fees Jan 6 - Jan 7, 2026 [](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/71000000/70580000/70579400/70579363/85dc8704.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579363/43d908e6.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) ![Outdoor dining](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579363/7ecf21b7.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) "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 $249 CA $709 total includes taxes & fees Jan 13 - Jan 14, 2026 [](https://www.expedia.ca/Anna-Maria-Hotels-Anna-Maria-Beach-Cottage-110G-Updated-Beach-Cottage.h70579363.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/63000000/63000000/62992200/62992152/54820e50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books](https://images.trvl-media.com/lodging/63000000/63000000/62992200/62992152/09e81533.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books](https://images.trvl-media.com/lodging/63000000/63000000/62992200/62992152/3d538ac7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/63000000/63000000/62992200/62992152/b18d8140.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Freshly Remodeled Island Suite w/ Pool & Pet Friendly [](https://www.expedia.ca/Anna-Maria-Hotels-Well-Appointed-Beach-Condo-With-Pool-Access.h62992152.Hotel-Information) Anna Maria 8.4/10 Very good (42) "Everything about the property was great, especially the location, which is walking distance away from restaurants and island shops." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ron H. CA $141 CA $467 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Anna-Maria-Hotels-Well-Appointed-Beach-Condo-With-Pool-Access.h62992152.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) ![Exterior](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579351/e17e2719.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) ![Interior](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579351/581411e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Adorable Cottage moments to beach w/ pool, beach gear, bikes [](https://www.expedia.ca/Anna-Maria-Hotels-Adorable-Cottage-Moments-To-Beach-W-Pool.h70579351.Hotel-Information) Anna Maria 9.8/10 Exceptional (14) "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 $353 CA $909 total includes taxes & fees Jan 13 - Jan 14, 2026 [](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) ![TV, DVD player](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579359/6d50f141.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) " 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 $300 CA $833 total includes taxes & fees Jan 13 - Jan 14, 2026 [](https://www.expedia.ca/Anna-Maria-Hotels-Anna-Maria-Beach-Cottage-110a-Old-Florida-Beach-Cottage-With-Modern-Amenities.h70579359.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=2026-01-05&endDate=2026-01-06®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 "The rooms are extremely nice and very clean. Every staff member that we encountered during our stay was super friendly. The location is perfect and within walking distance from just about anything you need. The beach is about 100 yards away from the location. We will definitely be back!!!" 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