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 ![](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 [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-10-14&endDate=2025-10-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-10-15&endDate=2025-10-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Anna Maria Island Historic Hotels ![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/ebba9faa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579361/933a3ccd.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 10/10 Exceptional (35) "Perfect, cutest cottage within steps of the beach." CA $250 CA $664 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Anna-Maria-Hotels-Anna-Maria-Beach-Cottage-110b-Updated-Studio-Beach-Cottage.h70579361.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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/74000000/73780000/73773600/73773534/17c42608.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/74000000/73780000/73773600/73773534/c0e9c959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dog friendly cottage - One block to the Bay! Anna Maria 9.4/10 Exceptional (8) "Check in and out process very easy!" CA $175 CA $449 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Anna-Maria-Hotels-Dog-Friendly-Cottage-One-Block-To-The-Bay.h73773534.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/95000000/94670000/94663700/94663686/1596962f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/95000000/94670000/94663700/94663686/6bef6cab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/95000000/94670000/94663700/94663686/5bf63d1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/95000000/94670000/94663700/94663686/d06bcc93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bo’s Beach Bungalow! Steps to Beach, Shops & Dining Anna Maria 8.6/10 Excellent (4) "Nice quiet area. About a block from beach! Short walk to Pine Ave with many restaurants and shops. House was nothing fancy but clean and comfortable. Had everything we needed. Only compliant was could use some more silverware. Hope it's available for us next year!" CA $127 CA $404 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Anna-Maria-Hotels-Adorable-Home-Near-The-Beach-Bos-Beach-Bungalow.h94663686.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/63000000/62990000/62982000/62981960/740dc148.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) ![Pool](https://images.trvl-media.com/lodging/63000000/62990000/62982000/62981960/627f1c1f.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) ### Freshly Remodeled Island Suite w/ Pool & Pet Friendly Anna Maria 9.2/10 Wonderful (56) "We absolutely enjoyed staying here and will be back. " [](https://www.expedia.ca/Anna-Maria-Hotels-Convenient-Condo-Near-The-Beach-WShared-Pool.h62981960.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579354/bc5a8235.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579354/b44b7d12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579354/ca968fa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand! Anna Maria 9.6/10 Exceptional (31) "Great location, cool little property and cabin. Perfect for a long weekend getaway!" CA $256 CA $690 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Anna-Maria-Hotels-Anna-Maria-Beach-Cottage-109G-Old-Florida-Beach-Cottage.h70579354.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/63000000/62990000/62981000/62980905/850c37da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/63000000/62990000/62981000/62980905/41159275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/63000000/62990000/62981000/62980905/e0fecaab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/63000000/62990000/62981000/62980905/b7beed72.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 (42) "Nice place for long weekend. Close to great restaurants and an easy walk to the beach." CA $162 CA $459 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Anna-Maria-Hotels-Budget-Friendly-Studio-WShared-Pool.h62980905.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/108000000/107130000/107121400/107121352/a444b7bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107130000/107121400/107121352/f13cfd30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/108000000/107130000/107121400/107121352/60795038.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107130000/107121400/107121352/e257f6f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Emerald Shores East! Walk to Beach! Anna Maria 9.6/10 Exceptional (4) "It was good " CA $196 CA $543 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Anna-Maria-Hotels-1-Min-To-Beach.h107121352.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/102000000/101090000/101082500/101082466/8d4b36ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101090000/101082500/101082466/9c50b6b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101090000/101082500/101082466/4f454277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cute Cottage Near Beach and Shops Anna Maria 10/10 Exceptional (2) "Beautiful home! So close to the beach, coffee, and shops. Will be back!" CA $227 CA $520 total includes taxes & fees Oct 15 - Oct 16 [](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/71000000/70580000/70579400/70579351/339be2ff.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) ![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) ![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) ### 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 $300 CA $832 total includes taxes & fees Oct 27 - Oct 28 [](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) ![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/71000000/70580000/70579400/70579348/380d9ac4.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 $256 CA $709 total includes taxes & fees Oct 18 - Oct 19 [](https://www.expedia.ca/Anna-Maria-Hotels-Anna-Maria-Beach-Cottage-107a-Old-Florida-Beach-Cottage.h70579348.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=2025-10-28&endDate=2025-10-29®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 "This resort is in a perfect location. Easy access to the beach, on-site pool, shopping, and dining. The staff is exceptional, from the front desk to the parking attendant. They are friendly, welcoming, informative and helpful. The rooms are spacious, clean, and stocked with all the essentials. We have stayed here many times and are never disappointed." [](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) - [All Inclusive Resorts and in Anna Maria](https://www.expedia.ca/Anna-Maria-Hotels-All-Inclusive-Hotel.0-0-d74028-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Anna Maria](https://www.expedia.ca/Anna-Maria-Hotels-Beach-Hotel.0-0-d74028-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Anna Maria](https://www.expedia.ca/Anna-Maria-Hotels-Boutique-Hotel.0-0-d74028-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - 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[Adults Only Resorts & in Orange Lake](https://www.expedia.ca/Orange-Lake-Orlando-Hotels-Adults-Only-Resorts.0-n553248635976473287-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in Orange Lake](https://www.expedia.ca/Orange-Lake-Orlando-Hotels-All-Inclusive-Hotel.0-n553248635976473287-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Orange Lake](https://www.expedia.ca/Orange-Lake-Orlando-Hotels-Beach-Hotel.0-n553248635976473287-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Orange Lake](https://www.expedia.ca/Orange-Lake-Orlando-Hotels-Couples-Resorts-Hotels.0-n553248635976473287-0-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Orange Lake](https://www.expedia.ca/Orange-Lake-Orlando-Hotels-Family-Hotel.0-n553248635976473287-0-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Golf Hotels in Orange Lake](https://www.expedia.ca/Orange-Lake-Orlando-Hotels-Golf-Hotel.0-n553248635976473287-0-tGolfHotel.Travel-Guide-Filter-Hotels) - [Hotels with a Lazy River in Orange Lake](https://www.expedia.ca/Orange-Lake-Orlando-Hotels-Hotels-With-A-Lazy-River.0-n553248635976473287-0-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels) - [Hotels with Free Airport Shuttle in Orange Lake](https://www.expedia.ca/Orange-Lake-Orlando-Hotels-Hotels-With-Free-Airport-Shuttle.0-n553248635976473287-0-tHotelswithFreeAirportShuttle.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in Orange Lake](https://www.expedia.ca/Orange-Lake-Orlando-Hotels-Hotels-With-Hot-Tubs.0-n553248635976473287-0-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Hotels with Waterslides in Orange Lake](https://www.expedia.ca/Orange-Lake-Orlando-Hotels-Hotels-With-Waterslides.0-n553248635976473287-0-tHotelswithWaterslides.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Orange Lake](https://www.expedia.ca/Orange-Lake-Orlando-Hotels-Luxury-Hotel.0-n553248635976473287-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Orange Lake](https://www.expedia.ca/Orange-Lake-Orlando-Hotels-Oceanfront-Hotels.0-n553248635976473287-0-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Orange Lake](https://www.expedia.ca/Orange-Lake-Orlando-Hotels-Pet-Friendly-Hotel.0-n553248635976473287-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Orange Lake](https://www.expedia.ca/Orange-Lake-Orlando-Hotels-Waterpark-Hotels.0-n553248635976473287-0-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Business Hotels in Sarasota](https://www.expedia.ca/Sarasota-Hotels-Business-Hotel.0-0-d602719-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Green Hotels in Sarasota](https://www.expedia.ca/Sarasota-Hotels-Green-Sustainable.0-0-d602719-tGreenSustainable.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Sarasota](https://www.expedia.ca/Sarasota-Hotels-Hotel-With-Pool.0-0-d602719-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with smoking rooms in Sarasota](https://www.expedia.ca/Sarasota-Hotels-Hotels-With-Smoking-Rooms.0-0-d602719-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels) - [Casino Hotels in St. Pete Beach](https://www.expedia.ca/St-Pete-Beach-Hotels-Casino-Hotel.0-0-d9802-tCasinoHotel.Travel-Guide-Filter-Hotels) - 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