Title: Anna Maria Island Chalets from CA $1,112 | 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) # Search Chalets in Anna Maria Island from CA $1,112 - ![](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 prices for these dates Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Anna Maria Island chalets ![Outdoor dining](https://images.trvl-media.com/lodging/104000000/103020000/103013100/103013017/9688cc9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103020000/103013100/103013017/64afde33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103020000/103013100/103013017/8886e179.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/104000000/103020000/103013100/103013017/f54100c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr & Studio [](https://www.expedia.ca/Siesta-Key-Hotels-Beach-Road-Condo-Private-Decks-Siesta-Key-Beach-Village-Walkability.h103013017.Hotel-Information) Siesta Key Village 10/10 Exceptional (2) "Location was terrific! Beach access was across the street and it was a short walk to restaurants and bars. Great set up for a family stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bobbi M. CA $2,743 CA $3,458 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Siesta-Key-Hotels-Beach-Road-Condo-Private-Decks-Siesta-Key-Beach-Village-Walkability.h103013017.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103070000/103064100/103064024/58a17c5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/104000000/103070000/103064100/103064024/62480ed5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103070000/103064100/103064024/93266b43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, video library, stereo](https://images.trvl-media.com/lodging/104000000/103070000/103064100/103064024/ae608647.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr [](https://www.expedia.ca/Siesta-Key-Hotels-Beach-Chalet-Deck-Siesta-Key-Village-And-Beach-Walkable.h103064024.Hotel-Information) Siesta Key Village 10/10 Exceptional (5) "We had a great time at Siesta key and this house was fantastic! Super easy check in/out, very clean, loves the beach chairs and umbrella - great touch!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy L. CA $918 CA $1,157 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Siesta-Key-Hotels-Beach-Chalet-Deck-Siesta-Key-Village-And-Beach-Walkable.h103064024.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825165/w1276h854x4y0-631b5ac3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825165/b95c27ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, video library, stereo](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825165/57f450d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825165/f18ae96f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr [](https://www.expedia.ca/Siesta-Key-Hotels-Chalet-Condo-W-Private-Deck.h102825165.Hotel-Information) Siesta Key Village 9.6/10 Exceptional (5) "Owner provided all the beach items and the place was clean and well kept." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John P. CA $899 CA $1,112 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Siesta-Key-Hotels-Chalet-Condo-W-Private-Deck.h102825165.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825161/da3b1cb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825161/b8314b80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825161/5a5c4e91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825161/8a02dc58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, Studio [](https://www.expedia.ca/Siesta-Key-Hotels-Chalet-Style-Suite-Condo-Private-Deck-Siesta-Key-Village-Beach-Walkable.h102825161.Hotel-Information) Siesta Key Village 6.0/10 (1) "Price point was really high for what you get. Small Great location! no ocean view Great communication uncomfortable bed fridge froze some of produce trees overgrown all over electrical wires within inches of the balcony very dangerous unsecure wifi unless reached out to " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason B. CA $524 CA $664 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Siesta-Key-Hotels-Chalet-Style-Suite-Condo-Private-Deck-Siesta-Key-Village-Beach-Walkable.h102825161.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&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FAnna-Maria-Island-Chalets.d553248622847118534-aaChalets.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FAnna-Maria-Island-Chalets.d553248622847118534-aaChalets.Travel-Guide-Accommodation) ## Top Anna Maria Island Hotel Reviews ![Seabreeze at Anna Maria Island Inn](https://images.trvl-media.com/lodging/17000000/16010000/16001900/16001812/a71dc126_y.jpg) ### Seabreeze at Anna Maria Island Inn 10/10 Excellent "Very easy and accommodating! Would definitely book again." [](https://expedia.ca/Sarasota-Hotels-Anna-Maria-Island-Inn.h16001812.Hotel-Information) ![Captain's Quarters at Anna Maria Island Inn](https://images.trvl-media.com/lodging/60000000/59790000/59789500/59789467/651a8200_y.jpg) ### Captain's Quarters at Anna Maria Island Inn 10/10 Excellent "Clean rooms only thing we missed not having was a microwave " [](https://expedia.ca/Sarasota-Hotels-Captains-Quarters-By-AMI-Locals.h59789467.Hotel-Information) ![Pelican Post at Anna Maria Island Inn](https://images.trvl-media.com/lodging/68000000/67680000/67676100/67676083/4174e2ab_y.jpg) ### Pelican Post at Anna Maria Island Inn 10/10 Excellent "Spotless and tidy " [](https://expedia.ca/Sarasota-Hotels-Pelican-Post.h67676083.Hotel-Information) ![Haley's at The Anna Maria Island Inn](https://images.trvl-media.com/lodging/1000000/900000/897700/897646/fc900ac2_y.jpg) ### Haley's at The Anna Maria Island Inn 10/10 Excellent "Had a wonderful stay at Hayley’s! The property was clean and modern looking. The staff was extremely kind. The location was great with a short 5 minute walk to the beach. Hope to be back!" [](https://expedia.ca/Sarasota-Hotels-Haleys-Couples-Retreat.h897646.Hotel-Information) ![Silver Surf Gulf Beach Resort](https://images.trvl-media.com/lodging/2000000/1050000/1045900/1045895/12fa4f1f_y.jpg) ### Silver Surf Gulf Beach Resort 10/10 Excellent "Clean room, nice staff, Christian based boutique, proximity to beach. Would definitely stay there again " [](https://expedia.ca/Sarasota-Hotels-Silver-Surf-Gulf-Beach-Resort.h1045895.Hotel-Information) ![Steps from Beach and Local Hotspots! Stay at Sunny Side Down!](https://images.trvl-media.com/lodging/109000000/108600000/108598400/108598339/w1277h849x3y3-a3c2a21c_y.jpg) ### Steps from Beach and Local Hotspots! Stay at Sunny Side Down! 10/10 Excellent "It was the first time for me. Everything was perfect. Location, communication, house in great condition and clean. I would do it again. Thank you" [](https://expedia.ca/Bradenton-Beach-Hotels-Steps-From-Beach-Trolley-To-Local-Hotspots-Stay-At-Sunny-Side-Down.h108598339.Hotel-Information) ![Anna Maria Beach Resort](https://images.trvl-media.com/lodging/74000000/73260000/73251000/73250924/aebd1d61_y.jpg) ### Anna Maria Beach Resort 10/10 Excellent "Loves it!! Every room has a gorgeous ocean view! " [](https://expedia.ca/Holmes-Beach-Hotels-Anna-Maria-Beach-Resort.h73250924.Hotel-Information) ![Anna Maria Sunsets - studio](https://images.trvl-media.com/lodging/40000000/39530000/39524600/39524590/c7ceb92e_y.jpg) ### Anna Maria Sunsets - studio 10/10 Excellent "I unfortunately did not get a chance to stay here as our plans changed. But the host was great and very communicative during all our interactions. He had many details and helpful tips had we stayed. Maybe one day we can make it there and stay in this studio. " [](https://expedia.ca/Sarasota-Hotels-Anna-Maria-Sunsets-Studio.h39524590.Hotel-Information) ![The Retreat at Anna Maria Island Inn](https://images.trvl-media.com/lodging/84000000/83510000/83500900/83500895/0ce71205_y.jpg) ### The Retreat at Anna Maria Island Inn 10/10 Excellent "Great Location Great staff Awesome accommodations Ill be back .......asap" [](https://expedia.ca/Bradenton-Beach-Hotels-The-Retreat-At-Anna-Maria-Island-Inn.h83500895.Hotel-Information) ## Find out more about Anna Maria Island ## Anna Maria Island Chalets information | Number of reviews | 12 | | ----------------- | --------- | | Accommodation | 0 Chalets | | Lowest Price | CA $1,112 | | Highest Price | CA $1,157 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Farmstay in Anna Maria ](https://www.expedia.ca/Anna-Maria-Agritourism.d74028-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Anna Maria ](https://www.expedia.ca/Anna-Maria-Apart-Hotels.d74028-aaApartHotels.Travel-Guide-Accommodation) - 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