Title: Anna Maria Island Chalets from CA $616 | 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 $616 - ![](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 In two weeks [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2026-05-01&endDate=2026-05-03&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) ![Dining](https://images.trvl-media.com/lodging/104000000/103020000/103013100/103013017/f54100c8.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) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/104000000/103020000/103013100/103013017/871e0aac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Siesta Key Village [](https://www.expedia.ca/Siesta-Key-Hotels-Beach-Road-Condo-Private-Decks-Siesta-Key-Beach-Village-Walkability.h103013017.Hotel-Information) 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 $2,322 CA $2,824 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Siesta-Key-Hotels-Beach-Road-Condo-Private-Decks-Siesta-Key-Beach-Village-Walkability.h103013017.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) ![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) ![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) ### Chalet in Siesta Key Village [](https://www.expedia.ca/Siesta-Key-Hotels-Chalet-Condo-W-Private-Deck.h102825165.Hotel-Information) 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 $954 CA $1,201 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Siesta-Key-Hotels-Chalet-Condo-W-Private-Deck.h102825165.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825159/f57fc95e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825159/afe28a17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825159/e83df062.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825159/6f45b857.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Siesta Key Village [](https://www.expedia.ca/Siesta-Key-Hotels-Chalet.h102825159.Hotel-Information) CA $1,951 CA $2,465 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Siesta-Key-Hotels-Chalet.h102825159.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) ![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) ![1 bedroom, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825161/c3cf09ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Siesta Key Village [](https://www.expedia.ca/Siesta-Key-Hotels-Chalet-Style-Suite-Condo-Private-Deck-Siesta-Key-Village-Beach-Walkable.h102825161.Hotel-Information) 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 $494 CA $616 total includes taxes & fees Jan 22 - Jan 23 [](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=2026-01-22&endDate=2026-01-23®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 ![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 "Amazing location! Clean and well kept! Adding a microwave and black out curtains would be a bonus because the room isnt dark at night due to the spot light above the door! " [](https://expedia.ca/Sarasota-Hotels-Pelican-Post.h67676083.Hotel-Information) ![Tortuga Inn Beach Resort](https://images.trvl-media.com/lodging/2000000/1060000/1054200/1054101/b1d10d73_y.jpg) ### Tortuga Inn Beach Resort 10/10 Excellent "Kitchen is fully functional, great for family get together" [](https://expedia.ca/Sarasota-Hotels-Tortuga-Inn-Beach-Resort.h1054101.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 "Great place , friendly staff! " [](https://expedia.ca/Sarasota-Hotels-Silver-Surf-Gulf-Beach-Resort.h1045895.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 "Excellent location, close to the beach." [](https://expedia.ca/Bradenton-Beach-Hotels-The-Retreat-At-Anna-Maria-Island-Inn.h83500895.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 "So we just need a bar!" [](https://expedia.ca/Holmes-Beach-Hotels-Anna-Maria-Beach-Resort.h73250924.Hotel-Information) ![Bridgewalk Resort](https://images.trvl-media.com/lodging/2000000/1050000/1045900/1045894/7186dbd7_y.jpg) ### Bridgewalk Resort 10/10 Excellent "The staff was very courteous, friendly and helpful." [](https://expedia.ca/Sarasota-Hotels-Bridgewalk-A-Landmark-Resort.h1045894.Hotel-Information) ![Bali Hai Beachfront Resort and Spa](https://images.trvl-media.com/lodging/37000000/36290000/36286200/36286167/5084dcca_y.jpg) ### Bali Hai Beachfront Resort and Spa 10/10 Excellent "Absolutely fantastic property. We absolutely loved our stay. Will be back for sure! " [](https://expedia.ca/Sarasota-Hotels-Bali-Hai-Beach-Resort.h36286167.Hotel-Information) ![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 "The room is beautiful! Brand new room with a cute ocean vibe. We got a ocean view with was really nice, but no microwave.. " [](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 "This is a nice room very close to the beach. It has a large pool, room is good size, great bed, and quiet. They provide beach chairs and parking. We arrived early and were able to enjoy the beach until our room was ready. The coffee I. The room was very good. I would recommend staying here. We also walked to many restaurants. And if you like walking/ running on the beach, it is the ideal spot. " [](https://expedia.ca/Sarasota-Hotels-Captains-Quarters-By-AMI-Locals.h59789467.Hotel-Information) ## Find out more about Anna Maria Island ## Anna Maria Island Chalets information | Number of reviews | 7 | | ----------------- | --------- | | Accommodation | 0 Chalets | | Lowest Price | CA $616 | | Highest Price | CA $2,824 | ## 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) - [B&B in Anna Maria ](https://www.expedia.ca/Anna-Maria-Bed-And-Breakfast.d74028-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Anna Maria ](https://www.expedia.ca/Anna-Maria-Chalets.d74028-aaChalets.Travel-Guide-Accommodation) - [Cottages in Anna Maria ](https://www.expedia.ca/Anna-Maria-Cottages.d74028-aaCottages.Travel-Guide-Accommodation) - 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