Title: Anna Maria Island Chalets from CA $858 | 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 prices for these dates In two weeks [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) In two months [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2026-05-22&endDate=2026-05-24&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/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) ![Dining](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825165/8a17245f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825165/64964fce.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 reviews) "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 $1,113 CA $1,417 total includes taxes & fees Feb 17 - Feb 18 [](https://www.expedia.ca/Siesta-Key-Hotels-Chalet-Condo-W-Private-Deck.h102825165.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825157/ab65f2ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825157/1221cc56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825157/43e30509.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825157/dddbac26.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-Condo-Private-Deck-Ocean-View-Siesta-Key-Village-Beach-Walkable.h102825157.Hotel-Information) Siesta Key Village 9.6/10 Exceptional (8 reviews) "Great location to beach, food and entertainment. All within walking distance. Unit was like home aeay from home." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda CA $674 CA $858 total includes taxes & fees Feb 23 - Feb 24 [](https://www.expedia.ca/Siesta-Key-Hotels-Chalet-Condo-Private-Deck-Ocean-View-Siesta-Key-Village-Beach-Walkable.h102825157.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) ![Interior](https://images.trvl-media.com/lodging/104000000/103070000/103064100/103064024/0d39daa6.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) ### 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 reviews) "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 $1,039 CA $1,322 total includes taxes & fees Feb 12 - Feb 13 [](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/103000000/102830000/102825200/102825143/437a5498.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825143/05b64e04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825143/d7d1972f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, video library, stereo](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825143/093d2125.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-Style-Private-Deck-Condo.h102825143.Hotel-Information) Siesta Key Village 9.4/10 Exceptional (6 reviews) "All the beach items were available for use , the room was clean , the staff was amazing, definitely will stay again . " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angie CA $1,123 CA $1,430 total includes taxes & fees Feb 23 - Feb 24 [](https://www.expedia.ca/Siesta-Key-Hotels-Chalet-Style-Private-Deck-Condo.h102825143.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825161/0bafc1eb.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/103000000/102830000/102825200/102825161/1d9838e2.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/c1f504ee.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 review) "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 $742 CA $945 total includes taxes & fees Feb 21 - Feb 22 [](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=2026-02-14&endDate=2026-02-15®ionId=553248622847118534&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Anna+Maria+Island%2C+Florida%2C+United+States+of+America®ionId=553248622847118534&latLong=27.504126%2C-82.714477&adults=2&startDate=2026-05-01&d1=2026-05-01&endDate=2026-05-04&d2=2026-05-04&lodging=VACATION_HOME) Condos [](https://www.expedia.ca/Hotel-Search?destination=Anna+Maria+Island%2C+Florida%2C+United+States+of+America®ionId=553248622847118534&latLong=27.504126%2C-82.714477&adults=2&startDate=2026-05-01&d1=2026-05-01&endDate=2026-05-04&d2=2026-05-04&lodging=CONDO) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Anna+Maria+Island%2C+Florida%2C+United+States+of+America®ionId=553248622847118534&latLong=27.504126%2C-82.714477&adults=2&startDate=2026-05-01&d1=2026-05-01&endDate=2026-05-04&d2=2026-05-04&lodging=APART_HOTEL) Villas [](https://www.expedia.ca/Hotel-Search?destination=Anna+Maria+Island%2C+Florida%2C+United+States+of+America®ionId=553248622847118534&latLong=27.504126%2C-82.714477&adults=2&startDate=2026-05-01&d1=2026-05-01&endDate=2026-05-04&d2=2026-05-04&lodging=VILLA) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Anna+Maria+Island%2C+Florida%2C+United+States+of+America®ionId=553248622847118534&latLong=27.504126%2C-82.714477&adults=2&startDate=2026-05-01&d1=2026-05-01&endDate=2026-05-04&d2=2026-05-04&lodging=APARTMENT) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Anna+Maria+Island%2C+Florida%2C+United+States+of+America®ionId=553248622847118534&latLong=27.504126%2C-82.714477&adults=2&startDate=2026-05-01&d1=2026-05-01&endDate=2026-05-04&d2=2026-05-04&lodging=COTTAGE) Houseboats [](https://www.expedia.ca/Hotel-Search?destination=Anna+Maria+Island%2C+Florida%2C+United+States+of+America®ionId=553248622847118534&latLong=27.504126%2C-82.714477&adults=2&startDate=2026-05-01&d1=2026-05-01&endDate=2026-05-04&d2=2026-05-04&lodging=HOUSE_BOAT) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Anna+Maria+Island%2C+Florida%2C+United+States+of+America®ionId=553248622847118534&latLong=27.504126%2C-82.714477&adults=2&startDate=2026-05-01&d1=2026-05-01&endDate=2026-05-04&d2=2026-05-04&lodging=CABIN) Residences [](https://www.expedia.ca/Hotel-Search?destination=Anna+Maria+Island%2C+Florida%2C+United+States+of+America®ionId=553248622847118534&latLong=27.504126%2C-82.714477&adults=2&startDate=2026-05-01&d1=2026-05-01&endDate=2026-05-04&d2=2026-05-04&lodging=RESIDENCE) ![](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 ![Anna Maria Beach Resort](https://images.trvl-media.com/lodging/74000000/73260000/73251000/73250924/aebd1d61_y.jpg) ### Anna Maria Beach Resort 10/10 Excellent "We love Jose! He was so kind to us. " [](https://expedia.ca/Holmes-Beach-Hotels-Anna-Maria-Beach-Resort.h73250924.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 "Great location, very clean, huge shower, beautiful heated pool. We just wish it was warmer to enjoy the beach and pool, bad timing on our part. We will definitely come again." [](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 "The area is wonderful, full of character and charm, the place itself is even better, lovely pool surrounded by a handful of cottages. The room was everything we wanted. Thank you - we will definitely visit again " [](https://expedia.ca/Sarasota-Hotels-Pelican-Post.h67676083.Hotel-Information) ![Bridgewalk Resort](https://images.trvl-media.com/lodging/2000000/1050000/1045900/1045894/7186dbd7_y.jpg) ### Bridgewalk Resort 10/10 Excellent "Staff were exceptionally friendly, rooms were super clean. Updated rooms. Great location." [](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 "We loved it here!! Defiantly would come back in the future" [](https://expedia.ca/Sarasota-Hotels-Bali-Hai-Beach-Resort.h36286167.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 "Super friendly staff, check in a breeze, maid service was excellent and the whole place was outstanding " [](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 "The Anna Maria Inn was a great location and property was clean and nice! The only few things we need to change is the outside lights are very bright inside the room all night, new coffee maker and a microwave! " [](https://expedia.ca/Bradenton-Beach-Hotels-The-Retreat-At-Anna-Maria-Island-Inn.h83500895.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 "Great location, super friendly staff, and were more than happy to put a bottle of champagne in our room before arrival! " [](https://expedia.ca/Sarasota-Hotels-Haleys-Couples-Retreat.h897646.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 "We had an excellent time. We were not happy with the room we booked since it did not have an ocean view. The staff were very helpful in upgrading us to a room with an ocean view. We did have to pay more, but it was worth it " [](https://expedia.ca/Sarasota-Hotels-Anna-Maria-Island-Inn.h16001812.Hotel-Information) ## Find out more about Anna Maria Island ## Anna Maria Island Chalets information | Number of reviews | 23 | | ----------------- | --------- | | Accommodation | 0 Chalets | | Lowest Price | CA $858 | | Highest Price | CA $1,430 | ## 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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