Title: Anna Maria Island Chalets from CA $765 | 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 [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two 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 three 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) In four months [Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2026-06-19&endDate=2026-06-21&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/103000000/102830000/102825200/102825143/437a5498.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) ![Smart TV, books, video library, stereo](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825143/b4f464c9.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) ### Chalet in Siesta Key Village [](https://www.expedia.ca/Siesta-Key-Hotels-Chalet-Style-Private-Deck-Condo.h102825143.Hotel-Information) 9.6/10 Exceptional (7 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 $1,357 CA $1,726 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Siesta-Key-Hotels-Chalet-Style-Private-Deck-Condo.h102825143.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) ![1 bedroom, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825157/107e4072.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 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) ### Chalet in Siesta Key Village [](https://www.expedia.ca/Siesta-Key-Hotels-Chalet-Condo-Private-Deck-Ocean-View-Siesta-Key-Village-Beach-Walkable.h102825157.Hotel-Information) 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 $678 CA $864 total includes taxes & fees Mar 7 - Mar 8 [](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) ![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) ![Interior](https://images.trvl-media.com/lodging/104000000/103070000/103064100/103064024/0d39daa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Siesta Key Village [](https://www.expedia.ca/Siesta-Key-Hotels-Beach-Chalet-Deck-Siesta-Key-Village-And-Beach-Walkable.h103064024.Hotel-Information) 10/10 Exceptional (6 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 $1,507 CA $1,918 total includes taxes & fees Mar 27 - Mar 28 [](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) ![Smart TV, books, video library, stereo](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825165/f9ae06d8.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) ![Dining](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825165/8a17245f.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 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 $1,357 CA $1,726 total includes taxes & fees Mar 13 - Mar 14 [](https://www.expedia.ca/Siesta-Key-Hotels-Chalet-Condo-W-Private-Deck.h102825165.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825161/0bafc1eb.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) ![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/103000000/102830000/102825200/102825161/8a02dc58.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 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 $603 CA $765 total includes taxes & fees Feb 26 - Feb 27 [](https://www.expedia.ca/Siesta-Key-Hotels-Chalet-Style-Suite-Condo-Private-Deck-Siesta-Key-Village-Beach-Walkable.h102825161.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103070000/103064100/103064031/f2036189.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, video library, stereo](https://images.trvl-media.com/lodging/104000000/103070000/103064100/103064031/8f479638.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103070000/103064100/103064031/d38e01b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103070000/103064100/103064031/e592d4a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Siesta Key Village [](https://www.expedia.ca/Siesta-Key-Hotels-Beach-Chalet-Condo-Ocean-View-Siesta-Key-Beach-Village-Walkability.h103064031.Hotel-Information) CA $2,110 CA $2,685 total includes taxes & fees Mar 27 - Mar 28 [](https://www.expedia.ca/Siesta-Key-Hotels-Beach-Chalet-Condo-Ocean-View-Siesta-Key-Beach-Village-Walkability.h103064031.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=2026-03-11&endDate=2026-03-12®ionId=553248622847118534&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AA_SPRING_PROMO_553248622847118534) ## 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=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=VACATION_HOME) 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=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=APART_HOTEL) 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=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=CONDO) 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=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&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=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&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=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&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=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&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=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&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=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&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 "Room was great, location was great, pool area was very clean and well kept, access to the beach was the icing on the cake. Highly recommend this resort." [](https://expedia.ca/Holmes-Beach-Hotels-Anna-Maria-Beach-Resort.h73250924.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 "Great location to restaurants, shops and the beach! Pool was a great plus and the rooms were very clean! Overall great stay and definitely would return!" [](https://expedia.ca/Sarasota-Hotels-Pelican-Post.h67676083.Hotel-Information) ![Driftwood at Anna Maria Island Inn](https://images.trvl-media.com/lodging/95000000/95000000/94993900/94993833/288b4afd_y.jpg) ### Driftwood at Anna Maria Island Inn 10/10 Excellent "Great little place!" [](https://expedia.ca/Holmes-Beach-Hotels-Driftwood-At-Anna-Maria-Island-Inn.h94993833.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 "Everything was perfect." [](https://expedia.ca/Sarasota-Hotels-Tortuga-Inn-Beach-Resort.h1054101.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 "Spacious suite with lovely balcony for coffee in the morning. Kitchenette that we didn’t end up using much because there are so many great places to eat within walking distance or a short bike or car rideFriendly staff, great location. Loved everything about this hotel. " [](https://expedia.ca/Sarasota-Hotels-Bali-Hai-Beach-Resort.h36286167.Hotel-Information) ![Bridgewalk Resort](https://images.trvl-media.com/lodging/2000000/1050000/1045900/1045894/7186dbd7_y.jpg) ### Bridgewalk Resort 10/10 Excellent "Yes Everyone did a great job. " [](https://expedia.ca/Sarasota-Hotels-Bridgewalk-A-Landmark-Resort.h1045894.Hotel-Information) ![Alamanda Villas](https://images.trvl-media.com/lodging/121000000/120120000/120114200/120114144/c4463db9_y.jpg) ### Alamanda Villas 10/10 Excellent "Very clean and the perfect location! Close to the beach, restaurants, and the grocery! We loved the heated pool in February. " [](https://expedia.ca/Holmes-Beach-Hotels-Alamanda-Villas.h120114144.Hotel-Information) ![Cedar Cove Resort and Cottages](https://images.trvl-media.com/lodging/9000000/8100000/8099700/8099611/0a89d66d_y.jpg) ### Cedar Cove Resort and Cottages 10/10 Excellent "Perfect spot in a sleepy beach town." [](https://expedia.ca/Sarasota-Hotels-Cedar-Cove-Resort-And-Cottages.h8099611.Hotel-Information) ![Seaside at Anna Maria Island Inn](https://images.trvl-media.com/lodging/36000000/35620000/35615900/35615805/2e87b391_y.jpg) ### Seaside at Anna Maria Island Inn 10/10 Excellent "Un lugar maravilloso que invita a disfrutar " [](https://expedia.ca/Sarasota-Hotels-Seaside-Inn.h35615805.Hotel-Information) ## Find out more about Anna Maria Island ## Anna Maria Island Chalets information | Number of reviews | 27 | | ----------------- | --------- | | Accommodation | 0 Chalets | | Lowest Price | CA $765 | | Highest Price | CA $2,685 | ## 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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