Title: Anna Maria Island Chalets  | 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)

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## Check prices for these dates

Next weekend

[Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select 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/104000000/103020000/103013100/103013017/8886e179.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 nearby](https://images.trvl-media.com/lodging/104000000/103020000/103013100/103013017/871e0aac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr & Studio

Siesta Key Village

10/10

Exceptional

(2)

"Property was well taken care of. Extras like coffee, shampoo, soaps, laundry, dishwasher, etc. was unexpected and very welcomed. Nice location and walk to beach was key to our stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Shellie K.

CA $1,729

CA $2,173 total

includes taxes & fees

Nov 4 - Nov 5

[](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/103000000/102830000/102825200/102825157/ab65f2ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825157/2efed104.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)

### Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, Studio

Siesta Key Village

9.8/10

Exceptional

(6)

"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 $792

CA $1,001 total

includes taxes & fees

Nov 22 - Nov 23

[](https://www.expedia.ca/Siesta-Key-Hotels-Chalet-Condo-Private-Deck-Ocean-View-Siesta-Key-Village-Beach-Walkable.h102825157.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825148/2e42fdb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825148/264c0268.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825148/411f9096.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825148/ff67d976.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, Studio

Siesta Key Village

8.0/10

Very good

(4)

"Great location"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sarah H.

CA $599

CA $753 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Siesta-Key-Hotels-Beach-Road-Condo-Private-Deck-Siesta-Key-Village-Beach-Walkable.h102825148.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)

![In-room safe, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825161/c3cf09ab.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 Rd, 300ft to Beach Access & 500ft to Siesta Key Village, Studio

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 $898

CA $1,129 total

includes taxes & fees

Nov 8 - Nov 9

[](https://www.expedia.ca/Siesta-Key-Hotels-Chalet-Style-Suite-Condo-Private-Deck-Siesta-Key-Village-Beach-Walkable.h102825161.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)

![Beach nearby](https://images.trvl-media.com/lodging/103000000/102830000/102825200/102825159/6f45b857.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 Rd, 300ft to Beach Access & 500ft to Siesta Key Village, 2bdr & Studio

Siesta Key Village

CA $1,947

CA $2,462 total

includes taxes & fees

Nov 15 - Nov 16

[](https://www.expedia.ca/Siesta-Key-Hotels-Chalet.h102825159.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.

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## Top Anna Maria Island Hotel Reviews

![Tortuga Inn Beach Resort](//images.trvl-media.com/lodging/2000000/1060000/1054200/1054101/b1d10d73_y.jpg)

### Tortuga Inn Beach Resort

10/10 Excellent

"Front office staff were very friendly and the place was very clean."

[](https://expedia.ca/Sarasota-Hotels-Tortuga-Inn-Beach-Resort.h1054101.Hotel-Information)

![The Retreat at Anna Maria Island Inn](//images.trvl-media.com/lodging/84000000/83510000/83500900/83500895/0ce71205_y.jpg)

### The Retreat at Anna Maria Island Inn

10/10 Excellent

"Beautiful room, convenient location, and excellent service! "

[](https://expedia.ca/Bradenton-Beach-Hotels-The-Retreat-At-Anna-Maria-Island-Inn.h83500895.Hotel-Information)

![Pelican Post at Anna Maria Island Inn](//images.trvl-media.com/lodging/68000000/67680000/67676100/67676083/4174e2ab_y.jpg)

### Pelican Post at Anna Maria Island Inn

10/10 Excellent

"Was perfect and safe. Walking distance to everything. "

[](https://expedia.ca/Sarasota-Hotels-Pelican-Post.h67676083.Hotel-Information)

![Bali Hai Beachfront Resort and Spa](//images.trvl-media.com/lodging/37000000/36290000/36286200/36286167/5084dcca_y.jpg)

### Bali Hai Beachfront Resort and Spa

10/10 Excellent

"Easy parking (even go golf carts!) Perfect location, and staff was super helpful and accommodating "

[](https://expedia.ca/Sarasota-Hotels-Bali-Hai-Beach-Resort.h36286167.Hotel-Information)

![Silver Surf Gulf Beach Resort](//images.trvl-media.com/lodging/2000000/1050000/1045900/1045895/12fa4f1f_y.jpg)

### Silver Surf Gulf Beach Resort

10/10 Excellent

"Love the Silver Surf! Friendly staff, spacious clean rooms, and beautiful beach. We stay there every time we go to AMI!"

[](https://expedia.ca/Sarasota-Hotels-Silver-Surf-Gulf-Beach-Resort.h1045895.Hotel-Information)

![Haley's at The Anna Maria Island Inn](//images.trvl-media.com/lodging/1000000/900000/897700/897646/fc900ac2_y.jpg)

### Haley's at The Anna Maria Island Inn

10/10 Excellent

"This was our 1st time in Anna Maria. It was a nice little beach town. The hotel was all renovated and really nice! Great location to everything. Easy walk down to the beach, and restaurants and shops super close as well. We enjoyed our stay here and would definitely come back! 😊 "

[](https://expedia.ca/Sarasota-Hotels-Haleys-Couples-Retreat.h897646.Hotel-Information)

![Anna Maria Beach Resort](//images.trvl-media.com/lodging/74000000/73260000/73251000/73250924/aebd1d61_y.jpg)

### Anna Maria Beach Resort

10/10 Excellent

"Theres not one thing i did mot like except the coffee maker was terrible defintely need an upgrade coffee not espresso "

[](https://expedia.ca/Holmes-Beach-Hotels-Anna-Maria-Beach-Resort.h73250924.Hotel-Information)

![Cedar Cove Resort and Cottages](//images.trvl-media.com/lodging/9000000/8100000/8099700/8099611/7751c173_y.jpg)

### Cedar Cove Resort and Cottages

10/10 Excellent

"Best view of the sunset from the room/balcony. Steps away from the beach."

[](https://expedia.ca/Sarasota-Hotels-Cedar-Cove-Resort-And-Cottages.h8099611.Hotel-Information)

![Seabreeze at Anna Maria Island Inn](//images.trvl-media.com/lodging/17000000/16010000/16001900/16001812/a71dc126_y.jpg)

### Seabreeze at Anna Maria Island Inn

10/10 Excellent

"Family friendly"

[](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 | |
| --- | --- |
| Accommodation | Chalets |
| Lowest Price | |
| Highest Price | |

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-   [Book Chalets in Anna Maria Island on Expedia.com](https://www.expedia.com/Anna-Maria-Island-Chalets.d553248622847118534-aaChalets.Travel-Guide-Accommodation)