Title: Book the Best Anna Maria Island Ski Hotels in 2025  | 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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# Find Ski Hotels in Anna Maria Island, FL

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## Check availability on Anna Maria Island Ski Hotels

Tonight

[Oct 29 - Oct 30](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-10-29&endDate=2025-10-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Oct 30 - Oct 31](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-10-30&endDate=2025-10-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

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Next weekend

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

## Top Anna Maria Island Ski Hotels

![Beach](https://images.trvl-media.com/lodging/23000000/22130000/22127600/22127530/w1400h930x0y3-50dc3034.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/23000000/22130000/22127600/22127530/c73b091a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/23000000/22130000/22127600/22127530/9f33c0cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/23000000/22130000/22127600/22127530/5ba3c4a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### August Ringling Room - Stay in a piece of Sarasota history - Downtown & Beaches

Central Sarasota

9.0/10

Wonderful

(15)

"Loved the atmosphere, books everywhere, coffee bar, live music, wine bar, and lack of pretentiousness."

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

Ann P.

CA $209

CA $315 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Sarasota-Hotels-August-Ringling-Room-Stay-In-A-Piece-Of-Sarasota-History-Downtown-Beaches.h22127530.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/25000000/24260000/24253100/24253065/bfa1f244.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/25000000/24260000/24253100/24253065/5d0c0eb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/25000000/24260000/24253100/24253065/3810f46f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/25000000/24260000/24253100/24253065/36d1ce5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tropical, private, downtown

Central Sarasota

9.6/10

Exceptional

(78)

"Place was perfect for our short stay! Great location, roomy enough for two adults and two small pups. Very cute inside, would stay here again! "

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

Stephanie L.

CA $70

CA $353 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Sarasota-Hotels-Very-Tropical.h24253065.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/20000000/19430000/19428500/19428409/2a095f61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/20000000/19430000/19428500/19428409/a61b3f38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/20000000/19430000/19428500/19428409/29047c22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/20000000/19430000/19428500/19428409/d8ef0648.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charles Ringling Room: 1 BR/1BA With Kitchen; 5 Mins. To Beach/Downtown

Central Sarasota

9.0/10

Wonderful

(20)

"I thought it would be close to museum"

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

Sally R.

CA $190

CA $321 total

includes taxes & fees

Oct 30 - Oct 31

[](https://www.expedia.ca/Sarasota-Hotels-Charles-Ringling-Room-1-Br1ba-With-Kitchen-5-Mins-To-Beachdowntown.h19428409.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84020000/84019300/84019299/45630ba2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/85000000/84020000/84019300/84019299/94895361.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84020000/84019300/84019299/bf781206.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/85000000/84020000/84019300/84019299/48f2bcc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Madeira Beach1 Waterfront & 2-3 minutes' Walk to the Beach

Madeira Beach

9.6/10

Exceptional

(10)

"It was a great place to stay and we will definately return."

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

Karen K.

CA $166

CA $454 total

includes taxes & fees

Oct 30 - Oct 31

[](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Madiera1-Waterfront-2-3-Minutes-Walktothe-Beach.h84019299.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/19000000/19000000/18994200/18994143/0ed55bbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/19000000/19000000/18994200/18994143/62fbdfe2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/19000000/19000000/18994200/18994143/d3d4460e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/19000000/19000000/18994200/18994143/32d395cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sunset Vistas Beach Front St. Pete Beach Treasure Island Clearwater Pool/parking

Sunshine Beach

9.6/10

Exceptional

(217)

"We had an amazing time here. It was clean and we had great views of the sunset every night. There were some beach chairs, toys, and towels already, so we did not have to go out and buy new ones. The owners were very responsive and kind. Would definitely come back. "

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

Sarah K.

CA $277

CA $627 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Sunset-Vistas-Direct-Beach-Front-Stpete-Beach-Treasure-Island-Clearwater.h18994143.Hotel-Information)

![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/19000000/19000000/18992200/18992190/0f584169.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/19000000/19000000/18992200/18992190/1810ba8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/19000000/18992200/18992190/b2962287.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/19000000/19000000/18992200/18992190/b82494bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sunset Vistas Beach Front St. Pete Beach Treasure Island Clearwater pool/parking

Sunshine Beach

9.8/10

Exceptional

(170)

"We enjoyed our stay very much. Only issues were low water pressure in bathroom sink and issues with the elevators. Look forward to staying again."

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

DAVID S.

CA $239

CA $583 total

includes taxes & fees

Nov 5 - Nov 6

[](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Beach-Condogreat-Views-Locationheated-Pooljacuzzigymfree-Parking-Wifi.h18992190.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/90000000/89260000/89253500/89253423/05147c5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89260000/89253500/89253423/da77e602.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/90000000/89260000/89253500/89253423/d9e8a6fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/90000000/89260000/89253500/89253423/21f6ac87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Serene Haven – Relax & Rejuvenate

North Kenwood

6.4/10

(8)

"Close to downtown. Lots of good restaurants and shopping near by"

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

DarShanna S.

CA $107

CA $336 total

includes taxes & fees

Oct 31 - Nov 1

[](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Tranquil-Retreat-Private-Entrance-Kitchen.h89253423.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111510000/111508300/111508293/15048a57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111510000/111508300/111508293/3f20a5ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/112000000/111510000/111508300/111508293/4690dc1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/112000000/111510000/111508300/111508293/140f8104.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pelicans Place | Your Family Beach Getaway Steps from Siesta Key Beach & Village

Siesta Key Village

9.6/10

Exceptional

(15)

"Great location! Cute little house with lots of potential. Needs some updating. Easy walk to everything. If you book bring a little speaker for the beach and a deck of cards. "

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

Myria K.

CA $805

CA $1,620 total

includes taxes & fees

Nov 29 - Nov 30

[](https://www.expedia.ca/Siesta-Key-Hotels-Pelicans-Place-Walk-To-Siesta-Key-Beach-Village.h111508293.Hotel-Information)

![Sun loungers, beach towels](https://images.trvl-media.com/lodging/24000000/23710000/23704300/23704256/w1400h930x0y3-b6294e57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/24000000/23710000/23704300/23704256/w1394h1044x3y3-7c7429e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/24000000/23710000/23704300/23704256/f2e8f222.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/24000000/23710000/23704300/23704256/ad905c49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Junior Suite - Large, 2 king beds, 1 private bath in great and historic location

Central Sarasota

9.4/10

Exceptional

(20)

"Great restaurant connected to the property. A bit noisy given the location next to Tamiami"

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

Dan

CA $209

CA $315 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Sarasota-Hotels-Otto-Ringling-Suite-Large.h23704256.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

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-   [Adults Only Resorts & in Orange Lake](https://www.expedia.ca/Orange-Lake-Orlando-Hotels-Adults-Only-Resorts.0-n553248635976473287-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels)
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