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 3 - Oct 4](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-10-03&endDate=2025-10-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Oct 4 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-10-04&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top Anna Maria Island Ski Hotels

![Exterior](https://images.trvl-media.com/lodging/25000000/24260000/24253100/24253065/bfa1f244.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)

![Miscellaneous](https://images.trvl-media.com/lodging/25000000/24260000/24253100/24253065/ea0f25fc.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)

### Tropical, private, downtown

Central Sarasota

9.6/10

Exceptional

(78)

"Clean, relaxing setting in a quaint neighborhood a short walk to downtown. "

CA $103

CA $392 total

includes taxes & fees

Oct 4 - Oct 5

[](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)

![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)

![Interior](https://images.trvl-media.com/lodging/20000000/19430000/19428500/19428409/29047c22.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)

### 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"

CA $180

CA $307 total

includes taxes & fees

Oct 6 - Oct 7

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

![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)

![Coffee and/or coffee maker](https://images.trvl-media.com/lodging/23000000/22130000/22127600/22127530/57eba4a1.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)

### 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."

CA $209

CA $315 total

includes taxes & fees

Oct 7 - Oct 8

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

CA $163

CA $455 total

includes taxes & fees

Oct 6 - Oct 7

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

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

![On the beach](https://images.trvl-media.com/lodging/69000000/68860000/68854500/68854454/493f5d42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/69000000/68860000/68854500/68854454/7ee305d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/69000000/68860000/68854500/68854454/25975003.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/69000000/68860000/68854500/68854454/e09f8ca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tropic Terrace Suite #4 - Beachfront Resort

Sunshine Beach

8.2/10

Very good

(12)

"Such a quiet place! We loved the access to walk down the beachfront on concrete on the beach side. We never once heard anyone outside of our space. Great place to go!!"

CA $321

CA $551 total

includes taxes & fees

Oct 4 - Oct 5

[](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Tropic-Terrace-Suite-4-Beachfront-Rental.h68854454.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)

![Marina](https://images.trvl-media.com/lodging/112000000/111510000/111508300/111508293/e2fa7ec7_edited_42cc.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)

![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111510000/111508300/111508293/3f20a5ed.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

(14)

"Great Location, convenient to beach and restaurants & shopping.. never drove anywhere in our time at Siesta Key!!"

CA $758

CA $1,590 total

includes taxes & fees

Oct 8 - Oct 9

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

![Marina](https://images.trvl-media.com/lodging/60000000/59660000/59652000/59651908/a763e703.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/60000000/59660000/59652000/59651908/650966d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/60000000/59660000/59652000/59651908/76228675.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/60000000/59660000/59652000/59651908/0abb609f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tropic Terrace Suite #48 - Beachfront Resort

Sunshine Beach

8.6/10

Excellent

(11)

"Lovely place to stay, very close to the endless sandy beach, loved the Boardwalk!"

CA $260

CA $472 total

includes taxes & fees

Oct 5 - Oct 6

[](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Tropic-Terrace-48-Beachfront-Rental.h59651908.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)

![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)

![Exterior](https://images.trvl-media.com/lodging/19000000/19000000/18992200/18992190/1810ba8a.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 had a great experience at the home in Broadkill! This was amazing for walks on the beach and easy access to many attractions. "

CA $251

CA $601 total

includes taxes & fees

Oct 10 - Oct 11

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

![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)

![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)

![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"

CA $209

CA $314 total

includes taxes & fees

Oct 6 - Oct 7

[](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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-17&endDate=2025-10-18&regionId=553248622847118534&adults=2&location_highlights_explore=ski&sort=RECOMMENDED&openPlayBack=true)

## Top Anna Maria Island Hotel Reviews

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