Anna Maria Island Vacations 2026 from CA $898

Anna Maria Island flight + hotel packages

Price found within the past 48 hours. Click for updated prices.

Hibiscus Suites - Gateway to Siesta Key

Save 100% on your flight

CA $898

per person

Dec 7 - Dec 13

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Tampa (TPA)

Book a stay at this business-friendly aparthotel in Sarasota. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

CA $1,180

per person

Dec 7 - Dec 13

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Tampa (TPA)

Book a stay at this beach hotel in Treasure Island. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.

Cedar Cove Resort and Cottages

Save 100% on your flight

CA $1,502

per person

Dec 7 - Dec 13

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Tampa (TPA)

Book a stay at this beach resort in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Bradenton Beach and Coquina Beach are located nearby.

The Avalon Club

Save 100% on your flight

CA $1,277

per person

Dec 7 - Dec 13

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Tampa (TPA)

Stay at this aparthotel in Clearwater Beach. Enjoy a fitness center, parking (surcharge), and in-room massages. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.

The Westin Sarasota

Central Sarasota

Save 100% on your flight

CA $1,260

per person

Dec 7 - Dec 13

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Tampa (TPA)

Book a stay at this spa hotel in Sarasota. Enjoy a full-service spa, 2 restaurants, and a rooftop terrace. Our guests praise the breakfast and the pool in our reviews. Popular attractions Lido Beach and Siesta Key Beach are located nearby.

Top Anna Maria Island hotels deals

Anna Maria Beach Resort

6306 Gulf Dr Holmes Beach FL

CA $569

CA $720 total

Sep 27 - Sep 28

includes taxes & fees

Book a stay at this beach hotel in Holmes Beach. Enjoy free WiFi, free parking, and a private beach. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Bradenton Beach and Anna Maria Beach are located nearby.

On private beach

Pool

Tropic Isle at Anna Maria Island Inn

101 22nd St Bradenton Beach FL

Free cancellation

Reserve now, pay when you stay

CA $261

CA $330 total

Sep 30 - Oct 1

includes taxes & fees

Stay at this hotel in Bradenton Beach. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Coquina Beach and Bradenton Beach are located nearby.

Pool

Pet-friendly

Bali Hai Beachfront Resort and Spa

6900 Gulf Dr Holmes Beach FL

CA $346

CA $438 total

Oct 20 - Oct 21

includes taxes & fees

Book a stay at this beach resort in Holmes Beach. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Bradenton Beach and Anna Maria Beach are located nearby.

Pool

Spa

Seabreeze at Anna Maria Island Inn

2218 Gulf Drive N Bradenton Beach FL

CA $289

CA $366 total

Sep 29 - Sep 30

includes taxes & fees

Book a stay at this beach apartment in Bradenton Beach. Enjoy free WiFi, free parking, and a private beach. Popular attractions Bradenton Beach and Coquina Beach are located nearby.

Pet-friendly

Parking included

The Retreat at Anna Maria Island Inn

2305 Gulf Dr N Bradenton Beach FL

CA $202

CA $256 total

Oct 21 - Oct 22

includes taxes & fees

Stay at this hotel in Bradenton Beach. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Bradenton Beach and Coquina Beach are located nearby.

Pool

Pet-friendly

Pelican Post at Anna Maria Island Inn

202 1st St N Bradenton Beach FL

CA $243

CA $307 total

Sep 30 - Oct 1

includes taxes & fees

Stay at this apartment in Bradenton Beach. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Coquina Beach and Bradenton Beach are located nearby.

Pool

Hot tub

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See all available properties in Anna Maria Island

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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.

Stay near popular Anna Maria Island attractions

A sunset over the ocean with a clear sky and calm waters.

Bean Point Beach

10.0/10 (1 review)

If a restful vacation is part of your travel plans, Bean Point Beach might be the perfect place to seek out during your trip to Anna Maria. Take in the museums and sunsets in the area.

See properties

Frequently asked questions

How much are vacation packages to Anna Maria Island?

Splash out on a one-of-a-kind experience in Anna Maria Island with a vacation package starting at CA $898. Reserving your flights, hotels and tours through Travelocity has never been easier. And even better, our great deals will leave you with extra cash for fun activities.

Where can I get the best vacation package deals for Anna Maria Island?

You can lock in terrific Anna Maria Island package deals with Travelocity. Mix and match from 400 air carriers and 1,000,000 properties worldwide and turn your travel dreams into reality.

Why should I purchase my Anna Maria Island vacation package via Travelocity?

With our Price Match Guarantee, we'll match any lower price you can find. Add to that our 24/7 customer support and high-quality service and the vacation of your dreams is well within reach.

Will I save money on my Anna Maria Island car rental if I bundle it with hotels and flights?

Combining your bookings into an Anna Maria Island vacation package will save you a tidy sum. You can combine a car and flight; a flight, hotel and car; or a car and hotel. There's no better way to explore the greater Anna Maria Island area than with your own rental car. You can also add tours and experiences to your Travelocity package.