Anna Maria Island Vacations 2025/2026 from CA $430

Q: 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.

Anna Maria Island flight + hotel packages

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

GALAXY HOTEL

Downtown St. Petersburg

per person

Oct 17 - Oct 22

found 22 hours ago

Roundtrip flight included

Toronto (YTO) to Tampa (TPA)

Stay at this 3.5-star business-friendly hotel in St. Petersburg. Enjoy free WiFi, breakfast (surcharge), and valet parking (surcharge). Popular attractions Tampa Bay and Salvador Dali Museum are located nearby.

The Avalon Club

per person

Oct 10 - Oct 13

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

Stay at this 4-star beach aparthotel in Clearwater Beach. Enjoy a beach locale, a fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Clearwater Beach and Sand Key Park are located nearby.

The Pointe Condos by Barsala

Port Tampa City

per person

Sep 8 - Sep 15

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Sarasota (SRQ)

Stay at this 4.5-star luxury aparthotel in Tampa. Enjoy free parking, in-room washers/dryers, and an in-room coffeemaker. Our guests praise the helpful staff in our reviews. Popular attractions Picnic Island Park and Picnic Island Beach are located nearby.

Twin Palms at Siesta

per person

Aug 29 - Sep 5

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Sarasota (SRQ)

Stay at this 3-star beach hotel in Siesta Key. Enjoy free WiFi, free parking, and private pools. Our guests praise the helpful staff in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.

Hibiscus Suites - Gateway to Siesta Key

per person

Aug 29 - Sep 5

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

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

Popular places to visit

Coquina Beach

Why not spend a carefree afternoon at Coquina Beach during your travels in Bradenton Beach? Wander the seaside or discover the area's sunsets.

Cortez Beach

Why not spend a carefree afternoon at Cortez Beach during your travels in Bradenton Beach? Stroll along the seaside or experience the area's entertainment venues.

Palmetto Avenue Beach

Why not spend a lazy afternoon at Palmetto Avenue Beach during your trip to Anna Maria? Wander the beaches or discover the area's sunrises.

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 $430. 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.