Anna Maria Vacation Packages 2026 from $385

Anna Maria flight + hotel vacation packages

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

Saddlebrook Resort

Wesley Chapel South

$385

per person

Feb 23 - Feb 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This resort features a golf course, a full-service spa, and 3 restaurants. Bring the family and enjoy the children's pool, playground, and kid-friendly dining. Enjoy the 2 outdoor pools and perks like free WiFi.

Delray House With Hot tub & Game Room

Palm River-Clair Mel

Save 100% on your flight

$399

per person

Feb 22 - Feb 26

found 1 hour ago

Roundtrip non-stop flight included

Boston (BOS) to Sarasota (SRQ)

A full-service spa, free self parking, and a virtual front desk are featured at this vacation home. Dry cleaning is also provided.

Family Home Tampa

Forest Hills

Save 100% on your flight

$629

per person

Feb 23 - Feb 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Sarasota (SRQ)

This guesthouse includes a garden and a virtual front desk. Take advantage of the free self parking.

The Residences at Siesta Key Beach by Hyatt Vacation Club

South Village

$2,221

per person

Mar 1 - Mar 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Sarasota (SRQ)

A private beach and an outdoor pool are featured at this smoke-free aparthotel. Relax with free beach cabanas, sun loungers, and beach umbrellas. Enjoy the gym and free perks like continental breakfast and valet parking.

SkyBeach Resort

Greater Pinellas Point

Save 100% on your flight

$566

per person

Feb 23 - Feb 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

A private beach, a marina, and 2 outdoor pools are all featured at this smoke-free hotel. Relax with beach cabanas, sun loungers, and beach umbrellas. Traveling on business? Take advantage of the express check-in, express check-out, and valet parking.

Top Anna Maria hotels deals

Updated bayside condo with heated pool - across the street from the beach

Anna Maria FL

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This condo features laundry facilities.

Pool

Kitchen

Lazy River! Mini Golf! Sleeps 16 Anna Maria Island - Nautical Situation

Anna Maria FL

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This vacation home features laundry facilities.

Washer

Dryer

Bayfront Home with Amazing Water Views! Private pool! – Breakaway

Anna Maria FL

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This vacation home features barbecue grills.

Pool

Kitchen

NOVEMBER SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog

Anna Maria FL

$941 nightly

$1,052 total

Jan 20 - Jan 21, 2026

Total with taxes and fees

This vacation home features a garden, laundry facilities, and barbecue grills.

Kitchen

Washer

NEW! Meet Me At Sunset! 3 Homes from the Beach!

Anna Maria FL

$1,407 nightly

$1,570 total

Dec 26 - Dec 27

Total with taxes and fees

This vacation home features a gym and a hot tub. A garden, laundry facilities, and barbecue grills are also on offer.

Hot Tub

Kitchen

Anna Cabana B: Pool Home, AMI North End, 2 Blocks to Beach by Anna Maria Life Vacation Rentals

Anna Maria FL

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This vacation home features a garden, laundry facilities, and barbecue grills.

Pool

Kitchen

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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.

Popular places to visit

Bean Point Beach

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.

Anna Maria City Pier

Explore the waterfront in Anna Maria with a trip to Anna Maria City Pier. Stroll along the beaches or discover the area's sunrises.

Anna Maria Island Museum and Historical Park

You can spend time browsing the exhibits at Anna Maria Island Museum and Historical Park in Anna Maria. Wander the beautiful beaches and seaside in the area.

Frequently asked questions

How much are vacation packages to Anna Maria?

You'll be pleasantly surprised — you could find yourself in Anna Maria for as low as $385. Let Travelocity save you time and money with our fantastic vacation packages. With flights, hotels and experiences all in one place, what's stopping you?

How long should my Anna Maria vacation be?

On average, people spend 4 nights in Anna Maria. However, that mightn't be nearly enough time for you. If you're eager to explore some of the region's off-the-beaten-path gems, why not add a couple of extra nights to your travel itinerary?

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

With at least 400 air carriers and 1,000,000 properties across the globe, you can't go wrong with Travelocity. Look through our extensive range and create your dream Anna Maria package deal. Don't you love it when trip planning is that easy?

Why should I purchase my Anna Maria vacation bundle via Travelocity?

We take the stress out of travel planning. Whether you're seeking a new destination to discover or want to make sure you get the best deal around, we've got your back. Our 24/7 customer care, excellent service and Price Match Guarantee mean you can confidently book with Travelocity.

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

With an Anna Maria vacation package, you can combine your car, hotel and flight bookings and save some serious money. If you want to uncover the best of this impressive destination, why not head to Universal Studios Florida? This famous sight is 100 mi from Anna Maria. With your own rental car, you'll be there before you know it.

Which airport is best for Anna Maria?

Many visitors choose to fly into Tampa Intl. Airport (TPA), 35 mi north of downtown Anna Maria. Others prefer Sarasota-Bradenton Intl. Airport (SRQ) (15 mi away from central Anna Maria) or St. Petersburg-Clearwater Intl. Airport (PIE) (25 mi away from central Anna Maria).

What is there to do in Anna Maria?

You'll feel a particular magic in the air as you wander through the streets of Anna Maria. Palmetto Avenue Beach and Island Players are just two landmarks that lure visitors to this fantastic city, so add them to your itinerary.

Where should I stay when visiting Anna Maria?

Many people spend their nights at the Sunrise Garden Resort By Vacasa. It's sure to be a great base for your Anna Maria escape.