Anna Maria Vacation Packages 2026 from $608

Anna Maria flight + hotel vacation packages

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

Captiva Beach Resort

South Village

Save 100% on your flight

$608

per person

Apr 27 - May 1

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

A private beach and an outdoor pool are featured at this smoke-free condo. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area, laundry facilities, and barbecue grills are also on offer.

Seaside at Anna Maria Island Inn

Save 100% on your flight

$2,044

per person

Apr 17 - Apr 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Sarasota (SRQ)

An outdoor pool is featured at this hotel, along with free WiFi in public areas and a safe deposit box.

Island Grand at TradeWinds

$1,241

per person

Apr 25 - May 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

A water park, 4 restaurants, and 5 outdoor pools are all featured at this resort. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Bring the family and enjoy the children's club, mini golf, and children's pool.

Kompose Boutique Hotel

Save 100% on your flight

$753

per person

Apr 23 - Apr 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.

Plaza Beach Hotel Beachfront Resort

Save 100% on your flight

$1,023

per person

Apr 30 - May 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

A private beach and an outdoor pool are featured at this hotel. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. There's fun for all ages with mini golf and a playground, and barbecue grills are available on site.

Top Anna Maria hotels deals

The Ballyhoo on Bean Point, 200 feet to a beautiful bayside beach and views!

Anna Maria FL

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A gym is featured at this cottage, along with laundry facilities and barbecue grills.

Kitchen

Washer

Love Shack on the Water Most desirable location on AMI

Anna Maria FL

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This apartment includes a garden and laundry facilities.

Kitchen

Washer

Naut 2 Shabby Cottage Next-Level Pool Area, Darling FL Cottage - Best of Both!

Anna Maria FL

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This vacation home features an outdoor pool and a hot tub. Laundry facilities and barbecue grills are also provided.

Pool

Hot Tub

Wake up on the waters of Tampa Bay in a north Anna Maria home.

Anna Maria FL

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

Kitchen

Washer

Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

Anna Maria FL

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This cottage features an outdoor pool and a hot tub. Families will appreciate the playground and onsite laundry facilities. Barbecue grills are provided for your convenience.

Pool

Hot Tub

Luxury waterfront home with a heated pool and spa!

Anna Maria FL

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A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.

Pool

Hot Tub

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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 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.

Island Players

You can get tickets for a performance at Island Players during your trip to Anna Maria. Stroll along the area's seaside, or simply savor its top-notch restaurants.

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 $608. 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.