Anna Maria Vacation Packages 2026 from $385

Anna Maria flight + hotel vacation packages

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

Hampton Inn Sarasota - I-75 Bee Ridge

Save 100% on your flight

$385

per person

May 26 - May 31

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

This hotel features an outdoor pool and a gym. Enjoy the hot tub and free perks like buffet breakfast and free self parking. Free WiFi in public areas, express check-in, and express check-out are also on offer.

Mar Bay Motel &Suites

Save 100% on your flight

$589

per person

Jun 23 - Jun 30

found 15 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A garden, a library, and a picnic area are also on offer.

voco Sarasota by IHG

Central Sarasota

Save 100% on your flight

$635

per person

Jun 1 - Jun 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 3 conference rooms, express check-out, and laundry service. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.

The Westin Sarasota

Central Sarasota

Save 100% on your flight

$749

per person

Jun 1 - Jun 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

A full-service spa, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Enjoy the 24-hour gym and perks like a free beach shuttle. You'll appreciate the a rooftop terrace, bar/lounge, and laundry facilities.

ChartHouse Clearwater Beach Marina Hotel

Save 100% on your flight

$606

per person

May 26 - May 31

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free WiFi. A rooftop terrace is on site, and self parking and a 24-hour front desk are also offered.

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

Adorable Cottage ONLY STEPS to Anna Maria Beach, No Roads to Cross! FREE WiFi & Trolley

Anna Maria FL

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A gym is featured at this vacation home, along with 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

CHARMING COTTAGE W/HEATED POOL, Close to Gulf & Bay Beach, FREE WiFi/Trolley, Dog*(See Note) Friendly!

Anna Maria FL

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This vacation home features an outdoor pool and a gym. A garden, laundry facilities, and concierge services are also on offer.

Pool

Kitchen

Lovely island home - 1 block to Pine Street, 2 dogs OK

Anna Maria FL

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

Pool

Kitchen

Duplex on North End of Anna Maria Island! With Pool and Grill

Anna Maria FL

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This vacation home features 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 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.

Anna Maria City Pier

After visiting Anna Maria City Pier, make a plan to see the other sights and activities in Anna Maria. Wander the beaches or discover the area's sunrises.

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.