Anna Maria Vacation Packages 2025/2026 from $374

Anna Maria flight + hotel vacation packages

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

Ocean Club Treasure Island Hotel

Save 100% on your flight

$374

per person

Oct 19 - Oct 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

This hotel features an outdoor pool and a hot tub. Relax with a drink at the poolside bar and enjoy perks like free self parking and free WiFi. A garden, luggage storage, and concierge services are also on offer.

Cedar Cove Resort and Cottages

$937

per person

Oct 4 - Oct 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

Free WiFi in public areas, a terrace, and a garden are available at this resort. A snack bar/deli, a picnic area, and luggage storage are also on offer.

voco Sarasota by IHG

Central Sarasota

Save 100% on your flight

$616

per person

Oct 20 - Oct 27

found 1 day ago

Roundtrip non-stop 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 Residences at Siesta Key Beach by Hyatt Vacation Club

Save 100% on your flight

$738

per person

Nov 9 - Nov 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

This aparthotel features an outdoor pool and a 24-hour gym. Spend a day at the beach kayaking, or relax with sun loungers and beach umbrellas. Guests will appreciate free perks like valet parking and WiFi in public areas.

GALAXY HOTEL

Downtown St. Petersburg

Save 100% on your flight

$550

per person

Nov 7 - Nov 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

This hotel features a coffee shop, wedding services, and valet parking. WiFi in public areas is free. Traveling on business? Take advantage of the 24-hour business center, conference center, and conference space.

Top Anna Maria hotels deals

Spacious 7-bedroom home in Anna Maria~ Putt Putt, Ping Pong, 3 blocks to beach!

$1,190 nightly

$1,330 total

Sep 7 - Sep 8

Total with taxes and fees

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

Pool

Hot Tub

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

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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

Pet Friendly Bay-Canal Waterfront! Tiki Bar 5BR, 5BA Huge Pool, 2 Kayaks/Bikes

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This vacation home features a water park, a garden, and laundry facilities. Families will appreciate the playground and barbecue grills.

Pool

Kitchen

Mimosa Bay: Waterfront Oasis w/ Heated Pool, Hot Tub & Bay Views

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A water park and a hot tub are featured at this smoke-free vacation home. Laundry facilities and barbecue grills are also provided.

Pool

Hot Tub

Tortuga Bay~Canal & Waterslide Putt Putt! KAYAKS & TIKI HUT

$1,177 nightly

$1,311 total

Sep 1 - Sep 2

Total with taxes and fees

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

Pool

Hot Tub

Adorable Beach cottage just steps Bean Point beach!

$502 nightly

$560 total

Sep 3 - Sep 4

Total with taxes and fees

This vacation home featured 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

Anna Maria Beach is beautiful. It's one of several beaches on Anna Maria Island and doesn't have any facilities, so it's less visited.

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.

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.

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 $374. 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.