Anna Maria Island Vacation Packages

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Your Anna Maria Island Vacation

Secure a vacation package to Anna Maria Island and enjoy travel on your own terms. You'll be charmed by its watersports, coastal beaches and fishing. Get your trip to Anna Maria Island off to a flying start by exploring its best cities. Bradenton Beach is one you cannot miss. Whether you're planning to travel for a few days or a few weeks, Expedia are here to help you organize your next dream Anna Maria Island vacation.

Top Anna Maria Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Barsala At The Wayland Condos

Barsala At The Wayland Condos

4 out of 5
Save 100% on your flight
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
7.6/10 Good! (10 reviews)
My little getaway was amazing!!! The studio was beautiful, had everything we needed I wasn't expecting a full kitchen with baking utensils as well. We had a blast the view was incredible. I loved the outside setup near the pool as well. Will definitely be booking another getaway real soon!!

Reviewed on Jun. 10, 2025

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
per person
Oct 6 - Oct 13
found 7 hours ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9.2/10 Wonderful! (1,040 reviews)
Wonderful reception

Reviewed on Jul. 14, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
per person
Aug 26 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (518 reviews)
No Complaints ...very clean, friendly staff. Very close to beach

Reviewed on Jul. 15, 2025

Innisbrook Resort

Innisbrook Resort

3.5 out of 5
Save 100% on your flight
per person
Oct 6 - Oct 13
found 7 hours ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
8.2/10 Very Good! (1,003 reviews)
Beautiful resort and wonderful location! The staff are very professional, warm and friendly. So much to do within the resort, but we did manage to visit Tarpon Springs too! We are already talking about our next visit!

Reviewed on Jul. 12, 2025

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
per person
Aug 26 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (2,352 reviews)
Staff was amazing the room was ok it better online. Overall experience was good

Reviewed on Jul. 14, 2025

Ready to book your vacation to Anna Maria Island?

 

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Anna Maria Island Hotel Deals

Anna Maria Beach Resort
Anna Maria Beach Resort
3.5 out of 5
6306 Gulf Dr, Holmes Beach, FL
The price is CA $581 per night from Aug 10 to Aug 11
CA $581
CA $735 total
Aug 10 - Aug 11
includes taxes & fees
9.2/10 Wonderful! (220 reviews)
"Beautiful relaxing resort! Staff very friendly and helpful."

Reviewed on Jul. 9, 2025

Anna Maria Beach Resort
Silver Surf Gulf Beach Resort
Silver Surf Gulf Beach Resort
3 out of 5
1301 Gulf Dr N, Bradenton Beach, FL
The price is CA $310 per night from Jul 29 to Jul 30
CA $310
CA $351 total
Jul 29 - Jul 30
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
"2nd year we have stayed here and we love it! Perfect location! Walking distance to beach, restaurants, bars, and shops! Always clean, spacious, and well taken care of. Our favorite part about staying here is the beach access with chairs and umbrellas provided by the hotel. Definitely recommend."

Reviewed on Jul. 2, 2025

Silver Surf Gulf Beach Resort
Bali Hai Beachfront Resort and Spa
Bali Hai Beachfront Resort and Spa
3.5 out of 5
6900 Gulf Dr, Holmes Beach, FL
The price is CA $421 per night from Aug 10 to Aug 11
CA $421
CA $533 total
Aug 10 - Aug 11
includes taxes & fees
8.4/10 Very Good! (564 reviews)
"Staff members were very efficient and helpful.The pool and beach were very nice. The suite on the pool side was comfortly furnished. For a resort , the entrance lobby coul be upgraded."

Reviewed on Jul. 1, 2025

Bali Hai Beachfront Resort and Spa
See all 3,583 properties in Anna Maria Island
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Discover the most popular places to visit in Anna Maria Island

Cortez Beach

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.

Cortez Beach

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.

Bean Point Beach

Historic Bridge Street Pier

Explore the waterfront in Bradenton Beach with a trip to Historic Bridge Street Pier. Wander the beautiful beaches or discover the area's beautiful sunsets.

Historic Bridge Street Pier

What to do in Anna Maria Island

Our Cruise gives you the best seat there is to the Skyway Bridge Light Show! Different display every night of the week!

Island Sunset and Skyway Light Show - 3hr Boat Cruise in St. Pete

CA $116
per adult
94% of travellers recommend
Island Sunset and Skyway Light Show - 3hr Boat Cruise in St. Pete
Anna Maria Island and Bradenton Beach: Parasailing Tour

Anna Maria Island & Bradenton Beach Parasailing Tour

CA $136
per adult
Anna Maria Island & Bradenton Beach Parasailing Tour
Clear Kayak LED Night Glass Bottom Tour - Anna Maria Island

Anna Maria Island - Clear Kayak LED Night Glass Bottom Tour

CA $89
per adult
90% of travellers recommend
Anna Maria Island - Clear Kayak LED Night Glass Bottom Tour
See all activities in Anna Maria Island

Frequently asked questions

How much does an Anna Maria Island vacation package cost?
Get ready to book, because a trip to Anna Maria Island starts from just CA $734. When you combine your hotels, flights and car rentals into a travel package, you'll score the best prices.
How do I get a cheap travel package to Anna Maria Island?
It's easy. Just bundle everything together. Flights, hotels and rental cars --- combine whatever you need into an Anna Maria Island vacation package to save loads of cash. Score even more bargains when you add extras such as experiences or tours to your booking. But that's not the only impressive part. You have the flexibility to customize your trip your own way. We offer more than 550 airlines and 1,000,000 hotel options globally, so that everyone has a chance to travel and live out those vacation dreams.
How far in advance should I book my Anna Maria Island vacation?
It's always wise to book early. Air carriers usually release flight tickets up to 12 months prior to departure, and this is an excellent opportunity to pick up some of the cheapest prices. Just been told you need to take your vacation time in a few weeks? That's fine too --- Expedia are never short on fantastic deals to send you off on the getaway of your dreams, at an affordable price.
What does an Expedia Anna Maria Island travel package include?
From flights and hotels to rental cars, Expedia can help you craft an Anna Maria Island package that suits you. Vacationing for a few weeks? Check out a rental car, hotel and flight bundle. If you're taking a short break, an airfare and hotel deal could suit you better. Experiences can also be added once you've made your booking. Our packages make it a cinch to plan and save.
What should I know before booking an Anna Maria Island travel package?
Whether it's adventure or relaxation you're chasing, an Anna Maria Island vacation package lets you plan your escape your way. Plus, you'll get access to great discounts when you combine your hotel with your rental car and flights. The more you bundle, the bigger the savings!
Can I choose my airline with an Anna Maria Island Expedia vacation package?
Yes, and with more than 550 airlines to select from globally, you're not short on choice. Have a look through the available options and see which airline best suits your budget and needs.
If I'm not able to travel, can I cancel my Anna Maria Island vacation package?
We totally get it --- life sometimes gets in the way of your plans. If you've locked in an Anna Maria Island vacation package and need to cancel or amend it, we're here to help. It's always worth visiting our Customer Service Portal first for information. But generally speaking, if you've booked your package within 24 hours, you may be able to amend or cancel your itinerary free of charge. If it's been more than 24 hours, your hotel, airline or car rental company may impose a charge.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.