Anna Maria Island Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
Westshore
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Sarasota (SRQ)
8.8/10 Excellent! (2,044 reviews)
The stay was awesome! Staff was great and very clean!

Reviewed on Aug. 12, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
per person
Sep 13 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (574 reviews)
As a travel agent I have traveled extensively and reviewed a plethora of properties. I would highly recommend Ocean Club. The check in area is small but it gets the job done. All condos are gulf front with beautiful views. Previous reviews remarked about the music from the pool- we were in room 206 which is almost directly above the pool and we didn’t have a problem. The actual Condo is very clean with everything you need for your stay- pots and pans, dishes, can opener, toaster, keurig (complete with a variety of pods), quality towels, and comfortable beds. There is also a full size washer and dryer in each unit. Others also remarked about “the trek” to the beach. Please remember that the waterline on a beach is variable and building codes require structures to be specific distances from the beach. Additionally, Florida law prohibits the destruction of certain grasses and sea oats. You can rent chairs and umbrellas on the beach OR there are plenty of umbrellas, chairs, sand toys,and floats that are in a communal area left by previous guests. There is a limit to one car per unit and with this parking is free. WiFi can be spotty as my partner did have to use her hotspot in order to work from our unit.

Reviewed on Aug. 12, 2025

The Avalon Club

The Avalon Club

4 out of 5
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (438 reviews)
Nice place...near the beach, would've rated it a 5 but I was denied a later checkout. Other than that a very nice place convenient to all the sites.

Reviewed on Aug. 8, 2025

Innisbrook Resort

Innisbrook Resort

3.5 out of 5
per person
Sep 22 - Sep 28
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Tampa (TPA)
8.2/10 Very Good! (1,005 reviews)
Room was already best possible. No upgrade necessary

Reviewed on Aug. 11, 2025

RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
per person
Sep 13 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.2/10 Very Good! (1,345 reviews)
Needs some upgrades on current rooms, but we had a great stay there

Reviewed on Aug. 11, 2025

Ready to book your vacation to Anna Maria Island?

 

Choose your dates

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 $447 per night from Sep 4 to Sep 5
CA $447
CA $566 total
Sep 4 - Sep 5
includes taxes & fees
9.2/10 Wonderful! (233 reviews)
"Beautiful property! Lots of amenities."

Reviewed on Aug. 7, 2025

Anna Maria 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 $365 per night from Sep 9 to Sep 10
CA $365
CA $463 total
Sep 9 - Sep 10
includes taxes & fees
8.4/10 Very Good! (586 reviews)
"Beautiful room, it was clean and had everything we needed. The attendant at the front desk was really nice and sweet and helpful and so were the other employees. It was right on the beach. They gave us complimentary drinks at the bar which was amazing! Would come back again."

Reviewed on Aug. 7, 2025

Bali Hai Beachfront Resort and Spa
Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn

3 out of 5
202 1st St N, Bradenton Beach, FL
The price is CA $247 per night from Sep 9 to Sep 10
CA $247
CA $313 total
Sep 9 - Sep 10
includes taxes & fees
9/10 Wonderful! (289 reviews)
"Great place near the beach to stay, the pool was very nice and had clean towels left in our room everyday"

Reviewed on Aug. 10, 2025

Pelican Post at Anna Maria Island Inn
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

Anna Maria Island and Bradenton: Sunset Kayak Dolphin Tour

Anna Maria Island and Bradenton: Sunset Kayak Dolphin Tour

CA $82
per adult
90% of travellers recommend
Anna Maria Island and Bradenton: Sunset Kayak Dolphin Tour
Picture 4 for Activity Bradenton: Anna Maria Island Guided Kayaking Manatee Tour

Bradenton: Anna Maria Island Guided Kayaking Manatee Tour

CA $75
per adult
100% of travellers recommend
Bradenton: Anna Maria Island Guided Kayaking Manatee Tour
Mangrove Tunnels

Exclusive Kayak Expedition: Exploring the Mangroves to Shell Key

CA $62
per adult
Exclusive Kayak Expedition: Exploring the Mangroves to Shell Key
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 $732. 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.

Other vacations you might like

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