Anna Maria Island Vacation Packages
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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.
Ocean Club Treasure Island Hotel
Price was CA $1,112, price is now CA $600 per person
CA $600
per person
Oct 2 - Oct 5
found 6 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9.6/10 Exceptional! (609 reviews)
Loved the condo, the access to the beach, in unit laundry, and convenience of the location. Gym and beach bar on site, would definitely come back!
Reviewed on Aug. 30, 2025
FUSION Resort Waterfront Suites
Price was CA $2,172, price is now CA $1,037 per person
CA $1,037
per person
Nov 15 - Nov 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9.2/10 Wonderful! (1,053 reviews)
The room was fantastic with a big wrap around balcony. Even though the weather did not cooperate, we all enjoyed chilling on the balcony with many trips to the pool. Beach was great. My only disappointment was they did not have any type of grill anywhere. I brought some really expensive steaks, burgers,hot dogs, which we had to cook in a pan.
The staff was fantastic and made sure we had everything we needed
Reviewed on Aug. 24, 2025
The Avalon Club
Price was CA $1,354, price is now CA $734 per person
CA $734
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9.4/10 Exceptional! (445 reviews)
Excellent place no word to explain how perfect everything was. We definitely go there from now on
Reviewed on Aug. 24, 2025
Inn on the Beach
Pass-a-Grille
Price was CA $2,192, price is now CA $1,251 per person
CA $1,251
per person
Nov 15 - Nov 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9.8/10 Exceptional! (330 reviews)
I loved the room and they supply so much beach towel a cooler there bikes looked like u can take the beach chairs to the beach and basically on the beach
Reviewed on Aug. 29, 2025
The Residences at Siesta Key Beach by Hyatt Vacation Club
Price was CA $3,031, price is now CA $1,752 per person
CA $1,752
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Sarasota (SRQ)
9.8/10 Exceptional! (284 reviews)
Beautiful apartment! Great city view on the balcony. Pool area was lovely.
Reviewed on Aug. 27, 2025
Anna Maria Island Hotel Deals
Anna Maria Beach Resort
6306 Gulf Dr, Holmes Beach, FL
The price is CA $392 per night from Oct 1 to Oct 2
CA $392
CA $497 total
Oct 1 - Oct 2
includes taxes & fees
Bali Hai Beachfront Resort and Spa
6900 Gulf Dr, Holmes Beach, FL
The price is CA $367 per night from Sep 2 to Sep 3
CA $367
CA $465 total
Sep 2 - Sep 3
includes taxes & fees
Pelican Post at Anna Maria Island Inn
202 1st St N, Bradenton Beach, FL
The price is CA $243 per night from Oct 1 to Oct 2
CA $243
CA $308 total
Oct 1 - Oct 2
includes taxes & fees
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.
Discover the most popular places to visit in Anna Maria Island
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.
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.
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.
What to do in Anna Maria Island
Anna Maria Island and Bradenton: Sunset Kayak Dolphin Tour
CA $83
per adult
90% of travellers recommend
Bradenton: Anna Maria Island Guided Kayaking Manatee Tour
CA $76
per adult
100% of travellers recommend
Anna Maria Island - Clear Kayak LED Night Glass Bottom Tour
CA $89
per adult
90% of travellers recommend
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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.