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ANNA MARIA ISLAND

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Annual Cruisin' Ocean City Maryland

Annual Cruisin' Ocean City Maryland
October - Ocean City Maryland

Anna Maria Island Beachfront Vacation Rentals | Beach Stays

Anna Maria Island is a seven-mile stretch of white sand beaches and gentle Gulf waters that feels worlds away from the bustle of mainland Florida. The island’s laid-back charm, walkable towns, and stunning beachfront properties make it a favorite for families, couples, and anyone chasing that “barefoot on the sand” kind of vacation. Here, beach cottages and modern coastal homes sit steps from turquoise water ideal for sunrise walks, paddleboarding, or simply watching the sunset melt into the Gulf from your deck.

Beachfront vacation rentals on Anna Maria Island offer a front-row seat to paradise. Stay on the shoreline and let the sound of the surf be your alarm clock. Spend your days exploring island shops and local seafood spots, or hop on the free trolley to visit the historic Anna Maria City Pier and lively Bridge Street. From Holmes Beach to Bradenton Beach, each stretch of sand has its own rhythm peaceful, sunny, and always inviting.

Beachfront Vacation Rentals On Anna Maria Island

Beau Soleil Seaside
$199/night
Home in Bradenton Beach Florida
2 Beds • 2 Full Baths • Sleeps 5
Beach Retreats
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Condo in Holmes Beach Florida
2 Beds • 2 Full Baths • Sleeps 4
Cheerful Rentals
Meant to Bee on AMI
$225/night
Home in Bradenton Beach Florida
2 Beds • 2 Full Baths • Sleeps 6
Beach Retreats
Aerial AMI Pier
$325/night
Home in Holmes Beach Florida
3 Beds • 3 Full Baths • Sleeps 6
Seabreeze Vacation
Sunset Beach
$514/night
Home in Holmes Beach Florida
4 Beds • 4 Full Baths • Sleeps 8
Lizzie Lus Island Retreat
Secluded Private Pool
$256/night
Home in Holmes Beach Florida
3 Beds • 3 Full Baths • Sleeps 6
BeachRentals.mobi
Front of Duplex
$268/night
Cottage in Holmes Beach Florida
2 Beds • 1 Full Bath • Sleeps 5
Lizzie Lus Island Retreat
Aerial AMI Pier
$207/night
Condo in Holmes Beach Florida
2 Beds • 2 Full Baths • Sleeps 6
Seabreeze Vacation
Barefoot Mermaid 1
$225/night
Apartment in Anna Maria Florida
2 Beds • 1 Full Bath • Sleeps 4
Salty Mermaid Real Estate & Vacation Rentals
Your Private Oasis and Outdoor Seating
$200/night
Home in Bradenton Beach Florida
3 Beds • 2 Full Baths • Sleeps 8
BeachRentals.mobi
Enjoy swimming, sunning and tiki fun
$213/night
Home in Holmes Beach Florida
2 Beds • 1 Full Bath • Sleeps 6
BeachRentals.mobi
Living Room
$220/night
Condo in Holmes Beach Florida
1 Bed • 1 Full Bath • Sleeps 4
Seabreeze Vacation

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