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ANNA MARIA ISLAND

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TRENDING

Annual Mad Dog Mandich Florida Keys Classic

Annual Mad Dog Mandich Florida Keys Classic
October - Islamorada Florida

Annual Shamrock Car Show And Poker Run

Annual Shamrock Car Show And Poker Run
March - Kill Devil Hills North Carolina

Anna Maria Island Beachfront Vacation Rentals

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.

Brachfront Vacation Rentals On Anna Maria Island

Casa Amiga
$529/night
Home in Anna Maria Florida
4 Beds • 4 Full Baths • Sleeps 10
Beach Retreats
Barefoot Mermaid 4
$220/night
Apartment in Anna Maria Florida
1 Bed • 1 Full Bath • Sleeps 3
Salty Mermaid Real Estate & Vacation Rentals
Aerial AMI Pier
$275/night
Condo in Bradenton Beach Florida
2 Beds • 2 Full Baths • Sleeps 4
Seabreeze Vacation
Heated Pool
$399/night
Home in Holmes Beach Florida
3 Beds • 3 Full Baths • Sleeps 6
Seabreeze Vacation
Aerial AMI Pier
Home in Bradenton Beach Florida
2 Beds • 2 Full Baths • Sleeps 6
Seabreeze Vacation
Sandcastle by the Sea
$261/night
Home in Holmes Beach Florida
2 Beds • 2 Full Baths • Sleeps 6
Beach Retreats
Sun Plaza West Unit 204
$225/night
Condo in Holmes Beach Florida
2 Beds • 2 Full Baths • Sleeps 6
Salty Mermaid Real Estate & Vacation Rentals
Mermaids Landing
$499/night
Home in Holmes Beach Florida
6 Beds • 4 Full Baths • Sleeps 12
Beach Retreats
Starfish Cove
$239/night
Home in Holmes Beach Florida
3 Beds • 2 Full Baths • Sleeps 6
Beach Retreats
Heated Pool & Spa
$299/night
Home in Holmes Beach Florida
2 Beds • 2 Full Baths • Sleeps 6
Seabreeze Vacation
Just Beachy
$699/night
Home in Holmes Beach Florida
4 Beds • 5 Full Baths • Sleeps 8
Beach Retreats
Private Heated Pool and Spa
$325/night
Home in Anna Maria Florida
3 Beds • 2 Full Baths • Sleeps 8
Seabreeze Vacation
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Find a Manager for Your Rental Property