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Anna Maria Island 4 Bedroom Vacation Rentals

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Anna Maria Island is a place where you can relax, enjoy the Florida sunshine and create memories that last forever. This Gulf Coast island has something for everyone and will offer you the best Florida beach vacation in the state.

There is an abundance of activities on the island in addition to spending the day on our amazing beaches. Take a sail, catch some large fish, see some dolphins, ride a jet ski, go paddleboarding or kayaking, play in the sand, swim in the ocean, walk our famous beaches and enjoy.

These four bedroom rentals are great for groups, multiple families, large families, and multi-couple vacations. Enjoy the spaciousness of our rentals. We are sure that there is more than enough room for everyone but if you need something bigger take a look at our 5+ bedroom vacation rentals. Our multi bedroom homes are spectacular! We also have stunning beachfront rentals throughout Holmes Beach, Bradenton Beach, and the City of Anna Maria.

These rentals can accommodate up to 10 guests or more.

Paradise on Pine
Paradise on Pine
Weekly $1750 - $6300 *
PoolLinen ServiceElevatorBBQ GrillInternetTable GamesDeck ChairsBoat Dock
Bed & Bath: 4/3.5 Sleeps: 12 Location: Anna Maria
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Sunchase Villa
Sunchase Villa
Weekly $1162 - $5600 *
BBQ GrillInternetDeck Chairs
Bed & Bath: 4/4.5 Sleeps: 8 Location: Anna Maria
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Aqua Cove
Aqua Cove
Weekly $2100 - $9800 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetTable GamesDeck ChairsBoat Dock
Bed & Bath: 4/3.5 Sleeps: 10 Location: Anna Maria
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Sundown North
Sundown North
Weekly $1400 - $5775 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/3 Sleeps: 10 Location: Anna Maria
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Bahama Breeze
Bahama Breeze
Weekly $1750 - $6300 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/3 Sleeps: 8 Location: Anna Maria
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Away To Play
Away To Play
Monthly $4668 - $20000 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 4/2.5 Sleeps: 8 Location: Holmes Beach
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Whispering Winds
Whispering Winds
Weekly $1295 - $3850 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/2 Sleeps: 8 Location: Anna Maria
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Avenue E By The Sea
Avenue E By The Sea
Weekly $1750 - $7000 *
PoolLinen ServiceElevatorBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 4/3.5 Sleeps: 8 Location: Holmes Beach
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Ocean Walk
Ocean Walk
Weekly $1925 - $8400 *
PoolSpaLinen ServiceBBQ GrillInternetVideo GamesTable GamesDeck Chairs
Bed & Bath: 4/3.5 Sleeps: 12 Location: Anna Maria
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Whispering Whale Retreat
Whispering Whale Retreat
Weekly $1400 - $5600 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 4/2 Sleeps: 10 Location: Anna Maria
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Bimini Breeze Beachhouse
Bimini Breeze Beachhouse
Weekly $1750 - $6300 *
PoolSpaBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 4/3 Sleeps: 10 Location: Bradenton Beach
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Pelican Villa
Pelican Villa
Weekly $1750 - $6300 *
PoolLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 4/3 Sleeps: 8 Location: Anna Maria
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Paradise Found
Paradise Found
Weekly $1750 - $6650 *
PoolSpaBBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 4/4.5 Sleeps: 8 Location: Bradenton Beach
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Casa Muratti
Casa Muratti
Weekly $1750 - $4900 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 4/3.5 Sleeps: 8 Location: Anna Maria
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Pineapple Key
Pineapple Key
Weekly $1575 - $6300 *
PoolSpaBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 4/2 Sleeps: 8 Location: Holmes Beach
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Summer Retreat
Summer Retreat
Weekly $1925 - $6300 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetVideo GamesTable GamesDeck Chairs
Bed & Bath: 4/4.5 Sleeps: 14 Location: Bradenton Beach
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Cabana Breeze
Cabana Breeze
Weekly $1750 - $7000 *
PoolLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 4/2 Sleeps: 10 Location: Anna Maria
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Sundown South
Sundown South
Weekly $1575 - $6300 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/3 Sleeps: 8 Location: Anna Maria
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Sunshine Reef
Sunshine Reef
Weekly $1925 - $7700 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/4 Sleeps: 10 Location: Anna Maria
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Breakaway
Breakaway
Weekly $2100 - $7700 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/2 Sleeps: 10 Location: Anna Maria
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Casa Laguna
Casa Laguna
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PoolSpaBBQ GrillInternetTable GamesDeck ChairsBoat Dock
Bed & Bath: 4/4 Sleeps: 11 Location: Longboat Key
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Island Retreat
Island Retreat
Weekly $1750 - $5600 *
PoolLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 4/3 Sleeps: 8 Location: Holmes Beach
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Villa Milano
Villa Milano
Weekly $1575 - $6300 *
PoolLinen ServiceElevatorBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 4/4 Sleeps: 8 Location: Holmes Beach
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Sunset Point
Sunset Point
Weekly $2100 - $8400 *
Linen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/3 Sleeps: 8 Location: Anna Maria
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Casa del Playa
Casa del Playa
Weekly $1400 - $4900 *
PoolSpaLinen ServiceInternetDeck Chairs
Bed & Bath: 4/3 Sleeps: 8 Location: Holmes Beach
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Breezy Beach
Breezy Beach
Weekly $1400 - $5600 *
SpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 4/4 Sleeps: 8 Location: Holmes Beach
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Hawaiian Hideaway
Hawaiian Hideaway
Weekly $1200 - $4725 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 4/2 Sleeps: 8 Location: Holmes Beach
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Ocean Breeze
Ocean Breeze
Weekly $1575 - $6300 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 4/3 Sleeps: 8 Location: Holmes Beach
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Riki Tiki
Riki Tiki
Weekly $1750 - $6300 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/4 Sleeps: 8 Location: Holmes Beach
More details >
Once Upon A Tide
Once Upon A Tide
Weekly $1925 - $5600 *
PoolLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 4/3.5 Sleeps: 8 Location: Anna Maria
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Blue Heron
Blue Heron
Weekly $1575 - $6300 *
PoolLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 4/3.5 Sleeps: 8 Location: Holmes Beach
More details >
LaPlage 2
LaPlage 2
Weekly $2100 - $6300 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetDeck Chairs
Bed & Bath: 4/3 Sleeps: 8 Location: Holmes Beach
More details >
Avalon
Avalon
Weekly $2450 - $9100 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetDeck Chairs
Bed & Bath: 4/3.5 Sleeps: 8 Location: Holmes Beach
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Egrets Nest
Egrets Nest
Weekly $1015 - $4725 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 4/2.5 Sleeps: 8 Location: Holmes Beach
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Skip to the Beach
Skip to the Beach
Monthly $8204 - $16800 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 4/4 Sleeps: 8 Location: Holmes Beach
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Island Dream
Island Dream
Weekly $2275 - $6300 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/4 Sleeps: 10 Location: Anna Maria
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Dancing Dolphin
Dancing Dolphin
Weekly $2500 - $7000 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/3.5 Sleeps: 8 Location: Anna Maria
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Coral Cove
Coral Cove
Weekly $1750 - $5600 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 4/3.5 Sleeps: 8 Location: Holmes Beach
More details >
Tarpon Pointe
Tarpon Pointe
Weekly $1750 - $6300 *
PoolBBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 4/3 Sleeps: 12 Location: Anna Maria
More details >
Waterside House
Waterside House
Weekly $1925 - $7700 *
PoolLinen ServiceElevatorBBQ GrillInternetTable GamesDeck ChairsBoat Dock
Bed & Bath: 4/5.5 Sleeps: 12 Location: Bradenton Beach
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*Rates shown are estimates. Excludes Taxes, Fees and Travel Insurance.
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