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Anna Maria Island 5+ Bedroom Vacation Rentals

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Anna Maria Island is the premier beach vacation location in Florida. Situated on the beautiful Gulf Coast, Anna Maria Island has so much to offer. Gorgeous beaches, great restaurants, and a never ending list of activities are all part of a great vacation here. Anna Maria Vacations has the best selection of vacation rentals to add to a memorable visit.

With some of the best coastline near or far, enjoy the simplicity of this pristine landscape and all of the coastal amenities that accompany this popular vacation destination.

Anna Maria Island is a great place for family vacations, weddings, a fun weekend with a group of friends and so much more. Here on this page you will find our rental homes with 5 or more bedrooms. These rental homes are perfect for multi family vacations as well. We have homes that have enough space for everyone.

These homes can accommodate up to 20 guests.

Tortuga Bay
Tortuga Bay
Weekly $2100 - $7000 *
PoolSpaLinen ServiceBBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 5/3 Sleeps: 10 Location: Anna Maria
More details >
Beach Side Paradise
Beach Side Paradise
Weekly $5600 - $17500 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 8/6 Sleeps: 16 Location: Bradenton Beach
More details >
Seaside Escape
Seaside Escape
Weekly $2100 - $9800 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 7/7.5 Sleeps: 15 Location: Bradenton Beach
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The Big Yellow House
The Big Yellow House
Weekly $2450 - $12600 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 5/4 Sleeps: 14 Location: Anna Maria
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Lighthouse Lagoon
Lighthouse Lagoon
Weekly $2100 - $7700 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/4 Sleeps: 14 Location: Anna Maria
More details >
Summer Breeze
Summer Breeze
Weekly $2100 - $7700 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/4 Sleeps: 14 Location: Anna Maria
More details >
Antigua Bay
Antigua Bay
Weekly $2450 - $8400 *
PoolSpaLinen ServiceBBQ GrillInternetVideo GamesTable GamesDeck Chairs
Bed & Bath: 5/4 Sleeps: 12 Location: Anna Maria
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Ocean Sunrise
Ocean Sunrise
Weekly $1575 - $4900 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 5/3.5 Sleeps: 12 Location: Bradenton Beach
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Ocean Sunset
Ocean Sunset
Weekly $3010 - $5600 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 5/4 Sleeps: 8 Location: Anna Maria
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Beachfront Paradise
Beachfront Paradise
Weekly $3500 - $14000 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 6/4.5 Sleeps: 18 Location: Bradenton Beach
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Bay View
Bay View
Weekly $2100 - $5880 *
PoolLinen ServiceBBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 5/4 Sleeps: 14 Location: Bradenton Beach
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Beachside Oasis
Beachside Oasis
Weekly $2100 - $8400 *
PoolBBQ GrillInternetVideo GamesDeck Chairs
Bed & Bath: 5/3.5 Sleeps: 14 Location: Bradenton Beach
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Casa del Sol
Casa del Sol
Weekly $2450 - $7700 *
PoolLinen ServiceBBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 5/3 Sleeps: 10 Location: Anna Maria
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Summer Sun
Summer Sun
Weekly $1750 - $8400 *
PoolSpaLinen ServiceBBQ GrillInternetVideo GamesTable GamesDeck Chairs
Bed & Bath: 5/5.5 Sleeps: 10 Location: Bradenton Beach
More details >
Coastal Horizons
Coastal Horizons
Weekly $2450 - $8400 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetDeck Chairs
Bed & Bath: 6/4 Sleeps: 12 Location: Bradenton Beach
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Pearl Beach
Pearl Beach
Weekly $2100 - $7700 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 6/4.5 Sleeps: 12 Location: Holmes Beach
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Montego Bay
Montego Bay
Weekly $2450 - $7700 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 5/4 Sleeps: 11 Location: Anna Maria
More details >
Beachbreeze
Beachbreeze
Weekly $2450 - $8400 *
PoolSpaLinen ServiceBBQ GrillInternetVideo GamesTable GamesDeck Chairs
Bed & Bath: 6/4.5 Sleeps: 12 Location: Holmes Beach
More details >
Caribbean Dream
Caribbean Dream
Weekly $2100 - $8400 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/4.5 Sleeps: 12 Location: Holmes Beach
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A Bean Point Paradise
A Bean Point Paradise
Weekly $2205 - $8400 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetDeck Chairs
Bed & Bath: 5/4 Sleeps: 12 Location: Anna Maria
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Atlantis Beach House
Atlantis Beach House
Weekly $2975 - $14000 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 9/6.5 Sleeps: 24 Location: Bradenton Beach
More details >
Sunset Surf
Sunset Surf
Weekly $2065 - $8330 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 6/4.5 Sleeps: 15 Location: Bradenton Beach
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Paradise Beach
Paradise Beach
Weekly $3500 - $18200 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 8/6.5 Sleeps: 17 Location: Bradenton Beach
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Bayfront Paradise
Bayfront Paradise
Weekly $2450 - $9100 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck ChairsBoat Dock
Bed & Bath: 5/4.5 Sleeps: 10 Location: Holmes Beach
More details >
Cabana Beach
Cabana Beach
Weekly $2100 - $7000 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/3.5 Sleeps: 10 Location: Holmes Beach
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Villa Portofino
Villa Portofino
Weekly $2100 - $6300 *
PoolBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/3.5 Sleeps: 10 Location: Holmes Beach
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View of the Gulf
View of the Gulf
Weekly $2450 - $11200 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 7/4.5 Sleeps: 14 Location: Holmes Beach
More details >
Tiki Beach
Tiki Beach
Weekly $2450 - $8400 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 6/5.5 Sleeps: 12 Location: Holmes Beach
More details >
Tropical Oasis
Tropical Oasis
Weekly $2450 - $14000 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 8/5 Sleeps: 16 Location: Holmes Beach
More details >
The Bayfront
The Bayfront
Weekly $2275 - $8400 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck ChairsBoat Dock
Bed & Bath: 6/4 Sleeps: 15 Location: Bradenton Beach
More details >
Bermuda Bay
Bermuda Bay
Weekly $2450 - $8400 *
PoolSpaLinen ServiceBBQ GrillInternetVideo GamesTable GamesDeck Chairs
Bed & Bath: 5/4 Sleeps: 14 Location: Anna Maria
More details >
Conch House
Conch House
Weekly $2100 - $8400 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 6/4.5 Sleeps: 12 Location: Holmes Beach
More details >
Willow Beach House
Willow Beach House
Weekly $2450 - $8400 *
SpaBBQ GrillInternetVideo GamesDeck Chairs
Bed & Bath: 5/3.5 Sleeps: 12 Location: Anna Maria
More details >
Lazy Lagoon
Lazy Lagoon
Weekly $2450 - $7700 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/5 Sleeps: 10 Location: Holmes Beach
More details >
Direct Beach View
Direct Beach View
Weekly $2450 - $8400 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/4.5 Sleeps: 10 Location: Anna Maria
More details >
Serenity Beach
Serenity Beach
Weekly $3150 - $14000 *
PoolSpaLinen ServiceBBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 5/4.5 Sleeps: 13 Location: Anna Maria
More details >
South Seas
South Seas
Weekly $2450 - $9100 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 6/4.5 Sleeps: 12 Location: Holmes Beach
More details >
Blue Water View
Blue Water View
Weekly $2450 - $8400 *
PoolLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 6/5 Sleeps: 12 Location: Holmes Beach
More details >
Coral Retreat
Coral Retreat
Weekly $2100 - $7000 *
PoolSpaLinen ServiceBBQ GrillInternetVideo GamesTable GamesDeck Chairs
Bed & Bath: 5/3.5 Sleeps: 10 Location: Holmes Beach
More details >
Gulf View Cottage
Gulf View Cottage
Weekly $1750 - $5600 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 5/3.5 Sleeps: 10 Location: Holmes Beach
More details >
The Rod and Reel Resort
The Rod and Reel Resort
Weekly $9030 - $28000 *
PoolSpaInternetTable GamesDeck Chairs
Bed & Bath: 11/8 Sleeps: 24 Location: Anna Maria
More details >
Beach Side Vista
Beach Side Vista
Weekly $1925 - $6300 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 7/5 Sleeps: 18 Location: Bradenton Beach
More details >
Summer House
Summer House
Weekly $2800 - $14000 *
PoolSpaLinen ServiceBBQ GrillInternetVideo GamesTable GamesDeck Chairs
Bed & Bath: 8/6 Sleeps: 16 Location: Holmes Beach
More details >
Surf View
Surf View
Weekly $2800 - $14000 *
PoolLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 8/6 Sleeps: 16 Location: Holmes Beach
More details >
Villa La Concha
Villa La Concha
Weekly $2450 - $8400 *
PoolSpaBBQ GrillInternetDeck Chairs
Bed & Bath: 5/4.5 Sleeps: 10 Location: Anna Maria
More details >
Whitecaps
Whitecaps
Weekly $2205 - $7000 *
PoolLinen ServiceElevatorBBQ GrillInternetDeck Chairs
Bed & Bath: 5/3.5 Sleeps: 12 Location: Anna Maria
More details >
Gulfside Oasis
Gulfside Oasis
Weekly $2450 - $8400 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 6/5 Sleeps: 12 Location: Holmes Beach
More details >
Anna Maria Grand Beach House
Anna Maria Grand Beach House
Weekly $7700 - $21000 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 9/9 Sleeps: 28 Location: Bradenton Beach
More details >
Hunters Point
Hunters Point
Weekly $2800 - $9800 *
Linen ServiceElevatorBBQ GrillInternetTable GamesDeck ChairsBoat Dock
Bed & Bath: 6/5.5 Sleeps: 12 Location: Cortez
More details >
Malibu Beach
Malibu Beach
Weekly $2800 - $14000 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 8/7.5 Sleeps: 16 Location: Holmes Beach
More details >
Harbor Side
Harbor Side
Weekly $1925 - $5600 *
PoolLinen ServiceBBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 5/3.5 Sleeps: 10 Location: Holmes Beach
More details >
Beach Haven
Beach Haven
Weekly $2800 - $14000 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 8/7.5 Sleeps: 16 Location: Holmes Beach
More details >
Gulf View Beach House
Gulf View Beach House
Weekly $1925 - $7700 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 5/3.5 Sleeps: 12 Location: Bradenton Beach
More details >
Mandalay Bay
Mandalay Bay
Weekly $4410 - $17500 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetVideo GamesTable GamesDeck ChairsBoat Dock
Bed & Bath: 7/7.5 Sleeps: 16 Location: Bradenton Beach
More details >
Tropical Hideaway
Tropical Hideaway
Weekly $2450 - $9800 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetDeck Chairs
Bed & Bath: 7/7 Sleeps: 16 Location: Bradenton Beach
More details >
Absolute Paradise
Absolute Paradise
Weekly $2100 - $8400 *
PoolSpaBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/4 Sleeps: 12 Location: Anna Maria
More details >
The Blue Horizon
The Blue Horizon
Weekly $4900 - $21000 *
PoolSpaElevatorBBQ GrillInternetDeck Chairs
Bed & Bath: 9/7.5 Sleeps: 21 Location: Bradenton Beach
More details >
Mojito Splash
Mojito Splash
Weekly $1925 - $7000 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/3.5 Sleeps: 10 Location: Holmes Beach
More details >
Bayblue
Bayblue
Weekly $2450 - $8400 *
PoolLinen ServiceElevatorBBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 6/4 Sleeps: 18 Location: Bradenton Beach
More details >
Sunset Paradise
Sunset Paradise
Weekly $2450 - $8400 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/4.5 Sleeps: 10 Location: Anna Maria
More details >
*Rates shown are estimates. Excludes Taxes, Fees and Travel Insurance.
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