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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.

Coral Retreat
Coral Retreat
Weekly $2100 - $6300 *
PoolSpaLinen ServiceBBQ GrillInternetVideo GamesTable GamesDeck Chairs
Bed & Bath: 5/3.5 Sleeps: 10 Location: Holmes Beach 4.75 (4 reviews)
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South Seas
South Seas
Weekly $2450 - $6650 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 6/4.5 Sleeps: 12 Location: Holmes Beach
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Beach Side Vista
Beach Side Vista
Weekly $1750 - $6720 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 6/4 Sleeps: 16 Location: Bradenton Beach
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Mandalay Bay
Mandalay Bay
Weekly $5600 - $17500 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetVideo GamesTable GamesDeck ChairsBoat Dock
Bed & Bath: 7/5.5 Sleeps: 20 Location: Bradenton Beach 5 (4 reviews)
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Paradise Point
Paradise Point
Weekly $2450 - $7700 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/4 Sleeps: 12 Location: Anna Maria
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Absolute Paradise
Absolute Paradise
Weekly $2275 - $7700 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/4 Sleeps: 14 Location: Anna Maria 5 (1 reviews)
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AMI Beach House
AMI Beach House
Weekly $2800 - $7700 *
PoolSpaBBQ GrillInternetDeck Chairs
Bed & Bath: 6/4.5 Sleeps: 14 Location: Holmes Beach
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Antigua Bay
Antigua Bay
Weekly $2275 - $7700 *
PoolSpaLinen ServiceBBQ GrillInternetVideo GamesTable GamesDeck Chairs
Bed & Bath: 5/4 Sleeps: 12 Location: Anna Maria 5 (2 reviews)
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Beachy Villa Vista
Beachy Villa Vista
Weekly $2450 - $7700 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/4.5 Sleeps: 12 Location: Holmes Beach 5 (12 reviews)
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Cabana Beach
Cabana Beach
Weekly $2254 - $5775 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 5/3.5 Sleeps: 10 Location: Holmes Beach 4.33333333333 (3 reviews)
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Summer Sunset
Summer Sunset
Weekly $2975 - $9800 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 6/6.5 Sleeps: 16 Location: Bradenton Beach
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Ocean Sunrise
Ocean Sunrise
Weekly $1750 - $5600 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 5/3.5 Sleeps: 12 Location: Bradenton Beach 5 (4 reviews)
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View of the Gulf
View of the Gulf
Weekly $2800 - $12880 *
PoolSpaBBQ GrillInternetDeck Chairs
Bed & Bath: 7/4.5 Sleeps: 16 Location: Holmes Beach 5 (3 reviews)
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Caribbean Dream
Caribbean Dream
Weekly $2450 - $7700 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/4.5 Sleeps: 12 Location: Holmes Beach
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Hunters Point
Hunters Point
Weekly $2450 - $6300 *
SpaLinen ServiceElevatorBBQ GrillInternetTable GamesDeck ChairsBoat Dock
Bed & Bath: 6/5.5 Sleeps: 12 Location: Cortez 5 (3 reviews)
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AMI Life
AMI Life
Weekly $2975 - $8750 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck ChairsBoat Dock
Bed & Bath: 5/3.5 Sleeps: 10 Location: Anna Maria
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Beach Side Paradise
Beach Side Paradise
Weekly $4200 - $18200 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetDeck Chairs
Bed & Bath: 7/6 Sleeps: 16 Location: Bradenton Beach
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Blue Water View
Blue Water View
Weekly $2450 - $7700 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 6/5 Sleeps: 14 Location: Holmes Beach 4.66666666667 (3 reviews)
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Southern Exposure
Southern Exposure
Weekly $2275 - $7700 *
PoolSpaElevatorBBQ GrillInternetDeck Chairs
Bed & Bath: 5/4.5 Sleeps: 12 Location: Anna Maria 5 (1 reviews)
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Direct Beach View
Direct Beach View
Weekly $2450 - $9100 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/4.5 Sleeps: 10 Location: Anna Maria 5 (2 reviews)
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Willow Beach House
Willow Beach House
Weekly $2975 - $7000 *
SpaBBQ GrillInternetVideo GamesTable GamesDeck Chairs
Bed & Bath: 5/3.5 Sleeps: 12 Location: Anna Maria 4 (1 reviews)
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Villa La Concha
Villa La Concha
Weekly $2450 - $7000 *
PoolSpaBBQ GrillInternetDeck Chairs
Bed & Bath: 6/4.5 Sleeps: 12 Location: Anna Maria
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Harbor Side
Harbor Side
Weekly $2100 - $5600 *
PoolSpaLinen ServiceBBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 5/3.5 Sleeps: 10 Location: Holmes Beach 4.5 (2 reviews)
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Summer Breeze
Summer Breeze
Weekly $2100 - $7560 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/4 Sleeps: 14 Location: Anna Maria
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Beachbreeze
Beachbreeze
Weekly $2450 - $7560 *
PoolSpaLinen ServiceBBQ GrillInternetVideo GamesTable GamesDeck Chairs
Bed & Bath: 6/4.5 Sleeps: 12 Location: Holmes Beach 5 (5 reviews)
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Coastal Horizons
Coastal Horizons
Weekly $2450 - $8400 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetDeck Chairs
Bed & Bath: 6/4 Sleeps: 12 Location: Bradenton Beach 5 (9 reviews)
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Villa Portofino
Villa Portofino
Weekly $2100 - $5600 *
PoolSpaBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/3.5 Sleeps: 10 Location: Holmes Beach
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Tropical Oasis
Tropical Oasis
Weekly $2450 - $7350 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetDeck Chairs
Bed & Bath: 5/4 Sleeps: 12 Location: Anna Maria 5 (9 reviews)
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Whitecaps
Whitecaps
Weekly $2205 - $5600 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/3.5 Sleeps: 12 Location: Anna Maria
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Tiki Beach
Tiki Beach
Weekly $2450 - $8400 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 6/5.5 Sleeps: 12 Location: Holmes Beach 5 (2 reviews)
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Pearl Beach
Pearl Beach
Weekly $2450 - $7350 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 6/4.5 Sleeps: 12 Location: Holmes Beach 5 (1 reviews)
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Casa del Sol
Casa del Sol
Weekly $2450 - $7560 *
PoolSpaLinen ServiceBBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 5/3 Sleeps: 14 Location: Anna Maria 5 (1 reviews)
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Gulfside Oasis
Gulfside Oasis
Weekly $2450 - $7700 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 6/5 Sleeps: 12 Location: Holmes Beach
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Lighthouse Lagoon
Lighthouse Lagoon
Weekly $2100 - $6300 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/4 Sleeps: 14 Location: Anna Maria
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Gulf View Cottage
Gulf View Cottage
Weekly $1750 - $4200 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 5/3.5 Sleeps: 10 Location: Holmes Beach 5 (1 reviews)
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Summer House
Summer House
Weekly $2800 - $13300 *
PoolSpaLinen ServiceBBQ GrillInternetVideo GamesTable GamesDeck Chairs
Bed & Bath: 8/6 Sleeps: 16 Location: Holmes Beach 5 (1 reviews)
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Bayblue
Bayblue
Weekly $2450 - $6650 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 6/4 Sleeps: 18 Location: Bradenton Beach 5 (2 reviews)
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Bermuda Bay
Bermuda Bay
Weekly $2275 - $7700 *
PoolSpaLinen ServiceBBQ GrillInternetVideo GamesTable GamesDeck Chairs
Bed & Bath: 5/4 Sleeps: 14 Location: Anna Maria 5 (1 reviews)
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Beachside Oasis
Beachside Oasis
Weekly $2450 - $8260 *
PoolSpaBBQ GrillInternetVideo GamesTable GamesDeck Chairs
Bed & Bath: 5/3.5 Sleeps: 14 Location: Bradenton Beach 4.5 (2 reviews)
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Anna Maria Grand Beach House
Anna Maria Grand Beach House
Weekly $5600 - $21000 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 9/9 Sleeps: 28 Location: Bradenton Beach 4.75 (4 reviews)
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The Rod and Reel Resort
The Rod and Reel Resort
Weekly $15589 - $19859 *
PoolSpaBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 11/8 Sleeps: 30 Location: Anna Maria 5 (4 reviews)
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Island Sol
Island Sol
Weekly $2100 - $6650 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 5/4 Sleeps: 14 Location: Bradenton Beach
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AMI Beach Fun
AMI Beach Fun
Weekly $2450 - $7560 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 5/3.5 Sleeps: 10 Location: Holmes 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 5 (3 reviews)
More details >
The Blue Horizon
The Blue Horizon
Weekly $4900 - $21000 *
PoolSpaElevatorBBQ GrillInternetDeck Chairs
Bed & Bath: 9/7.5 Sleeps: 21 Location: Bradenton Beach 4.85714285714 (7 reviews)
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The Bayfront
The Bayfront
Weekly $2275 - $6300 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck ChairsBoat Dock
Bed & Bath: 6/4 Sleeps: 15 Location: Bradenton Beach 4.5 (2 reviews)
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The Big Yellow House
The Big Yellow House
Weekly $2450 - $10850 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 5/4 Sleeps: 14 Location: Anna Maria 5 (3 reviews)
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A Bean Point Paradise
A Bean Point Paradise
Weekly $2275 - $7560 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetDeck Chairs
Bed & Bath: 5/4.5 Sleeps: 12 Location: Anna Maria 5 (3 reviews)
More details >
Ocean Sunset
Ocean Sunset
Weekly $3150 - $6300 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 5/3 Sleeps: 10 Location: Anna Maria
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*Rates shown are estimates. Excludes Taxes, Fees and Travel Insurance.
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