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City of Anna Maria Vacation Rentals

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Looking for a vacation rental in the City of Anna Maria? You’ve come to the right place. The City of Anna Maria will leave you hypnotized by her beauty after your first visit, captivated only by swimming in her crystal clear waters and burying your feet into the soft, golden sand. The city that has something for everyone never disappoints. During the day you can go explore the beaches as well as enjoy some extracurricular water activities such as jet skiing, kayaking, paddleboarding, parasailing, fishing, and dolphin watching. Because of its perfect placement in the North of the Island, the City of Anna Maria has some of the most picturesque views and sunsets that the Gulf has to offer. The quaint art galleries, old school ice cream shops, and vintage shops just adds to the charm that the City of Anna Maria exudes.

The City of Anna Maria boasts some of the most upscale vacation rentals on the Gulf. Instead of dealing with the chaos of a busy city every day or a boring weekly commute, you could fall in the love with the City of Anna Maria by booking your perfect vacation rental now. The City of Anna Maria is sure to capture you immediately and the hardest thing you will have to do is having to leave when it all comes to a close. After a warm day in the sun, you will enjoy the cool night air coming into your bedroom window as it comes off the ocean. The combination of the salty air and clear starry skies will leave an everlasting memory you will take with you for a lifetime. Every vacation rental we offer has amazing views that guarantee a spectacular experience no matter which rental you choose!

The City of Anna Maria has some of the most superb rental properties in the area, including some amazing beachfront vacation rentals. No matter what type of coastal view you’re looking for, we have them from the Bay to the Gulf. We have vacation rentals that come in all shapes in sizes, no matter how big or small your group is. You can browse our website to view our available vacation rentals in the city of Anna Maria. No matter what your needs are, we have the necessary accommodations to suit them. We have so many options, we’re guaranteed to find you the perfect vacation rental fit for your great escape to the City of Anna Maria!

Southern Breeze 4
Southern Breeze 4
Weekly $749 - $1925 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 2/1 Sleeps: 6 Location: Anna Maria
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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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Beach Escape
Beach Escape
Weekly $1750 - $4725 *
PoolSpaBBQ GrillInternetDeck Chairs
Bed & Bath: 3/2.5 Sleeps: 8 Location: Anna Maria
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Whispering Whale Retreat
Whispering Whale Retreat
Weekly $1400 - $4725 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 4/2 Sleeps: 10 Location: Anna Maria
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Anna Maria Cottage
Anna Maria Cottage
Weekly $2000 - $6160 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 3/3 Sleeps: 6 Location: Anna Maria
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Aqua Cove
Aqua Cove
Weekly $2100 - $7700 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetTable GamesDeck ChairsBoat Dock
Bed & Bath: 4/3.5 Sleeps: 10 Location: Anna Maria
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The Rod and Reel Resort
The Rod and Reel Resort
Weekly $10500 - $28000 *
PoolSpaInternetTable GamesDeck Chairs
Bed & Bath: 11/8 Sleeps: 24 Location: Anna Maria
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Shells and Sunshine
Shells and Sunshine
Weekly $1575 - $5600 *
Linen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 3/2 Sleeps: 8 Location: Anna Maria
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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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Heron House
Heron House
Weekly $1575 - $5600 *
PoolLinen ServiceInternetDeck Chairs
Bed & Bath: 3/3 Sleeps: 10 Location: Anna Maria
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Limelight
Limelight
Weekly $1400 - $4725 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 3/2 Sleeps: 6 Location: Anna Maria
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Southern Breeze 6
Southern Breeze 6
Weekly $749 - $1925 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 2/1 Sleeps: 6 Location: Anna Maria
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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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A Sandbox by the Sea
A Sandbox by the Sea
Weekly $1400 - $4725 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 2/2 Sleeps: 6 Location: Anna Maria
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Hidden Oasis
Hidden Oasis
Weekly $1100 - $3605 *
InternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 4 Location: Anna Maria
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Moondance
Moondance
Weekly $1295 - $3850 *
Linen ServiceInternetDeck Chairs
Bed & Bath: 2/1.5 Sleeps: 4 Location: Anna Maria
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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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Direct Beach View
Direct Beach View
Weekly $2450 - $8400 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/4.5 Sleeps: 10 Location: Anna Maria
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Sunshine Reef
Sunshine Reef
Weekly $1925 - $6300 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/4 Sleeps: 10 Location: Anna Maria
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Low Tide
Low Tide
Weekly $1050 - $2688 *
InternetDeck Chairs
Bed & Bath: 2/1 Sleeps: 4 Location: Anna Maria
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Absolute Paradise
Absolute Paradise
Weekly $2100 - $8400 *
PoolSpaBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/4 Sleeps: 12 Location: Anna Maria
More details >
Acacia Breeze
Acacia Breeze
Weekly $1575 - $6300 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck ChairsBoat Dock
Bed & Bath: 3/3 Sleeps: 12 Location: Anna Maria
More details >
Montego Bay
Montego Bay
Weekly $2450 - $7700 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 5/4 Sleeps: 11 Location: Anna Maria
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Las Palmas
Las Palmas
Weekly $2100 - $3997 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 3/2 Sleeps: 10 Location: Anna Maria
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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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Sunny Side Up
Sunny Side Up
Weekly $1000 - $3500 *
BBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 2/2 Sleeps: 6 Location: Anna Maria
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A Snails Place
A Snails Place
Weekly $1350 - $3850 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 3/2 Sleeps: 6 Location: Anna Maria
More details >
Bay Bungalow
Bay Bungalow
Weekly $1100 - $4725 *
PoolLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 3/2 Sleeps: 8 Location: Anna Maria
More details >
Tortuga Bay
Tortuga Bay
Weekly $2100 - $7000 *
PoolSpaLinen ServiceBBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 5/3 Sleeps: 10 Location: Anna Maria
More details >
Sundown South
Sundown South
Weekly $1525 - $4725 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/3 Sleeps: 8 Location: Anna Maria
More details >
High Tide
High Tide
Weekly $1000 - $2835 *
InternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 4 Location: Anna Maria
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Southern Breeze 5
Southern Breeze 5
Weekly $749 - $1925 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 2/1 Sleeps: 6 Location: Anna Maria
More details >
Whispering Winds
Whispering Winds
Weekly $1295 - $3850 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/2 Sleeps: 8 Location: Anna Maria
More details >
Bahama Breeze
Bahama Breeze
Weekly $1750 - $6300 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/3 Sleeps: 8 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 >
Willow Beach House
Willow Beach House
Weekly $2450 - $9800 *
SpaBBQ GrillInternetVideo GamesDeck Chairs
Bed & Bath: 5/3.5 Sleeps: 12 Location: Anna Maria
More details >
Southern Breeze 3
Southern Breeze 3
Weekly $749 - $1925 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 2/1 Sleeps: 6 Location: Anna Maria
More details >
Sundown North
Sundown North
Weekly $1400 - $4550 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/3 Sleeps: 10 Location: Anna Maria
More details >
Carefree Cay
Carefree Cay
Weekly $1600 - $3850 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 3/2.5 Sleeps: 6 Location: Anna Maria
More details >
Sunset Paradise
Sunset Paradise
Weekly $2100 - $8400 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/4.5 Sleeps: 10 Location: Anna Maria
More details >
Tarpon Pointe
Tarpon Pointe
Weekly $1750 - $6300 *
PoolBBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 4/3 Sleeps: 12 Location: Anna Maria
More details >
Island Breeze
Island Breeze
Weekly $1400 - $4200 *
PoolSpaBBQ GrillInternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 6 Location: Anna Maria
More details >
Anna Maria Chateau
Anna Maria Chateau
Weekly $1400 - $5600 *
PoolLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 3/2 Sleeps: 8 Location: Anna Maria
More details >
Dancing Dolphin
Dancing Dolphin
Weekly $2500 - $7000 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/3.5 Sleeps: 8 Location: Anna Maria
More details >
Casa del Sol
Casa del Sol
Weekly $2450 - $7700 *
PoolLinen ServiceBBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 5/3 Sleeps: 10 Location: Anna Maria
More details >
Island Dream
Island Dream
Weekly $2275 - $6300 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/4 Sleeps: 10 Location: Anna Maria
More details >
Tahiti Bay
Tahiti Bay
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PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/4 Sleeps: 14 Location: Anna Maria
More details >
Southern Breeze 1
Southern Breeze 1
Weekly $749 - $1925 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 2/1 Sleeps: 6 Location: Anna Maria
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 >
Antigua Bay
Antigua Bay
Weekly $2450 - $8400 *
PoolSpaLinen ServiceBBQ GrillInternetVideo GamesTable GamesDeck Chairs
Bed & Bath: 5/4 Sleeps: 12 Location: Anna Maria
More details >
The Laguna Beach
The Laguna Beach
Weekly $1750 - $4725 *
PoolSpaBBQ GrillInternetDeck Chairs
Bed & Bath: 3/2 Sleeps: 6 Location: Anna Maria
More details >
Campbell House
Campbell House
Weekly $1575 - $3850 *
PoolSpaBBQ GrillInternetDeck Chairs
Bed & Bath: 3/2.5 Sleeps: 6 Location: Anna Maria
More details >
Sunchase Villa
Sunchase Villa
Weekly $1162 - $4900 *
BBQ GrillInternetDeck Chairs
Bed & Bath: 4/4.5 Sleeps: 8 Location: Anna Maria
More details >
Sunset Point
Sunset Point
Weekly $2100 - $6300 *
Linen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/3 Sleeps: 8 Location: Anna Maria
More details >
Breakaway
Breakaway
Weekly $2100 - $7700 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/2 Sleeps: 10 Location: Anna Maria
More details >
Magnolia Breeze
Magnolia Breeze
Weekly $1000 - $3500 *
BBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 2/2 Sleeps: 5 Location: Anna Maria
More details >
Lighthouse Lagoon
Lighthouse Lagoon
Weekly $2100 - $7700 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/4 Sleeps: 14 Location: Anna Maria
More details >
Ocean Walk
Ocean Walk
Weekly $1925 - $7700 *
PoolSpaLinen ServiceBBQ GrillInternetVideo GamesTable GamesDeck Chairs
Bed & Bath: 4/3.5 Sleeps: 12 Location: Anna Maria
More details >
Southern Breeze 2
Southern Breeze 2
Weekly $749 - $1925 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 2/1 Sleeps: 6 Location: Anna Maria
More details >
Seaside
Seaside
Weekly $1750 - $6300 *
Linen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 3/2.5 Sleeps: 10 Location: Anna Maria
More details >
Casa on the Beach
Casa on the Beach
Weekly $1134 - $5600 *
PoolLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 3/3 Sleeps: 8 Location: Anna Maria
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
More details >
Bay Breeze Bungalow
Bay Breeze Bungalow
Weekly $1750 - $6300 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 3/3.5 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 >
Bermuda Bay
Bermuda Bay
Weekly $2450 - $8400 *
PoolSpaLinen ServiceBBQ GrillInternetVideo GamesTable GamesDeck Chairs
Bed & Bath: 5/4 Sleeps: 14 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 >
The Beach House
The Beach House
Weekly $1400 - $3850 *
BBQ GrillInternetDeck Chairs
Bed & Bath: 3/2.5 Sleeps: 7 Location: Anna Maria
More details >
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
More details >
*Rates shown are estimates. Excludes Taxes, Fees and Travel Insurance.
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