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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!

Breakaway
Breakaway
Weekly $1750 - $5600 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/2 Sleeps: 10 Location: Anna Maria 4.8 (5 reviews)
More details >
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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Cabana Breeze
Cabana Breeze
Weekly $1750 - $8400 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 4/2 Sleeps: 10 Location: Anna Maria
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Room 3 Rod and Reel Resort
Room 3 Rod and Reel Resort
Weekly $2338 - $2737 *
PoolSpaBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 2/1 Sleeps: 6 Location: Anna Maria
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Southern Breeze 5
Southern Breeze 5
Weekly $749 - $2100 *
PoolSpaBBQ GrillInternetDeck Chairs
Bed & Bath: 2/1 Sleeps: 6 Location: Anna Maria
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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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Campbell House
Campbell House
Weekly $1953 - $3850 *
PoolSpaBBQ GrillInternetDeck Chairs
Bed & Bath: 3/2.5 Sleeps: 6 Location: Anna Maria
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Gulf Front Paradise
Gulf Front Paradise
Weekly $3500 - $11900 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 4/4.5 Sleeps: 10 Location: Anna Maria
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Moondance
Moondance
Weekly $1295 - $3150 *
SpaLinen ServiceInternetDeck Chairs
Bed & Bath: 2/1.5 Sleeps: 4 Location: Anna Maria 4.33333333333 (3 reviews)
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Anna Maria Cottage
Anna Maria Cottage
Weekly $1750 - $4620 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 3/3 Sleeps: 6 Location: Anna Maria
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High Tide
High Tide
Weekly $1001 - $3010 *
SpaInternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 4 Location: Anna Maria
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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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Acacia Breeze
Acacia Breeze
Weekly $1736 - $4760 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck ChairsBoat Dock
Bed & Bath: 3/3 Sleeps: 12 Location: Anna Maria 5 (6 reviews)
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Room 2 Rod and Reel Resort
Room 2 Rod and Reel Resort
Weekly $2338 - $2737 *
PoolSpaBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 2/1 Sleeps: 6 Location: Anna Maria
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Pelican Villa
Pelican Villa
Weekly $1750 - $4725 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/3 Sleeps: 8 Location: Anna Maria 4 (1 reviews)
More details >
Sunshine Reef
Sunshine Reef
Weekly $1925 - $5600 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/4 Sleeps: 10 Location: Anna Maria 5 (5 reviews)
More details >
The Rod and Reel Resort
The Rod and Reel Resort
Weekly $14882 - $22001 *
PoolSpaBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 11/8 Sleeps: 30 Location: Anna Maria 5 (4 reviews)
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Whispering Winds
Whispering Winds
Weekly $1295 - $3850 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/2 Sleeps: 8 Location: Anna Maria
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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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Southern Breeze 1
Southern Breeze 1
Weekly $749 - $2450 *
PoolSpaBBQ GrillInternetDeck Chairs
Bed & Bath: 2/1 Sleeps: 6 Location: Anna Maria
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Limelight
Limelight
Weekly $2002 - $3850 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 3/2 Sleeps: 6 Location: Anna Maria 4.5 (2 reviews)
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AMI Life
AMI Life
Weekly $3185 - $8750 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck ChairsBoat Dock
Bed & Bath: 5/3.5 Sleeps: 10 Location: Anna Maria
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Room 7 Rod and Reel Resort
Room 7 Rod and Reel Resort
Weekly $1428 - $2667 *
PoolSpaBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 1/1 Sleeps: 4 Location: Anna Maria 5 (2 reviews)
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Southern Breeze 6
Southern Breeze 6
Weekly $749 - $2100 *
PoolSpaBBQ GrillInternetDeck Chairs
Bed & Bath: 2/1 Sleeps: 6 Location: Anna Maria
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Sunset Point
Sunset Point
Weekly $2450 - $7000 *
SpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/3 Sleeps: 8 Location: Anna Maria 5 (1 reviews)
More details >
Anna Maria Island Breeze
Anna Maria Island Breeze
Weekly $1400 - $3780 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 2/2 Sleeps: 6 Location: Anna Maria
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Sunny Side Up
Sunny Side Up
Weekly $1001 - $2975 *
SpaBBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 2/2 Sleeps: 6 Location: Anna Maria 4.33333333333 (3 reviews)
More details >
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)
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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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Lighthouse Lagoon
Lighthouse Lagoon
Weekly $2100 - $7000 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/4 Sleeps: 14 Location: Anna Maria
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Low Tide
Low Tide
Weekly $1001 - $2688 *
SpaInternetDeck Chairs
Bed & Bath: 2/1 Sleeps: 4 Location: Anna Maria 2.5 (2 reviews)
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Montego Bay
Montego Bay
Weekly $2275 - $7700 *
PoolSpaBBQ GrillInternetDeck Chairs
Bed & Bath: 5/4 Sleeps: 12 Location: Anna Maria 4 (2 reviews)
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Tropical Oasis
Tropical Oasis
Weekly $2100 - $7525 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetDeck Chairs
Bed & Bath: 5/4 Sleeps: 12 Location: Anna Maria 5 (8 reviews)
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The Beach House
The Beach House
Weekly $1400 - $4620 *
SpaBBQ GrillInternetDeck Chairs
Bed & Bath: 3/2.5 Sleeps: 7 Location: Anna Maria
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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
More details >
FantaSea
FantaSea
Weekly $2604 - $4550 *
PoolSpaLinen ServiceBBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 3/3 Sleeps: 8 Location: Anna Maria
More details >
A Ray of Sunshine
A Ray of Sunshine
Weekly $1505 - $3500 *
PoolSpaBBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 3/3 Sleeps: 6 Location: Anna Maria 5 (1 reviews)
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Coastal Serenity
Coastal Serenity
Weekly $2100 - $5600 *
PoolSpaBBQ GrillInternetDeck Chairs
Bed & Bath: 4/3.5 Sleeps: 10 Location: Anna Maria
More details >
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)
More details >
Dancing Dolphin
Dancing Dolphin
Weekly $2499 - $6930 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/3.5 Sleeps: 10 Location: Anna Maria 5 (1 reviews)
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 (2 reviews)
More details >
Heron House
Heron House
Weekly $1575 - $4725 *
PoolSpaLinen ServiceInternetDeck Chairs
Bed & Bath: 3/3 Sleeps: 10 Location: Anna Maria 5 (1 reviews)
More details >
Pelican Cove
Pelican Cove
Weekly $1225 - $2450 *
PoolSpaLinen ServiceBBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 2/2 Sleeps: 4 Location: Anna Maria
More details >
Reef Romance
Reef Romance
Weekly $2450 - $6300 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/4.5 Sleeps: 8 Location: Anna Maria
More details >
Ocean Walk
Ocean Walk
Weekly $1925 - $6300 *
PoolSpaLinen ServiceBBQ GrillInternetVideo GamesTable GamesDeck Chairs
Bed & Bath: 4/3.5 Sleeps: 12 Location: Anna Maria 5 (2 reviews)
More details >
Bay Bungalow
Bay Bungalow
Weekly $1449 - $4725 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 3/2 Sleeps: 8 Location: Anna Maria 5 (4 reviews)
More details >
Casa on the Beach
Casa on the Beach
Weekly $2100 - $4550 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 3/3 Sleeps: 6 Location: Anna Maria 4.16666666667 (6 reviews)
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Island Dream
Island Dream
Weekly $2198 - $5600 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/4 Sleeps: 10 Location: Anna Maria
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Ocean Sunset
Ocean Sunset
Weekly $3150 - $6300 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 5/3 Sleeps: 10 Location: Anna Maria
More details >
Bahama Breeze
Bahama Breeze
Weekly $1750 - $5250 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 4/3 Sleeps: 8 Location: Anna Maria 5 (1 reviews)
More details >
Room 5 Rod and Reel Resort
Room 5 Rod and Reel Resort
Weekly $1358 - $2037 *
PoolSpaBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 1/1 Sleeps: 2 Location: Anna Maria
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Southern Breeze 4
Southern Breeze 4
Weekly $749 - $2100 *
PoolSpaBBQ GrillInternetDeck Chairs
Bed & Bath: 2/1 Sleeps: 6 Location: Anna Maria
More details >
Southern Breeze 2
Southern Breeze 2
Weekly $749 - $2100 *
PoolSpaBBQ GrillInternetDeck Chairs
Bed & Bath: 2/1 Sleeps: 6 Location: Anna Maria 4 (1 reviews)
More details >
Sunchase Villa
Sunchase Villa
Weekly $1505 - $4725 *
SpaBBQ GrillInternetDeck Chairs
Bed & Bath: 4/4.5 Sleeps: 8 Location: Anna Maria 4 (2 reviews)
More details >
Beach Paradise
Beach Paradise
Weekly $1750 - $5425 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 4/4 Sleeps: 10 Location: Anna Maria
More details >
Summer Breeze
Summer Breeze
Weekly $2100 - $7560 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/4 Sleeps: 14 Location: Anna Maria
More details >
Southern Breeze 3
Southern Breeze 3
Weekly $749 - $2100 *
PoolSpaBBQ GrillInternetDeck Chairs
Bed & Bath: 2/1 Sleeps: 6 Location: Anna Maria 4.5 (2 reviews)
More details >
Room 4 Rod and Reel Resort
Room 4 Rod and Reel Resort
Weekly $1358 - $2037 *
PoolSpaBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 1/1 Sleeps: 2 Location: Anna Maria
More details >
Casa Muratti
Casa Muratti
Weekly $1750 - $4200 *
PoolSpaBBQ GrillInternetDeck Chairs
Bed & Bath: 4/3.5 Sleeps: 8 Location: Anna Maria 5 (2 reviews)
More details >
Willow Beach House
Willow Beach House
Weekly $2450 - $7700 *
SpaBBQ GrillInternetVideo GamesTable GamesDeck Chairs
Bed & Bath: 5/3.5 Sleeps: 12 Location: Anna Maria 4 (1 reviews)
More details >
Anna Maria Chateau
Anna Maria Chateau
Weekly $1400 - $5600 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 3/2 Sleeps: 8 Location: Anna Maria 3.75 (4 reviews)
More details >
Paradise on Pine
Paradise on Pine
Weekly $1750 - $5460 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetTable GamesDeck ChairsBoat Dock
Bed & Bath: 4/3.5 Sleeps: 12 Location: Anna Maria
More details >
Las Palmas
Las Palmas
Weekly $2100 - $3500 *
PoolSpaBBQ GrillInternetDeck Chairs
Bed & Bath: 3/2 Sleeps: 10 Location: Anna Maria
More details >
Aqua Cove
Aqua Cove
Weekly $2100 - $5600 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetTable GamesDeck ChairsBoat Dock
Bed & Bath: 4/3.5 Sleeps: 10 Location: Anna Maria 4 (1 reviews)
More details >
Shells and Sunshine
Shells and Sunshine
Weekly $1575 - $3850 *
SpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 3/2 Sleeps: 8 Location: Anna Maria
More details >
Room 6 Rod and Reel Resort
Room 6 Rod and Reel Resort
Weekly $2002 - $3367 *
PoolSpaBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 2/1.5 Sleeps: 6 Location: Anna Maria 5 (1 reviews)
More details >
Absolute Paradise
Absolute Paradise
Weekly $2275 - $7700 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/4 Sleeps: 14 Location: Anna Maria 5 (1 reviews)
More details >
The Big Yellow House
The Big Yellow House
Weekly $2450 - $10500 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 5/4 Sleeps: 14 Location: Anna Maria 5 (3 reviews)
More details >
Beach Escape
Beach Escape
Weekly $1750 - $4200 *
PoolSpaBBQ GrillInternetDeck Chairs
Bed & Bath: 3/2.5 Sleeps: 8 Location: Anna Maria
More details >
Magnolia Breeze
Magnolia Breeze
Weekly $1001 - $3850 *
SpaBBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 2/2 Sleeps: 5 Location: Anna Maria 5 (2 reviews)
More details >
Once Upon A Tide
Once Upon A Tide
Weekly $1925 - $5600 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 4/3.5 Sleeps: 8 Location: Anna Maria 5 (5 reviews)
More details >
Hidden Oasis
Hidden Oasis
Weekly $1050 - $2975 *
SpaInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 4 Location: Anna Maria 5 (3 reviews)
More details >
Angelfish
Angelfish
Weekly $1001 - $3150 *
SpaBBQ GrillInternet
Bed & Bath: 3/2 Sleeps: 8 Location: Anna Maria
More details >
Room 1 Rod and Reel Resort
Room 1 Rod and Reel Resort
Weekly $1127 - $1568 *
PoolSpaInternetTable GamesDeck Chairs
Bed & Bath: 1/1 Sleeps: 2 Location: Anna Maria
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 5 (2 reviews)
More details >
Seaside
Seaside
Weekly $1750 - $7504 *
SpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 3/2.5 Sleeps: 10 Location: Anna Maria 5 (1 reviews)
More details >
Whispering Whale Retreat
Whispering Whale Retreat
Weekly $1400 - $3850 *
PoolSpaBBQ GrillInternetDeck Chairs
Bed & Bath: 4/2 Sleeps: 10 Location: Anna Maria
More details >
Room 8 Rod and Reel Resort
Room 8 Rod and Reel Resort
Weekly $1778 - $3178 *
PoolSpaBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 1/1 Sleeps: 2 Location: Anna Maria
More details >
Tarpon Pointe
Tarpon Pointe
Weekly $1750 - $4725 *
PoolSpaBBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 4/3 Sleeps: 10 Location: Anna Maria 5 (4 reviews)
More details >
Island Breeze
Island Breeze
Weekly $1400 - $3150 *
PoolSpaBBQ GrillInternetDeck Chairs
Bed & Bath: 2/2 Sleeps: 6 Location: Anna Maria 4 (1 reviews)
More details >
A Snails Place
A Snails Place
Weekly $1400 - $3500 *
PoolSpaBBQ GrillInternetDeck Chairs
Bed & Bath: 3/2 Sleeps: 6 Location: Anna Maria 3 (1 reviews)
More details >
*Rates shown are estimates. Excludes Taxes, Fees and Travel Insurance.
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