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Anna Maria Island Luxury Vacation Rentals

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While Anna Maria Vacations entire business model is based on hand selecting the best rental properties for our guests to experience, there is a very special group of “luxury” properties within our fantastic portfolio. Our luxury grand homes and condos are located on both the Gulf and Bay waters and offers the best upscale experience that the Island has to offer. We also have luxury inland homes just a few minute stroll to the beach. Large luxury homes up to 9 bedroom or just a fantastic 3 bedroom with all the amenities you could ever want- we have got what the discerning traveler is looking for.

Anna Maria Island will have you ensnared after your first visit, especially after meeting her crystal clear waters and burying your feet into the soft, warm sand; you may never want to leave. The Island has something for everyone. During the day you can go fishing, dolphin watching, paddle boarding, kayaking, sailing, or ride a jet ski. Want some downtime from the hustle and bustle? Take some time to slow things down and go swimming in the Gulf of Mexico or walk on our world renowned beaches. The days may be warm and the air is crisp but as the night settles in, the air gets cooler, the water curls at your doorstep, and the night envelopes you in its tranquility.

Anna Maria Island boasts some of the finest beachfront vacation rentals in all of Florida. There is no place better to leave the noise of the city behind and wake up to waves and sun at your doorstep. The Island is pleasantly perfect for any kind of getaway including but not limited to a honeymoon, a yearly family vacation, or simply a spur-of-the-moment getaway. Several of our luxury vacation rentals are very spacious- plenty large enough to accommodate multiple families or multiple generations of families. Unlike most other Florida tropical resort destinations, Anna Maria Island offers an experience like no other, unadulterated from the real world, extending candid memories that will last you a lifetime. After booking your luxury vacation rental, the only problem you will encounter is not wanting to leave!

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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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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Gulfside Oasis
Gulfside Oasis
Weekly $2450 - $8400 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 6/5 Sleeps: 12 Location: Holmes Beach
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Hunters Point
Hunters Point
Weekly $2800 - $9800 *
Linen ServiceElevatorBBQ GrillInternetTable GamesDeck ChairsBoat Dock
Bed & Bath: 6/5.5 Sleeps: 12 Location: Cortez
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Blue Water View
Blue Water View
Weekly $2450 - $8400 *
PoolLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 6/5 Sleeps: 12 Location: Holmes Beach
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LaPlage 7
LaPlage 7
Weekly $1925 - $5600 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetDeck Chairs
Bed & Bath: 3/2.5 Sleeps: 6 Location: Holmes Beach
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Serenity Beach
Serenity Beach
Weekly $3150 - $14000 *
PoolSpaLinen ServiceBBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 5/4.5 Sleeps: 13 Location: Anna Maria
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Bradenton Beach Club Unit F
Bradenton Beach Club Unit F
Weekly $1750 - $5600 *
PoolSpaElevatorBBQ GrillInternetDeck Chairs
Bed & Bath: 3/2.5 Sleeps: 6 Location: Bradenton 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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Sunset Paradise
Sunset Paradise
Weekly $2100 - $9100 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/4.5 Sleeps: 10 Location: Anna Maria
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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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The Blue Horizon
The Blue Horizon
Weekly $4900 - $21000 *
PoolSpaElevatorBBQ GrillInternetDeck Chairs
Bed & Bath: 9/7.5 Sleeps: 21 Location: Bradenton Beach
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Seaside
Seaside
Weekly $1750 - $6300 *
Linen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 3/2.5 Sleeps: 10 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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Tropical Oasis
Tropical Oasis
Weekly $2450 - $14000 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 8/5 Sleeps: 16 Location: Holmes Beach
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Carefree Cay
Carefree Cay
Weekly $1600 - $3850 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 3/2.5 Sleeps: 6 Location: Anna Maria
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Malibu Beach
Malibu Beach
Weekly $2800 - $14000 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 8/7.5 Sleeps: 16 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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Bayfront Paradise
Bayfront Paradise
Weekly $2450 - $10500 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck ChairsBoat Dock
Bed & Bath: 5/4.5 Sleeps: 10 Location: Holmes Beach
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Summer Sun
Summer Sun
Weekly $1925 - $8400 *
PoolSpaLinen ServiceBBQ GrillInternetVideo GamesTable GamesDeck Chairs
Bed & Bath: 5/5.5 Sleeps: 10 Location: Bradenton Beach
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LaPlage 5
LaPlage 5
Weekly $1925 - $5600 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetDeck Chairs
Bed & Bath: 3/3 Sleeps: 6 Location: Holmes Beach
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Surf View
Surf View
Weekly $2800 - $14000 *
PoolLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 8/6 Sleeps: 16 Location: Holmes Beach
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Acacia Breeze
Acacia Breeze
Weekly $1575 - $6300 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck ChairsBoat Dock
Bed & Bath: 3/3 Sleeps: 12 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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Willow Beach House
Willow Beach House
Weekly $2450 - $9800 *
SpaBBQ GrillInternetVideo GamesDeck Chairs
Bed & Bath: 5/3.5 Sleeps: 12 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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Beachfront Paradise
Beachfront Paradise
Weekly $3500 - $15400 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 6/4.5 Sleeps: 18 Location: Bradenton Beach
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Summer Breeze
Summer Breeze
Weekly $2100 - $8400 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/4 Sleeps: 17 Location: Anna Maria
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Avalon
Avalon
Weekly $2450 - $9100 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetDeck Chairs
Bed & Bath: 4/3.5 Sleeps: 8 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
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Pearl Beach
Pearl Beach
Weekly $2100 - $8400 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 6/4.5 Sleeps: 12 Location: Holmes Beach
More details >
Absolute Paradise
Absolute Paradise
Weekly $2100 - $8400 *
PoolSpaBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/4 Sleeps: 12 Location: Anna Maria
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Coastal Sunset
Coastal Sunset
Weekly $1750 - $5600 *
PoolLinen ServiceElevatorInternetDeck Chairs
Bed & Bath: 3/2.5 Sleeps: 6 Location: Holmes Beach
More details >
A Snails Place
A Snails Place
Weekly $1350 - $3850 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 3/2 Sleeps: 6 Location: Anna Maria
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Caribbean Dream
Caribbean Dream
Weekly $2100 - $8400 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/4.5 Sleeps: 12 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 >
Summer House
Summer House
Weekly $2800 - $14000 *
PoolSpaLinen ServiceBBQ GrillInternetVideo GamesTable GamesDeck Chairs
Bed & Bath: 8/6 Sleeps: 16 Location: Holmes Beach
More details >
Riki Tiki
Riki Tiki
Weekly $1750 - $6300 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/4 Sleeps: 8 Location: Holmes Beach
More details >
Mandalay Bay
Mandalay Bay
Weekly $5250 - $17500 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetVideo GamesTable GamesDeck ChairsBoat Dock
Bed & Bath: 7/7.5 Sleeps: 16 Location: Bradenton Beach
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*Rates shown are estimates. Excludes Taxes, Fees and Travel Insurance.
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