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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!

Gulf View Suite 105
Gulf View Suite 105
Weekly $320 - $775 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 2 Location: Holmes Beach
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Gulf View Suite 101
Gulf View Suite 101
Weekly $320 - $775 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 4 Location: Holmes Beach
More details >
Beachfront Paradise
Beachfront Paradise
Weekly $4200 - $15960 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetDeck Chairs
Bed & Bath: 6/4.5 Sleeps: 18 Location: Bradenton Beach
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Dancing Dolphin
Dancing Dolphin
Weekly $2500 - $8316 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/3.5 Sleeps: 10 Location: Anna Maria
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Gulf View Room 213
Gulf View Room 213
Weekly $195 - $475 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 4 Location: Holmes Beach
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Gulf View Room 208
Gulf View Room 208
Weekly $215 - $475 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 5 Location: Holmes Beach
More details >
Deluxe King Gulf View Rm 209
Deluxe King Gulf View Rm 209
Weekly $215 - $495 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 3 Location: Holmes Beach
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Gulf View Room 203
Gulf View Room 203
Weekly $215 - $475 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 4 Location: Holmes Beach
More details >
Sunset Paradise
Sunset Paradise
Weekly $2450 - $9072 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/4.5 Sleeps: 10 Location: Anna Maria
More details >
Gulfside Oasis
Gulfside Oasis
Weekly $2450 - $9072 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 6/5 Sleeps: 12 Location: Holmes Beach
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Tropical Oasis
Tropical Oasis
Weekly $2100 - $9660 *
PoolLinen ServiceElevatorBBQ GrillInternetDeck Chairs
Bed & Bath: 5/4 Sleeps: 12 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
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Summer House
Summer House
Weekly $2400 - $15120 *
PoolSpaLinen ServiceBBQ GrillInternetVideo GamesTable GamesDeck Chairs
Bed & Bath: 8/6 Sleeps: 16 Location: Holmes Beach
More details >
Mango Breeze
Mango Breeze
Weekly $1750 - $4725 *
PoolLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 4/3.5 Sleeps: 10 Location: Holmes Beach
More details >
Deluxe King Resort View Rm 112
Deluxe King Resort View Rm 112
Weekly $175 - $425 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 3 Location: Holmes Beach
More details >
Deluxe King Gulf View Rm 207
Deluxe King Gulf View Rm 207
Weekly $215 - $495 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 3 Location: Holmes Beach
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A Snails Place
A Snails Place
Weekly $1400 - $4200 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 3/2 Sleeps: 6 Location: Anna Maria
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Aqua Cove
Aqua Cove
Weekly $2100 - $6720 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetTable GamesDeck ChairsBoat Dock
Bed & Bath: 4/3.5 Sleeps: 10 Location: Anna Maria
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Riki Tiki
Riki Tiki
Weekly $1925 - $6720 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/4 Sleeps: 8 Location: Holmes Beach
More details >
Deluxe King Resort View Rm 107
Deluxe King Resort View Rm 107
Weekly $195 - $450 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 3 Location: Holmes Beach
More details >
Aqua Reef
Aqua Reef
Monthly $5600 - $10080 *
PoolBBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 2/2 Sleeps: 4 Location: Holmes Beach
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Coastal Sunset
Coastal Sunset
Weekly $1750 - $5040 *
PoolLinen ServiceElevatorInternetDeck Chairs
Bed & Bath: 3/2.5 Sleeps: 6 Location: Holmes Beach
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Absolute Paradise
Absolute Paradise
Weekly $2275 - $9240 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/4 Sleeps: 14 Location: Anna Maria
More details >
Resort View Suite 110
Resort View Suite 110
Weekly $295 - $695 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 4 Location: Holmes Beach
More details >
Beach Paradise
Beach Paradise
Weekly $1750 - $6300 *
PoolLinen ServiceElevatorBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 4/4 Sleeps: 10 Location: Anna Maria
More details >
Room 6 Rod and Reel Resort
Room 6 Rod and Reel Resort
Weekly $2597 - $3367 *
PoolSpaBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 2/1.5 Sleeps: 6 Location: Anna Maria
More details >
Deluxe King Gulf View Rm 104
Deluxe King Gulf View Rm 104
Weekly $195 - $475 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 3 Location: Holmes Beach
More details >
FantaSea
FantaSea
Weekly $2600 - $4725 *
PoolSpaLinen ServiceBBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 3/3 Sleeps: 8 Location: Anna Maria
More details >
Blue Water View
Blue Water View
Weekly $2450 - $9072 *
PoolLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 6/5 Sleeps: 14 Location: Holmes Beach
More details >
Seaside
Seaside
Weekly $1750 - $7504 *
Linen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 3/2.5 Sleeps: 10 Location: Anna Maria
More details >
View of the Gulf
View of the Gulf
Weekly $2450 - $11200 *
PoolBBQ GrillInternetDeck Chairs
Bed & Bath: 7/4.5 Sleeps: 16 Location: Holmes Beach
More details >
The Rod and Reel Resort
The Rod and Reel Resort
Weekly $14000 - $22000 *
PoolSpaBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 11/8 Sleeps: 30 Location: Anna Maria
More details >
Hunters Point
Hunters Point
Weekly $2800 - $7700 *
Linen ServiceElevatorBBQ GrillInternetTable GamesDeck ChairsBoat Dock
Bed & Bath: 6/5.5 Sleeps: 12 Location: Cortez
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Pearl Beach
Pearl Beach
Weekly $2275 - $8400 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 6/4.5 Sleeps: 12 Location: Holmes Beach
More details >
Resort View Room 108
Resort View Room 108
Weekly $195 - $540 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 2 Location: Holmes Beach
More details >
A Bean Point Paradise
A Bean Point Paradise
Weekly $2275 - $9072 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetDeck Chairs
Bed & Bath: 5/4 Sleeps: 12 Location: Anna Maria
More details >
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
More details >
Room 8 Rod and Reel Resort
Room 8 Rod and Reel Resort
Weekly $2338 - $3178 *
PoolSpaBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 1/1 Sleeps: 2 Location: Anna Maria
More details >
Gulf View Room 102
Gulf View Room 102
Weekly $195 - $775 *
PoolLinen ServiceInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 2 Location: Holmes Beach
More details >
Resort View Suite 111
Resort View Suite 111
Weekly $295 - $6925 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 5 Location: Holmes Beach
More details >
Island Sol
Island Sol
Weekly $2100 - $7980 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 5/4 Sleeps: 10 Location: Bradenton Beach
More details >
AMI Beach House
AMI Beach House
Weekly $2800 - $7700 *
PoolSpaBBQ GrillInternetDeck Chairs
Bed & Bath: 6/4.5 Sleeps: 14 Location: Holmes Beach
More details >
Gulf View Suite 211
Gulf View Suite 211
Weekly $320 - $775 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 4 Location: Holmes Beach
More details >
Southern Exposure
Southern Exposure
Weekly $2275 - $7700 *
PoolSpaBBQ GrillInternetDeck Chairs
Bed & Bath: 5/4.5 Sleeps: 12 Location: Anna Maria
More details >
Reef Romance
Reef Romance
Weekly $2450 - $7560 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/4.5 Sleeps: 8 Location: Anna Maria
More details >
Summer Breeze
Summer Breeze
Weekly $2100 - $9072 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/4 Sleeps: 14 Location: Anna Maria
More details >
Beach Side Paradise
Beach Side Paradise
Weekly $4200 - $21000 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetDeck Chairs
Bed & Bath: 7/6 Sleeps: 16 Location: Bradenton Beach
More details >
Deluxe King Gulf View Rm 212
Deluxe King Gulf View Rm 212
Weekly $195 - $475 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 3 Location: Holmes Beach
More details >
Deluxe King Resort View Rm 114
Deluxe King Resort View Rm 114
Weekly $175 - $425 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 3 Location: Holmes Beach
More details >
Resort View Room 113
Resort View Room 113
Weekly $175 - $425 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 4 Location: Holmes Beach
More details >
Bayside Paradise
Bayside Paradise
Weekly $1785 - $6720 *
PoolLinen ServiceBBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 4/3 Sleeps: 10 Location: Holmes Beach
More details >
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
More details >
Resort View Suite 106
Resort View Suite 106
Weekly $320 - $775 *
PoolSpaLinen ServiceInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 2 Location: Holmes Beach
More details >
Anna Maria Grand Beach House
Anna Maria Grand Beach House
Weekly $5600 - $25200 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 9/9 Sleeps: 28 Location: Bradenton Beach
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 >
AMI Life
AMI Life
Weekly $3185 - $10500 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck ChairsBoat Dock
Bed & Bath: 5/3.5 Sleeps: 10 Location: Anna Maria
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
More details >
Deluxe King Gulf View Rm 204
Deluxe King Gulf View Rm 204
Weekly $215 - $495 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 3 Location: Holmes Beach
More details >
LaPlage 5
LaPlage 5
Weekly $1750 - $5460 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetDeck Chairs
Bed & Bath: 3/3 Sleeps: 6 Location: Holmes Beach
More details >
Acacia Breeze
Acacia Breeze
Weekly $1736 - $5460 *
PoolSpaLinen ServiceBBQ GrillInternetTable GamesDeck ChairsBoat Dock
Bed & Bath: 3/3 Sleeps: 12 Location: Anna Maria
More details >
Mandalay Bay
Mandalay Bay
Weekly $5600 - $20160 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetVideo GamesTable GamesDeck ChairsBoat Dock
Bed & Bath: 7/5.5 Sleeps: 20 Location: Bradenton Beach
More details >
Ocean Walk
Ocean Walk
Weekly $1925 - $7560 *
PoolSpaLinen ServiceBBQ GrillInternetVideo GamesTable GamesDeck Chairs
Bed & Bath: 4/3.5 Sleeps: 12 Location: Anna Maria
More details >
The Blue Horizon
The Blue Horizon
Weekly $4900 - $25200 *
PoolSpaElevatorBBQ GrillInternetDeck Chairs
Bed & Bath: 9/7.5 Sleeps: 21 Location: Bradenton Beach
More details >
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
More details >
Gulf View Room 202
Gulf View Room 202
Weekly $215 - $495 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 2 Location: Holmes Beach
More details >
LaPlage 7
LaPlage 7
Weekly $1925 - $5600 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetDeck Chairs
Bed & Bath: 3/2.5 Sleeps: 6 Location: Holmes Beach
More details >
Coastal Serenity
Coastal Serenity
Weekly $2100 - $6720 *
PoolSpaBBQ GrillInternetDeck Chairs
Bed & Bath: 4/3.5 Sleeps: 10 Location: Anna Maria
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 >
Resort View Suite 115
Resort View Suite 115
Weekly $265 - $750 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 5 Location: Holmes Beach
More details >
Hidden Cove 1
Hidden Cove 1
Weekly $1204 - $4620 *
PoolLinen ServiceInternetDeck Chairs
Bed & Bath: 2/2.5 Sleeps: 4 Location: Holmes Beach
More details >
Deluxe King Resort View Rm 109
Deluxe King Resort View Rm 109
Weekly $195 - $450 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 3 Location: Holmes Beach
More details >
Bradenton Beach Club Unit F
Bradenton Beach Club Unit F
Weekly $1750 - $5040 *
PoolSpaElevatorBBQ GrillInternetDeck Chairs
Bed & Bath: 3/2.5 Sleeps: 6 Location: Bradenton Beach
More details >
Deluxe King Gulf View Rm 214
Deluxe King Gulf View Rm 214
Weekly $195 - $495 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 3 Location: Holmes Beach
More details >
Caribbean Dream
Caribbean Dream
Weekly $2275 - $7700 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/4.5 Sleeps: 12 Location: Holmes Beach
More details >
Mermaids Dream
Mermaids Dream
Weekly $1400 - $4620 *
PoolLinen ServiceElevatorInternetTable GamesDeck Chairs
Bed & Bath: 3/3 Sleeps: 6 Location: Holmes Beach
More details >
Gulf View Room 103
Gulf View Room 103
Weekly $195 - $475 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 4 Location: Holmes Beach
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 >
Gulf Front Suite 201
Gulf Front Suite 201
Weekly $395 - $6801 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 5 Location: Holmes Beach
More details >
Gulf View Suite 210
Gulf View Suite 210
Weekly $320 - $775 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 4 Location: Holmes Beach
More details >
Paradise Point
Paradise Point
Weekly $2450 - $9240 *
PoolLinen ServiceElevatorBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 5/4 Sleeps: 12 Location: Anna Maria
More details >
A Ray of Sunshine
A Ray of Sunshine
Weekly $1505 - $4200 *
PoolSpaBBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 3/3 Sleeps: 6 Location: Anna Maria
More details >
Aqua Bay
Aqua Bay
Weekly $2275 - $6300 *
PoolSpaLinen ServiceBBQ GrillInternetDeck ChairsBoat Dock
Bed & Bath: 4/3 Sleeps: 8 Location: Holmes Beach
More details >
Gulf View Suite 215
Gulf View Suite 215
Weekly $320 - $750 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 4 Location: Holmes Beach
More details >
Island Dream
Island Dream
Weekly $2200 - $6720 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 4/4 Sleeps: 10 Location: Anna Maria
More details >
Gulf View Suite 206
Gulf View Suite 206
Weekly $340 - $775 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 4 Location: Holmes Beach
More details >
Gulf Front Paradise
Gulf Front Paradise
Weekly $3500 - $11900 *
PoolSpaLinen ServiceElevatorBBQ GrillInternetTable GamesDeck Chairs
Bed & Bath: 4/4.5 Sleeps: 10 Location: Anna Maria
More details >
The Anna Maria Luxury Suite
The Anna Maria Luxury Suite
Weekly $395 - $895 *
PoolSpaLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/2 Sleeps: 5 Location: Holmes Beach
More details >
Gulf View Suite 205
Gulf View Suite 205
Weekly $240 - $775 *
PoolLinen ServiceBBQ GrillInternetDeck Chairs
Bed & Bath: 1/1 Sleeps: 4 Location: Holmes Beach
More details >
*Rates shown are estimates. Excludes Taxes, Fees and Travel Insurance.
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