A beach scene with palm trees, lounge chairs, and umbrellas on the sand near the ocean under a clear blue sky.
A small white house with a fenced entrance, surrounded by green lawn and palm trees, under a bright blue sky with fluffy clouds.
Two canopy beds with blue bedding, a round rug, wicker stools, patterned floor, and a cozy, coastal-themed decor in a bright room.
Two people relaxing on lounge chairs on a wooden deck, with a striped awning above.
Dates
Wed, 30 Jul - Thu, 31 Jul
Guests
2 Adults

Welcome to Paradise

Eight Destinations. One Island Experience.

Anna Maria Island Inn offers an exclusive collection of eight uniquely curated beachfront and island properties, each thoughtfully designed to deliver a premium coastal escape. From sophisticated Gulf-front sanctuaries to lush tropical retreats, every location offers a perfect blend of privacy, elegance, and comfort for the modern traveler.

A scenic beach with clear turquoise water, white sand, and seaside houses under a bright blue sky with clouds in the distance.
A modern backyard with a swimming pool, palm trees, lounge chairs, and a wooden deck, surrounded by a white fence and a house.
A scenic beach with clear turquoise water, white sand, and seaside houses under a bright blue sky with clouds in the distance.
A modern backyard with a swimming pool, palm trees, lounge chairs, and a wooden deck, surrounded by a white fence and a house.

From luxe beachfront retreats like Seaside to nostalgic hideaways like Haley’s and tropical suites across Tropic Isle, each property caters to a different vacation style. Choose the style that best suits your vision for the ideal Anna Maria Island getaway!

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Island Accommodations

Anna Maria Island Stays

Anna Maria Island is a warm and welcoming destination for everyone who loves sunshine and white sand. We offer multiple ways to make the most of your island vacation. Explore our beachfront, poolside, and group accommodations below.

All Properties

Beach scene with lounge chairs, umbrellas, a wooden deck, and palm trees under a clear blue sky, adjacent to a building.

OCEANFRONT

Beachfront

Seaside

Upscale rooms with direct Gulf views and instant beach access—designed for premium seaside relaxation.

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A beachfront deck with a table, chairs, and an umbrella overlooks the sandy beach and ocean under a blue sky with clouds.

OCEANFRONT

Beachfront

Seabreeze 

Located on a quieter stretch of beach with upstairs and downstairs rooms - perfect for couples or families.

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A backyard features a modern pool with a wooden deck, surrounded by palm trees, lounge chairs, and a patio dining area.

WALK TO THE BEACH

Bayside

Captain’s Quarters

Four stylish tropical units each with a king bed, shared pool & hot tub, steps from the Gulf and historic Bridge Street.

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The image shows a sunny pool area with lounge chairs, umbrellas, and palm trees, set against a backdrop of a clear blue sky and clouds.

WALK TO THE BEACH

Bayside

Pelican Post

A tropical garden hideaway with a resort-style pool & hot tub, just steps to the beach and Bridge Street shops.

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A sunny backyard with a pool, blue chairs, and lush tropical trees and plants under a clear blue sky.

HOLMES BEACH

Available September

Driftwood

Reopening soon. A cozy, seven room property in Holmes Beach, two blocks from soft white sand & local shops.

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A swimming pool with lounge chairs and striped umbrellas, surrounded by white buildings, set against a backdrop of palm trees and blue sky.

HOLMES BEACH

Available September

Haley’s

Reopening soon. An iconic 1950s Florida‑style accommodations, with pool access, tropical charm & steps from beaches.

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A backyard mini-golf course with palm trees and a small bench is visible next to a pool area and modern house.

WALK TO THE BEACH

Beachside

The Retreat

Newly renovated poolside suites across from beach with a putting green, pool & hot tub, perfect for families & groups.

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The image shows a tropical pool deck with sun loungers, palm trees, and a clear blue sky in the background.

WALK TO THE BEACH

Available September

Tropic Isle

Tropical oasis across from the beach, with heated pool, oceanview rooms & private patios for poolside escape.

Explore

Curated Island Adventures

Explore Anna Maria Island

Create unforgettable memories with Prime Vacations’ Exclusive Experiences. From serene walks at Bean Point Beach to relaxing afternoons at Bayfront Park and vibrant outings in Bradenton, Florida, adventure awaits. Enjoy private yacht charters, guided island tours, and handpicked local activities. Whether you crave excitement or relaxation, discover the very best of Anna Maria Island and beyond crafted for comfort, luxury, and lasting memories

Area Guide

A person relaxes on a long wooden pier extending into a vast body of water, under a clear blue sky with scattered clouds, ending at a structure.
A group of people is celebrating, clinking champagne glasses together outdoors, suggesting a festive occasion or gathering.
A scenic beach at sunset with vibrant pink and orange clouds, gentle waves, and a wide sandy shore.

Curated Island Adventures

Explore Anna Maria Island

Create unforgettable memories with Prime Vacations’ Exclusive Experiences. From serene walks at Bean Point Beach to relaxing afternoons at Bayfront Park and vibrant outings in Bradenton, Florida, adventure awaits. Enjoy private yacht charters, guided island tours, and handpicked local activities. Whether you crave excitement or relaxation, discover the very best of Anna Maria Island and beyond crafted for comfort, luxury, and lasting memories

Area Guide

Anna Maria Islands Inn

Stay 2, Get 1 FREE

Get a FREE third night when you stay anytime from 8/10-12/18/25. Blackout dates apply; no promotional code required.

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