7 charming Anna Maria beach cottages for a seaside retreat

the beach of Anna Maria Island
Vacation home on Anna Maria Island with an outdoor pool

We’ve packed our big towels and our floppy sun hats. We’ve slathered ourselves in sunblock. Now, all we need is a cozy spot to rest our sandy, sun-sleepy selves before we do it all again. When the beach is calling, these Anna Maria beach cottages make a picture-perfect home base.

The pool area of a cottage rental in Anna Maria.

Mangrove Cottage

This dog-friendly Anna Maria cottage has room for six people, along with a patio, a private pool, and a welcoming environment. The beach is also just a short walk away for added convenience.

Anna Maria beach vacation rental.

Starfish Beach Cottage #3

There is no better way to reset and recharge than walking along the warm sandy beach while listening to the tide ebb and flow.

Luxurious outdoor pool of a vacation home in Holmes Beach, FL.

Almost Gulf Front

After a day of seashell hunting, return home for a family meal in this airy Anna Maria beach cottage. The back patio—with a private saltwater pool, lush landscaping, and a tiki bar—is perfect for an evening beverage and some light reading.

palm trees out front of the Sea Palm Cottage on anna maria island

Sea Palm Cottage

The beach is just a block away from this sunny three-bedroom cottage, and the lush foliage adds a tropical flair right outside your door.

Blue vacation rental with a cobblestone style driveway in Anna Maria, FL.

Sunset Glow

Beach cottage on the outside, high-end ocean retreat on the inside. Take advantage of the private pool, updated kitchen, and beach access a block and a half away.

Large vacation home with an outdoor pool and a yard with palm trees in Holmes Beach, FL.

3 Oars

This Holmes Beach cottage has three bedrooms, a private pool, and an inviting backyard with a gas grill.

a patio with a table and beach chairs overlooking the sand dunes

Dolphin Watch

Yes, the sand really is right there. Sit back and soak up the views at this two-bedroom Anna Maria beach cottage.

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