When you’re traveling all the way to an idyllic spot like Anna Maria Island, it really pays to go the extra mile (or half-block) and book a getaway right on the sand. These seven Anna Maria gulf front rentals will upgrade your next beach weekend to the ultimate retreat.

Wine Down

wine down anna maria island | vacasa

Treat yourself: Not only is there an amazing ocean view and direct beach access, but there’s also a private heated pool and hot tub.

Tour Wine Down.

Sea Song

anna maria island rental oceanfront view

This sweet beach bungalow combines classic architecture with lots of natural light and a partially-covered patio that leads right down to the sand. Pick an Adirondack chair and admire unobstructed ocean views.

Tour Sea Song.

Vista Grande 1: Sul Mare

anna maria island oceanfront home

Feeling a little fancy? Choose this upscale Anna Maria gulf front property. Even the building’s pool and hot tub have ocean views.

Tour Vista Grande 1: Sul Mare.

Vista Grande 3 Penthouse

view from Vista Grande 3 Penthouse

If you’re feeling really fancy, then choose this penthouse suite. The ocean is practically in your living room with two walls of windows.

Tour Vista Grande 3 Penthouse.

Water’s Edge 205 South

Water’s Edge 205 South

This gulf front home in Holmes Beach is a bit more laid-back, with a bright interior and nice views of both the pool and the beach.

Tour Water’s Edge 205 South.

A Gulf Front Getaway

anna maria island condo rental

Keep cool in this condo with a north-facing view and a lovely gulf front pool. You can access the beach right from the deck.

Tour A Gulf Front Getaway.

Honey Beach House

gulf front anna maria rental | vacasa

Follow the little paving stones through the seagrass to the sand, or stay on the porch with a book and a glass of lemonade. This gulf front home in Holmes Beach is even dog-friendly.

Tour Honey Beach House.

Still searching for the perfect getaway? Browse all Anna Maria gulf front rentals

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Author: Hannah Morrison

Hannah hails from Telluride, CO and currently lives in Portland, where she works as writer, editor, and unofficial resident poet for Team Vacasa. You'll often find Hannah singing and dancing down the sidewalk, making really tall sandwiches, and planning her next long run.