Long stays on Anna Maria Island
Long Stay Rentals on Anna Maria Island
Planning a 30 to 180 day stay? These guides cover snowbird travel, monthly rentals, and long-term beach living with a relaxed, family-friendly vibe. Dogs 35 lbs or less are welcome.
Long stay guide
Snowbird Rentals
Seasonal living on Anna Maria Island.
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Long stay guide
Monthly Beach Rentals
Seasonal living on Anna Maria Island.
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Long stay guide
Winter Stays
Seasonal living on Anna Maria Island.
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Long stay guide
3-Month Stays
Seasonal living on Anna Maria Island.
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Long stay guide
Extended Stays
Seasonal living on Anna Maria Island.
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Long stay guide
Remote Work Stays
Seasonal living on Anna Maria Island.
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Long stay guide
Retiree Travel
Seasonal living on Anna Maria Island.
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Long stay guide
Quiet Winter Rentals
Seasonal living on Anna Maria Island.
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Long stay guide
Long-Term Beach Living
Seasonal living on Anna Maria Island.
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Long stay guide
Work From the Beach
Seasonal living on Anna Maria Island.
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Long stay guide
Snowbird Community
Seasonal living on Anna Maria Island.
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Long stay guide
Furnished Long Stays
Seasonal living on Anna Maria Island.
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Long stay guide
Kitchen for Long Stays
Seasonal living on Anna Maria Island.
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Long stay guide
Washer and Dryer Stays
Seasonal living on Anna Maria Island.
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Long stay guide
Low-Noise Neighborhoods
Seasonal living on Anna Maria Island.
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Long stay guide
Grocery Walkability
Seasonal living on Anna Maria Island.
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Long stay guide
Healthcare Access
Seasonal living on Anna Maria Island.
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Long stay guide
Seasonal Relocations
Seasonal living on Anna Maria Island.
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Long stay guide
Second-Home Feel
Seasonal living on Anna Maria Island.
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Long stay guide
Repeat Guest Stays
Seasonal living on Anna Maria Island.
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Ready for a longer island stay?
Build your season around beach mornings, pool afternoons, and a calm pace that feels like home.