Long stays on Anna Maria Island
Long Stay Rentals on Anna Maria Island
Planning to stay longer than a week? Every stay at The Sandbox is at least 7 nights, and a longer stay can be any length after that, priced at the seasonal weekly rate ($1,495 to $3,495 a week, depending on the season, plus a $315 departure clean, a $60 non-refundable security fee, administrative and reservation fees, and taxes). There is no separate monthly rate or discount. These guides cover snowbird travel, month-long stays, and long-term beach living with a relaxed, family-friendly vibe. One dog up to 35 lb is welcome with approval.
Coming for the winter? Start with our guide to a snowbird rental on Anna Maria Island.
Planning 28 nights or more? Contact us and we will help you line up the weeks.
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
Groceries and Essentials
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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Prefer No-Pet Extended Stays?
If you need a pet-free home for a longer stay, our sister property has a strict no-pet policy.
Bay to Beach House
A separate home with a strict no-pet policy. Check its own site for rates, minimum stays and availability.
View Extended StaysReady for a longer island stay?
Build your season around beach mornings, pool afternoons, and a calm pace that feels like home.