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SandboxBeach House

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 Stays

Ready for a longer island stay?

Build your season around beach mornings, pool afternoons, and a calm pace that feels like home.