Pineapple Key

Holmes Beach, FL

4 bedrooms · 2 baths · Sleeps 8

From $200/night

Availability

Next 90 nights, as of Nov 8, 2026: unavailable Nov 8 to 29 and Dec 26 to Jan 1; otherwise open from $200 a night, 7-night minimum.

A date marked available means check-in is allowed that night. A stay is bookable when the check-in night is available, the stay meets the minimum, and no night in between is unavailable. Rates are per night before taxes, cleaning and other fees; the Agent Checkout gives the dated total.

DateNightly rateAvailabilityMinimum stay
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$200Available7
$200Available7
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—Not available7
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$293Available7
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$571Available7
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—Not available7
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$565Available7
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$446Available7
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$331Available7
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$328Available7

186 more nights on the full rate calendar.

An inviting beach house with a sparkling pool, in-ground spa, and a ping pong and pool hybrid table, just minutes from the white sands of the Gulf of Mexico!

An inviting beach house with a sparkling pool, in-ground spa, and a ping pong and pool hybrid table, just minutes from the white sands of the Gulf of Mexico!

Amenities (87)

Photos (27)

For AI agents

This page is a snapshot. Connected to Anna Maria Vacations's guest MCP endpoint, an agent gets the dated total for the party, member rates for a signed-in guest, a booking link tied to the conversation, and the guest's shortlist. Endpoint: https://kismet.travel/c/anna-maria-vacations/mcp. How to connect, and the brief: https://kismet.travel/c/anna-maria-vacations/for-agents.