Where Stories Become Stays
When you share your most memorable Staypineapple story on Instagram, it could earn you a free two-night stay AND a spotlight on our page!
At Staypineapple, every stay tells a story — share yours, and it might get a sequel! We’re passionate about creating experiences that leave lasting memories, and we want to hear yours. Share your most memorable Staypineapple moments on Instagram, and it could earn you a free two-night stay AND a spotlight on our page!
Each month, we’ll select one guest story and treat that guest to a stay. Whether it was a special trip, a friendly team member who made you smile, or simply a cozy spot to unwind after an adventure, we want to know what made your stay unforgettable.
Here’s how to share:
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Pick a photo or video that captures the memory of your stay
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Post it on Instagram
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Tag @staypineapple
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Direct Message (DM) us the word 'STORY'
We read every submission because seeing how we help make your stays truly special is why we do what we do. So, start posting, start storytelling, and maybe your story will soon get the Staypineapple sequel it deserves.
Be sure to read our terms & conditions here.
WHERE STORIES BECOME STAYS FAQS
How do I enter?
Post an original in-feed Instagram post or Reel sharing your Staypineapple stay, tag @staypineapple, and DM us the word “STORY.”
Do Instagram Stories count?
No. Only new in-feed posts and Reels qualify.
Does my account need to be public?
Yes. Accounts must be public at time of entry and winner selection.
How many times can I enter?
Guests may submit multiple unique posts per month. However, the same story or content cannot be submitted.
Can I enter again if I've won before?
Yes, previous winners are eligible to enter future monthly periods.
How will I know if I've won?
Winners are contacted directly via Instagram Direct Messages from the verified @staypineapple account. We will not message you from any other account.