Roaming Pineapple
Roaming Pineapple
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Vacation Homes for Real Families — Dogs, Kids, and All of It

Family of four enjoying the beach, facing the sea.

Family is Everything

As a young family ourselves, creating safe and beautiful spaces for families to enjoy quality time and share adventures together is our passion. We thought of everything so you don't have to!

Pets are family too

Every property in our collection has been road-tested by the most important members of our team — Indy and Cindy, our Aussies. They've evaluated the floors (easy-clean), the yard situation (fenced), the sleeping arrangements (their spot on the couch), and the general vibe. If it passes the pup test, it makes the portfolio. Your dogs aren't an afterthought here — they're part of why we built this. Follow Indy's adventures at @Indy_the_Aus. 

A straw hat and sunglasses beside a packed suitcase on an orange surface.

Cultivate Curiosity

Travel and fostering curiosity is a big part of our lives. But when traveling, we have come to love having the conveniences of our own home available to us. This is a very important consideration as we furnish each property with your needs top of mind.  

Ready to find your spot?

→ The Princess Tide — Corolla, Outer Banks NC (sleeps 16, heated pool, dog-friendly)→ The Beech Hut — Beech Mountain, NC (creekside roundhouse, ski-in proximity, dog-friendly)

Copyright © 2026 Roaming Pineapple - All Rights Reserved.

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