Roaming Pineapple
Roaming Pineapple
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Retreat, Relax, Refresh, Repeat

Thoughtfully designed vacation homes where memories happen

Beach waves, mountain mornings, and spaces your whole family will love.

Our Luxury Vacation Rentals

North Carolina

Front Facade of The Princess Tide Beach house for rent

The Princess Tide - Corolla, NC

Steps from the beach

Private heated Pool & Hot Tub

Dog Friendly

Kid-centric extras!


Guests call this 5 star home a "Wonderful Getaway" and "a Little Oasis" and a "great summer retreat for family and friends"

The Beech Hut - Beech Mountain

Unique creek-side roundhouse

Close to Beech Mtn Ski Resort

Fire pit & Hot tub

Dog Friendly with fenced yard


Guests call this 5 star home a "very cool round house" saying its "cozy and comfy" have "lovely relaxing summer evenings" 

About Roaming Pineapple

Our Story

We are a North Carolina family who loves traveling with out kids and dogs, slowing down together and making memories along the way. After years of staying in rentals that felt impersonal, we decided to create spaces that feel warm, thoughtful and easy to enjoy. 


Roaming Pineapple homes are designed for connection - beach days, mountain mornings, shared meals, and cozy evenings after big adventures. Wherever you roam, we hope your stay feels effortless and meaningful.

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