Seaside Cottage Rentals

Check out our expanded list of beach cottages and find your own slice of paradise.

Oahu, Hawaii

This Hawaiian beach rental comes complete with a stunning view.

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Oahu Hideaway

Jean Allsopp

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Life moves slowly on Oahu―at least on the windward side of the island. Glitzy tourist destinations seem far removed, and visitors to the quiet beach town of Kailua feel as though they’ve stepped onto a separate isle. So, if you’re seeking a vacation rental an ocean away from everyday worries, we’ve discovered your getaway.

The 70-year-old, three-bedroom Windsurf cottage retains its original charm with just a few modifications. The breezy house has jalousie and sliding windows, eliminating the need for air-conditioning. Interior and exterior board-and-batten walls and slightly bowed floorboards attest to the home’s authenticity. Sure, there are quirks and imperfections. But here, renters experience an old-school beach shack still enjoying its heyday.

The owners chose chunky bamboo furniture and Hawaiian bark-cloth pillows to underscore a classic beach vibe. The place is stocked with funky accessories, such as hula girl lamp bases and glass-float light fixtures. “We wanted Old Hawaiian style to suit the character of the house and lift guests’ spirits,” says the owner.

A lava-rock wall encloses 25,000 square feet of flawless, green landscaping adjacent to a quiet stretch of sand. Renters can windsurf, kiteboard, snorkel, or simply relax in the sun. Ambitious guests may rent a kayak nearby and undertake a vigorous, 40-minute paddle to the Mokuluas, twin islands visible from the home’s yard. Daring visitors cliff-jump into Sharks Cove, while less adventurous friends enjoy a leisurely picnic.

Windsurf offers renters a rare opportunity to revisit Old Hawaii on a pristine property that overlooks one of the world’s finest beaches. Guests tell us they return home with a renewed spirit and only one regret―that they couldn’t extend their stay.

(published July 2007)

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