Kaaawa Vacation Rentals

Kaaawa vacation rentals offer a quiet, authentic escape along Oahu’s lush windward coast. Nestled between the mountains and sea, this small coastal town is ideal for travelers seeking peace, nature, and the rhythm of real island life-far from the crowds of Waikiki.

Choose from oceanfront cottages, hillside homes with sweeping views, and cozy beach bungalows perfect for couples or families. Many Kaaawa rentals come with lanais, full kitchens, and easy access to secluded beaches where you can watch sunrises, snorkel, or just breathe in the salty breeze.

Kaaawa is a gateway to outdoor adventure-minutes from Kualoa Ranch, Crouching Lion hike, and scenic drives along the coastline. It’s the kind of place where you can fall asleep to waves and wake up to birdsong, surrounded by dramatic cliffs and clear blue water.

Whether you're here for romance, unplugging, or exploring, Kaaawa vacation rentals offer the charm, comfort, and local flavor of a true Hawaiian hideaway.

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Recently Update Home!Quiet Beach Community! Come to the Country & Escape Crowds!

Leave the city behind, escape the crowds! Breath the fresh ocean air from our large ocean view lanai! The home was renovated just a couple years ago and has been well maintained every since. Everything is like new, including furniture and
Registration Number: GE-035-956-3264-01, 510110100000, TA-035-956-3264-01

2 bedroom
2 bathroom
Sleeps 4

from $276

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Kaaawa Home With Mountain View’s - 30 Day Min

This Hawaiian home gives you the best of both worlds, nestled up close to the Koolau mountains with an ocean view. The house will accommodate 6 guests. Incl 3 bd/1ba, a kitchen & plenty of living space. We aim to make this space feel like your
Registration Number: GE-191-572-9920-01, 51014032, TA-191-572-9920-01

3 bedroom
1 bathroom
Sleeps 6

from $190

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The Plantation Estate

Cool ocean and mountain breezes welcome you to 'The Ko'olau Plantation Estate' your perfect Hawaiian Hideaway with over 60,000 square feet of outdoor space. With breathtaking ocean views and 25 feet from edge of property to the ocean. The
Registration Number: GE-079-352-4736-01, TA-079-352-4736-01

9 bedroom
9 bathroom
Sleeps 14

from $3,427

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