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A coastal landscape with a mountain range, a town, and a clear blue sea.

Windward Coast Beach Vacations

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Top Beach vacation packages in Windward Coast

Price found within the past 48 hours. Click for updated prices.
  • Dock
    Sep 15 - Sep 21

    Paradise Bay Resort + Flight

    Kahaluʻu
    6 nights
    3.5 star property
    8.8/10 - Excellent (1,000 reviews)
    "Very relaxing. Great location with wonderful views."
    Reviewed July 25, 2026
    Roundtrip • Tokyo (HND) - Oahu (HNL)
    HND - HNL • Nonstop HNL - HND • Nonstop
    Save 100% on your flight
    ￥448,664
    ￥265,348
    per traveler
    found 1 day ago
    Paradise Bay Resort

Discover the most popular places to visit in Windward Coast

A beach with clear turquoise water, a sandy shore, and several boats lined up on the right.

Lanikai Beach

9.2/10 (3,293 reviews)
Nothing says vacation like spending a lazy day at Lanikai Beach, a popular beach in Kailua. You can seek out the snorkeling spots while in the area.

Find your perfect Windward Coast beach vacation

How do I book the best Windward Coast beach vacation packages?

Life’s a beach when you dive into our brilliant Windward Coast beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in Windward Coast?

A rental steps from the shore creates an amazingly affordable Windward Coast beach vacation. Seaside sojourns during low season start from ￥265,347. Prices and availability are subject to change. Additional terms may apply.

How can I book the best family beach vacations in Windward Coast?

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a Windward Coast beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a Windward Coast vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find Windward Coast beach vacation deals?

Sort your search results by deals to delight in amazing Windward Coast beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a Windward Coast beach trip with free cancellation and/or flexible dates?

Just like the Windward Coast tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my Windward Coast beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Windward Coast. (OK, maybe not that last part.)