Windward Coast Beach Vacations

Book a Beach Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

4 Night Beach vacations in Windward Coast

Price found within the past 48 hours. Click for updated prices.
Paradise Bay Resort
Don't see what you're looking for?
See all available trips from Columbus to Windward Coast
View all trips

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 $891. 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.)

Top Beach Windward Coast Hotels

Paradise Bay Resort

Paradise Bay Resort

3.5 out of 5
47-039 Lihikai Drive, Kaneohe, HI
  • 20 min drive from Lanikai Beach
Make the most of this fantastic location, as you'll be close to Kahaluu Beach when booking a stay at this hotel. An outdoor pool and a hot tub are just some ...
8.6/10 Excellent! (1,001 reviews)

Travelers like: close to beach, outdoor pool

Travelers say...
"Nice place"

Reviewed on Aug 18, 2025

Paradise Bay Resort
Award Winner - Hawaii's Hidden Hideaway - Bed and Breakfast

Award Winner - Hawaii's Hidden Hideaway - Bed and Breakfast

Kailua
  • 12 min walk from Lanikai Beach
Make the most of this fantastic location, as you'll be close to Lanikai Beach with a vacation at this bed & breakfast. A hot tub, beach towels, and sun loungers ...
9.2/10 Wonderful! (80 reviews)
"Very nice. Great location. Comfy bed. Beautiful plants."

Reviewed on Jul 17, 2025

Award Winner - Hawaii's Hidden Hideaway - Bed and Breakfast
PRIVATE BEACHFRONT RENTAL

PRIVATE BEACHFRONT RENTAL

Kailua
  • 5 min drive from Lanikai Beach
Stroll along the shore in Kailua, as you'll be near Kailua Bay Beach with a stay at this bed & breakfast. Amenities at PRIVATE BEACHFRONT RENTAL include beach ...
10/10 Exceptional! (140 reviews)

Travelers like: on the beach, sun loungers, beach towels

Travelers say...
"This was such a lovely little escape. Tucked into a quiet little street and with the beach as your backyard. The room was super comfortable and spotlessly clean. Shari was so friendly and communicative if we had any questions, but everything was so clearly lined out and navigated, it felt like home ..."

Reviewed on Aug 19, 2025

PRIVATE BEACHFRONT RENTAL
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.