Windward Coast Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Top Windward Coast Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Luana Waikiki Hotel & Suites

Luana Waikiki Hotel & Suites

3.5 out of 5
Waikiki
Price was CA $2,046, price is now CA $1,207 per person
CA $1,207
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Honolulu (HNL)
8.8/10 Excellent! (1,580 reviews)
The hotel was great staff very helpful

Reviewed on Jul 13, 2026

Ilikai by Luana Hawaii Vacation Rentals

Ilikai by Luana Hawaii Vacation Rentals

3 out of 5
Waikiki
Price was CA $4,330, price is now CA $1,842 per person
CA $1,842
per person
Sep 5 - Sep 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Honolulu (HNL)
8.8/10 Excellent! (58 reviews)
A bit dated room but good location. Amenities are great and beach access was very close.

Reviewed on Feb 23, 2026

Ala Moana Hotelcondo by Luana Vacation Rental

Ala Moana Hotelcondo by Luana Vacation Rental

3.5 out of 5
Ala Moana
Price was CA $3,392, price is now CA $1,634 per person
CA $1,634
per person
Sep 5 - Sep 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Honolulu (HNL)
7.6/10 Good! (258 reviews)

Paradise Bay Resort

Paradise Bay Resort

3.5 out of 5
Kahaluʻu
Price was CA $2,959, price is now CA $1,618 per person
CA $1,618
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Honolulu (HNL)
8.8/10 Excellent! (1,001 reviews)
This place is a hidden gem!! Tucked away in a beautiful town on a peaceful, serene bay with amazing staff!! Marissa was most helpful with recommendations that did not disappoint. I will definitely be returning.

Reviewed on Jul 13, 2026

Stay Hotel Waikiki

Stay Hotel Waikiki

3 out of 5
Waikiki
Price was CA $1,999, price is now CA $1,232 per person
CA $1,232
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Honolulu (HNL)
8/10 Very good! (1,859 reviews)
Everything about the stay was great.

Reviewed on Jul 13, 2026

Where to stay in Windward Coast

Find the best Windward Coast areas and neighborhoods for the activities you enjoy most. Learn more about Windward Coast
A tropical beach with clear turquoise waters, two small islands, and a dense palm tree line.

Lanikai

While Lanikai isn't home to many top sights, Lanikai Beach and Lanikai Pillboxes Trailhead are some notable places to visit nearby.

Find hotels in Lanikai

Ready to book your vacation to Windward Coast?

 

Choose your dates

Windward Coast Hotel Deals

Hilton Hawaiian Village Waikiki Beach Resort

Hilton Hawaiian Village Waikiki Beach Resort

4.5 out of 5
2005 Kalia Rd Honolulu HI
The price is CA $416 per night from Aug 11 to Aug 12
CA $416
CA $586 total
Aug 11 - Aug 12
includes taxes & fees
8.4/10 Very good! (9,500 reviews)
"ELEVATORS ARE TOO SLOW VERY SLOW TAKE ME ABOUT 5 MINUTE TO GET ONE ELEVATOR , THE LINE OF PEOPE WAITING WAS CRAZY"

Reviewed on Jul 14, 2026

Hilton Hawaiian Village Waikiki Beach Resort
Sheraton Waikiki Beach Resort

Sheraton Waikiki Beach Resort

4.5 out of 5
2255 Kalakaua Ave Honolulu HI
Fully refundableReserve now, pay when you stay
The price is CA $777 per night from Aug 7 to Aug 8
CA $777
CA $1,009 total
Aug 7 - Aug 8
includes taxes & fees
9.2/10 Wonderful! (3,253 reviews)
"Hotel was great, however the check in process was terrible. They hold the check in time exactly until the exact time. We arrived early obviously understanding the check in time expectations. However upon arriving 4 hours early and expressing we had a young g child. It feeling well and anything they ..."

Reviewed on Jul 14, 2026

Sheraton Waikiki Beach Resort
'Alohilani Resort Waikiki Beach

'Alohilani Resort Waikiki Beach

5 out of 5
2490 Kalakaua Avenue Honolulu HI
The price is CA $444 per night from Aug 13 to Aug 14
CA $444
CA $621 total
Aug 13 - Aug 14
includes taxes & fees
8.6/10 Excellent! (4,119 reviews)
"Second year in a row staying here. Very convenient location and resort offers all that you need."

Reviewed on Jul 14, 2026

'Alohilani Resort Waikiki Beach
See all 7,347 properties in Windward Coast
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Windward Coast attractions

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.
See properties

Frequently asked questions

How much does a Windward Coast vacation package cost?
Discover the best of Windward Coast from as little as CA $1,207. Choose from a wonderful selection of rental cars, hotels and flights to suit every budget and style. You can pick up even more discounts when you add a few tours or experiences to your vacation package.
How do I get a cheap travel package to Windward Coast?
Combining your hotel and flight with Expedia won't just save valuable time — it'll save you a few dollars too. A Windward Coast vacation package makes it a breeze to put together your dream adventure. With more than 550 airlines around the world to choose from, finding flights that suit your busy schedule won't be difficult. Not only that, we have over 1,000,000 hotel options globally to take your pick of. Now that's choice! Whatever your budget, Expedia puts more of the world within your reach.
What are the top hotels in Windward Coast?
Travelers journeying to Windward Coast often make a booking at Less Than A One Minute Walk To Kailua Beach or Private Beachfront Rental. You'll find them in Lanikai. Another great neighborhood is Kalama Tract. Cute 2 Bedrooms Plantation Home With Ac and Hawaii's Hidden Hideaway Bed And Breakfast are well-liked options in this area.
How far in advance should I book my Windward Coast vacation?
It's difficult to pick the best time for airfares, but we generally say the earlier, the better. Plenty of international flights on Expedia become available to compare up to 12 months in advance. If you can't book ahead, don't worry. Low prices appear from time to time within a few weeks of departure dates.
What does an Expedia Windward Coast travel package include?
That's up to you. You can select from a variety of Windward Coast bundles, such as a flight, hotel and rental car. You can also book a hotel with a flight, or a flight with a rental car. Once you've made your booking, you can add the fun stuff like experiences and tours. Whatever your Windward Coast vacation looks like, you'll save!
What should I know before booking a Windward Coast travel package?
Whether it's adventure or relaxation you're seeking, a Windward Coast vacation package lets you organize your escape your way. Plus, you'll get access to great discounts when you combine your accommodations with your flights and rental car. The more you bundle, the more you'll save!
Can I choose my airline with a Windward Coast Expedia vacation package?
Definitely. Expedia has over 550 partner airlines to pick from globally. With such a huge range of choice, finding the right carrier to take you to Windward Coast will be a snap.
If I'm not able to travel, can I cancel my Windward Coast vacation package?
Whether it's your hotel or flight, yes, you can amend or cancel it. Booked your Windward Coast vacation package in the last 24 hours? You may be able to make changes or cancellations at no cost. For bookings made more than 24 hours ago, you may be charged a fee by your airline, hotel or car rental company. For more information, check out our Customer Service Portal. We're here to help you every step of the way.

Explore a world of travel with Expedia

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