Windward Coast Vacation Packages

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  • Better together

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

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

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Top Windward Coast Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Ala Moana Hotelcondo by Luana Vacation Rental

Ala Moana Hotelcondo by Luana Vacation Rental

3.5 out of 5
Ala Moana
Price was CA $2,450, price is now CA $1,284 per person
CA $1,284
per person
Aug 14 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Honolulu (HNL)
7.6/10 Good! (258 reviews)

Ilikai by Luana Hawaii Vacation Rentals

Ilikai by Luana Hawaii Vacation Rentals

3 out of 5
Waikiki
Price was CA $4,593, price is now CA $1,962 per person
CA $1,962
per person
Aug 28 - Sep 4
found 10 hours 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

@ Marbella Lane - Paradise Point Close to Beaches

@ Marbella Lane - Paradise Point Close to Beaches

5 out of 5
Price was CA $5,280, price is now CA $3,546 per person
CA $3,546
per person
Sep 14 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Honolulu (HNL)
10/10 Exceptional! (1 review)
Everything was perfect! Thank you to the Marbella Team, our stay was excellent. We enjoyed everything Mākaha valley had to offer. Especially the amazing sunsets! 10/10 would recommend

Reviewed on Dec 24, 2025

Holiday Surf Hotel

Holiday Surf Hotel

2.5 out of 5
Waikiki
Price was CA $2,373, price is now CA $1,657 per person
CA $1,657
per person
Aug 27 - Sep 3
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Honolulu (HNL)
6.6/10 (70 reviews)
The place is dated, but very clean. The property manager was very helpful, courteous and pleasant. Great location

Reviewed on Jan 18, 2026

@ Marbella Lane - Stunning Gem w/ MT & Ocean Views

@ Marbella Lane - Stunning Gem w/ MT & Ocean Views

3 out of 5
Price was CA $6,160, price is now CA $4,371 per person
CA $4,371
per person
Sep 15 - Sep 22
found 23 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Honolulu (HNL)
No reviews

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

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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
Fully refundableReserve now, pay when you stay
The price is CA $400 per night from Jul 15 to Jul 16
CA $400
CA $568 total
Jul 15 - Jul 16
includes taxes & fees
8.4/10 Very good! (9,413 reviews)
"Very busy resort. Great if you like to be where the action is. Lots of restaurants within walking distance. Staff were very helpful, property clean."

Reviewed on Jul 8, 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 $751 per night from Jul 11 to Jul 12
CA $751
CA $979 total
Jul 11 - Jul 12
includes taxes & fees
9.2/10 Wonderful! (3,230 reviews)
"Very good, very very very well located, and clean"

Reviewed on Jul 7, 2026

Sheraton Waikiki Beach Resort
Hyatt Regency Waikiki Beach Resort & Spa

Hyatt Regency Waikiki Beach Resort & Spa

4 out of 5
2424 Kalakaua Ave Honolulu HI
Fully refundableReserve now, pay when you stay
The price is CA $396 per night from Aug 1 to Aug 2
CA $396
CA $563 total
Aug 1 - Aug 2
includes taxes & fees
9/10 Wonderful! (5,270 reviews)
"The Staff was great. The rooms could use a make over… the furniture looks warm and out dayed"

Reviewed on Jul 8, 2026

Hyatt Regency Waikiki Beach Resort & Spa
See all 7,374 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
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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 $1,284. 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.

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