Windward Coast Vacation Packages

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    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.
Romer House Waikiki

Romer House Waikiki

4 out of 5
Waikiki
Price was CA $2,148, price is now CA $1,437 per person
CA $1,437
per person
Oct 8 - Oct 15
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Honolulu (HNL)
8.8/10 Excellent! (916 reviews)
It was close to everything including the beach. Very nice rooms and staff.

Reviewed on Jul 17, 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 $15,661, price is now CA $5,493 per person
CA $5,493
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip 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 $15,541, price is now CA $5,721 per person
CA $5,721
per person
Aug 19 - Aug 23
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

Paradise Bay Resort

Paradise Bay Resort

3.5 out of 5
Kahaluʻu
Price was CA $2,652, price is now CA $1,644 per person
CA $1,644
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Honolulu (HNL)
8.8/10 Excellent! (1,009 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

2BR/2BA Condos in Kuhio at Waikiki with Parking!

2BR/2BA Condos in Kuhio at Waikiki with Parking!

2 out of 5
Waikiki
Price was CA $4,920, price is now CA $3,267 per person
CA $3,267
per person
Aug 20 - Aug 24
found 1 hour ago
Roundtrip flight included
Vancouver (YVR) to Honolulu (HNL)
10/10 Exceptional! (1 review)
The Condo was very comfortable and in excellent condition. Location was amazing , just a very short walk to Waikīki Beach. We had an awesome stay - I give this property and vacation company the highest rating!

Reviewed on Jan 6, 2025

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 $401 per night from Aug 1 to Aug 2
CA $401
CA $568 total
Aug 1 - Aug 2
includes taxes & fees
8.4/10 Very good! (9,418 reviews)
"It was a nice place to stay, wasn’t very happy to pay $500 fee to SELF park my Rental car for a week."

Reviewed on Jul 18, 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 $798 per night from Aug 18 to Aug 19
CA $798
CA $1,033 total
Aug 18 - Aug 19
includes taxes & fees
9.2/10 Wonderful! (3,256 reviews)
"Excellent location and pool. Water slide was a blast and close to the beach. Lots of food and shopping to walk. Housekeeping was especially attentive and friendly. Would definitely staff here again"

Reviewed on Jul 18, 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 $321 per night from Aug 17 to Aug 18
CA $321
CA $473 total
Aug 17 - Aug 18
includes taxes & fees
9/10 Wonderful! (5,277 reviews)
"Clean and professional"

Reviewed on Jul 17, 2026

Hyatt Regency Waikiki Beach Resort & Spa
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 $1,437. 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.