Kalawao County Vacation Packages

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Top Kalawao County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Castle at Moloka'i Shores

Castle at Moloka'i Shores

3 out of 5
Price was CA $2,112, price is now CA $1,758 per person
CA $1,758
per person
Jul 21 - Jul 31
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Hoolehua (MKK)
7.2/10 Good! (182 reviews)
In all it was good. A toaster would have been nice and air conditioning

Reviewed on Jun 2, 2026

Hotel Moloka'i

Hotel Moloka'i

3 out of 5
Price was CA $2,504, price is now CA $1,922 per person
CA $1,922
per person
Jul 13 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Hoolehua (MKK)
8.2/10 Very Good! (678 reviews)
This hotel is very charming and old-fashioned in the best way. The rooms are spacious and modern, but the outside look and feel of the hotel is very quaint. The extremely helpful young woman at the front desk seemed to know everything about the island and was able to answer every question we asked. We were busy while we were there, so we didn't have a chance to use the pool, but it looked clean and inviting. We did use the laundry facilities (laundry detergent is available in the vending machine). Our room had a large bathroom (sink outside of the toilet/showr room but still separated from the bedroom), refrigerator, microwave, coffee set up, and very comfortable mattresses and pillows. The property is well maintained and quiet (well, except for the chickens, but they didn't really bother us and can be heard anywhere, any time in HI). We didn't have great cell service, but I realized too late that the hotel offers free calls to anywhere in the US, which is cool. The restaurant is closed, which is a shame, because it looks like it would be fun, and we would have liked an additional dining option. We would definitely stay here again if we have the good fortune to return to Molokai!

Reviewed on Jun 5, 2026

Four Seasons Resort Lanai

Four Seasons Resort Lanai

5 out of 5
Price was CA $5,803, price is now CA $5,376 per person
CA $5,376
per person
Aug 17 - Aug 21
found 8 hours ago
Roundtrip flight included
Vancouver (YVR) to Lanai City (LNY)
9.8/10 Exceptional! (227 reviews)
Beautiful property. Fabulous service. If you want stay in a nice hotel in Lana’i, this is the only game in town.

Reviewed on Apr 25, 2026

Sensei Lanai, A Four Seasons Resort

Sensei Lanai, A Four Seasons Resort

5 out of 5
Price was CA $4,810, price is now CA $4,480 per person
CA $4,480
per person
Aug 17 - Aug 21
found 8 hours ago
Roundtrip flight included
Vancouver (YVR) to Lanai City (LNY)
9.8/10 Exceptional! (144 reviews)
The spa was the best one I have ever been to. Great amenities, and gorgeous place overall. The staff was incredibly kind. Would love to be back

Reviewed on May 16, 2026

Wavecrest

Wavecrest

3 out of 5
Price was CA $2,253, price is now CA $2,184 per person
CA $2,184
per person
Aug 17 - Aug 21
found 8 hours ago
Roundtrip flight included
Vancouver (YVR) to Hoolehua (MKK)
9/10 Wonderful! (6 reviews)
The unit was lovely and well appointed. Even nicer than the pictures and that never happens. Pool is great. Neighbors are quiet. I very much enjoyed it.

Reviewed on Jan 10, 2026

Kalawao County Hotel Deals

Hilton Vacation Club Ka'anapali Beach Maui

Hilton Vacation Club Ka'anapali Beach Maui

4 out of 5
104 Ka'anapali Shores Place Kaanapali HI
The price is CA $369 per night from Jun 21 to Jun 22
CA $369
CA $487 total
Jun 21 - Jun 22
includes taxes & fees
9/10 Wonderful! (1,022 reviews)
"Staff was really friendly and helpful. Location was perfect. Amenities were great. Loved it"

Reviewed on Jun 5, 2026

Hilton Vacation Club Ka'anapali Beach Maui
The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua

5 out of 5
1 Ritz-Carlton Drive Kapalua HI
The price is CA $1,250 per night from Jun 7 to Jun 8
CA $1,250
CA $1,582 total
Jun 7 - Jun 8
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
"We loved this hotel. While it's not a classic 'on the beach' resort, beaches are close by and the overall setting is beautiful. We had one of the 'fire lanai' rooms which turned out to be a great choice. The staff was great too. Next time we go to Maui, we plan to stay here again!"

Reviewed on Jun 2, 2026

The Ritz-Carlton Maui, Kapalua
Aston Kaanapali Shores

Aston Kaanapali Shores

3.5 out of 5
3445 Lower Honoapiilani Hwy Lahaina HI
Fully refundableReserve now, pay when you stay
The price is CA $583 per night from Jun 7 to Jun 8
CA $583
CA $733 total
Jun 7 - Jun 8
includes taxes & fees
8.8/10 Excellent! (4,121 reviews)
"Amazing views and very spacious for family. Nice beach and pools!"

Reviewed on Jun 5, 2026

Aston Kaanapali Shores
See all 3,624 properties in Kalawao County
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.
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Frequently asked questions

How much does a Kalawao County vacation package cost?
Choose from any combination of car rentals, flights and hotels, and you can be vacationing in Kalawao County from just CA $1,758. And the more you bundle, the more cash you save. The vacation of your dreams has never been more affordable.
How do I get a cheap travel package to Kalawao County?
Just imagine all the wonderful things you could do in Kalawao County with a pile of extra cash in your wallet. Watch your savings stack up when you combine your travel bookings into a Kalawao County vacation package. You have loads of choice with Expedia too. In fact, you can take your pick of more than 550 air carriers and 1,000,000 properties around the world. Whether you're vacationing with the family or adventuring alone, organizing a trip to Kalawao County is better with a package.
How far in advance should I book my Kalawao County vacation?
Reserving your tickets early with Expedia means one less thing to worry about. Many air carriers advertise prices up to a year in advance. Typically, this is the cheapest time to book. If circumstances have left you booking late, incredible deals to Kalawao County sometimes become available just a few weeks before departure.
What does an Expedia Kalawao County travel package include?
That depends on you. You can choose from a range of Kalawao County bundles, such as a hotel, rental car and flight. You can also book a flight and a hotel, or a flight with a rental car. Once you've made your booking, you can add on the fun stuff like tours and activities. Whatever your perfect Kalawao County trip looks like, get set to save!
What should I know before booking a Kalawao County travel package?
Whether it's relaxation or adventure you're chasing, a Kalawao County 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 bigger the savings!
Can I choose my airline with a Kalawao County Expedia vacation package?
With a vacation package, the choice is in your hands. Whether you'd prefer to fly to Kalawao County in business or coach, simply select from the available airline options. Expedia has access to more than 550 airline partners across the world.
If I'm not able to travel, can I cancel my Kalawao County vacation package?
Because we know life can be unpredictable, the answer is yes. For further details, check out our Customer Service Portal. But generally speaking, if you've booked your Kalawao County vacation package in the last 24 hours, you may be able to cancel or change it free of charge. Your airline, hotel or car rental company may impose a fee if you made your booking a while ago.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.