Kalawao County Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 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 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 $1,655, price is now CA $1,358 per person
CA $1,358
per person
Jun 1 - Jun 10
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Hoolehua (MKK)
7.2/10 Good! (179 reviews)
The room and property was nice but could be cleaner. Overall, the staff was nice and friendly but communication for additional fees, such as cleaning amount did not match what reflected on Expedia, the hotel could do better to email tenants prior to arriving just confirming the exact amounts so what to expect is clearer. The stay was good. No complaints of the room. However, the spa was not hot.

Reviewed on Sep 15, 2025

Hotel Moloka'i

Hotel Moloka'i

3 out of 5
Price was CA $2,371, price is now CA $1,995 per person
CA $1,995
per person
Jul 5 - Jul 12
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Hoolehua (MKK)
8.2/10 Very Good! (663 reviews)
No kitchen, shopping center and restaurants nearby

Reviewed on Apr 6, 2026

Four Seasons Resort Lanai

Four Seasons Resort Lanai

5 out of 5
Price was CA $7,800, price is now CA $6,738 per person
CA $6,738
per person
May 14 - May 18
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Lanai City (LNY)
9.8/10 Exceptional! (225 reviews)
We are "stuck" here for an extra 2 days due to the Kona stirm. Staff have been exceedingy patient and friendly and accommodating during this challenging peroid. They even got me to the local emergency room for treatment of an acute injury. Our room was gorgeous!

Reviewed on Mar 14, 2026

Sensei Lanai, A Four Seasons Resort

Sensei Lanai, A Four Seasons Resort

5 out of 5
Price was CA $4,276, price is now CA $3,764 per person
CA $3,764
per person
May 14 - May 18
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Lanai City (LNY)
9.8/10 Exceptional! (139 reviews)
Transformative experience! Highly recommended - unlike any other vacation!

Reviewed on Aug 18, 2025

Wavecrest

Wavecrest

3 out of 5
Price was CA $2,875, price is now CA $2,793 per person
CA $2,793
per person
May 28 - Jun 7
found 1 day 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 $442 per night from May 7 to May 8
CA $442
CA $573 total
May 7 - May 8
includes taxes & fees
9/10 Wonderful! (1,009 reviews)
Our family had a great stay here! Loved the pool and ocean was walkable. The location was great too, lots of things around. Overall wonderful stay

Reviewed on Apr 11, 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 $1,175 per night from May 10 to May 11
CA $1,175
CA $1,492 total
May 10 - May 11
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
Very clean rooms. Good staff.

Reviewed on Apr 13, 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 $442 per night from Apr 15 to Apr 16
CA $442
CA $565 total
Apr 15 - Apr 16
includes taxes & fees
8.8/10 Excellent! (4,056 reviews)
Two pools! Two hot tubs, a spa! So much stuff to do. A restaurant and lots of things in walking distance.

Reviewed on Apr 12, 2026

Aston Kaanapali Shores
See all 3,850 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 $1,358. 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.