Kalaupapa Holidays

  • Plan, book, travel with confidence
    • payments icon
    Better together
    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Top hotels in Kalaupapa

Aston Kaanapali Shores
Aston Kaanapali Shores
3.5 out of 5
3445 Lower Honoapiilani Hwy, Lahaina, HI
The price is S$602 per night from 8 Dec to 9 Dec
S$602
includes taxes & fees
8 Dec - 9 Dec
8.4/10 Very Good! (3,352 reviews)
"Several people we visited were “owners” at AKS and were very friendly; one even said “thank you for staying at Shores; I hope you make the choice to stay here again.” The view out our balcony of the pool area and the ocean from afar was beautiful."

Reviewed on 25 Nov,2024

Aston Kaanapali Shores
The Ritz-Carlton Maui, Kapalua
The Ritz-Carlton Maui, Kapalua
5 out of 5
1 Ritz-Carlton Drive, Kapalua, HI
The price is S$1,216 per night from 1 Dec to 2 Dec
S$1,216
includes taxes & fees
1 Dec - 2 Dec
9/10 Wonderful! (1,000 reviews)
"Had a wonderful stay for our anniversary and we definitely will be back! The service was impeccable and everyone was SO friendly wherever we went in the hotel, even the housekeeping when passing in the halls. It's so rare these days, even in top hotels. Breakfast was a little overpriced for the ala ..."

Reviewed on 17 Nov,2024

The Ritz-Carlton Maui, Kapalua
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 S$429 per night from 27 Nov to 28 Nov
S$429
includes taxes & fees
27 Nov - 28 Nov
8.6/10 Excellent! (1,006 reviews)
"Convenient to restaurants and activities"

Reviewed on 25 Nov,2024

Hilton Vacation Club Ka'anapali Beach Maui
See all 3,302 properties in Kalaupapa
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.

Frequently asked questions

How much does a Kalaupapa holiday package cost?
Choose from any combination of hotels, flights and car rentals, and you can be holidaying in Kalaupapa from just . And the more you bundle, the more dollars you save. Your dream holiday has never been more affordable.
How do I get a cheap travel package to Kalaupapa?
One of the simplest ways to save cash (and time) is to bundle your bookings with Expedia. Flights, hotels, rental cars and activities — we’ve got it all. Pick a combination that best suits you and see your savings stack up. We know a package deal is never one-size-fits-all. That’s why we offer more than 550 airlines and 1,000,000 properties worldwide, which lets you customize your Kalaupapa getaway.
How far in advance should I book my Kalaupapa holiday?
It all depends on the air carrier, but you can generally browse through international flights on Expedia up to a year in advance. While it’s generally recommended to book ahead of time, lucky customers occasionally find a cheaper seat just weeks before their intended journey.
What does an Expedia Kalaupapa travel package include?
It all boils down to what kind of escape you’re planning. Kalaupapa holiday deals can include flights, car rentals and hotels. You can mix and match to find the bundle that fits your needs. You can also add on experiences and activities after you’ve booked to get even bigger discounts.
What should I know before booking a Kalaupapa travel package?
Booking all the parts of your holiday together is an excellent way to save. Bundle your car rentals, flights and hotels into one little package. But hotels aren’t your only option. Expedia offers all sorts of properties, including holiday rentals like beach villas and city apartments. You’ve got choices galore!
Can I choose my airline with a Kalaupapa Expedia holiday package?
Expedia has access to more than 550 partner airlines worldwide, so you sure can! Simply choose the airline you want and put together your ideal Kalaupapa trip.
If I'm not able to travel, can I cancel my Kalaupapa holiday package?
It’s good to know that you can cancel your Kalaupapa booking if your travel plans have been upended. Whether you’ll incur a penalty or not depends on your hotel, airline or car rental company. It may be possible to cancel or change your booking free of charge if you booked in the last 24 hours. Head to our Customer Service Portal for more information.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.