Kalaupapa Vacations from $780

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Your Kalaupapa Vacation

The exciting city of Kalaupapa is calling. Immerse yourself in everything it has to offer with a Kalaupapa vacation package that's customized to you. Be sure to spend some time sightseeing during your trip to Kalaupapa. Kalaupapa National Historical Park and St. Philomena Church are some popular places to visit. Don't put off exploring this destination any longer. The perfect Kalaupapa vacation is a couple of clicks away with Expedia.

The Latest Kalaupapa vacation packages

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 $873, price is now $780 per person
$780
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Hoolehua (MKK)
7.2/10 Good! (164 reviews)
Lovely oceanfront condo with beautiful clean pool. Cant remember the security guards name but she was so nice and friendly to talk story with.

Reviewed on Aug 15, 2025

Hotel Moloka'i

Hotel Moloka'i

3 out of 5
Price was $1,194, price is now $999 per person
$999
per person
Oct 23 - Oct 27
found 19 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Hoolehua (MKK)
8.2/10 Very Good! (622 reviews)
Excellent staff and location. Beautiful grounds complete with Molokai chickens and cats. Excellent parking. . Effective air conditioning.. Quiet and peaceful on the ocean.

Reviewed on Aug 18, 2025

Paniolo Hale

Paniolo Hale

2 out of 5
Price was $985, price is now $882 per person
$882
per person
Nov 13 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Hoolehua (MKK)
No reviews
Ke Nani Kai

Ke Nani Kai

2 out of 5
Price was $970, price is now $870 per person
$870
per person
Nov 13 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Hoolehua (MKK)
8/10 Very Good! (1 review)
Molokai Shores

Molokai Shores

2 out of 5
Price was $959, price is now $861 per person
$861
per person
Nov 13 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Hoolehua (MKK)
6/10 (2 reviews)
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Discover the most popular places to visit in Kalaupapa

Kalaupapa National Historical Park

4.5/5(356 reviews)

Explore the great outdoors at Kalaupapa National Historical Park, a lovely green space in Kalaupapa. Stroll along this relaxing area's seaside, or simply enjoy its bars.

Kalaupapa National Historical Park

St. Philomena Church

You can learn about the history of Kalaupapa with a trip to St. Philomena Church. Stroll along this relaxing area's seaside, or simply enjoy its bars.

St. Philomena Church

Kalaupapa Hotel Deals

Aston Kaanapali Shores

Aston Kaanapali Shores

3.5 out of 5
3445 Lower Honoapiilani Hwy, Lahaina, HI
Fully refundableReserve now, pay when you stay
$171 nightly
The price is $202 total per night from Sep 15 to Sep 16
$202 total
Sep 15 - Sep 16
Total includes taxes and fees
8.6/10 Excellent! (3,669 reviews)
"Love it will be back forsure thank you"

Reviewed on Aug 19, 2025

Aston Kaanapali Shores
The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua

5 out of 5
1 Ritz-Carlton Drive, Kapalua, HI
$904 nightly
The price is $1,066 total per night from Aug 29 to Aug 30
$1,066 total
Aug 29 - Aug 30
Total includes taxes and fees
9/10 Wonderful! (1,001 reviews)
"The staff is very attentive and friendly."

Reviewed on Aug 15, 2025

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
$276 nightly
The price is $325 total per night from Sep 7 to Sep 8
$325 total
Sep 7 - Sep 8
Total includes taxes and fees
8.8/10 Excellent! (1,010 reviews)
"I truly have nothing to complain about. Everything was great. Awesome staff. The room is big. There isn’t a stove in the room, but there is an electric grill and a rice cooker, which did the trick. Also there are lots of barbecues close to the pool, so, cooking was not an issue. There is cafe downstairs ..."

Reviewed on Aug 18, 2025

Hilton Vacation Club Ka'anapali Beach Maui
See all 3,495 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.

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Frequently asked questions

How much does a Kalaupapa vacation package cost?
You'll find cheap prices from $780 on Expedia for your Kalaupapa break. However, a range of factors like the hotel choice, length of stay and season will determine how much your vacation to Kalaupapa costs.
What are the cheapest months to go to Kalaupapa?
September, October and December are the best times to look for cheap Kalaupapa vacation packages. Choosing to travel in quieter months means you can generally find reduced prices on flights and accommodations.
How many days is enough for Kalaupapa?
The ideal length for your Kalaupapa vacation depends on what you'd like to do and see. Typically, a handful of days to a week will give you plenty of time to hit all the top sights and discover some hidden gems along the way.
Is it worth booking a vacation package to Kalaupapa?
It's easy to see why a Kalaupapa vacation is on the must-do list of many travelers. Well-known attractions like Kalaupapa National Historical Park are just the beginning of what you can explore here.
How to find the best Kalaupapa package deals?
Finding a cheap Kalaupapa package deal is easy with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, apply a couple of filters and see what's available. You can fine-tune your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most affordable Kalaupapa package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Kalaupapa vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking flights and hotels individually. Better still, you can tailor your Kalaupapa escape to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Kalaupapa?
If you have your Kalaupapa travel dates locked in, book as soon as you can to grab some unbeatable deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Kalaupapa?

  1. Choose your travel dates: The things you want to do in Kalaupapa and your preferred season can help you decide when to travel.
  2. Plan your budget wisely: As well as the cost of your hotel, you should consider other expenses. These include transportation, flights and food. Also, set aside a little extra for unexpected expenses that could crop up during your trip to Kalaupapa.
  3. Explore Kalaupapa with Expedia's trip planning tool: Gain insights into the leading attractions and best properties for your trip to Kalaupapa. You can also save your favorite places, collaborate with your group and manage your plans in one place.
  4. Decide how long to go for: Now that you're up to speed on Kalaupapa, you can figure out the right length of your break. Put together a draft plan and give yourself enough time for all the things you want to do.
  5. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a tailored Kalaupapa vacation package.
  6. Add on experiences and excursions: Have a look at our travel guide to find some awesome things to do in Kalaupapa. Book tickets or make reservations as soon as you can to save time and avoid the hassle of searching for activities once you arrive.

Does Expedia offer Book Now, Pay Later Kalaupapa vacation packages?
Your Kalaupapa trip should be a relaxing escape from your busy life, not a reason for money-related stress. So to allow you more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.