Kaupulehu Holidays

Photo by Sascia EmMa

  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 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

Where to stay in Kaupulehu

Find the best Kaupulehu areas and neighborhoods for the activities you enjoy most. Learn more about Kaupulehu
Aerial view of Kahikolu Congregation Church, Kealakekua Bay, Big Island, Hawaii, United States of America, North America

Holualoa Village

While visiting Holualoa Village, you might make a stop by sights like Sadie Seymour Botanical Garden and Honl's Beach.

Find hotels in Holualoa Village

Top hotels in Kaupulehu

Four Seasons Resort Hualalai

Four Seasons Resort Hualalai

5 out of 5
72-100 Ka'upulehu Drive Kailua-Kona HI
The price is S$1,823 per night from 29 Apr to 30 Apr
S$1,823
29 Apr - 30 Apr
includes taxes & fees
9.6/10 Exceptional! (484 reviews)
It’s the Four Seasons… enough said.

Reviewed on 6 Apr, 2026

Four Seasons Resort Hualalai
Kona Village, A Rosewood Resort

Kona Village, A Rosewood Resort

5 out of 5
72 300 Maheawalu Drive Kailua-Kona HI
The price is S$2,087 per night from 22 Apr to 23 Apr
S$2,087
22 Apr - 23 Apr
includes taxes & fees
9.4/10 Exceptional! (84 reviews)
Gorgeous property with lovely staff

Reviewed on 15 Apr, 2026

Kona Village, A Rosewood Resort
PACIFIC 19 Kona

PACIFIC 19 Kona

3.5 out of 5
75-5646 Palani Rd Kailua-Kona HI
Fully refundableReserve now, pay when you stay
The price is S$331 per night from 21 Apr to 22 Apr
S$331
21 Apr - 22 Apr
includes taxes & fees
8.4/10 Very Good! (2,539 reviews)
Decent place to stay, but hidden fees that are not advertised, like $25 for parking a car and a separate $25 "convenience fee" ... for coffee in the morning??

Reviewed on 17 Apr, 2026

PACIFIC 19 Kona
See all 5,541 properties in Kaupulehu
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 Kaupulehu holiday package cost?
You can pick up a holiday package to this popular destination on Expedia. However, how much your holiday to Kaupulehu costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Kaupulehu?
August, October and December are the best times to search for cheap Kaupulehu holiday packages. Travelling in less busy months means you can usually find better prices on flights and hotels.
How many days is enough for Kaupulehu?
The ideal duration for your Kaupulehu holiday depends on what you'd like to do and see. Usually, a handful of days to a week will give you enough time to hit all the leading sights and discover some hidden treasures along the way.
How to find the best Kaupulehu package deals?
Bagging a cheap Kaupulehu package deal is a breeze with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, apply a few filters and see what's available. You can fine-tune your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to view the most affordable Kaupulehu package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Kaupulehu holiday as a package?
An Expedia holiday package could land you great savings when compared to booking flights and stays separately. Better still, you can personalise your Kaupulehu getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a holiday package to Kaupulehu?
Land fantastic discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Kaupulehu trip.
How to plan a trip to Kaupulehu?

  1. Choose the right time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to Kaupulehu.
  2. Set a budget: Factor in expenses such as flights, transportation and food when calculating how much to set aside for your trip to Kaupulehu. Then, pick a property that matches your budget, whether that's an economical option or a more luxurious getaway.
  3. Determine how many days away: Start by listing all the activities and attractions you'd like to get to in Kaupulehu. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a customised Kaupulehu holiday package.

Popular places to visit

Kua Bay

Kua Bay

Leave the crowds behind and head to this hidden beach paradise, one of Hawaii Island’s best-kept secrets.

Kua Bay

Four Seasons Resort Hualalai Golf Course

Play a round of golf in Kailua-Kona at Four Seasons Resort Hualalai Golf Course, and enjoy other activities such as snorkelling. Wander through the beautiful beaches and seaside in this romantic area.

Four Seasons Resort Hualalai Golf Course

Kaʻupulehu Cultural Center

Enjoy an outing to Kaʻupulehu Cultural Center during your stay in Kailua-Kona. Stroll along the seaside or discover the sunsets in this romantic area.

Kaʻupulehu Cultural Center

Things to do

Big Island Manta Ray Night Snorkel

Big Island Manta Ray Night Snorkel

S$121
per adult
96% of travellers recommend
Big Island Manta Ray Night Snorkel
Snow covering the top of the Mauna Kea volcano in Hawaii

Mauna Kea Summit & Stars Adventure

S$423
per traveller
90% of travellers recommend
Mauna Kea Summit & Stars Adventure
Big Island GOAT Experience: Mauna Kea Summit, Sunset & Stars

Big Island GOAT Experience: Mauna Kea Summit, Sunset & Stars

S$371
per adult
94% of travellers recommend
Big Island GOAT Experience: Mauna Kea Summit, Sunset & Stars
See all activities in Kailua-Kona

* 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.