Kaupulehu Holidays

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Price found within the past 48 hours. Click for updated prices.
Fairway Villas Waikoloa by OUTRIGGER

Fairway Villas Waikoloa by OUTRIGGER

3 out of 5
Price was S$3,339, price is now S$2,690 per person
S$2,690
per person
10 May - 15 May
found 14 hours ago
Return flight included
Singapore (SIN) to Kailua-Kona (KOA)
8.8/10 Excellent! (503 reviews)
The condo was fairly clean. Furnishings are dated, but functional. Blanket on bed was so old and pilled I thought I was at great grandmas house! One coffee table obviously had something spilled on it, and coasters were actually stuck to table. The showerhead sprayed right in my face and couldn’t be adjusted too much without spay handle falling off. Kitchen was equipped with what I needed, although I never cooked any meals there. Appliances updated. Nice to have washer/dryer. TV was good, Internet was down (Spectrum) came back on but messed up cable atv, only used Roku afterwards. Great vacation and would recommend Fairway Villas.

Reviewed on 25 Feb, 2026

Mauna Lani, Auberge Collection

Mauna Lani, Auberge Collection

5 out of 5
Price was S$4,658, price is now S$3,405 per person
S$3,405
per person
10 May - 15 May
found 14 hours ago
Return flight included
Singapore (SIN) to Kailua-Kona (KOA)
9.4/10 Exceptional! (1,002 reviews)
Truly, an exceptional experience! We have visited several Auberge properties over the years and while the chain always provides an excellent experience, the Mauna Lani surpassed all of them! From our warm greeting to the hotel, to the fabulous hotel grounds and amenities, to the helpful staff, nothing was left undone. The lobby of the Mauna Lani is nothing short of breathtaking, with a wide array of gathering areas and comfortable nooks. The beachfront areas had gorgeous views and the property amenities included free snorkeling gear, paddle boards, and fun activities, like a tour of their impressive fish ponds. The Mauna Lani left us luxuriated, relaxed and feeling that aloha spirit!

Reviewed on 18 Feb, 2026

Fairmont Orchid Gold Experience

Fairmont Orchid Gold Experience

5 out of 5
Price was S$6,032, price is now S$4,679 per person
S$4,679
per person
10 May - 15 May
found 14 hours ago
Return flight included
Singapore (SIN) to Kailua-Kona (KOA)
9.6/10 Exceptional! (71 reviews)
All of the above! Was a great stay and exceeded my expectations all around.

Reviewed on 20 Feb, 2026

Fairmont Orchid

Fairmont Orchid

4.5 out of 5
Price was S$4,418, price is now S$3,601 per person
S$3,601
per person
10 May - 15 May
found 14 hours ago
Return flight included
Singapore (SIN) to Kailua-Kona (KOA)
9.2/10 Wonderful! (1,002 reviews)
This was a very special Christmas treat! The hotel is spectacular at Christmas and we had the best stay!

Reviewed on 19 Jan, 2026

Waikoloa Beach Marriott Resort & Spa

Waikoloa Beach Marriott Resort & Spa

4 out of 5
Price was S$4,132, price is now S$3,463 per person
S$3,463
per person
10 May - 15 May
found 14 hours ago
Return flight included
Singapore (SIN) to Kailua-Kona (KOA)
8.6/10 Excellent! (1,003 reviews)
Location, excellent and friendly bar and hotel service staff.

Reviewed on 21 Feb, 2026

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$2,038 per night from 1 Mar to 2 Mar
S$2,038
1 Mar - 2 Mar
includes taxes & fees
9.6/10 Exceptional! (481 reviews)
The room was decent but prime ocean view isn't always full ocean view. customer service is pretty mediocre for the price. Food is good for breakfast. Would avoid beach house for dinner. Pool side drinks are mediocre. Overall probably would recommend staying at the Kona Village hotel next door. They ...

Reviewed on 27 Feb, 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$2,068 per night from 7 Mar to 8 Mar
S$2,068
7 Mar - 8 Mar
includes taxes & fees
9.6/10 Exceptional! (75 reviews)
Excellent service, great location, great rooms, highly recommended!

Reviewed on 5 Feb, 2026

Kona Village, A Rosewood Resort
Royal Kona Resort

Royal Kona Resort

4 out of 5
75-5852 Alii Dr Kailua-Kona HI
Fully refundableReserve now, pay when you stay
The price is S$336 per night from 22 Mar to 23 Mar
S$336
22 Mar - 23 Mar
includes taxes & fees
8.2/10 Very Good! (2,859 reviews)
Room.was great....wifi everywhere on the resort. Beautiful grounds and awesome view!

Reviewed on 28 Feb, 2026

Royal Kona Resort
See all 5,644 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 from S$2,690 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 which includes a beach and a coastal town

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

See whales from up-close

Whale Watching On The Big Island

S$125
per adult
76% of travellers recommend
Whale Watching On The Big Island
Hawaii’s GOAT Experience: Mauna Kea Summit, Sunset & Stars

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

S$367
per adult
94% of travellers recommend
Big Island GOAT Experience: Mauna Kea Summit, Sunset & Stars
Captain Cook Reef Snorkeling of Kealakekua Bay

Captain Cook Reef Snorkeling of Kealakekua Bay

S$102
per adult
Captain Cook Reef Snorkeling of Kealakekua Bay
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.