Kailua-Kona Luxury Vacations

Book a Luxury Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ¥109,000 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 Luxury vacation packages in Kailua-Kona

Price found within the past 48 hours. Click for updated prices.
Royal Kona Resort

Royal Kona Resort

Historic Kailua Village
¥259,812
per person
Oct 17 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Kailua-Kona (KOA)
8.2/10 Very Good! (2,981 reviews)
Aston Kona by the Sea

Aston Kona by the Sea

Holualoa Village
¥310,220
per person
Oct 17 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Kailua-Kona (KOA)
8.8/10 Excellent! (1,263 reviews)
NA

Reviewed on Aug 3, 2026

Four Seasons Resort Hualalai

Four Seasons Resort Hualalai

Kaupulehu
¥638,721
per person
Sep 13 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Kailua-Kona (KOA)
9.6/10 Exceptional! (499 reviews)
Kanaloa at Kona by OUTRIGGER

Kanaloa at Kona by OUTRIGGER

Keauhou
¥472,332
per person
Oct 9 - Oct 16
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Kailua-Kona (KOA)
8.6/10 Excellent! (555 reviews)
The positives are that the condo is spacious, the resort complex is beautiful, and the pool area is excellent. The location is also convenient for exploring the Kona area. However, the condo itself feels quite dated. The furniture, kitchen, bathrooms, and appliances are all older than expected, and the cookware was heavily scratched and should be replaced. Another disappointment was that air conditioning requires an additional fee, which we only realized after making the reservation. Since the top floor becomes very warm during the day, air conditioning feels more like a necessity than an optional upgrade. It's also worth noting that the condo requires climbing stairs just to reach the entrance, and because it's a two-level unit, carrying luggage during check-in and check-out can be inconvenient. Overall, this is a nice place in a well-maintained complex, but we expected a more updated condo for the price. We've stayed in other condos on the Big Island that were more modern and provided a better overall experience, so this one didn't feel like the best value. We enjoyed our stay, but we would likely choose a different property next time

Reviewed on Aug 6, 2026

Don't see what you're looking for?
See all available trips from Tokyo to Kailua-Kona
View all trips

5* Luxury vacations in Kailua-Kona

Price found within the past 48 hours. Click for updated prices.
Four Seasons Resort Hualalai

Four Seasons Resort Hualalai

Kaupulehu
¥638,721
per person
Sep 13 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Kailua-Kona (KOA)
9.6/10 Exceptional! (499 reviews)
Don't see what you're looking for?
See all available trips from Osaka to Kailua-Kona
View all trips

4 Night Luxury vacations in Kailua-Kona

Price found within the past 48 hours. Click for updated prices.
Kona Coast Resort

Kona Coast Resort

Keauhou
¥86,142
per person
Sep 26 - Sep 30
found 23 hours ago
Roundtrip flight included
Honolulu (HNL) to Kailua-Kona (KOA)
9.2/10 Wonderful! (1,458 reviews)
Minimal amount of ADA accessible units although we requested wheelchair accessible units.

Reviewed on Aug 7, 2026

Holua Resort

Holua Resort

Keauhou
¥99,504
per person
Sep 26 - Sep 30
found 23 hours ago
Roundtrip flight included
Honolulu (HNL) to Kailua-Kona (KOA)
9.2/10 Wonderful! (1,003 reviews)
This property was great for teens being able to have a little space and a comfortable bed rather than a pull out sofa. The AC was fantastic as we had extremely humid and hot weather during our visit. There are 6 small pools + hot tubs on the property which are cleaned and maintained regularly. Staff was friendly and welcoming. Beware they send you to a 'concierge' desk to claim your key cards but it is a heavy time share pitch. The property and some details are a bit run down so not a good start. The closet bars/hangers were thick with dust and the furniture needs some upholstery cleaning as do the vents/filters for the AC units. There was a 'designated smoking bench' right below our balcony so that ended many morning coffees quickly. Nice that they have the benches but a more thoughtful placement would be better. There was a strong chemical smell coming from the dishwasher. We ran it once to see if that would clear out any left over soap, etc. but discovered the machine was actually broken and the smell was likely an epoxy used to glue plastic parts back together. We didn't use the dishwasher for the entire visit. No big deal. When they suggest you store ALL food in the fridge, you should. They get bugs and ants due to the weather, etc. The parking didn't bother us but it is a two level garage and a little walk to get to your place. If you need a ride in a golf cart, one of the staff will happily pick you up or drop you off. There isn't ocean access. Wouldn't return.

Reviewed on Aug 3, 2026

Kanaloa at Kona by OUTRIGGER

Kanaloa at Kona by OUTRIGGER

Keauhou
¥131,182
per person
Sep 26 - Sep 30
found 23 hours ago
Roundtrip flight included
Honolulu (HNL) to Kailua-Kona (KOA)
8.6/10 Excellent! (555 reviews)
The positives are that the condo is spacious, the resort complex is beautiful, and the pool area is excellent. The location is also convenient for exploring the Kona area. However, the condo itself feels quite dated. The furniture, kitchen, bathrooms, and appliances are all older than expected, and the cookware was heavily scratched and should be replaced. Another disappointment was that air conditioning requires an additional fee, which we only realized after making the reservation. Since the top floor becomes very warm during the day, air conditioning feels more like a necessity than an optional upgrade. It's also worth noting that the condo requires climbing stairs just to reach the entrance, and because it's a two-level unit, carrying luggage during check-in and check-out can be inconvenient. Overall, this is a nice place in a well-maintained complex, but we expected a more updated condo for the price. We've stayed in other condos on the Big Island that were more modern and provided a better overall experience, so this one didn't feel like the best value. We enjoyed our stay, but we would likely choose a different property next time

Reviewed on Aug 6, 2026

Don't see what you're looking for?
See all available trips from Honolulu to Kailua-Kona
View all trips

Things to do

Young girl holding a sea urchin on the glass bottom boat in the Pacific Ocean near the Big Island of Hawaii

Glass-Bottom Boat Tour in Waikoloa

¥7,981
per adult
94% of travellers recommend
Glass-Bottom Boat Tour in Waikoloa
Deluxe Snorkel & Dolphin Watch

4.5hr Snorkel & Dolphin Watch includes breakfast & Lunch plus a 20ft slide

¥18,117
per adult
96% of travellers recommend
4.5hr Snorkel & Dolphin Watch includes breakfast & Lunch plus a 20ft slide
Captain Cook Dinner Cruise to Kealakekua Bay from Kailua Pier

Captain Cook Dinner Cruise to Kealakekua Bay from Kailua Pier

¥31,920
per adult
90% of travellers recommend
Captain Cook Dinner Cruise to Kealakekua Bay from Kailua Pier
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.