Kailua-Kona Luxury Vacations

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Top Luxury vacation packages in Kailua-Kona

Price found within the past 48 hours. Click for updated prices.
Aston Kona by the Sea

Aston Kona by the Sea

Holualoa Village
Save 100% on your flight
¥133,048
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
Honolulu (HNL) to Kailua-Kona (KOA)
8.8/10 Excellent! (1,268 reviews)
Beautiful… would stay here again, in a heartbeat!!

Reviewed on Aug 26, 2026

Royal Kona Resort

Royal Kona Resort

Historic Kailua Village
Save 100% on your flight
¥151,666
per person
Sep 26 - Oct 3
found 17 hours ago
Roundtrip flight included
Honolulu (HNL) to Kailua-Kona (KOA)
8.2/10 Very Good! (2,975 reviews)
The hotel was just okay, it seemed a bit old-fashioned, and they're trying to update it. Last night, we had issues with the AC, so we had to switch rooms. We ended up with a sea view, which was amazing! The pool lady was super nice and sweet, so overall, it was a good stay.

Reviewed on Aug 25, 2026

Kanaloa at Kona by OUTRIGGER

Kanaloa at Kona by OUTRIGGER

Keauhou
Save 100% on your flight
¥194,425
per person
Oct 2 - Oct 6
found 19 hours ago
Roundtrip flight included
Honolulu (HNL) to Kailua-Kona (KOA)
8.6/10 Excellent! (560 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

Four Seasons Resort Hualalai

Four Seasons Resort Hualalai

Kaupulehu
¥842,878
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kailua-Kona (KOA)
9.6/10 Exceptional! (500 reviews)
Went there everything is beautiful but the most amazing thing is the people!!!!!

Reviewed on Aug 11, 2026

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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
¥842,878
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kailua-Kona (KOA)
9.6/10 Exceptional! (500 reviews)
Went there everything is beautiful but the most amazing thing is the people!!!!!

Reviewed on Aug 11, 2026

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

4 Night Luxury vacations in Kailua-Kona

Price found within the past 48 hours. Click for updated prices.
Aston Kona by the Sea

Aston Kona by the Sea

Holualoa Village
Save 100% on your flight
¥133,048
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
Honolulu (HNL) to Kailua-Kona (KOA)
8.8/10 Excellent! (1,268 reviews)
Beautiful… would stay here again, in a heartbeat!!

Reviewed on Aug 26, 2026

Holua Resort

Holua Resort

Keauhou
Save 100% on your flight
¥142,493
per person
Oct 2 - Oct 6
found 19 hours ago
Roundtrip flight included
Honolulu (HNL) to Kailua-Kona (KOA)
9.2/10 Wonderful! (1,005 reviews)
Very nice and clean for an older complex. The staff were always helpful. But the parking lot is so far away from some units. Occasionally the cart would stop and offer a ride. But they were not always around.

Reviewed on Aug 26, 2026

Kanaloa at Kona by OUTRIGGER

Kanaloa at Kona by OUTRIGGER

Keauhou
Save 100% on your flight
¥194,425
per person
Oct 2 - Oct 6
found 19 hours ago
Roundtrip flight included
Honolulu (HNL) to Kailua-Kona (KOA)
8.6/10 Excellent! (560 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

Top Luxury Kailua-Kona Hotels

Four Seasons Resort Hualalai

Four Seasons Resort Hualalai

72-100 Ka'upulehu Drive Kailua-Kona HI
  • 32 min drive from Kailua Pier
Pamper yourself with an extravagant stay at Four Seasons Resort Hualalai, where you'll find jetted bathtubs and premium bedding. Deluxe amenities at this resort ...
9.6/10 Exceptional! (501 reviews)
"Went there everything is beautiful but the most amazing thing is the people!!!!!"

Reviewed on Aug 11, 2026

Four Seasons Resort Hualalai
Hampton Inn by Hilton Kailua-Kona Bay

Hampton Inn by Hilton Kailua-Kona Bay

75-5739 Alii Dr Kailua-Kona HI
  • 5 min walk from Kailua Pier
Take a lavish vacation in Kailua-Kona. Popular amenities include an outdoor pool, a terrace, and a garden.
6.8/10 (993 reviews)
"We did not stay at Uncle Billys hotel. It was closed but we were booked at a hotel 7 miles away"

Reviewed on Jan 1, 2022

Hampton Inn by Hilton Kailua-Kona Bay
Royal Kona Resort

Royal Kona Resort

75-5852 Alii Dr Kailua-Kona HI
  • 13 min walk from Kailua Pier
Pamper yourself with a luxe vacation at Royal Kona Resort. Sought-after amenities at this hotel include a spa, an outdoor pool, and a restaurant.
8.4/10 Very Good! (2,972 reviews)
"The hotel was just okay, it seemed a bit old-fashioned, and they're trying to update it. Last night, we had issues with the AC, so we had to switch rooms. We ended up with a sea view, which was amazing! The pool lady was super nice and sweet, so overall, it was a good stay."

Reviewed on Aug 25, 2026

Royal Kona Resort
See all 3,647 properties in Kailua-Kona
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.

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
Kona Catamaran Sail aboard Spirit of Aloha from Honokohau Harbor

Kona Catamaran Day or Sunset Sail aboard Spirit of Aloha

¥14,205
per adult
96% of travellers recommend
Kona Catamaran Day or Sunset Sail aboard Spirit of Aloha
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.