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.
Royal Kona Resort
Historic Kailua Village
Price was $590, price is now $584 per person
$584
per person
Nov 24 - Nov 26
found 9 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kailua-Kona (KOA)
8.2/10 Very Good! (2,697 reviews)
Gorgeous view! Friendly staff. Check in was really slow. Their computers seemed to be slow. Great wifi in room. No microwave in room. Beautiful lagoon for swimming. Lovely resort. Comfy beds and pillows. Great AC.
Reviewed on Oct 24, 2025
Four Seasons Resort Hualalai
Kaupulehu
Save 100% on your flight
Price was $7,064, price is now $5,567 per person
$5,567
per person
Jan 1 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Kailua-Kona (KOA)
9.6/10 Exceptional! (471 reviews)
What an amazing property but even more importantly what a superamazing staff!!
Ryan deserves all the credit. Her quick thinking kindness solved our issue so elegantly. This is indeed a VIP in all the senses. The fact that she is so likeablle made it even better!!
Isiah from in room dining was great and easy to talk to.
Chayan on check in made us feel like ohana!
Greg upon check out conitnued to make us feel wanted and loved.
Overall, a lovely property and a great experience but once again Ryan deserves the biggest mahalo nui loa!!
Thank you four seasons
Aloha and malama till we see you again
Reviewed on Oct 15, 2025
Aston Kona by the Sea
Holualoa Village
Price was $2,811, price is now $2,101 per person
$2,101
per person
Dec 27 - Dec 31
found 22 hours ago
Roundtrip flight included
San Antonio (SAT) to Kailua-Kona (KOA)
8.8/10 Excellent! (1,124 reviews)
The room class that I had ordered was not available upon check in. A two Bedroom and ocean front. They gave me in a room that had a wall right in front of the best part of the view. My impression is they don’t place the Expedia reservations in a priority spot. I would call the hotel prior to arrival to confirm room assignment.
Reviewed on Oct 23, 2025
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View all trips5* Luxury vacations in Kailua-Kona
Price found within the past 48 hours. Click for updated prices.
Four Seasons Resort Hualalai
Kaupulehu
Save 100% on your flight
Price was $7,064, price is now $5,567 per person
$5,567
per person
Jan 1 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Kailua-Kona (KOA)
9.6/10 Exceptional! (471 reviews)
What an amazing property but even more importantly what a superamazing staff!!
Ryan deserves all the credit. Her quick thinking kindness solved our issue so elegantly. This is indeed a VIP in all the senses. The fact that she is so likeablle made it even better!!
Isiah from in room dining was great and easy to talk to.
Chayan on check in made us feel like ohana!
Greg upon check out conitnued to make us feel wanted and loved.
Overall, a lovely property and a great experience but once again Ryan deserves the biggest mahalo nui loa!!
Thank you four seasons
Aloha and malama till we see you again
Reviewed on Oct 15, 2025
Don't see what you're looking for?
See all available trips from Columbus to Kailua-Kona
View all trips3 Night Luxury vacations in Kailua-Kona
Price found within the past 48 hours. Click for updated prices.
Royal Kona Resort
Historic Kailua Village
Price was $1,245, price is now $1,099 per person
$1,099
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kailua-Kona (KOA)
8.2/10 Very Good! (2,697 reviews)
Gorgeous view! Friendly staff. Check in was really slow. Their computers seemed to be slow. Great wifi in room. No microwave in room. Beautiful lagoon for swimming. Lovely resort. Comfy beds and pillows. Great AC.
Reviewed on Oct 24, 2025
Four Seasons Resort Hualalai
Kaupulehu
Save 100% on your flight
Price was $7,064, price is now $5,567 per person
$5,567
per person
Jan 1 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Kailua-Kona (KOA)
9.6/10 Exceptional! (471 reviews)
What an amazing property but even more importantly what a superamazing staff!!
Ryan deserves all the credit. Her quick thinking kindness solved our issue so elegantly. This is indeed a VIP in all the senses. The fact that she is so likeablle made it even better!!
Isiah from in room dining was great and easy to talk to.
Chayan on check in made us feel like ohana!
Greg upon check out conitnued to make us feel wanted and loved.
Overall, a lovely property and a great experience but once again Ryan deserves the biggest mahalo nui loa!!
Thank you four seasons
Aloha and malama till we see you again
Reviewed on Oct 15, 2025
Aston Kona by the Sea
Holualoa Village
Price was $1,921, price is now $1,529 per person
$1,529
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Kailua-Kona (KOA)
8.8/10 Excellent! (1,124 reviews)
The room class that I had ordered was not available upon check in. A two Bedroom and ocean front. They gave me in a room that had a wall right in front of the best part of the view. My impression is they don’t place the Expedia reservations in a priority spot. I would call the hotel prior to arrival to confirm room assignment.
Reviewed on Oct 23, 2025
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View all trips4 Night Luxury vacations in Kailua-Kona
Price found within the past 48 hours. Click for updated prices.
Kona Coast Resort
Keauhou
Price was $2,352, price is now $1,732 per person
$1,732
per person
Dec 25 - Dec 29
found 21 hours ago
Roundtrip non-stop flight included
Oakland (OAK) to Kailua-Kona (KOA)
9.2/10 Wonderful! (1,370 reviews)
Didn't care for the property and the condo at all. Just not our vibe and no beach access. Like walking around a neighborhood in suburb not Hawaii
Reviewed on Oct 24, 2025
Holua Resort
Keauhou
Price was $2,451, price is now $1,794 per person
$1,794
per person
Dec 25 - Dec 29
found 21 hours ago
Roundtrip non-stop flight included
Oakland (OAK) to Kailua-Kona (KOA)
9.2/10 Wonderful! (1,009 reviews)
We enjoyed our stay. Very quiet and very comfortable. Had everything we needed. Bed was lovely. Staff service was good!
What was not so good is the unit needs a remodel. Cabinets are very worn. Curtains were torn in places. But there was a card in the unit that said a complete remodel is happening in 2026. That is good news!
Reviewed on Oct 20, 2025
Four Seasons Resort Hualalai
Kaupulehu
Price was $8,367, price is now $6,501 per person
$6,501
per person
Jan 1 - Jan 5
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Kailua-Kona (KOA)
9.6/10 Exceptional! (471 reviews)
What an amazing property but even more importantly what a superamazing staff!!
Ryan deserves all the credit. Her quick thinking kindness solved our issue so elegantly. This is indeed a VIP in all the senses. The fact that she is so likeablle made it even better!!
Isiah from in room dining was great and easy to talk to.
Chayan on check in made us feel like ohana!
Greg upon check out conitnued to make us feel wanted and loved.
Overall, a lovely property and a great experience but once again Ryan deserves the biggest mahalo nui loa!!
Thank you four seasons
Aloha and malama till we see you again
Reviewed on Oct 15, 2025
Don't see what you're looking for?
See all available trips from Columbus to Kailua-Kona
View all tripsAll you need to know about luxury vacations in Kailua-Kona
What can I expect from a luxury Kailua-Kona vacation?
Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Kailua-Kona vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views.
How can I find all-inclusive luxury vacation packages in Kailua-Kona?
By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5* filter to find truly sensational stays. You barely need to lift a finger.
Can I book a cheap Kailua-Kona luxury vacation?
Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at $584. Prices and availability are subject to change. Additional terms may apply.
How can I book a luxury family vacation in Kailua-Kona?
Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi.
Can I book a package in Kailua-Kona with a luxury vacation home?
A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package.
How can I find the best luxury vacation deals in Kailua-Kona?
Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months.
Can I book a luxury holiday in Kailua-Kona with free cancellation and/or flexible dates?
Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan.
Why should I book my luxury trip to Kailua-Kona with Expedia?
A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind.
Top Luxury Kailua-Kona Hotels
Four Seasons Resort Hualalai
72-100 Ka'upulehu Drive, Kailua-Kona, HI
Four Seasons Resort Hualalai is a sumptuous 5-star beach property where you can treat yourself to jetted bathtubs and premium bedding. Deluxe amenities at this ...
9.6/10 Exceptional! (471 reviews)
What an amazing property but even more importantly what a superamazing staff!! Ryan deserves all the credit. Her quick thinking kindness solved our issue so elegantly. This is indeed a VIP in all the senses. The fact that she is so likeablle made it even better!! Isiah from in room dining was great ...
Reviewed on Oct 15, 2025
Hampton Inn by Hilton Kailua-Kona Bay
75-5739 Alii Dr, Kailua-Kona, HI
Take a lavish vacation in Kailua-Kona. Popular amenities include an outdoor pool, a terrace, and a garden.
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
Royal Kona Resort
75-5852 Alii Dr, Kailua-Kona, HI
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.
8.2/10 Very Good! (2,710 reviews)
Great place.
Reviewed on Oct 20, 2025
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.