Kailua-Kona Luxury Vacations

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Flight and Luxury hotel deals in Kailua-Kona

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

Royal Kona Resort

Historic Kailua Village
CA $1,694
per person
Oct 14 - Oct 20
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Kailua-Kona (KOA)
8.2/10 Very good! (2,976 reviews)
Aston Kona by the Sea

Aston Kona by the Sea

Holualoa Village
CA $2,120
per person
Oct 14 - Oct 20
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Kailua-Kona (KOA)
8.8/10 Excellent! (1,263 reviews)
This place was probably top notch 25 years ago. The grounds and scenery were very nice. Parking was good in the garage and staff was helpful. The unit we had was very dated, stained rugs, a couple of live roaches (sometimes happens in this climate), advertised with washing machine and dryer, but the washing machine leaked all over the floor and would not run (very disappointing when your counting on being able to wash clothes on a long trip) Overall it was just ok, not someplace I would visit again.

Reviewed on Aug 7, 2026

Kanaloa at Kona by OUTRIGGER

Kanaloa at Kona by OUTRIGGER

Keauhou
CA $2,228
per person
Oct 14 - Oct 20
found 18 hours ago
Roundtrip flight included
Montreal (YMQ) to Kailua-Kona (KOA)
8.6/10 Excellent! (558 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
CA $12,998
per person
Oct 20 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Kailua-Kona (KOA)
9.6/10 Exceptional! (499 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 holidays in Kailua-Kona

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

Four Seasons Resort Hualalai

Kaupulehu
CA $12,998
per person
Oct 20 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Kailua-Kona (KOA)
9.6/10 Exceptional! (499 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 Columbus to Kailua-Kona
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3 Night Luxury holidays in Kailua-Kona

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

Royal Kona Resort

Historic Kailua Village
CA $1,317
per person
Sep 18 - Sep 21
found 20 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Kailua-Kona (KOA)
8.2/10 Very good! (2,976 reviews)
Aston Kona by the Sea

Aston Kona by the Sea

Holualoa Village
CA $1,464
per person
Sep 18 - Sep 21
found 20 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Kailua-Kona (KOA)
8.8/10 Excellent! (1,263 reviews)
This place was probably top notch 25 years ago. The grounds and scenery were very nice. Parking was good in the garage and staff was helpful. The unit we had was very dated, stained rugs, a couple of live roaches (sometimes happens in this climate), advertised with washing machine and dryer, but the washing machine leaked all over the floor and would not run (very disappointing when your counting on being able to wash clothes on a long trip) Overall it was just ok, not someplace I would visit again.

Reviewed on Aug 7, 2026

Kanaloa at Kona by OUTRIGGER

Kanaloa at Kona by OUTRIGGER

Keauhou
CA $1,505
per person
Sep 18 - Sep 21
found 20 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Kailua-Kona (KOA)
8.6/10 Excellent! (558 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

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See all available trips from Columbus to Kailua-Kona
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4 Night Luxury holidays in Kailua-Kona

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

Holua Resort

Keauhou
CA $1,481
per person
Sep 19 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Kailua-Kona (KOA)
9.2/10 Wonderful! (1,005 reviews)
Royal Kona Resort

Royal Kona Resort

Historic Kailua Village
CA $1,524
per person
Sep 19 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Kailua-Kona (KOA)
8.2/10 Very good! (2,976 reviews)
Aston Kona by the Sea

Aston Kona by the Sea

Holualoa Village
CA $1,820
per person
Sep 19 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Kailua-Kona (KOA)
8.8/10 Excellent! (1,263 reviews)
This place was probably top notch 25 years ago. The grounds and scenery were very nice. Parking was good in the garage and staff was helpful. The unit we had was very dated, stained rugs, a couple of live roaches (sometimes happens in this climate), advertised with washing machine and dryer, but the washing machine leaked all over the floor and would not run (very disappointing when your counting on being able to wash clothes on a long trip) Overall it was just ok, not someplace I would visit again.

Reviewed on Aug 7, 2026

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

Plan the perfect luxury Kailua-Kona vacation with Expedia

What are some benefits when booking luxury Kailua-Kona vacations?

When you book a luxury Kailua-Kona vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax.

How can I find all-inclusive luxury vacations in Kailua-Kona?

If you're looking for something luxurious in Kailua-Kona, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together.

Can I book a cheap luxury vacation?

While luxury vacations tend to be on the more costly end of the spectrum, ranging from CA $1,317, there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to 19. After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first.

Are there luxury spa vacations?

Yes, luxury spa vacations are available and quite popular in Kailua-Kona. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search.

What should I look for in a luxury family vacation in Kailua-Kona?

When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout Kailua-Kona.

Can I book last-minute luxury vacations?

Yes, last-minute bookings are often available in Kailua-Kona. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces.

What can help me find the best luxury vacation deals in Kailua-Kona?

You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of Kailua-Kona or travelling to more obscure destinations altogether can often lead to lower prices.

Can I book a luxury vacation that is fully refundable?

Yes, fully refundable reservations are sometimes available on luxury vacation packages in Kailua-Kona. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking.

Why should I book my luxury vacation with Expedia?

When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings.

Luxury Hotels in Kailua-Kona

Four Seasons Resort Hualalai

Four Seasons Resort Hualalai

72-100 Ka'upulehu Drive Kailua-Kona HI
  • 32 min drive from Kailua Pier
Book a stay at this luxury resort in Kailua-Kona. Enjoy free WiFi, free parking, and 7 outdoor pools. Popular attractions Four Seasons Resort Hualalai Golf Course ...
9.6/10 Exceptional! (500 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
Stay at this hotel in Kailua-Kona. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Magic Sands Beach and Kahalu'u Beach Park ...
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
Book a stay at this beach hotel in Kailua-Kona. Enjoy a full-service spa, breakfast (surcharge), and a fitness center. Our guests praise the pool and the restaurant ...
Royal Kona Resort
See all 3,385 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

Deluxe Snorkel & Dolphin Watch

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

CA $159
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

CA $125
per adult
96% of travellers recommend
Kona Catamaran Day or Sunset Sail aboard Spirit of Aloha
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

CA $70
per adult
94% of travellers recommend
Glass-Bottom Boat Tour in Waikoloa
See all activities in Kailua-Kona

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.