Find 5 Star Hotels in Kailua, HI from ￥72,832

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Check availability on Kailua 5 Star Hotels

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Dec 23 - Dec 24
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Jan 2 - Jan 4

Our top choices for Kailua 5-star hotels

Balcony
2 2 Oceanview Modern Resort Vistas

2 2 Oceanview Modern Resort Vistas

2 2 Oceanview Modern Resort Vistas
5.0 star property
Central Kihei
10.0 out of 10, Exceptional, (5)
"This condo was great! Great ocean views, and the beach was beautiful! The condo owners thought of everything!"
United States
Jarrod
2 2 Oceanview Modern Resort Vistas
Luxury Apartment, Ocean View | Living area | Hulu, streaming services
Oceanfront Kihei Paradise Vistas

Oceanfront Kihei Paradise Vistas

Oceanfront Kihei Paradise Vistas
5.0 star property
Central Kihei
10.0 out of 10, Exceptional, (2)
"This property was clean, quiet, and had excellent security. The barbecue grill was easy to use. They had sandless beach towels, which worked so well. The view was beautiful! I want to go again next year. "
United States
Mae
Oceanfront Kihei Paradise Vistas
Luxury Condo | Living area | 90-inch Smart TV with digital channels, Hulu, streaming services
Centrally Located Elegant Vistas

Centrally Located Elegant Vistas

Centrally Located Elegant Vistas
5.0 star property
South Kihei
10.0 out of 10, Exceptional, (1)
"Love this Kihei home! Centrally located! It is very clean. We love that they have beach chairs and towels on hand. Overall great experience stay!"
United States
Edwin
Centrally Located Elegant Vistas
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Kailua.
Hilton Grand Vacations Club Maui Bay Villas

Hilton Grand Vacations Club Maui Bay Villas

575 S Kihei Road Kihei HI
The price is ￥56,648 per night from Jan 14 to Jan 15
￥56,648
￥72,832 total
Jan 14 - Jan 15, 2026
includes taxes & fees
9/10 Wonderful! (222 reviews)
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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.

Learn more about Kailua

Check out Garden of Eden Arboretum and Maui Garden Of Eden - Botanical Gardens & Arboretum—just a couple of the sights around Kailua.

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Frequently asked questions

How much does it cost to stay in a 5-star hotel in Kailua?
The amount you pay for a 5-star hotel in Kailua can vary according to what time of year you travel and how long you plan to be away, among a number of factors. Take advantage of our price per night filter and other search tools to find the best deal on a plush stay.

  • Search for the lowest price per night from ￥72,832

What makes a hotel 5 stars in Kailua?
In Kailua, a hotel needs to provide a certain amount of upscale amenities to earn 5 stars. These may include on-site gyms, spas and saunas, gourmet restaurants, premium bedding, complimentary luxury toiletries and more. What also sets 5-star hotels apart is their guest-focused standard of service. You can look forward to things like in-room massages, nightly turn-down services and concierge services. Some may also offer special touches such as a welcome gift.
Are there any 5-star all-inclusive resorts in Kailua?
Use our handy filters to find a high-end retreat in Kailua where everything you need is included. From there, narrow down your results for resorts that have 5 stars and are described as "All inclusive." The main thing on the schedule at these stays? Pure enjoyment and indulgence.