A lush green valley with a coastline.

Hawaii Island Luxury Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ₩1,660,000 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 Hawaii Island

Price found within the past 48 hours. Click for updated prices.
  • Sep 7 - Sep 12

    Waikoloa Beach Marriott Resort & Spa + Flight

    Waikoloa
    5 nights
    4.5 star property
    8.6/10 - Excellent (1,001 reviews)
    Roundtrip San Jose (SJC) - Kona Coast (KOA)
    SJC - KOA1 stop KOA - SJC2 stops
    Save 100% on your flight
    ₩3,055,518
    ₩2,148,422
    per traveler
    found 9 hours ago
    Waikoloa Beach Marriott Resort & Spa
  • Sep 7 - Sep 12

    Fairmont Orchid Gold Experience + Flight

    Kamuela
    5 nights
    5.0 star property
    9.4/10 - Exceptional (91 reviews)
    "Absolutely loved everything about the Fairmont Gold experience. I would sincerely recommend staying with a Fairmont Gould, as there was an amazing breakfast, great staff, own concierge, nicer floor.. the food options for breakfast or actually a great money saver with really high-quality food versus going to the restaurants. Amazing food options at the hotel, great amenities. Snorkeling in the lagoon with sea turtles and hundreds of tropical fish. Luau on property."
    Reviewed July 15, 2026
    Roundtrip San Jose (SJC) - Kona Coast (KOA)
    SJC - KOA1 stop KOA - SJC2 stops
    Save 100% on your flight
    ₩4,644,580
    ₩3,422,207
    per traveler
    found 9 hours ago
    Fairmont Orchid Gold Experience
  • Sep 7 - Sep 12

    Fairmont Orchid + Flight

    Kohala Coast
    5 nights
    4.5 star property
    9.2/10 - Wonderful (1,002 reviews)
    Roundtrip San Jose (SJC) - Kona Coast (KOA)
    SJC - KOA1 stop KOA - SJC2 stops
    Save 100% on your flight
    ₩3,269,098
    ₩2,441,395
    per traveler
    found 9 hours ago
    Fairmont Orchid
  • Sep 7 - Sep 12

    Kona Village, A Rosewood Resort + Flight

    Kaupulehu
    5 nights
    5.0 star property
    9.4/10 - Exceptional (94 reviews)
    "amazing resort, extremely family friendly with every amenity you can imagine. the service is top notch, the food is good, and the setting is unbelievable. I will definitely be a guest again and I hope they continue to uphold their current standards."
    Reviewed July 24, 2026
    Roundtrip San Jose (SJC) - Kona Coast (KOA)
    SJC - KOA1 stop KOA - SJC2 stops
    Save 100% on your flight
    ₩8,143,081
    ₩6,484,910
    per traveler
    found 9 hours ago
    Kona Village, A Rosewood Resort
  • Sep 7 - Sep 12

    Four Seasons Resort Hualalai + Flight

    Kaupulehu
    5 nights
    5.0 star property
    9.6/10 - Exceptional (498 reviews)
    Roundtrip San Jose (SJC) - Kona Coast (KOA)
    SJC - KOA1 stop KOA - SJC2 stops
    Save 100% on your flight
    ₩8,342,728
    ₩6,906,017
    per traveler
    found 9 hours ago
    Four Seasons Resort Hualalai

Discover the most popular places to visit in Hawaii Island

Top Luxury Hawaii Island Hotels

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.

All you need to know about luxury vacations in Hawaii Island

What can I expect from a luxury Hawaii Island vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Hawaii Island 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 Hawaii Island?

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 Hawaii Island 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 ₩2,148,421. Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in Hawaii Island?

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 Hawaii Island 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 Hawaii Island?

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 Hawaii Island 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 Hawaii Island 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.