Kahoolawe Luxury Vacations

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Top Luxury vacation packages in Kahoolawe

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

Royal Lahaina Bungalows & Spa

$1,268

per person

Dec 6 - Dec 12

found 14 hours ago

Roundtrip non-stop flight included

Burbank (BUR) to Kahului (OGG)

7.8/10 Good! (27 reviews)

Hotel Wailea Maui

Wailea

Save 100% on your flight

$2,903

per person

Dec 6 - Dec 12

found 23 hours ago

Roundtrip non-stop flight included

Burbank (BUR) to Kahului (OGG)

9.4/10 Exceptional! (1,002 reviews)

Everything was excellent, form the location to the incredible food!

Reviewed on Sep 22, 2026

Fairmont Kea Lani Maui

Wailea

Save 100% on your flight

$3,085

per person

Dec 6 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Burbank (BUR) to Kahului (OGG)

9.6/10 Exceptional! (1,002 reviews)

Great experience and would highly recommend.

Reviewed on Sep 27, 2026

Hana-Maui Resort, a Destination by Hyatt Residence

Hana Town Center

Save 100% on your flight

$1,796

per person

Dec 6 - Dec 12

found 23 hours ago

Roundtrip non-stop flight included

Burbank (BUR) to Kahului (OGG)

9.2/10 Wonderful! (1,001 reviews)

Loved the location, beautiful property!

Reviewed on Sep 19, 2026

Andaz Maui at Wailea Resort - a concept by Hyatt

Wailea

Save 100% on your flight

$2,773

per person

Dec 6 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Burbank (BUR) to Kahului (OGG)

9.2/10 Wonderful! (1,001 reviews)

We really enjoyed our stay. We booked 2 weeks but ended up leaving a couple days early because of the potential hurricane threat. Staff was amazing!! Everyone was so very friendly! Loved the walking path to other hotels, shops, restaurants! Rooms were nice, loved the coffee, chips, cookies, cute reusable bag provided. Wished it had another mirror somewhere to get ready while another was showering and wished there was more space for clothes. Though again we were there for 2 weeks so had a lot. They had full sized shampoo, conditioner, body wash, ironing board and cloths steamer, nice hair dryer and robes. Small reusable water bottles with ice and water available on each floor. Food by the pool was good. We rented a car for part of our stay, so super close to Kīhei for food, other beaches, shops but $60/day to park and had to use valet. Pools were beautiful! Reef safe sunscreen 30 & 50 were provided at every pool. We were a little disappointed that 2 pools were being worked on and we didn’t know it beforehand. Very noisy at one pool M-F for hours. And limited shady spots, and if windy, shade umbrellas had to come down. You could purchase cabanas in the shade for an extra $250 I believe but many sat empty at all pools. Beach was rough after the storm (can’t be helped because of weather) but no one was working on steps, path to get down to the beach. Other hotels were on it days after it happened… just something to be prepared, aware of. We were able to snorkel.

Reviewed on Sep 28, 2026

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5* Luxury vacations in Kahoolawe

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

Royal Lahaina Bungalows & Spa

$1,268

per person

Dec 6 - Dec 12

found 14 hours ago

Roundtrip non-stop flight included

Burbank (BUR) to Kahului (OGG)

7.8/10 Good! (27 reviews)

Hotel Wailea Maui

Wailea

Save 100% on your flight

$2,903

per person

Dec 6 - Dec 12

found 23 hours ago

Roundtrip non-stop flight included

Burbank (BUR) to Kahului (OGG)

9.4/10 Exceptional! (1,002 reviews)

Everything was excellent, form the location to the incredible food!

Reviewed on Sep 22, 2026

Fairmont Kea Lani Maui

Wailea

Save 100% on your flight

$3,085

per person

Dec 6 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Burbank (BUR) to Kahului (OGG)

9.6/10 Exceptional! (1,002 reviews)

Great experience and would highly recommend.

Reviewed on Sep 27, 2026

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3 Night Luxury vacations in Kahoolawe

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

Aloha Chic Penthouse Vistas

Central Kihei

$953

per person

Dec 3 - Dec 6

found 18 hours ago

Roundtrip flight included

Los Angeles (QLA) to Kahului (OGG)

10/10 Exceptional! (5 reviews)

The place was beautiful, clean, and well equipped with supplies. The location was perfect for us with amazing views and sunsets.

Reviewed on Jul 3, 2026

Hotel Wailea Maui

Wailea

Save 100% on your flight

$2,719

per person

Dec 24 - Dec 27

found 1 day ago

Roundtrip flight included

Seattle (SEA) to Kahului (OGG)

9.4/10 Exceptional! (1,002 reviews)

Everything was excellent, form the location to the incredible food!

Reviewed on Sep 22, 2026

Fairmont Kea Lani Maui

Wailea

$2,083

per person

Nov 10 - Nov 13

found 18 hours ago

Roundtrip non-stop flight included

Ontario Intl. Airport (ONT) to Kahului (OGG)

9.6/10 Exceptional! (1,002 reviews)

Great experience and would highly recommend.

Reviewed on Sep 27, 2026

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4 Night Luxury vacations in Kahoolawe

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

Maui Banyan Vacation Club

South Kihei

$1,033

per person

Nov 21 - Nov 25

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Kahului (OGG)

8/10 Very Good! (392 reviews)

We were pleasantly surprised how nice and how large the unit was. We loved the view of the path and gardens from the balcony. The only glitch was that when we arrived, the door code we were given didn't work. But this was quickly resolved - the lady at the front desk just reset it to a new code and we were in.

Reviewed on Sep 25, 2026

Maui Beach Vacation Club

North Kihei

$1,316

per person

Nov 21 - Nov 25

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Kahului (OGG)

8.4/10 Very Good! (937 reviews)

The only problem with the resort was the rooms do not have AC and it got a little bit hot!

Reviewed on Sep 28, 2026

Hotel Wailea Maui

Wailea

Save 100% on your flight

$2,783

per person

Nov 21 - Nov 25

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Kahului (OGG)

9.4/10 Exceptional! (1,002 reviews)

Everything was excellent, form the location to the incredible food!

Reviewed on Sep 22, 2026

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What can I expect from a luxury Kahoolawe vacation?

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

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 Kahoolawe 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 $953. Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in Kahoolawe?

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 Kahoolawe 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 Kahoolawe?

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 Kahoolawe 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 Kahoolawe 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.