Kahoolawe Adventure Vacations

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Top Adventure vacation packages in Kahoolawe

Price found within the past 48 hours. Click for updated prices.
Maui Vista – Maui Condo & Home

Maui Vista – Maui Condo & Home

South Kihei
$1,109
per person
Oct 13 - Oct 19
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
8.6/10 Excellent! (54 reviews)
Everything was great

Reviewed on Feb 1, 2026

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea
$2,198
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
9.4/10 Exceptional! (1,000 reviews)
My husband and I had an incredible honeymoon stay. We couldn't recommend Hotel Wailea enough!! The team are all so lovely and attentive and all went out their way to give us the best experience. Shannon was an absolute star organising an itinerary prior to arrival so everything was so smooth and easy. Would definitely recommend the in-room Lomi Lomi couples massage and hiring e-bikes with Bear. Shoutout to Sunny also for her help on the front desk and assistance with our postcards! Our hotel room was spacious, comfortable and had a breathtaking ocean view and sofa balcony loungers. We were also very grateful to the valet team for all their assistance chauffeuring us around Wailea and the beaches. The food was utterly divine, in particular the Bird Cage was a highlight, superb menu and sake. The breakfasts also were so fresh! Not to mention the moreish cocktail menu and bites by the pool! The ariel and flow yoga with Andrea and outrigger canoe experience were also fantastic. We couldn't fault it and was the most perfect honeymoon. Thank you all so so much again. We look forward to returning one day X

Reviewed on Sep 6, 2026

The Residences at Kamaole Sands Resort

The Residences at Kamaole Sands Resort

South Kihei
$1,301
per person
Nov 12 - Nov 15
found 20 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
10/10 Exceptional! (5 reviews)
Bonus was there were beach chairs, towels and an umbrella. We only used two chairs as our family were busy snorkeling or boarding away while 1-2 sat out and rested. Clean, right down from beach park 3...stocked pantry got some add-ons and pots and pans enough to allow us making most of our meals. Great times and great communication from host. Thanks! Lucas

Reviewed on Aug 30, 2026

Courtyard Maui Kahului Airport

Courtyard Maui Kahului Airport

$1,224
per person
Oct 20 - Oct 25
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
9.2/10 Wonderful! (1,000 reviews)
AC Hotel by Marriott Maui Wailea

AC Hotel by Marriott Maui Wailea

Wailea
$1,358
per person
Oct 20 - Oct 25
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
9.2/10 Wonderful! (283 reviews)
Would choose ac by Marriott again

Reviewed on Sep 3, 2026

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5* Adventure vacations in Kahoolawe

Price found within the past 48 hours. Click for updated prices.
Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa

$1,325
per person
Nov 4 - Nov 9
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
8/10 Very Good! (26 reviews)
Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea
$2,198
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
9.4/10 Exceptional! (1,000 reviews)
My husband and I had an incredible honeymoon stay. We couldn't recommend Hotel Wailea enough!! The team are all so lovely and attentive and all went out their way to give us the best experience. Shannon was an absolute star organising an itinerary prior to arrival so everything was so smooth and easy. Would definitely recommend the in-room Lomi Lomi couples massage and hiring e-bikes with Bear. Shoutout to Sunny also for her help on the front desk and assistance with our postcards! Our hotel room was spacious, comfortable and had a breathtaking ocean view and sofa balcony loungers. We were also very grateful to the valet team for all their assistance chauffeuring us around Wailea and the beaches. The food was utterly divine, in particular the Bird Cage was a highlight, superb menu and sake. The breakfasts also were so fresh! Not to mention the moreish cocktail menu and bites by the pool! The ariel and flow yoga with Andrea and outrigger canoe experience were also fantastic. We couldn't fault it and was the most perfect honeymoon. Thank you all so so much again. We look forward to returning one day X

Reviewed on Sep 6, 2026

Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

Wailea
Save 100% on your flight
$2,648
per person
Oct 14 - Oct 19
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
8.6/10 Excellent! (1,008 reviews)
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3 Night Adventure vacations in Kahoolawe

Price found within the past 48 hours. Click for updated prices.
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

Wailea
Save 100% on your flight
$1,235
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
9.2/10 Wonderful! (1,008 reviews)
Loved this resort

Reviewed on Sep 12, 2026

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea
Save 100% on your flight
$1,414
per person
Dec 3 - Dec 6
found 24 hours ago
Roundtrip flight included
Ontario Intl. Airport (ONT) to Kahului (OGG)
9.4/10 Exceptional! (1,000 reviews)
My husband and I had an incredible honeymoon stay. We couldn't recommend Hotel Wailea enough!! The team are all so lovely and attentive and all went out their way to give us the best experience. Shannon was an absolute star organising an itinerary prior to arrival so everything was so smooth and easy. Would definitely recommend the in-room Lomi Lomi couples massage and hiring e-bikes with Bear. Shoutout to Sunny also for her help on the front desk and assistance with our postcards! Our hotel room was spacious, comfortable and had a breathtaking ocean view and sofa balcony loungers. We were also very grateful to the valet team for all their assistance chauffeuring us around Wailea and the beaches. The food was utterly divine, in particular the Bird Cage was a highlight, superb menu and sake. The breakfasts also were so fresh! Not to mention the moreish cocktail menu and bites by the pool! The ariel and flow yoga with Andrea and outrigger canoe experience were also fantastic. We couldn't fault it and was the most perfect honeymoon. Thank you all so so much again. We look forward to returning one day X

Reviewed on Sep 6, 2026

Wailea Beach Villas

Wailea Beach Villas

Wailea
$2,168
per person
Nov 12 - Nov 15
found 20 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
9.8/10 Exceptional! (199 reviews)
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4 Night Adventure vacations in Kahoolawe

Price found within the past 48 hours. Click for updated prices.
Maui Banyan Vacation Club

Maui Banyan Vacation Club

South Kihei
$1,117
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
8/10 Very Good! (388 reviews)
Very nice room. Amazing stay!

Reviewed on Sep 9, 2026

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea
$2,198
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
9.4/10 Exceptional! (1,000 reviews)
My husband and I had an incredible honeymoon stay. We couldn't recommend Hotel Wailea enough!! The team are all so lovely and attentive and all went out their way to give us the best experience. Shannon was an absolute star organising an itinerary prior to arrival so everything was so smooth and easy. Would definitely recommend the in-room Lomi Lomi couples massage and hiring e-bikes with Bear. Shoutout to Sunny also for her help on the front desk and assistance with our postcards! Our hotel room was spacious, comfortable and had a breathtaking ocean view and sofa balcony loungers. We were also very grateful to the valet team for all their assistance chauffeuring us around Wailea and the beaches. The food was utterly divine, in particular the Bird Cage was a highlight, superb menu and sake. The breakfasts also were so fresh! Not to mention the moreish cocktail menu and bites by the pool! The ariel and flow yoga with Andrea and outrigger canoe experience were also fantastic. We couldn't fault it and was the most perfect honeymoon. Thank you all so so much again. We look forward to returning one day X

Reviewed on Sep 6, 2026

Maui Beach Vacation Club

Maui Beach Vacation Club

North Kihei
$1,142
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
8.4/10 Very Good! (937 reviews)
The building was right at the street. Too much driving car noise. There was no house keeping available. Across street was the beach but not appropriate for swimming

Reviewed on Sep 11, 2026

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Find awesome Kahoolawe adventure vacations

How can I book the best Kahoolawe adventure trips?

Choose your own adventure in Kahoolawe, whether that’s a white-knuckle experience or a weekend walk. Read the reviews of the adventures that have gone before to be sure your chosen stay is your idea of fun.

How can I plan the perfect Kahoolawe family adventure vacation?

Adventure awaits when you select the family-friendly filter. There’s plenty of excitement for all ages in Kahoolawe. Just make sure to check your chosen escapade is within the realms of can-do for the whole clan and will have the whole team grinning.

Can I book all-inclusive Kahoolawe adventure vacation packages?

By refining your filters, you can explore all-amazing, all-adventurous, all-inclusive vacation packages. Amp up the extravagance with a few more filters too. Pick pristine pools, sensational spas, or wondrous waterparks for a sensational adventure getaway.

Why should I book a Kahoolawe adventure vacation for couples?

Book a Kahoolawe couples adventure vacation for the ultimate in romance and memory-making. Stunning scenery, heart-racing happenings, and the grandeur of the great outdoors—it’s the best way to bond.

How can I find the best deals on adventure packages in Kahoolawe?

It’s easy to unleash fabulously affordable adventures. Enter the dates for your caper, then sort your search results by price or deals.

Can I book an adventure vacation package in Kahoolawe with free cancellation and/or flexible dates?

Yes! When you’re searching for a great getaway, filter by payment option for free cancellation, so a change of plans won’t mess up your adventures. You’ll find buy now, pay later options, too, for full-on flexibility.

Why should I book a Kahoolawe adventure trip with Expedia?

Adventure, airfare, accommodation, ATOL protection, and activities—all on one site. And that’s just the benefits that begin with A.

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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.